The Wisdom Wall

“Yes. Get rid of them. Build a, build a professional service organization. Hire more SEs who can do it. Customer success. Look, people think that's blasphemy. I get it. I don't believe in it. I inherited our customer success when Frank came in and he gave it to me. I got rid of it. It was an expense that I didn't see…”

“The ultimate measuring stick for a head of sales is can you hire great people and make them productive? And to me, productive means within six months, can a sales rep get onboarded Understand how to sell the product, generate their own pipeline, and then close on a, you know, north of 250,000 dollars of new ACV a…”

“I'm like, that's the most idiotic thing I've ever heard in my entire life, because who gives a crap about your brand when you're fifty million dollars in revenue?”

“when I'm talking to founders, like when they're looking for heads of sales, what I say is go find that someone, A, who's, who's been a second line manager or B, a head of sales at a crappy software company. And that's been successful. That's hit their numbers. Because can you imagine if you actually could sell a crappy…”

“If you've never done sales and you come into a startup, you're not learning anything. There's no one teaching. The founder doesn't know how to do sales”

“And so, to me, whether you call it customer success or professional services, you have to show that they can at least be breakeven, those people. If they're a cost of sale, then I think they're, it's not worthwhile.”

“So PLG is great, but if you want to sell to the enterprise, the enterprise is hyper-political, and you have to have a sales process to do that. And at some point, The PLG motion will fail you, or it won't get you to that, that large enterprise. And if you aspire to sell the large enterprise, you need a sales mode. I…”

“No one's really your friend. You have a job to do, and you have an obligation to shareholders.”

“I think it's a mistake for a founder to hire a chief revenue officer right away, because the getting rid of a chief revenue officer is going to be more painful versus, Hey, you have a VP of sales and you can hire over them and you can make that VP of sales a Head of North America or head of the East or West or whatever…”

“those large enterprises, especially in an early stage startup, they will suck the life out of that startup because they will say, I need these hundred features.”

“Founders love product marketers. They understand the product and they're going to build this marketing literature and stuff like that. That's a waste of time. The marketing team needs to generate pipeline.”

“if you do not go on eight sales calls a week, if you do not become a student of what you sell, you will fail. You might be a really nice person, but if you don't do those two things, you're going to fail.”

“A hundred percent. Like that's a, that's a good lesson is like, A single person should not be the litmus test because you don't know if they're doing the things that you do. As the sales leader, you should be, be a leading from the front sales leader. You should understand how to sell the product. You should understand…”

“I've seen that, you know, the board of directors is saying this person stinks and they don't. It's more that the founders aren't listening to customers. They're not building the right product.”

“the, the industry expertise does not matter as much as like you being successful selling an enterprise technology.”

“If they're doing three, four million dollars, don't pat yourself on the back because that means you're missing opportunities. You're missing a opportunity in the market because they're just sitting there and they're fat and happy.”

“it's silly to pay a sales team on something that's just like an on-demand contract. No way. We never, you should never do that because it it's, it's not durable revenue and there's risk.”

“I think like you have to go in and you have to then sell, like in a consumption model, you have to get usage. So like we talk about forward deployed engineers. Okay. Well, that's an ideal situation to deploy a forward deployed engineer or professional services person, which I think, you know, that's the right approach,…”

“So a good way to find out if a second line manager is failing, just look at their travel schedule. If they're, if they are not, if they are lowest on the totem pole on their, on their travel reports means they're not working.”

“no pain, no deal, no champion, no deal. And, and the way that you develop a champion is you look at the metrics. You show them how to use those metrics to get the deal done. So, like, I, medic doesn't change, and people want it, want to say AI makes it different. I don't believe that at all.”

“What has not changed is if you have the guts to pick up the call, the phone, call me, leave a voicemail, text me, email me, call me again, that there's nothing, nothing replacing that because dude, like all these CIOs are getting inundated, inundated with AI prospecting.”

“Founder led sales is great. I think founder led sales should always happen, especially when you're innovating on your product and you're learning. So I'm a huge fan of the founders being a part of the sales process, but ultimately I want the founders building product and building a world-class product and building a…”

“if you don't generate your own pipeline, if you don't go on eight face-to-face meetings a week, You're probably gonna fail.”

“I hate whale hunting only. And the reason I hate whale hunting only as a sales leader is it's too spiky. And spikes get you fired. Spikes on one end are great, but if you miss a quarter, guess what? The head of sales, you're, you're fired.”

“For the high end of the market, it works well. Palantir shows that. For the mid-market, it is not a scalable business.”

“Zoom does not tell you what's happening in an office. You don't know if you have a tyrant running a country for you unless you're there. And you're going and having coffee with someone, you're having breakfast with someone, you're having dinner with them, a beer, a glass of wine, whatever it is, but like, go find those…”

“a good way to test that champion. If they are real champion is will they actually bring you to the economic buyer?”

“a good sales rep uses us as a pawn. I always say, I'm an actor in the sales reps movie. They're the director. They can use me however they want. If they make me the director, good luck, and you're probably going to fail.”

“If you go out on a sales call, and the person doesn't know what the hell they're talking about, and they've been on the job for six months, yeah, you're going to be in a world of hurt, and you should just cut bait.”

“I think CEOs, founders like to blame other people for failures. Sales, sales is probably the first person to get the finger pointed at.”

“pretty much the number one pain point of any startup CEO is they would need help building a sales team.”

“if we can build outbound sales organizations, sale-led growth engines, um, and then you can pile in PLG on top of it, you, you have best of both worlds.”

“when you're scaling, it's, it's six. But at scale, like, if you're not growing as fast, and you're not hiring as fast, and you have a bunch of productive reps that have been in the seat for six months or longer, you can have, like, eight or nine.”

“I think it's really important. To have this really close relationship between sales and marketing and for marketing to treat sales as their customer.”

“the advice I would give to these founders is go find a sales leader that you like and put them on your board, or at least have them as an advisor.”

“every week have your head of sales, send out an email of what they did. Now, if it, if you have too big of a company, then send it just to the leadership team, but let them know like, Hey, this is what I did this week, because then all of a sudden you can start figuring out is this person working or not.”

“And that transparency that I had around what I was doing, and they, I developed credibility with them, even though sometimes what I said was not always right, because I'm not this database expert, it made, made this relationship with these engineers strong, and they trusted me, and then they started building product…”

“just look at how long your sales cycle is. How long does it take you to close one deal? And that's what you look at is how long does it take to open up a new pipeline opportunity and then bring it to closure. That's really what productivity is.”

“you can fail, like, you can fail in the mid-market a bunch, and then not be super consequential. If you fail in the, in the, you know, Fortune 100, Good luck getting another, another chance.”

“What I found was that people would actually, if they pay for something, even if you're splitting the cost of it with the customer, a lot of times when they pay for something versus get something for free, they value it more.”

“The immediate gratification is, is definitely something that, uh, that I enjoy. But it's always like, it never ends, because once you have a good quarter, it's on to the next quarter, and you're a loser all over again, so.”

“The reality is, is that if you're out there trying to convince people that they have a problem, that's an 18 month to 24 month sales cycle.”

“So with Snowflake being a consumption model, you could see the dial turn real time. I look at revenue on a daily basis. And if a customer goes up really fast or down really fast, it sets off alarm bells because I don't want them to overspend because all of a sudden they'll be really mad at me. And I don't want, and if…”