Dave Kellogg

“By the way, for whatever it's worth, I don't actually think customer success should report to sales. I think that's a stress reaction to save money. I think the company hits a downturn. There's too much sales expense, which customer success is usually classifi…”

“There's two ways to solve that problem. One is to have super consistent pricing, which in my experience in enterprise is very difficult. The other is to have very complicated pricing. So it's very hard for them to figure out who got the better deal.”

“The low-hanging fruit on efficient growth is a dispassionate, calm analysis of what sectors do we sell to.”

“I'd say a 1.5 or less is in enterprise. I mean, here we are back to your question. The bigger the deals, the more permission you have. So an enterprise, I might go one five. In SMB, I might go one O.”

“As an operator, I actually just do it on new ARR. My first order CAC is just, it's not net new, because net new introduced churn. You just made my metric more complicated, right? You made it easier to cheat. You took away some of its meaning.”

“If I were screening companies I would, I tend to want to use compound metrics. The more I'm trying to fix broken things, the more I want atomic metrics.”

“I think most startups, when they make that argument to me, I think they're vastly underestimating the size of their market. That if you have a really, really big market, That, that you haven't picked all the low hanging fruit.”

“And by the way, if you asked, like, the most recent study, I think, said one oh five. The reason I said one oh eight is I just can't make my mouth say one oh five. But I think it may have come down from one 20 to one oh five, to be honest, and I think it's thr…”

“Churn forecasting to me is actually easier than new sales forecasting.”

“So, so I just think CS for it, I am, if a VP of sales misses their forecast, I'm somewhat understanding. To me, it's I'm not very sympathetic to a VP of CS that misses their forecast, because how is it that you didn't know?”

“And a good forecast looks like this, gently upsloping to the actual number you sell. Notice I've never talked about quota. Because forecast is not about quota.”

“Some sales managers use the forecast as a club to kind of push the reps around. Like if I could just in a moment of week is get you commit to one 20, then I can hold it against you for the rest of the quarter. First, I don't think that's great sales management…”

“So I like hiring three at a time but not for the Hunger Games effect, for the controlled experiment effect.”

“I would say somewhere between six and 12 months in enterprise.”

“The hardest case is not firing somebody who's not selling. That's easy. The hardest case is keeping somebody who's not selling.”

“In my world, there's three different types of calls. Let me just define them. I think the There's a forecast call, there's a pipeline scrub, and there's a deal review. Purpose of forecast call is to come up with a forecast. Should be all numbers. One of my sid…”

“As a CEO founder, I think you just need to look at the materiality of the deal to the quarter. And like, are you What's the word? But negligence in your duties. Like at some level, if the deal is material of the quarter, you better be in it deep.”

“You don't make the software. So your only job is to sell the software. You're not a technical resource. You don't help customers deploy. So this is kind of the, you had one job argument, right? Like you had one job. And it's like, let's just remember, that's w…”

“By the way, everyone should have a closed plan, and every time you hear one of those excuses, it should go on in the closed plan.”

“The company got acquired on the last day of the quarter, all purchasing got frozen. Okay! Right? That we couldn't have seen coming, right? But it needs to literally be that level of act of God, right, before It's before it's an excusable reason for a slip.”

“Selling through curiosity is just amazing, because most salespeople are, in some ways, they're too busy trying to prove how smart they are, be tough and confident, and it's just so humble a place to come from”

“There's a great metaphor, Harry, which is when do you stop squeezing a wet rag? When the water stops coming out, right? So as long as there's water coming out, I'm going to keep squeezing, and then even then, when the water stops coming out, what do you do? On…”

“I think Outbound actually worked better four years ago than it does today, because I think everyone's doing it, and people are getting flooded with it, and they don't like getting called on their cell phone, they're not answering their regular phone, and you c…”

“The other thing, so I imagine this all as a matrix of vertical versus use case, and every time you're hopping a cell, it's danger, right? Like you know how to sell the custom publishing use case to publishers. Can I sell it to airlines? First, the first one is…”

“If I was advising a young person where to go, if you wanted to found a company in two or three years, I'd say product, not engineering.”

“If and when you replace a founder, which was extremely unpopular for the last five years, but I think will get more popular going forward, you will tend to replace them with a GTM person.”

“So if I were a founder of one of these companies, I'd be very aggressive right now to get myself known and established in the market, because this market will organize, right? We're in the chaos phase of the market, and so from the vendor side, this will organ…”

“The most common form of misleading is what I call cherry picking, right? You just don't put up the bad numbers, right? You put up different numbers every quarter.”

“That the companies I work with that kind of have their metrics act together, Don't have the deja vu problem because the numbers are telling us what's not working.”

“And when I give the forecast to the board, I want to give a 90% confidence interval. So I'm giving them the lower bound of a 90% confidence interval. Now people hate that. And if people get scared when you use those words, I have advice. Just say you get to mi…”

“I actually think the best way to segment them is by aspiration. That, that if we could, and nobody offers these yet, but I want you to just consider this concept that we should segment benchmarks by aspiration, which is if I want to sell for 18 times EBITDA in…”

“I competed against the company that did one dollar renewals. And they would juice their churn rate so they could offset their SAS metrics.”

