The Wisdom Wall

“And, and the folks with the highest usage may actually have the most incentive to leave. It's not a clear correlation to success, right?”

“Customers will prefer, prefer a great eye to a mediocre human. They'll prefer a great eye that solves their problem today, that knows the answer, to someone that has to get an engineer and an appointment to you next week, that doesn't know, that says I'm just new to the account because your old account manager quit…”

“it's better to give a precious lead to an ad to a B plus AI than to give it to someone in sales. That's going to quit, not show up or screw up the deal.”

“It doesn't, you don't need to return to office for high performers. The best people will get it done. They'll get it done from Antarctica or they'll get it done in the office, but the mid performers just don't work from home, right? They barely work. And so they, they want to supervise them for 40 hours. It's not about…”

“The tactical answer for more kumbaya people is probably cut half your sales team. This always works. Concentrate your leads in tougher times. It may not work at Matt. Maybe it doesn't work at zoom info scale, but even at fifty million, it's going to work.”

“You gotta play in categories where you lose most deals to win. This is a weird thing. You gotta play in categories where you lose most deals.”

“If growth has slowed, it is not a downturn or macro. It's a little bit of it. It is that you have fallen out of product market fit. If two years ago you were growing a hundred percent and today you're growing. It is not just the market. It is that you do not have the mark, the product the market wants anymore. You…”

“It's always your fault when someone doesn't work out... It's you didn't do the work. You didn't figure out if they were the right fit. They never know. You can never know enough about a company before you join. It's impossible.”

“So far, since I've been involved in SAS since 2005, we have not gotten any more efficient. In sales and marketing, we've gotten more efficient at other things.”

“I think if you have humans in a renewal, you're you have failed your customers. You have failed your customers. If you need sales or success or account, it doesn't mean that the margin, you don't need help. I'm not saying you don't need to parachute in on 10% of your deals, but if 80% of your deals can't sell for new,…”

“Uh, they're tough on all of us, and I really think as founders, we should do everything humanly possible to have no non-performance layoffs. I mean, we have recurring revenue. You should be able to predict the next quarter or two. You should be a little embarrassed if you have to do layoffs, even though a lot of us do…”

“You can brute force high NRR with longer term deals. You can brute force NRR if you threaten customers when they leave with an inability to get their data. You can, you can brute force NRR by having out of bound price increases, 30 or 40% a year.”

“with a few exceptions, I don't have any empathy for startups that had decent growth during 2021 and have, have slowed to zero. Ok, I don't have any empathy. You really have no customers? Really none? No. What it really means is your product wasn't valuable enough. It means you no longer have product market fit. It…”

“Unless your customers are in New York, unless you're doing financial services or some parts of ad tech or otherwise, going to New York is the worst idea. Uh, you get none of the, almost none of the benefits of being in the Bay Area. You don't get the customers here. You don't get the ecosystem. You don't get the…”

“Once you give up free trials, you will never go back, and you will be able to have terrible onboarding, and you will be able to have all this friction behind the scenes, and you will be able to have many broken processes and things, and you will never build great software if you abandon your free trial.”

“I think it is a self-inflicted wound for a lot of systems of record and SaaS centers as they jack up the prices because seats are going down and agents are going up and they jack up the price for access. It's incense us finally to put more and more of our data outside of that system of record and then forget about the…”

“you're going to lose in the vendor war if you're not the one that not just is recommended in AO, but where the agent says, I will just do it with this, with this API.”

“What's changed is the agents have so much context. They're aware of so much that every single day when you log in, especially with you, when you log in with 10 K now our AI VP of revenue, it has new things that wants to build and do. It's not a software tool. It's not a workflow automation, right? I mean, it's not…”

“The agent made the call for a heat map vendor We'd never heard of, and we, we didn't even, we didn't even need to do more diligence. You trusted the agent. Someone lost a 50, 20, a twenty-k deal out there to an agent, and you, they were never, and this paid vet, this other, this SaaS vendor was never even in the deal.…”

“these models, um, are goal-seeking, right? And they want to finish projects. So Replit just wants, Amelia, you know this, Replit wants to finish. Replit wants to finish, and so does CloudCode if you use it on an own. But when, but if you use Cloud on top of it, It, it countermands that. It gets Replit to slow down and…”

“moats still exist in the age of AI, but they're just like shallower, so you better fucking deliver value.”

“it is more tiring to be managing 21 agents. It is not. I don't know that it's more work. I'm still reflecting on it, but it is a higher cognitive load than people.”

“And so your goal should not be to reproduce 80% of your best person, but the goal should be to find areas where the goal is higher than human.”

“if you talk to folks like at Finn or Intercom or Gorgias or Sierra and others, they're all saying that there's convergence that support sales and marketing are all converging because once you can AI-ify them, you don't want to have three different agents, right? You want one.”

“to get to the level of autonomy you want, you don't need humans in the loop. Okay. That that's not autonomy, right? What you need is humans on the loop constantly, the exceptions kicked out to them.”

“That will, in many cases, either deliver instant ROI or really replace humans, and it is so jaw-droppingly valuable that you can charge two to 10 times more than your software.”

“the biggest takeaway is don't, still don't build it if you can buy it. We love Tenk and QB, they're part of our families, and I hate to say this, but we would dump both of them if there was an off the shelf tool. We wouldn't turn them off. This is the strange anthropomorphizing we do with AI, but we would stop using…”

“if you run them in the dev environment permanently, like we're doing, you get an extra agent that has an infinite context window and infinite history.”

“what's better is if your team is Lagging or resistant, just go hire one reasonably senior person that is all in here. One. And, and folks will start quitting when they don't want to work at that pace anyway. You got to hire them ideally at the VP level above, and they're just going to do it. Just create a new role, VP…”

“If you build a 60% solution. No, one's going to pay for it.”

“view FDs as one of your most important assets to getting renewals, retention, NPS, word of mouth, virality. Don't, don't look at FDs as a cost center. This was the mistake we made in customer success a generation ago. And this is why customer success was cut to zero and repurposed into a sales function because it was…”

“It might be the API that gets us to switch, not the humans, not the chocolates, not the gift certificate, but if the API is better, works better with our agents, we might spend a couple hours. It takes to move over our key accounts to ramp because it's the agent that matters.”

“If you haven't gotten any outbound to work, Buying an AI to do it isn't, it's not going to help you. You have to prove it. Any of the agents we use, any of the dozens of agents we use, we are taking a playbook that at least works a little bit.”

“So there's no economic justification, uh, for software costs to building these apps, right? Uh, you can buy them for 10 grand, like it makes no economic sense. Um, so you have to really need something that you can't buy today.”

“If growth isn't accelerating, you're not an AI company.”

“You're not going to VibeCode Salesforce for real, but you know what you can VibeCode? Something for demo day that looks really good.”

“investors are expecting insane levels of growth. Insane levels of growth, right? They want, like, the idea that you can go from one to a hundred in a year is now seen as what you want to invest in.”

“There's no great answers to the question that some great businesses will compound to Epic rates, but they're unfundable now, and they would have been fundable two years ago.”

“You have to own the agents on your platform, or the agents will take away all the value.”

“A lot of the agents we use, um, are pushing down market to be more self-service. So far that doesn't work. So far, I will say for the most part, agents that require deep training cannot be self-trained.”

“I don't think that is the right answer for 99.8% of the world. It might work for owner, and I'd love to learn from you. It might work for us, but most folks should not think about, most folks should realize you need a, you need a nerdy human managing your agents.”

“You could have it all. You could have lifestyle, quality of life, work from home, work for 20 or 30 hours a week, exceed quota for a lot of structural reasons. That doesn't exist anywhere today. Even the fastest growing startups, um, they're either lean or they're back in the office or they're high intensity. There…”

“if you're not in existing invest, uh, vendors that are able to increase pricing and you're not in a top AI initiative, the number of vendors are shrinking or flat.”

“If you've been doing this for a while, your VCs are just going to check out on you. They're just, it's just not again, like putting all your money into anthropic. It's just natural. If your company is around six, seven, eight, nine, 10 years, and you're looking at this chart, you know what your job is as an investor,…”

“AI is about more than being productive. Ultimately it's about replacing or augmenting humans and delivering relatively rapid and massive ROI, much more than traditional workflow and database software.”

“profitable is not enough unless you're utterly insanely profitable like Zoom. For every dollar Zoom brings in, 50 cents goes to the bottom line.”

“Atlassian got incredibly successful selling JIRA and other products for five bucks a month with discounts to folks at companies. Now folks will spend 400 dollars, in some cases, 5000 dollars on cursor. That's why it goes to a billion.”

“these guys are blowing up because the products unlock huge TAM expansion, huge TAM expansion by replacing a lot of humans, a lot of SDR. And none of these guys would be remotely as successful if they had to charge like traditional SaaS companies.”

