CEO

“We think, I always tell people, we see three distinct breakpoints for CEOs. The first is around 40 or 50 people and that's usually where communications break down. You can't just rely on osmosis to get information out in the company anymore. You gotta actually…”

“And then a thousand is really interesting, because at a thousand, like if you're interacting From a reporting relationship with more than, I'd say, six to 10 people, you're really probably doing something wrong. Spending most of your time externally, and then …”

“Year five is where it gets tough. You get tired. And the best CEOs and VPs and teams push through to that sixth year. And the other ones, it's tough. You see a lot of transition in five years. You see a lot of folks handing the reins to other folks.”

“Most founders are going to have the big idea to start the company, and they're going to have many ideas that are all top priorities, and so I think it's the job of the VP of product to be able to not just prioritize those ideas but really do the analysis and g…”

“The trap that companies will fall into is, ah, that you've got the CEO with some vision of, like, here's this customer problem, and I'm gonna build this product. But they've never actually been a product person, and breaking down that kind of generic vision in…”

“If you're not spending your time with your average customer and figuring out, you know, why is this particular customer nowhere near as big as this other bank I mentioned earlier? It's, on paper, it's the same size. Why isn't that really happening, and what ar…”

“And to me, when you get into your B, it's still important as a CEO to spend half your time with your customers, with your existing customers, with your prospects.”

“If you're not one of the primary sellers for your company's product in the early days, to me you have no business starting and running the company”

“So my job changes probably at least every six months. And every time I need to learn a new job, and every time I don't know if I'll be great at the next job I feel like, one, having, ah, a coach is useful, and it can be a different coach every six months.”

“You don't have to hold onto these things like CEO or C whatever or blah, blah, blah for ego because you'll still get the credit. Your ego is going to be fine. You're going to get the ego stuff anyway, which is cool.”

“Around that size the primary job of a CEO has to start switching to management. And usually for a pre-product market fit company, the primary job of the CEO should be to focus on product market fit.”

“The number one cause of CEO death is misalignment with the board.”

“If you're getting the board slides out 24 hours or less before the board meeting, you're not looking good, almost regardless.”

“And if you're CEO of the company, you cannot allow warring princes in your company. Everybody sees it. The whole company knows if two E staffers are at war.”

“If I'm not keeping the board busy, Helping me drive the company, they are going to come in with ideas and ways to help that I may not find helpful.”

“The backdrop of global pandemic change is so enormous that you can kind of sneak in anything you want. And we see I see that talking to other CEOs today, not my customers, just like, There's essentially a group therapy SAS CEO round table. And it's like, oh, t…”

“I think every CEO should have a driver-based model where you play with sales productivity, sales turnover, sales ramp time, marketing is a percent of sales, cost per sale. You put these various drivers in and you can see what happens to your business, see thei…”

“Too many CEOs think that like marketers can convince PR people and journalists to write about anything. And the reality is journalists don't give a shit about your product unless it is truly doing something innovative or unless it's breaking rules and they'll …”

“Information on a brand and a product rarely evokes emotion. Information about people does. Right. And this is why every CEO should be the face of their company. People will attach to that.”

“I think if you get, if you make everyone responsible 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?”

“Until you're big, until you're at 40, fifty million, when board meetings really are about money around the table, right? Until that phase, board meetings are at least 50% for your management team to present. There is nothing, few things more valuable to a CEO …”

“The great marketers don't spend money on, on programs that don't perform, right? So I think this is true, but I blame the CEOs for lowering the bar on hiring for VPs.”

“I think the number one mistake I've seen founders make is they hold people's feet to the fire on all those cells, and I think that's wrong. I think it's demotivating. I think it doesn't reflect an understanding of the fact that the model deviates from reality.…”

“What I have found over and over is if you have a founder or a CEO with a particularly large vision, they're thinking 20 years out. They're thinking big, far reaching, you know, wide kind of visions, and it's the job of the CMO to bring it down to the one year,…”

“Put a list together of what needs to be done with your exec team, and go through each item on the list, and assign That whatever it is to somebody on the team. And if you can't get through that task list, initiative list, whatever it is, with your name not bei…”

“There was no advantage for this CEO to set the target at forty million dollars in the first place. What you should have done with hindsight, is reached out to the board before the meeting, said, what does a successful twenty-twenty-two look like to you all? Th…”

“As a past CRO, it's really critical that you and the CEO have the same answer. So it doesn't matter which answer it is that you have, but have the same answer.”