“Even layer one has taken me with certain companies I work with quarters. And I walk in every time I have this kind of entrepreneurial blind spot going, this is going to be easy. Me, head of FP&A, CFO, we'll get this nailed in 30 days, 60 days. Every time I do …”

“The change management is hard. It may require staff upgrades, particularly key analytics roles like RevOps, FP&A. Sometimes those people are not that strategic. They're not that fast, right? That they're good at making a budget and they're good at getting comp…”

“They produce a nature-based PNL, not a function-based PNL, and you can't do SAS metrics off a nature-based PNL.”

“Templates build trust. Why? Because there's no cherry picking, and the most common form of misleading is cherry picking.”

“The goal is to not have conversation about metrics, but conversations about the business using metrics.”

“If you step back and take a more kind of macro view on it, you should try to raise money about every two years.”

“You know, one interesting thing about this phenomenon is you can often take the size of somebody's round and divide it by eight to 10 and get a pretty good approximation of their burn rate.”

“You might go out thinking you're gonna raise twenty-five million, and in this world, find out that you can raise 50. Should you take the 50? In my opinion, yes.”

“The perverse thing about this is, the better your category, the more likely that is to happen. If you're selling some very Focused vertical SaaS app, you're unlikely to find a spending arms race, right? But if you're in some horizontal platform category, peopl…”

“So, if you find yourself in this situation, it's probably a sign that you're in a really good category, but you either need to play to win, and go out raise the other guy, or you need to find pivot into some sub-segment where you're not directly competing with…”

“I did a year at Salesforce in the middle of all that, and I was mentioning Zendesk. I was like, hey, there's these guys called Zendesk, and they might be a problem for, like, our customer service business and I got the kind of uh-oh moment where, like, oh, and…”

“The last three I just exclude is politics, period. Because what you're saying is you want your function to be more important than the other function. So I throw those out.”

“Avoid this fake either or framing, which is you need to speak like you're vision driven. So when you're talking to customers and analysts, the markets, talk about the desired end state. Talk about the vision. Don't talk about competition. When you're building …”

“Their OTE, their on-target earnings, is 300 K. They're gonna cost a 180 K for two-thirds, and you can adjust these numbers to your local market, but do the exercise, right? So I'm hiring a seller. I'm hiring two-thirds of an SC. I'm hiring two-thirds of an SDR…”

“And the people who got you from zero to 10 are almost by definition figure it outers, right? If a scale it upper joined your company at zero million dollars, they probably quit pretty quickly.”

“I've worked with many startups where the figure it out sales VP had to leave when we hit ten million. And I always feel bad about that, because I don't actually think they have to leave. I think they should be redeployed. Like, my answer is, what do you do wit…”

“Scaling is very different. It's about a small number of amazing process and infrastructure oriented leaders leveraging a large number of great, but not necessarily amazing people, right? They're not solving problems. They're building systems and processes. Qua…”

“Anyone with an idea is trying to help, and your job is to listen, to understand the idea, and then by and large not do it, right? Because if you have a good plan and a good strategy, you need to go execute that.”

“The U.S. Has geography and vertical industry, right, they're correlated. Like, if you're focused on pharma, you go to New Jersey, finance New York City, entertainment LA, and sometimes for a company, I actually recommend, even if you don't have to be verticall…”

“A lot of people do NFL cities, which I think is a terrible strategy, but you could do that if you want. Just, if there's a football team, put salespeople there. Not, not my recommended one, but people do it.”

“Don't hire a VP of sales, hire a director. And let them try and earn the job.”

“To me, the definition of that should be customer verifiable, right? With one phone call, I should be able to verify that, and that one's easy. I just call the customer and say, do you think our product can solve your problem? Because that's what solution fit c…”

“I literally did a consulting gig with a company that had 100 X pipeline coverage. Can you imagine? So their pipeline was a hundred times bigger, and they still missed their numbers. So, so think about that. And the answer is they don't have what I call pipelin…”

“You don't want to raise money from a VC who wants you to be a billion dollars, and you want to sell it a hundred million. I've had friends who wanted to sell it a hundred million. VCs wouldn't let them, right? Because they'll say, no, we're blocking the sale b…”

“You're confused by ill-defined terminology and process, most marketers are not that rigorous in their thinking and you're drawn into conflict between sales and marketing, right?”

“If the category hasn't formed yet, you're probably in a why-buy-one mode. Hey, I know there's this thing you never heard of. Let me tell you why you should buy one. If there is a category, and there's five vendors in it, and there's a magic quadrant, you're pr…”

“The fact of the matter is, if you're talking to your buyer, and it's a high consideration purchase, they will have time to read a twelve-page white paper. They will have time to go to a one-hour demo, right?”

“People want references who remind them of themselves. So, this is a large part of the whole Crossing the Chasm book, is you can't take a, you know, technology pioneer and reference them against a pragmatist. It doesn't work.”