“Even if you grew a 50% this year, if your competitor grew a hundred percent and you, you know, you're at the same AR, sorry, got a normal idea. You lost this year.”

“The fastest growing AI companies are burning more AI and their gross margins are lower, but their burn multiples are also lower because they're adding so much revenue.”

“And you want them to double next year, and they need to triple their team, move on from that executive.”

“agents will actually may make our moats even weaker and shallower because if the agents can just take prompt, if I can take a prompt from one app and give it to another app, my switching costs have gone down radically.”

“The way an AI agent works for sales for GTM is you figure out something that works with your team with humans. You figure out an email, an outreach, a script, a set of objections that you overcome, a set of questions. You, you nail it yourself, just like it has always been at Sastra since the beginning. Humans figure…”

“The real bar is better than the average human with 24, seven consistency. And that's which, that's what you're going to see in these emails, like pretty good. With not a lot of errors. That's, that's good enough to crush it.”

“And I really think, especially in 20, 26, we're all going to work in these heterogeneous worlds where we mix AIs and humans and imagining that I somehow mind talking to a great AI is backwards. A great AI is often going to add more value than a mediocre human.”

“If you can't get that help. Don't buy the vendor. Don't buy the vendor, no matter how slick the salesperson is AI or human. If you're not going to get the help to train and deploy. I'd rather have a worse vendor that will give me the help day and night.”

“You just need enough data for these tools to work. You don't need 10 years of data. Six months is enough. You need a volume of actionable data.”

“No matter how great your app is, there just isn't any budget at the CIO office. It's all being consumed by AI and price increases.”

“You don't really need twenty million, right? You might need 20,000 great words of content that are recent on your product. It might be enough to make the AI great.”

“This is, you will get more benefits, but you do not get time back. You lose time. You lose time with these agents.”

“There's no set and forget, no matter what anybody tells you in 20, 25, maybe in 20, 26. Uh, but there's, there's no set and forget.”

“The main learning is only do this if you can't buy it from 99% of you. Like it's cool, but we did this for content review and other things, and we'll show you where there is no off the shelf app, but, but don't roll your own. Buy, buy, don't build, right? Use for B to B stuff. There's a lot of cool things you can vibe…”

“none of these names are as important as putting in the reps and the work. And Amelia will show you the actual date in a second. These are all great apps. We stand behind them. We recommend them for sure. But you could pick another two. The most important thing is training them deeply and doing it Every day. So many of…”

“all of these apps have their own OAuth built in. That is secure. That has been hardened. And everyone goes in and I know Replit the best because that's where I've spent time, but they all have the same ultimate. They're all more similar than they're different. And you're like, oh, I don't want to use the Replit OAuth…”

“If you build unit tests and this is, if you go back to the craziness that happened to me on social media, the agent, when it, first of all, the agent wants you to be happy. So we'll make up data. That's number one issue. We'll say it passed the test when it didn't. But the worst thing is when it fails the test. It will…”

“If you seriously want to put a simple, but real B to B app into production with real users, collecting real information and charging for it for real, and you want it to be any good budget a month. A month and 60% of your time will be QA and testing.”

“VCs are now looking for trillion dollar outcomes. People have decided that every couple of years, there'll be another open AI. Not every week. There'll be a trillion dollar company.”

“after a hundred, if you're growing less than 30%, it's big yellow light, right? And if after a hundred million, you're growing less than 20%, you fell out of product market fit. A hundred million. You have so many thousands of customers. They should be telling their friends and they should be leaving and going to new…”

“Most sales reps want to earn 80% of what they can for 30% of the work.”

“if they don't understand what they're going to do about the fact that search is going from SEO to chat CPT, and I don't know the answer, but I know the issues probably can't hire them.”

“You get higher output. You get higher quality, but you, but there's no less work trade off here. That does not seem to exist in high quality GTM AI today. More work for more, for better output.”

“the IPO bar today is 50% growth at five hundred million, okay? Now that's not a billion dollar IPO, that's a much bigger IPO.”

“I firmly believe that even if you do raise VC for most folks, a one and done is the best approach. Raise a little bit of seed money and then call it a day. Don't take the stress and pressure.”

“profitability efficiency is great. It may be necessary. It may be necessary. If you don't have capital, if you're bootstrapped, if you've spent all your money, the public markets are demanding that everybody be, be more efficient, but it's not enough. So profitable. Hooray. No one cares.”

“Interview 30 kids of any age and be religious about this. Just only hire one you would buy your own product from. Don't give on this. I don't care whether they worked at Toast. I don't care if they worked at Owner. I don't care if they were the first person in at Service Titan.”

“You, to be a venture backed company, you have to go from zero to two hundred million in 10 years. Do a spreadsheet. If you don't triple, triple, double from a million, you will never get to two hundred million in a decade. It just won't happen.”

“You don't have product market fit until you have no cus more customers than you know why. If you know exactly how you got every customer and it's hard and you're not, and you're like our other guy who was great. He said a million, but they don't know how to get to two. He's got happy customers. Great. You can have in…”

“The truth is we talk about on the internet that like it's a choice, but the truth is the venture capital is a niche product. It's a weird product. It requires T three D two growth. Most folks are not experiencing T three, two growth. Or don't appear to have the potential for it in the early days. So they just can't…”

“I believe AI is as much table stakes, more table stakes at a tactical level than it is budget enabler at a meta level, at a high level. I think you have to do it. And it's hard, but it may not actually increase your revenue.”

“if it's scale, if you can't grow your new logos, 20% a year, you're in decay. Okay. 20% a year plus 120% NRR. I know it doesn't totally sum, but that's your 40% growth at scale.”

“Because every five to 10 years, you have to re-found a company. It's so hard just to keep up with bugs. It's so hard just to keep up with feature requests. It's so hard to build the product you built 10 years ago, right?”

“You can't, even if you build the products in a year, it takes so long for that revenue to get material, doesn't it? Two, three years. So if you start now at a hundred million or two hundred million in revenue to try to go to IPO, you're fracked.”

“You basically got to have 700 people when you get to two hundred million in ARR. And that may sound, hey, what does that mean for me? I'm not at two hundred million in ARR today. Roll it back to where you are. You can bridge some of the gap with capital, but at the end of the day, to be efficient, to survive in today's…”

“I wouldn't let them start until they know the product folds. I wouldn't let them start. Now, best of all is literally give them the, if you really think they're so great, give them the offer, agree on the comp, agree on the equity and say, you know what? Now take a month before you even show up and go learn the, I…”

“make sure, even in a stretch candidate, that they have hired two to three salespeople that hit quota before. Not 20, not 200, but it's not enough if they inherited a team. It's not enough if they were on a sales team. It's not enough if they were an SDR that got promoted to manager but never hired any of the SDRs that…”

“And so they're not gonna, they're not gonna give you credit because you're profitable. They're not gonna give you credit for lower growth because of macro issues. But what they will do is they get a little blind to hyper growth. Like they're so deaf because fewer companies are hyper growing. The ones that are…”

“Agencies for BDRs and SDRs never work with a few exceptions. The reason they never work is because with. 20 clients, you never learn the product.”

“the number one reason I see startups struggle at your stage. In today's world is they hire a VP of sales that either doesn't want to sell. Or doesn't ever want to learn the product.”

“I would never give anyone an offer letter before they give you a demo from CRO to junior SDR.”

“I used to not be sure. Now I think it's a hundred percent required. They've got to sell themselves. And if you hear hesitation in their voice, they ain't gonna do it. If you hear a maybe, don't make the hire.”

“Not a hundred percent of the time, but at least 90% of the time sales falls.”

“If your CTO by today, isn't sure how to, doesn't, isn't sure how to integrate AI into your product. Ask yourself if you need a new CTO. It doesn't mean get rid of them, but your competitiveness, I think is going to continue to decay and accelerate.”

“magically bolting on a PLG motion to a sales led thing is not an instant solution to marketing. It's I see so many folks that they're struggling. What are you going to do? Our product's 60,000 dollars a year. Oh, we're going to go PLG. What does that mean? We're not quite sure, but it's going to be self-serve. It's…”

“I think the worst of all of this, what has made it the worst is when we've all decided that customer success should be part of sales. The worst of all of these trends, because what we've done is weaponized customer success. We've taken the one person in the company. Who, if they're actually good and not lazy and do any…”

“funds are structured for this funds are looking for ten billion dollar exits. It actually puts a lot of pressure on folks that are doing pretty good. They'll just, if you, if a V, the only way a VC can make money is not just if you exit for a billion, which is pretty hard. Pretty hard to exit for a billion, but it has…”

“There is no magical AI line budget at big companies. There is no magical thing. Stuff is being cut to fund these initiatives”

“If your new customer growth is not growing half of your, of your top line, your revenue growth, you are shrinking in relevance. You are shrinking in market share and your future is at risk.”

“Growth is twice as important as profitability. So track both, but profitability is not the goal.”