“The CEO, you know, can commit himself to things that your sales team will never be able to commit to.”

“One, if you can recruit people better than you should still be the CEO, and two, I think you have to have a curious mind.”

“I view the CEO as the proxy for sales and marketing. Like if the CEO is great with some help, maybe you and I can, we're working on a search together day. We can help you find a sales and marketing leader. But I don't really care who you have at a hundred K in…”

“One thing that's been consistent, and I bet most sales leaders would agree with this, is that the buying decisions, which used to be with the functional lead, which in our case is the chief people officer, are now oftentimes getting pushed to the CFO, sometime…”

“The best CEOs recruit 20 to 30% of the time. Constantly. 20 to 30. If you're not spending 20 to 30% of your time as a CEO recruiting after a million or two in revenue, you're not getting the job done.”

“The weird thing about CEOs, Even of huge companies, is almost all of them open all their emails. They sit in front of their phones, and their computers, and look, they don't open the dumb emails, and they don't go to the promotions tab, ok?”

“There's three jobs for the CEO, and this is true when you're Series A and it's true when you're Series F. You gotta keep money in the bank, you have to sell the vision internally and externally, and you have to fire yourself by hiring people to do jobs better …”

“Another friend of mine has this expression from Machiavelli that warring princes means one thing, a weak king. And if you're CEO of the company, you cannot allow warring princes in your company. Everybody sees it. The whole company knows if two E staffers are …”

“The number one cause of CEO death is misalignment with the board.”

“And this notion of having a sell by date, it may not be polite, but often board members have it, and if they have it, I'd advise you to understand what they are. And to try and reframe the issue that it shouldn't be that John or Mary is with the company or not…”

“That's how you lose interest in meeting with a direct report, and I view the non-desire to meet with one as a huge warning sign that you should inspect.”

“The whole thing falls apart when you have some vision as a founder, CEO, entrepreneur, or even if you're a functional leader, and the people underneath you don't believe the same things, it's all a house of cards.”

“Almost every CEO that I talk to that goes past about 50 engineers runs into exactly this problem, and they realize they haven't spent enough time on this, so I can't overemphasize it, spending enough time on this.”

“CEOs read like every email. Every email. And it's just, they don't, Howard's nodding his head. Even when he was running Yext, 22 quarters is a public. He didn't respond to any of them. And if the email was great, if it was like, if it was going to solve one of…”

“The actual number of paid customers that go live is in the eighties. They're often, as CEOs, we think, oh God, it must be 96%. And they're often shocked when they look at the data and they're like, oh my God, it's 81% of our customers go live, right? They're a…”

“Don't hire the jaded. The one literally four minutes in your interview, they're telling you how the CEO or the VC screwed them over... Don't hire them. They're going to think the same thing of you about three weeks in.”

“Which is to be a CEO like you got to be like constantly, I think you got to spend 20 to 30% of your time soft recruiting execs.”

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

“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 …”

“The CEO, for whatever reason, in the early days, maybe loved is the wrong word, but he enjoyed managing, he managed 12 SDRs himself before he hired a sales leader... So greenhouse got to ten million through outbound, right?”

“If you hire someone that you don't a hundred percent believe in it, zero percent chance it's going to work out.”

“You should always, regardless of size, the CEO should be actively involved, you know, at least 10% of their time to 20% engaged with customers and partners.”

“And I see so many executives flame out weeks two through 20 or 50, and it's not that they weren't great. It's just, they were never aligned with the CEO.”

“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…”

“I'm the last generation of CEOs to say, maybe you are too, that we only had human employees.”

“I also advise some companies Sit on board of companies, and there are some companies where the leadership, the mandate doesn't come from a leadership level, and nothing is happening in those organizations. The CEO really need to say this is one of our top prio…”