“If your sales led motion slows down, I will tell you the simple answer. And this is so important. You have fallen out of product market fit.”

“If you don't architect around this in the beginning, it's almost impossible to add it later.”

“No one on planet Earth needs another SaaS product. They don't. Every company out there, all the Fortune 500 and Global 2000, they seem to work just fine. With whatever CRM, or marketing automation, or ABM, or whatever tool, they work just fine. They don't need any change. Like, the bar is really high to get someone to…”

“I would just fire anyone that isn't metrics oriented. Literally, you don't need anybody today. You have the wrong people. First of all, I don't think you should ever hire anyone that isn't metrics oriented, but it's usually a sign of someone that should either not be a VP. Or should be somewhere much larger than you're…”

“There basically are no rounds north of two hundred million dollar valuations because for an investor to make 10 X on a two hundred million dollar valuation with dilution, you have to have a two and a half billion dollar IPO. There just aren't very many. Most SaaS companies aren't even worth two billion dollars today.”

“If you hire someone from something that is great, but easier to sell and yours is harder, they will fail almost always.”

“in enterprise, it's often around a hundred customers in a group. In mid-market, it's a thousand. And in SMB, you're lucky to get to 10,000 customers without hitting significant headwinds, ok? So my, my rough, way too rough rules are enterprise, mid-market, SMB. Before you get even halfway to a hundred, a thousand or…”

“The biggest mistake I see from like, Two-ish million to ten million that founders make is they over-diversify. They cross a couple million in revenue. They finally have something. It's more than beer money. It's real. And they're like, okay, well, we're strong in insurance. I want to do all these other things. It's too…”

“Don't raise venture capital, or at least let me qualify it with an asterisk and a dagger. Don't raise more than five to ten million. Don't go to the double digits if you don't want IPO.”

“what I see again and again is I see founders who are pretty good and they hire rep after rep after rep that worked at Dropbox or whatever, and a hundred percent failure rate. Again, and again, and again, and again, and again.”

“I think if you exit founder led sales and vertical SAS before ten million, you fail.”

“PLG is like cloud. It's actually nothing. It is an amorphous term that properly used describes a set of actions and motions that is helpful. Improperly used makes no sense. There are no cloud magicians. If you don't, you can't hire someone to magically cloudify your application and you can't hire, there are no PLG…”

“If you can get it to ten million, you have good NRR, and the founders don't quit, Like, even if you're growing 30%, build a spreadsheet. You will go from 10 to a hundred if you're patient enough.”

“If you can, the right, the perfect time to hire the VP of sales is when you have two scaled reps.”

“If you hire someone that hired zero reps themselves, it never works.”

“Private equity firms will buy any SaaS company with high NRR, um, that are break even north of twenty million.”

“VCs prefer bootstrapped, but they are not willing to give you credit on growth. That's how I'd summarize. They're not willing to say, oh, well, look, 50% growth is okay. It's because you didn't have money, but if I give you money, you'll accelerate to a hundred. A founder might believe that, but no VC is going to take…”

“when I hear that we win every deal, I just know it means you're not doing any marketing. You're not doing any marketing and you're likely not doing any outbound in sales either.”

“At the end of the day, the metric everyone's going to talk about is NRR, going to a Ron's point. Every public company reports it, but GRR is more important.”

“what you usually find is if you get rid of the good but not great VP of sales, And don't have a plan. Don't have someone to replace her or him. Don't have a strategy. I see companies go into a spiral they often struggle to recover from.”

“And a simp, a simplistic way to boil it all down is, one, we have to revert back to sales closing three to five times what they take home. Three, at least three X for SMB, at least four X for mid-market, five X for enterprise. And you have to budget in there the cost of the support of the team. And so that may have to…”

“If you're doubling, you can raise venture capital. If you're growing 65%, that's still pretty good growth. You can't raise money.”

“Once the top public companies are trading at about 10 X on average, 10 X or above, that's normalcy for venture. And you can make a spreadsheet and you can talk about why and how ownership works out to distributions and, but it's pretty hard to build a three X venture fund in SAS if, if we don't have 10 X multiples.”

“what no VC wants on planet Earth Is slower growth and profitability. No VC wants that trade-off. Because going back to the earlier point, the game is to go from one to two million to a hundred million in seven to 10 years.”

“So M&A, like, you think M&A should pick up in, when, when things are calmer, but it does, it doesn't happen that way, right? Now, to some extent, there's a little bit of, like, you know, the Tomo Bravos and the Vistas, they, they have some insulation from this, but even they don't, like, Vista is struggling to close…”

“So if you can do it in, in single digit millions, I think that's my challenge. Try to do it in, try to fully localize your app in, in single digit millions, right?”

“the thing is, SAS is not really that interesting without a hundred percent NRR from SMBs and like a 120% from the enterprise, because you can kind of sleepwalk. I mean, not literally, but it's what makes the business model work is that the revenue recurs, right?”

“somewhere between 10 and twenty million in revenue, depending on your sales motion, the models converge. The models converge. So, if you have twenty million in revenue and you're bootstrapped, and you're willing to spend all 20, right, you can basically hire as many people as a venture-backed startup can.”

“I don't think there's any such thing as an MVP in SaaS. Yeah. If you want to be a B to C guy, great. I, I hate that term too. I, the term I use, and I, I should, I used to talk about it a lot in the early days of Saster, but you want a minimum sellable product, not viable product. Uh, MVP is a crappy, uh, pre-milestone…”

“somehow in seven to 10 years, you've got to get to a hundred plus million in revenue. Okay, you, you just have to, and, and really today it probably has to be closer to two hundred million because that's when you can really IPO, right, approaching two hundred million.”

“There's still delusion across all of the markets, and I still anger founders when I bring it up. I still get Toxic comments, but you just have to assume absent evidence, you're unfundable. Like, go find, go get a term sheet, or just go get someone you trust to tell you, hey, Harry, if you hit ten million growing to…”

“Um, you know, it, it's very hard for most employees to make money on anything that doesn't have a ten billion dollar plus outcome. It's very hard to get rich as an employee.”

“Exits are rare. They're really, really rare, and VCs don't talk this way, and Twitter doesn't talk this way.”

“If you do a brief strategic retreat as a startup, it's fine. Take a quarter, get your house in order, right? Get rid of that terrible VP, cut your burn rate. But if you stay in strategic retreat for a year, you never pull out of it, right?”

“If you can't raise any money at all today, like if you're unfundable, I don't think you're going to be fundable at the end of the year. Ok, if you're, if you're, if you're fundable today, but you don't, you don't like the metrics, you don't like the valuation, you, you double the end of this year and you see some…”

“Investors are hoping for a hundred percent growth at a hundred million ARR. That's what you can back into. Today, and it's crazy, investors want a hundred percent growth at a hundred ARR.”

“Like it's, it's hyper risky to hire a head of sales, even a stretch one before you have two reps that hit quota because a head of sales job is to hire reps three through 300, not to create product market fit, not to create the playbook, but to take a really rough playbook That's, that it's not really clear why it's…”

“even if you don't ship another feature this year, you can go back, and you can upgrade your support next week, and you can do some of it next week, and you can do over four to six weeks, and your MPS will go up, your sales will go up a little bit, Your NRR will go up, and people will just be happier”

“Even if they're a stretch VP, even if they're, this might be their first VP role, if they don't have one or two queued up, zero, uh, approaching zero percent chance they make it.”

“If they don't have anyone good in 30 days, realize by day 60 you may need to move them out, as painful as it is, right?”

“we all, we all just really start with a 10 X feature. One little thing that matters to a buyer that someone else doesn't do or ignores or doesn't have time to do anymore. That's what matters, not, not immediately building, being irreplaceable your first year. It's not going to happen.”

“Your first, the sales reps you hire as a CEO, you have to be willing to buy from them.”

“literally move out your bottom 10%, and your revenue will literally go up in less than one sales cycle.”

“a great VP of sales should make an impact in one sales cycle or less.”

“just remember time never turns a mediocre VP into a good one. It just never does. And especially never listen to your VCs or investors that tell you this.”

“I've never seen a single VP of sales succeed that didn't bring in one or two good people with them immediately when they joined. Never seen it. Not once.”

“I'd rather have an expert in my product that's a decent closer than an amazing closer that doesn't understand the product. They won't close anything until your brand is just, is just mega.”

“it's a terrible sign if 80% of your deals close. It means you're doing no marketing. It means you're literally doing no marketing or outbound if 80% of your deals close.”

“there's no freaking efficiencies in sales in SaaS. Like, you get engineering efficiencies. Everyone can use your same code base, but you barely get any efficiencies in sales once you hit a billion in ARR, and I don't think too many people here hit a billion in ARR. It is linear.”

“Having customer, if you have enough trust with your head of customer success, have them have to accept the customer. This is the only hack I've seen. Not that the commission is delayed until deployment or, or renewal, but CS has to accept it.”

“If you, if you don't have those two AEs and you hire a VP of sales, 80% of the time it doesn't work because there's nothing for them to work with, right?”

“The toolkit is roughly the same for every startup at a given ACV, at a given price point. So make sure they've sold in cloud, in SaaS at your price point, ok? Otherwise, don't fall in love with them.”

“What makes them 10 X, and it took me a long time to figure this out, is that, um, they can change their playbook. 90% of sales reps, and this works out the bigger you get. They sell exactly the same way.”

“I've found that in true enterprise, like real enterprise, the founder is often the VP of sales until ten million.”

“basically a hundred X ARR startup has to at least quintuple next year with high quality revenue, at least quintuple, right?”

“and as long as you're even at a million and a half in revenue, whatever that OT, the on target earnings, The total amount you pay him or her, as you can see in the match, he or she will pay for themselves.”

“But I think, actually, of all the bad hires you can make, VP of sales is the worst because it's far worse than no hire at all, right?”

“whether you're doing poorly or well, if that person can't come in and increase the revenue in one sales cycle that comes out of them, it is hopeless. Right? There is no excuse, because either they're going to do a better job with what you have or not.”

“As long as your deal size isn't like a million dollars or more, it's about a million and a half in revenue. Ok, and a million and a half in revenue, You've probably got at least a hundred customers, 50 customers, 80, you've got a statistically significant number of customers, you've been at it for a little while, ok?”

“Folks that I know that are enterprise that they get to a few million revenue. They try to build a free trial later. It's too late. Their DNA is too gone. They, everything's manual. Everything's manual data entry, manual this, manual that, manual that, and you'll never have a beloved product.”

“I haven't logged in in six months and you're raising my pricing. That's it. That's an F you, right? At least don't increase prices on your users that haven't logged in. That's my, that's what's triggering to raise price on a product you haven't used, right?”

“These are now just APIs. All these craft skills that were, or dark arts are now just APIs.”

“Not only do you have to deliver a beautiful app, it has to surprise and delight you at least once a quarter where your jaw drops that it does something you didn't even expect because of AI. Your jaw should drop because of the agentic capabilities of a B to B product. Then I'm going to stay.”

“planning, planning when the world is stable, there's a really good ROI. When the world is unstable, put all your planning time into building better product faster.”

“to get us to move from one of our products to another, it's gotta be like twice as good. Now it's gotta be twice as good or it's not worth it, or they have to stop innovating.”

“I think all vendors today should offer immediately cancelable contracts with no risk, an instant downgrade and full data portability.”

“the meta lesson for me is, you know, guardrails are technical debt. Too many guardrails are debt, right? They can break the product.”

“the agents are going to ask for different features. Than humans. The agents care about rate limiting. The agents care about how often they can interact with the product. The agents care, uh, they, they don't care about the UX and the UI, right? So they're gonna grade a lot of these products a lot more harshly than a…”

“this may become our jobs at the end of the day is, is the, the agent will have the right ideas. It will have the data. It will make the best proposition, but ultimately it will, there'll be some, even though it'll be smarter than us and some of us, there will be some level of expertise in life experience. It won't have…”

“If you don't monitor there's each day and you do what, and you do a classic SAS buying process, which is by deploying forget. Your agents will, will drift. They'll take shortcuts and they'll, and they'll in their own cute way, they'll live.”

“Now I think it's one of your top, top metrics, because if your usage is falling for your app, you have stealth churn. That is a canary in the coal mine. It's not, this is a real red light.”

“And the reality is agents actually in their own way, as powerful as they are, we love it. From an onboarding perspective, they add more friction in many cases to your product. It's a frictionful process. You're forcing customers who don't understand agents to train them.”

“So what we found is if, and it might be hard to quantify that, maybe it isn't, but if you get above a certain line, if you invest the time to train your agent, if you read the email exceptions every day, if you upload all the documents, you're going to find this concern that folks don't want to talk to an AI is…”

“You need to recruit somebody else on their team and, and divide and conquer and make sure you have two. You gotta have two, right? I mean, one's hard enough. There's a lot of, in the early days of AI agents, when we talk to folks, there's very few people at a lot of organizations that can do this. It's not that hard,…”

“Mediocre ROI is dead. Is just dead. Products that just give you productivity bounces that no one's going to buy that stuff today.”

“what you should do with the agents now is they're pretty good. You can do this in Claude code. You can do it in Replit. You can do it in Lovable is ask them, um, uh, to do the deepest security audit possible on your app at least once every month or two. And they're pretty good at it. And it will, it, it, it, I'm not…”

“I think for the future, I think our learning is listen, that AI marketing tools, no matter what vendors say are not nearly as mature as the sales tools, which are not nearly as mature as coding or support tools, right?”

“So it's the, the, the reason they fail today is that people don't roll up their sleeves and train the agent themselves.”

“it used to be years before vendors would have feature parody right now. Now we're down to weeks.”

“If you didn't re-accelerate and you weren't in market with a great agent, a great agentic product this year, you get a D minus, but you don't get enough because you got through the year, but you can't get a D next year.”

“An agent can't today figure out, make something that isn't working work. But if you know what's working, and then this is important, you train the agent with it, then you get 24 seven infinite firepower backing up your best practices.”

“These apps that need to be trained with forward deployed engineers and work. I don't think very many of them are less than 30 or 50,000 dollars a year. And a lot of them actually try to kind of have a price point that's approaching a hundred K like 60 K a year base base, and then 20 or 30 K they want you to pay for the…”

“actually, ChatGPT and friends benefit you if you have high authority, but you're lower, lower in Google because they don't care. They're just looking for the best piece of content to answer a question.”

“It's so much better to get back to someone with a 90% perfect answer in real time than any brutal other process. There's just no excuse.”

“There's no way you're going to build an artisan, a Salesforce, a gamma. You could build the little bits of it. I mean, there's just no way there's too many man hours”

“not only will these AI agents cut corners on security, if you don't know about security, you won't even know the corners it's been cut.”

“They're wonderful, but they are all unstable. I have to basically every day fix and update these apps. Who's going to do that for you? Who's going to do that for you? They do not maintain themselves.”

“ask any great developer, how excited are you to take over a vibe coded app? You're going to hear spaghetti code. Don't want to own it. Don't want to fix it. They don't want to do it.”

“at the end of the day, all these sites look like Claude. Once you see one Replit or Lovable site and you can just smell it. Um, you know, there, someone was saying that like, 30% of this YC class, uh, vibe coded their app. And I, I want to see a couple. I'm like, I, that one's Replit. One's Lovable. Like I can see it…”

“You have to understand how these AI agents work and that they're goal seeking. And that means they'll fabricate data. They'll fabricate results. They'll lie to finish a project.”

“And if you look on the internet again, a lot of folks will tell you, 80, 90, 95% of vibe coded prosumer vibe coded apps are never finished. At best case, their prototypes have never finished, and this is number one reason that people don't get their arms around that the aging is not truthful, and you need to, you need…”

“I actually think the traditional playbook act, not with saying what Kyle and I talked about this morning. If you have intense product market fit, it works fine. Open AI is doing field events. Open AI is doing webinars. Open AI has as swag open. I mean, but open AI has so much product market fit, right? The playbook…”

“And so the irony of this, all of this is as much as sales and marketing changes, probably the one thing that won't change is brand marketing.”

“I think if your second product is smaller than your first, you're not multi-product because it doesn't get you anywhere. If you get to a hundred million and it takes you two years to launch a product that can only do fifty million, it doesn't get you anywhere, right? It's gotta be bigger.”

“No one, no matter what anybody says, the only reason any investor cares about AI is because they want insane growth. They don't really care.”

“he put the data in Snowflake, and he's like, okay, let me compare that to churn. And he found out the very best sales reps in the SMB motion had the highest churn, because they were shoving deals down the pipe. And so actually, none of the best reps were his best reps.”

“You need S tier orchestration to create S tier output. That's the learning.”

“honestly, you could pick a slightly worse tool, but if you invest the time and effort, it's going to be dramatically better than what you have today. Right. The key is investing in the orchestration and the QA.”

“I think reskilling is tough. I just showing up with, with a recipe that you got on ChatGPT to your marketing team doesn't count as being an AI native.”

“for any deal, even approaching a hundred million, you should hire a banker, right? You, it always pays for itself. I think. Always, I found, and I don't want to do it out of order. It was one of my top 10 mistakes. As a founder, if you don't hire a banker, even if they don't get you another offer, which they probably…”

“Why aren't you? It's because you're not growing fast enough when you're playing games.”

“AI is also the rebirth of freemium, rebirth of free trial. We expect to try this stuff. For free and you've got to work around the cost.”

“I'm going to argue until you're at mass scale, until you're at the Salesforce scale, don't add any friction to the sales process. There is an argument when you're at hundreds of millions of revenue to add friction. There is an argument that friction itself is a qualifier, especially for your sales team, that you don't…”

“So what do you do? You raise prices again and again, and you push more and more enterprise and abandon your smaller customers, which may help you make the quarter, but oftentimes is abandoning the future to hit your present goals.”

“Maybe you think co-pilots are silly, but if there's budget in your space, go build a co-pilot.”

“The other thing you can't talk about is like people that are jaded or broken a little, Training isn't gonna help. Like, a team trip to Miami is not gonna help. You gotta gently move them out. Like, now. You're better with half the employees, as small as you are, that all want to be there than folks polluting the…”

“And what I learned for him is don't hire anyone where the first line in their bio, whatever, wherever it is, isn't hacker.”

“If you have even a million dollars in a geo outside your home geo or North America, and it's growing quickly, just hire a full-time person there you trust to get it to two million to four to eight to 16. People wait until 10, 20, thirty million in a geo to hire a leader there. No, just like centralized customer…”

“give them an unsigned off, give them a signed offer letter, but don't ask them to countersign until they're all in that way. The pressure's off, right? Here's your comp. Here's your title. Here's your equity. It's signed. If you need two weeks to make sure you believe in the plan, if you need two weeks to go talk to a…”

“I think it's more whether demand gen should report to an aggressive sales leader who says I've had an all of enough and I used to be against it for the reasons, but now I'm seeing it work up to a point because at least they can get more results versus a lackadaisical marketing organization.”

“never, never hire a CRO that everybody loves because there's so much bias across the team. There has to be some, like someone has to be threatened by the CRO or you're not making the right hire.”

“when you hire a great sales leader, assign it, you don't get any time back in sales. It's just used differently. You'll just be more efficient.”

“All, so many veterans that work 10 years, wherever, they don't really learn the product before they start. I'm just, I just, I'm just gonna use the HubSpot playbook. I'm just gonna use the whatever playbook. And people are tired and they just want a job and they don't learn the product and they just all fail.”

“I don't think there's a PLG motion to magically adopt at zero dollars in revenue.”

“For a private equity firm, anything north of twenty million growing more than 20% that's breakeven, they will buy with a hundred. And here's the key with a hundred percent NRR or more, it is an asset to a PE firm.”

“If you can get thousands of people using your product for 10 K a month or 10 K a year or more, go sell it. If you can get millions of people using your products so that a few percent can convert, go build Canva. But don't be in the middle. Don't be a small number of folks that will convert. That's death. Just putting…”

“This is the other mistake a lot of folks make that come from a sales background. They don't realize how great a self-serve product has to be like so much better than enterprise, any enterprise or even mid-market product in the world. Like the onboarding doesn't have to be that good because you have a customer success…”

“We don't really, none of us need more software. Nope. No business in the world. Nobody's in the United States is failing a few security issues aside because they don't have a software vendor. Like the world kind of works on a day to day basis. We actually don't need any new products.”

“if the money's okay and you and your co-founders are like, you know what? Competition is pretty good. And you know what? We are worried that our growth is good, but not great. And we are worried that we're not that good at the gen AI side. We're worried about this. Whether those worries are surmountable or not, if the…”

“In the early days, just get close to customers. It almost doesn't matter whether you get, you don't need to optimize pricing. Kill basic, keep it, do a little A-B testing if you can, but it don't matter. Just close them, right?”

“Find someone that's doing it for the right reasons to accelerate their career. Okay. Not someone that's a fuddy-duddy, not someone that's been a CEO 11 times. They're not going to have the energy you have, and it's not going to work out. They've got to have a reason that this is their shot.”

“No one needs your product unless you have a 10 X feature.”

“The right sequence is VP marketing, VP sales, VP of product.”

“If you don't gain energy meeting with customers, maybe you should find another CEO.”

“My rough rule of thumb today is 20, 30, zero. So what I mean is to get a PE firm interested in you, you've got to hit Twenty million ARR... now not a hundred percent growth, 30% or higher... And then zero percent has to be your losses.”

“it takes three years to really churn from a business process from one vendor to another. It takes a year to get upset, another year to qualify, and that third year to do change management. We think they're not churning, but it, sometimes it's a 36 month process to lose a customer.”

“Sell to your ICP. It tastes good, but if you do this more than four quarters, the competition is going to pass you by. They're just going to pass you by, right?”

“Now, the number one way I think you build a relationship in sales today, no matter what is being a product expert, Are you literally the biggest guru in the data space, sales data space, the biggest guru in your industry, and you learn a little bit how to ask for the close. You don't even, you will destroy the…”

“The number one issue I'm seeing from five million to five hundred million in the companies I've invested in over the last 11 years is being too slow to go multi-product.”

“The second product has to be bigger than the first and it's tough. And you have to sequence it properly too early. You'll burn out the team and you'll burn out the market, but too late and growth will decay.”

“I think if you do the math, you, you almost have to earn at least 10 K a year from these very small businesses to make the math work.”

“if you make a critical hire and VP of sales or any role at your startup, VP of anything, it's your fault.”

“Sales has no efficiencies whatsoever in it. You need even more people the bigger you get. It has dis-efficiencies of scale.”

“80% of the VPs of sales candidates that founders that I know invest in work with ask me to meet. 80%, bring me this guy, gal, whenever, no gender. They just, they won't do the sales themselves.”

“Salesforce is coming up on thirty billion, and Mark Benioff's still out there hustling and meeting with customers. If you're a VP of sales and gunner or CRO, pass. Don't matter what else you like them.”

“If your model is like, 20%, 50%, 80% outbound, and you want it to go up and you love this head of sales, But they've only done inbound, zero percent chance of success.”

“I think in the enterprise AI and automation are about cutting headcount. Let's cut half of the thousand agents we have doing support. My thesis is vertical SAS is blowing is going to blow up because there just aren't anyone to do the work. There's just no, first of all, it's 22 bucks an hour instead of 13, but I just…”

“when fear sets in sales, it, it's almost unrecoverable. It's the one symptom where if you're ever deciding, should I give my VP of sales more time? We've talked about this for years since after. The numbers aren't improving, but things look okay, or this or that looks okay. The number one way whether to keep ahead of…”

“Don't hire someone that's a product marketer. You don't need at 2,000,005 million, even ten million air. You don't need 11 pages on your marketing site explaining How different segments of your market are critical.”

“You don't need a corporate marketer. You don't need a brand expert at your stage until you have a brand. When you, when everyone has heard of you, you can hire a corporate or brand marketer.”

“If you like a marketer. If they're smart, if they're intelligent, look at their LinkedIn and see what their first line is. If it says strategist, thank them, send them a blue pen with your logo on and do not hire them. Trust me, not 99% of the time.”

“A great VP of sales will literally give the CEO a quota.”

“In today's world, if you go into a bake-off, a competitive bake-off, and your competitor is making real or fake promises with AI, and you cannot compete, you're going to get slaughtered, especially in the enterprise.”

“For public companies, growth is still worth twice as much as profitability for startups. It's probably four to 10 times.”

“You can't hire folks with three jobs or want to be fractional or want to run two businesses on the side or want to see how it goes or think they can be a fractional CRO for seven companies at the same time. It's too hard out there. You can't hire the broken, the bitter and the fractional, even if it's all you can find,…”

“The first executives today, the VP of sales, VP of marketing, even VP of CS, VP of product. They got to carry it back today for real. They got to, they got to, and it doesn't, it's if they don't, they never will. They'll never, they'll, we changed too much. They needed too much of a team. They'll never learn the…”

“In founder-led sales, unfortunately, you can't hire the diverse type of rep that a great CRO or VP of sales can hire. They have to be narrow. They have to be people that work on your wavelength, that talk the way you talk, that can do no look passes, that you can send one Slack, not a hundred a day, not being pummeled…”

“A great head of sales that will actually carry a bag. A great head of marketers is actually willing to do a campaign themselves or to put together an event themselves. The great ones are always accretive. This is like a recurrent Sastra post for 12 years. A great head of sales will come in and take your 50 leads and…”

“Nine times out of 10 innovation, innovating on pricing is a terrible idea because it confuses your market.”

“there's these day one high attached vendors that make these applications blow up and the rest struggle, which doesn't mean you shouldn't do them, but it does mean it probably can't be everything for you.”

“the only way you get time back when you hire a VP of sales is if the last product they sold was truly harder to sell. If it's truly, they go into an environment that in every way is easier, right? Then you get some time back because they already did it. They already learned how to sell that tough, Vertical SAS or…”

“What I have learned is if they already know the product, if they're already a customer, if they've already sold it, sure, like they could just be a manager. But I think 80% of VPs of sales today should close when they start. 80 to 90%, they gotta close.”

“once you approach 10% market share in your, not, not in the whole world, but in your core ICP, your core market, it starts to slow down at 10%.”

“data is, data's like security. It can't be solved. Like, you can't solve security because someone else is going to figure out how to, how to take advantage of anything, and so that, that's why security is one of the most dynamic spaces, because it's not solvable, right? Data's not solvable. Data is not, you will never…”

“if you do a great weekly webinar, it always works. This is, this is so true. We even do it ourselves at Sastr. If every single week at the same time, at Wednesday at 10 a.m., you do a webinar for prospects and customers, and the first week only one comes and people are grouchy, and the next week two, and then three,…”

“instead of writing great content for SEO, you outsource it to some crappy agency that recycles chat, TBD content. You know how often that works? Nunts. None. None.”

“Where you want to hire a head of product usually as a founder is not to make the product better. It's when the product gets too complicated.”

“A stretch VP doesn't have 80 people. But they better have two or one. And when you go to interview that stretch VP of sales, stretch head of sales, ask them who they're going to bring with you. It's one of my classic can interview questions on sasser.com and ask them and ask them and, You don't need 50. That's, that's…”

“VCs love bootstrap companies. If you talk to Excel partners, one of the top VCs at all times, they'll say our favorite investments were Atlassian, right, which I think they bought 20% of, bootstrapped. Qualtrics, bootstrapped, on and on. Why do VCs like bootstrapped? There's no one else on the cap table.”

“And also you sometimes hear bad advice from the hyper successful. Sometimes the folks that are so successful so quickly also can sort of give you wrong advice inadvertently if you're doing pretty darn good, but not great.”

“Ask VCs for advice when you want money. Ask for money when you want advice. This is terrible advice.”

“If in a sales cycle, things are not improving on several core metrics and sales, they never will.”

“after even a couple million in ARR, you can afford any higher if they're accretive.”

“I have never in SAS in B to B with, The high margins we have, with the recurring revenue we have, with the upsell opportunities that we generally have. I have never seen a great VP of any role, sales, marketing, customer sales, eng or product, not be a creative.”

“The junior product person is your first product hire. Never works.”

“The junior marketer might work a tiny bit. Maybe you get some tweets, um, and in some instances, but you never get MQLs and SQLs and leads and the whole thing.”

“If nothing, if you have leads and nothing's closing nothing, it's not the sales team because Those leads are good. They're coming in. They, they, they found something they like. Um, at least some of them should be closing.”

“A great VP is always cheaper than a mediocre manager for 50% less.”

“I see so many founders that think they can be the VP of product at 1015, twenty million in ARR. You can't, you don't have 50 hours a week to be VP of product.”

“you can also have pretty good CAC and long CLTV and go bankrupt.”

“most marketers in SAS will never hit their goals if you don't give them credit for the free ones for word of mouth, because it's everything to marketing is expensive, right?”

“I track this with SAS companies and it's a niche metric, but it's super interesting in terms of long-term health, which is the ratio of revenue growth to new customer growth on a percentage basis. So I like to see at least a sort of a two to one ratio. Like if, if you're growing 50%, I like to see you adding at least…”

“my rule is if your, if your ARR ever goes down, it's not ARR. ARR may grow, may grow slowly or more, or more quickly, but when you see a startup where the ARR has gone up and down, I'm like, okay, I, I gotta dig in here, because whatever it is, it ain't, it ain't an ARR, right?”

“This is my number one tip. It always works. It always works. You, you have to constantly every month do an L four M analysis. Okay. You do not need 20 people in finance or operations or planning to do this. Any founder can do this. Take your financials, and all you need is your top line and your bottom line. How much…”

“The biggest danger I see with founders is they get a crap model from their finance team. I see this all the time. It's worst of all, the worst of all mistake is a lot of founders these days, wait to hire a VP of finance or director of finance, let alone a CFO. Instead they hire a director of operations, some smart kid…”

“Every, every SAS company I know of that gets to 30, forty million that is profitable or cashflow neutral. Someone wants to buy it because they're going to miss the quarter. Someone out there, it may not be Monday, but some public company or company about to go public would love an extra 30, forty million of ARR to bolt…”

“I would actually, and this is different advice from some, I would keep that mix as long as your funding allows it. Knowing almost nothing about your business, but pattern matching. Because when you make the solution worse, you lose some of your magic.”

“A great VP of sales is in one quarter you're selling more, ok? Whether you're selling 10% more or a hundred percent more, that's a sign of a great, that in one quarter or less or one sales cycle, it's materially better.”

“And the sign of, another sign of a bad VP of sales is it gets immediately better when they leave. Because the rest of the team steps up.”

“The answer is always be, be 90% transparent, and do what the business needs to be done, and be open about it. And sometimes they will quit, but it's, it's ok. Like, it sucks, but it's ok. You, don't, don't hide the ball, don't try to do a stealth search”

“I don't think there's any karma out there. I've decided after all these years that the people that mistreated me, many of them did pretty well.”

“The number one reason I see these failures happen is when the CEO's like pretty good, they're committed, they'll do it for 10 years, they'll run up the hill, they'll, they'll hustle, they'll get the sales, but the CTO isn't that good.”

“Um, there are a lot of sales leaders who have only done inbound, ok? They have only responded to leads. They should not manage SDRs if humanly possible. They almost all fail.”

“Your first 50 employees, your first 50, have to be pirates or romantics. They have to be pirates or romantics. You know what I'm talking about. These are folks on your team that for reasons that almost don't make sense, live in, lead startups.”

“I do think that CS, a good CS team should have an expansion goal, ok? But I don't think CS, we, at Sastra, we're tiny, we get threatened by our vendors at renewal time. That's the wrong way to run customer success.”

“however you do pricing the enterprise, it should be as if you should be comfortable every other customer knowing what every customer is paying. Then it simplifies your life.”

“Imagine you're re-earning a fraction of the deal. That always works, doesn't it? To keep, keep it going. It never doesn't work.”

“Actually, I think most folks wait too long to have an EMEA office. Um, you at least want to do it by the time you have a couple million in revenue to service those customers, right?”

“rule of 40 kind of implies that mediocre growth is okay if you're profitable, and that's the disservice. It's, no VC is interested in mediocre growth that's profitable, like we started this earlier. No one's interested in the rule of 30. We really, VCs want rule of 100.”

“categories have more rooms for number one than sometimes VCs realize, right? And that has certainly happened as SaaS and cloud has expanded, especially with vertical SaaS.”

“cutting the marketing budget to zero wrong answer, right? Let them optimize what they can do with a million and trust in your team.”

“layoffs don't really solve anything. They're just little, they're little snacks, right? They make little incremental changes, but layoffs don't create growth on their own, right?”

“This is why CAC is such a flawed metric, because if your customer, let's say your, your average deal size is five K, a five K a year customer. You're, you're actually not gonna have anything that's, where you can spend 5000 dollars to get a 5000 dollar customer. You're gonna have a lot of stuff that's viral, that's…”

“If you sell for 10 X or more than you raise, like, it's all pretty good. No matter what, it gets worked out.”

“So founders have this investing superpower that money managers don't have, which is they know who's better than them. But if in SaaS and B to B, if you do that pre-revenue, you really can't be sure.”

“It's not a volume game. It's not, Tiger Global made it look like it, they had a good play. But really, the great ones, they, you know in 20 minutes. In fact, you often know before you meet them.”

“as a founder, I think you should give up free at the, you should try to never give it up no matter what the team wants. Cause your product always gets clunky when you do.”

“you gotta know how your peer set is doing, because if you don't, you don't actually know how you're doing in these environments. If you're growing faster than your competitors and you've got 10 years of runway, everyone should get a Christmas bonus. If you have, if you are, can have 10 years of runway, hooray, but you…”

“The loser-ist thing as a founder you can say to a VC, right, they make you sound like a loser, and I literally never use the word loser, right, it's terrible, but it's true, is we didn't grow that fast last month because we were fundraising.”

“if you're not sure, I always tell founders, just do it. Even if you have the revenue, even if you have, if there's a missing slice, like, just go to Harvard, MIT, and Stanford, get it done, and it's, it's, it's worth it, right?”

“as soon as you have even a hand, 10, 20 customers, you can hire a great senior growth marketer demand gen to get you more leads. So hire that person as early as you can find her or him.”

“by ten million or so in ARR, you have convergent evolution. These paths converge. By ten million ARR, you have, if you bootstrap to ten million ARR, you're generating enough cash to hire all the VPs you want, ok?”

“the real truth is you're too late at five million.”

“My view for what it's worth, I, I'd be curious, your thoughts is no matter what happened last year, I think all the time I've been in SaaS, including the founder, there's been an anchor valuation, which is 10 X AR.”

“an insider tip, if you are fundraising, figure out, now's a good time from new funds and newer VCs that have less Baggage.”

“The problem with small layoffs. Like if you lay off a small number of people, a lot of them are not the best people. So great. Like some company lays off four percent, like there are gems there and go find the gems and hire them. There really are gems in every company and layoffs suck, but usually they're cutting the…”

“there becomes these parody things where marketing is more important than product, but it, it's pretty uncommon, but before 10, 20, thirty million in revenue, and sometimes a lot later, so.”

“the best ones don't really want to be mentors anymore, and the mediocre ones want to be mentors, right?”

“When you hire a VP of sales or director or whatever, head of sales, this is how many minutes you get back in your day. Zero. Now. Now. What does happen is if they're any good, they re, they rework your calendar. Instead of the CEO being the opener, and the middler, and the closer, they handle the closing, and they…”

“Get two AEs that hit quota. One's not enough. If it's one, you don't know why. If it's one, the VP of sales doesn't know why. If it's two, the VP of sales, VP of sales is a hiring job mainly. If you have two hitting quota and the VP of sales is good, even if they're new, even if they're a stretch VP, they'll figure out…”

“Your marketing site should be better than your product. It should be prettier. It should work well. It does, you don't have to write a lot of code on your marketing site, ok?”

“In the U.S., your best AEs should be making 300,000 for SMB, half million for mid-market, and a million dollars for enterprise.”

“The only reason an individual contributor sales rep should leave your company is for a promotion. They can't get at your company.”

“You're almost better off without a week, with no VP than even a mediocre VP.”

“You do not have to sequence it perfectly, and we've, we've talked about this on Sastr. It's a classic post of what order to sequence it in, but the real key to understand, and this is not intuitive until you're later, is any great VP is accretive.”

“every customer you lose in SaaS is sort of a failure. Someone failed. Sales oversold it. Your product let them down, or CS let them down. No one, no one buys SAS products for fun. It's not fun to deploy, test, and roll out a SAS app in your company, and every single time they churn, you have failed a customer”

“It's actually a completely weak sign when a VP of sales is missing a quarter, and he says, well, you know what, I'm not going to make it, but let's raise prices so that we can make my plan. It's a cookie. You raise prices on your base once. It works once. You can't raise it every quarter.”

“we'd like 10 to 15 qualified meetings per SDR, and the best ones can do 15 to 20, and the best ones always generate about two million in pipe per year.”

“And 98% of you, 96% of you, I think, make the same mistake. You hire a junior person. Ok, I'm gonna go hire, I'm gonna go hire a product manager that worked on one pixel at Twilio, or worked on one little thing at some great company. They don't know how to ship products into production. A manager is not enough. Your…”

“you can't freeze hiring and hit the plan. You can't cut your way to growth. It doesn't work. Whatever your issues are, cutting, sometimes you have to cut if you have two months of burn, but you can never cut your way to growth, and it especially doesn't work in sales.”

“this deferential relationship to your investors, it is, um, It can be subtly toxic if you let it go on for too long. It can be, they don't know, and they will even many of them will even encourage it. They're used to it. They're used to this slightly Imperial relationship”

“For sales, marketing, product, and engineering, I would not take, I would not, if I'm scaling, hire someone that does not have a pure SaaS broker. There's too many, there's too many folks that do. There's no point in hiring a salesperson that hasn't sold SaaS. I ain't gonna take that risk.”

“you can't have product-led growth Isn't actionable unless you have instrumentation around it, right? What is actionable, right? What is the difference between product-led growth and classic freemium self-service, um, viral word of mouth, which we've been doing for as long as we had collaboration software, internet…”

“when you don't see that, my rule is, and I've made this mistake since, don't invest. No matter how much you love the founder, you can love them as humans. They can be doing very well. But if, if you don't have this crazy 20 year commitment to building something huge, um, It's hard to make money in venture.”

“When you meet a winner, when you meet a winner, you buy all the shares. Now, if you can buy a quarter of the company, you buy a quarter of the company. If you can buy two percent of the company, you buy two percent of the company. But you either buy all of them or none.”

“What does a mediocre VP of sales do if there's sixty million in the bank? They spend it all. They spend, the mediocre ones, a hundred percent of them spend it all.”

“long sales cycles don't matter at scale north of 20, thirty million in revenue. You're lining up so many deals at the same time that long sales cycles don't matter because if you have a hundred deals in flight, it, it, it, it actually, it actually starts to happen very predictably, right?”

“how many active investments can you be number one in? And it might be five. Like the traditional, the old school metric for board seats was, it was supposed to be 10, ok, but when you started to run the place, it would be 20. Ok, if you go back and talk, when you do the 20 BCU talks, they would be on the Arthur Rocks,…”

“The work you force your management team to put into those slides for each board meeting forces organization, self-discipline, reporting, goal analytics that otherwise they just don't bother to do in Notion. They don't do it. They just write a stream of consciousness or an update to a table.”

“you get to 10 to a hundred, With almost no sales team, not quickly, not quickly.”

“I think if you get, if you make everyone responsible for, for gross retention and net retention, they're gonna bang their heads on the table. You gotta pick a CEO like what's more important and it's gotta be net retention, right?”

“If you, if you have cost effective, high quality humans, that is the single best investment you can make in software.”

“For the first 30 days, no employee has to do anything but shadow. There is no quota. There are no sales. You should not even do your own call. You will not get a lead. You are paired with Sam or Abigail or Jody in any role, but, but especially sales and marketing. And you're not, we're not expecting anything out of you…”

“that fear, it's, I've never seen it cured. I've never seen that fear of the next year's number. Um, you should have anxiety, but that's not fear. Anxiety is, I don't know if these five ideas will work, but I'm going to try it. They, they should work.”

“no matter how enterprise your app is, it should have a self-service component. Because if it does, you will be able to figure out how to get to the atomic element of this app without training, right? If you have no self-service, you can, you can skip, you can have as many explainers and trainers, and I don't care.…”

“Every trusted brand has gotten a boost.”

“If this person did not successfully hire at least three to four good reps, even if they're young, they're not a VP of sales, ok? If they inherited a team that was somewhat successful, they didn't recruit any of them, They're not a VP of sales.”

“one of the best, the biggest ways you can waste money is making someone a player coach for too long, because they gotta bring these people in. You can do it for a quarter, right? Prove them out, have them hold a quota, but if you've got this person holding a quota on their own, as an individual contributor in addition…”

“And it turns out a mediocre VP of sales that's just closing the deals you would have closed otherwise, but taking 300,000 dollars out of your own pocket is clearly a cost center. It's a frustrating, painful, expensive cost center. But a great VP of sales, and I, and I learned this when I went from my crappy VP of sales…”

“we know that the Oracle VP doesn't work. Salesforce is the same as Oracle today, right?”

“If you hired a VP of sales and all, he, he or she keeps all the reps you have, that's trouble, ok? Because they know that they're not all, They're not all great. They can't, if you have three or four folks on your team, the bottom person, like, you, you're not a sales manager. They can't be that great. I can tell you…”

“If you're at a startup, right, for me, pipeline is a sign of failure, right? How much revenue are you going to close this month? I don't need to see the charts, and I don't need to see seven million dollars next to Comcast, or twelve million dollars next to whoever, right? Because that stuff's all crap. Like, it…”

“Sometimes you do need to hire this person because you're burnt out and you need leverage, but this person will be gone by a million and a half in revenue. I can tell you nine times out of 10, the person that, that's totally smart, 160 IQ, loves your product, can talk to them in a day, but has no experience managing a…”

“But my real point is, if you hire someone that's two stages above where you're at and bring them in, high, high chance of failure, right? You know, I think you can risk doing one stage above. So in other words, if you're doing one million, Right? Um, I think you can risk hiring someone that's only done 10 to fifty…”

“If your product today is, say, 300 bucks a month, ok, and that's great, but next, but you're starting to get a few bigger customers, and your goal next year is do 20 K deals, 20 K ACV deals. If this person has sold at 20 K, he or she will have developed the skills necessary for your company, no matter what it does.”

“A sales team that sits together in the same room, open style, performs better.”

“I think if you are in a top tier accelerator, uh, and, and you don't get funded quickly, there is a bit of a black star, a scarlet mark. It's not huge, but if you're, it's not just YC, but if you're in a top program, there's an assumption that Bessemer has an army of analysts that all the big funds that, that…”

“what startups, my recommendation as a rule is don't ask people to take salary cuts. I know you're the hottest startup that there's ever been that no one's ever heard of, but don't ask people to take salary cuts unless you have to.”

“You have to pay twice. You have to pay sales for revenue that comes in after the contract is signed, and you have to pay customer success, however you're going to pay them, for the work they do. And when work overlaps over an extended period of time, you just have to double pay.”

“I would caution you, I would say 92 times out of a hundred, that is a, that is, um, The wrong business model.”

“having a, a modest amount of a customer success manager's, uh, money tied to either expansion in the account or NPS in their accounts and having it be around 10%, 15% of their total compensation is, is a good starter.”

“My obvious learning is that people over index on variable comp. You pay someone a 100,000 dollars a year with a 2000 dollar bonus. You know what they do all day long? Whatever they get the 2000 dollar bonus for. That's all they do.”

“We mock a lot of this stuff, like billboards, uh, early as founders, because, like, there's no way we're going to get leads. It's not about leads, right? It's about reinforcing the brand and supporting that, and then I've heard of it. You do it just right, it can even work at like a million in revenue.”

“But ultimately, you're not taking money out of his personal pocket. When you go to a law firm, I mean, what, I don't know what the biggest Harvey deal is. Let's imagine it's 20,000,030 million a year, ok? That's got to come either from another substitute tool, like I'm taking that on my other budget, right? Or the…”

“The thing about headless is it also makes it much easier to bifurcate our data and put some into outside of the system of record and some in because the agent, the headless version of your CRM or SFA or system of record, well, it has no problem up to a point pulling in from three different systems of record, right?”

“When an agent can only do a task, you check the task, but when an agent can decide things, you need an opinion about every decision it makes, and it makes a lot of them, and some of them it doesn't even tell you about.”

“When you've been building products, you, you just, the path of least resistance is to use what the agent recommends, right?”

“The bar is in the, is, is better than the top Team could do on figma in 30 days. The, the bar is what can we do with nobody in an hour? Or 10:05 minutes. It's, it's pretty good.”

“You launch an agent for support. You realize they could do marketing. They can do sales. They can do pre-sales. They can do screen. Like almost any well-trained agent can do more than what you intended to do.”

“Find your, find your tool nerd that hacks marketing tools and just put them in charge of all this stuff. Internal is always better than external, right? But here, man, only hired if no one in the third, he can do it.”

“You want to know when you have the right sales team in your company, when the customers hound them for months and years after, when they, when they added so much value in the sales process that even when they're handed off to someone else in the org, they don't do it. They still go back to Bobby or Lindsey. That's the…”

“when you hook up APIs, the agent will come up with use cases for the API you didn't even know existed, right?”

“By, by the time we'd added the 14th guardrail, the 14th exception, everything was an exception. Everything got bounced. And so everything started to break and we had to rebuild it from scratch and get rid of almost all of those rules, like throw away all these rules.”

“For the stuff we're talking about, for building GTM agents, for building Autonomous dashboards, autonomous tracking. You're gonna struggle to, if you just do this reasonably thoughtfully, you're gonna, you're not even gonna spend a thousand bucks a month, right?”

“when, when you're reading the output of an agent, you don't, you can't just ask yourself actually anymore if it's good because it just might be good. In fact, Claude keeps getting better. So by the end of the year, the output might be borderline great. Okay. You have to ask yourself, would I buy my own product from…”

“the API is the future of software, because we can all interface with APIs now, right? APIs used to be just for your engineers and used to developers. Now anyone can access your API. So I could, uh, democratized.”

“agents are goal-seeking, right? Most of them under the hood are, are clawed. It'll be more, we use Gemini ourselves too. We'll use more open ad. Most of them are clawed, but it doesn't matter. They're goal-seeking. And, and that still creates a certain laziness, which is they go just as far as they think they can to…”

“your APIs used to be, unless you were, unless your company was an API, unless you were Stripe or something, it was, it was often a niche portion of your platform that a lot of folks didn't even touch or understand because only developers could use it. Now anyone can use your API. Anyone can use your API.”

“if both of you guys could take out, say, four million next year, um, just put it away, might not be the worst idea for a media business, right?”

“if you get over the nut, if you think about the nut, and they're high, this is why it's a terrible business, but if you get over it, it's almost pure profit. That extra person you charge a ripoff ticket to for 2500 bucks, that costs you 80 bucks, right?”

“if I had to advise people that are earlier on their journey, find something in your go to market motion that just isn't getting done or is getting done very at a very mediocre level. Then put an agent, don't try to replace what's working well. Do that as your 10th agent or your 20th”

“agents are too much work to train every agent. That you're going to use in GTM, including clay, including the rest requires weeks of training before you can go live.”

“Your job is to radically increase the functionality of your product so you can tap into what buyers want to buy right now, not what they wanted to buy in 20, 23, let alone 20, 21.”

“instead of the traditional five to six percent of prospects being in market a month, which is a way a lot of marketers think about things, right? I'm going to, I'm going to try to reach everyone in my, in my universe. But the only 20% are really in my ICP and of that 20%, maybe four to five to six percent are in…”

“If you can't sell it yourself, the AI can't sell it for you. It's that simple.”

“If, if a prospect can have a wonderful time, get their questions answered for real without a used car salesman and book a meeting in real time, you're going to close more, whether it's one percent more or 20% more, it's much better.”

“Voice is not a lot of work to train on your voice. It's a little bit of work, and video is two orders of magnitude more work, so just sequence them in.”

“that's what you really want to do is to Is for AI to be your steroids for content creation, not to create the core nucleus that becomes trite and boring”

“As great as these tools are, they do not enable lazy marketing. What they enable is better marketing and much more of it. Everyone wants an autopilot. Everyone wants to buy a tool and disappear. It does not work that way.”

“Don't just set and forget and buy. You will learn nothing. You will learn absolutely nothing. Be part of a deployment to see how it really works. Otherwise you'll never really learn.”

“This is one of the biggest lies in a lot of AI B to B applications that they magically work out of the box without training. They don't.”

“be wary of super cheap apps. Be wary of super cheap. It's not that we're not getting there. It's not that everything isn't going to get better, but it's, you can't cut the corner on training. So if instead of 50 grand a year, you're buying a solution that's, that's 500 dollars a month or 50 dollars a month. I'm not…”

“you have to read your sales team's emails. Cause they're probably terrible. Even today they're terrible. Even with AI, they're probably terrible. Slow down and audit everything.”

“I would almost pick that vendor. The one that you have the most confidence you can onboard on, not the smooth, smoothest deck or sales process or best demo.”

“Force, if you're going to vibe code it, break it up into its components and then have more pages than you would think. You're almost going back in time in some ways to have a lot of pages, but it will save your sanity. I built a massively complicated app that was all one page and I, then it was just impossible to fix…”

“build an app in 10 or 15 minutes. It will come up with ideas for you. It will have you sign off on an action plan and then it will roll out. And at first it will look kind of cool. And then you'll start clicking on things and half of it won't work. And half of the buttons will be placeholders. And a lot of the stuff…”

“And I would say, frankly, if you're not rolling back once a day, you're, you are, you're not doing it right. This is your, this is how you can fix things that are otherwise unfixable, but you, but rolling back to a week ago, I mean, there's a million reasons that becomes impossible. There's a hundred checkpoints. You…”

“professional investors, if you don't have the pedigree, if you don't have the numbers, like the growth, or you don't have, or you're not in a super hot space, it's three, three risks too many. Like if you have to even precede inception, investors don't take all three risks.”

“I find almost every founder gets the ratio of enterprise to bolt on wrong, right?”

“You know, if no one's ever heard of you and you have no base to email from, no matter how well you do, you're not going to see these results.”

“even if you have all your data in, even if you have it all in, you may have to QA it every single day for the first couple of months.”

“Almost all of them can only do one or two workflows. They can't do everything you want.”

“another reason deals falls apart, the SVP leaves or is fired. That's actually a top reason for like sub billion dollar deals is the head of the business unit retires or is kicked out or is fired all of a sudden. That's not on the, it's not on his or her priority list.”

“Founders way underestimate how big a deal it is for an acquirer. It's so much work. It's so distracting. It's years of commitment. Forget about the money. The money often doesn't matter.”

“when a potential buyer says build, buy or partner, right? That's usually internal, uh, code word for we're thinking about buying, but we're not quite there yet, but we're pretty close. Like they're not really thinking about build or partner or they'd be partnering or they would have already partnered with you or they'd…”

“founders will see a decline in market share before VCs can see it before anyone can see it, you'll smell it. You'll go walk into that deal and you'll start losing deals. But you're still growing at a hundred percent or 80 or 200%.”

“And the harder it is to leave, man, the more stressful it is to buy.”

“Everyone has this magical first sales rep. That somehow Out of all the folks, they are the one that could sell the product in the early days, okay? And there's different versions of it, but if you talk, if you want to have fun, anytime you talk to a founder north of a 10 millionaire, ask him if they had a magical sales…”

“Not only do you have to drive up NRR and drive down churn and solve those 82 feature gaps and build that integration, but you got to add a layer if you really want to do it. And the best teams, the most agile teams, the ones that are killing it are doing this.”

“As long as you break even on a new layer. As long as you break even on a new initiative, it's worth it. As long as your core is efficient, not every marketing campaign has to have perfect ROI. Not every sales motion has to be profitable instantly. It just has to average out to something that's decent.”

“everyone regrets not going multi-product earlier.”

“A core product, a second core product has to unlock much, much, much more budget for a discreet reason than the first.”