Latest / The Official SaaStr Podcast: SaaS | Founders | Investors / How to Hire a Great VP of Sales Today: The New, Latest Edition with Jason Lemkin (Video + Pod)
Transcript
- 0:00SPEAKER_00: Thanks for coming.
- 0:00SPEAKER_00: Originally,
- 0:01SPEAKER_00: this first date was just going to be networking,
- 0:04SPEAKER_00: brain dating in the back,
- 0:06SPEAKER_00: but we decided to throw together some extra sessions.
- 0:09SPEAKER_00: It always happens.
- 0:10SPEAKER_00: I asked Christophe to do the bootcamp for VC and I thought, what could I do for bootcamp?
- 0:15SPEAKER_00: And I thought I could update some of the earliest things we've been doing for 12
- 0:19SPEAKER_00: years on Sastr on hiring a great VP of sales.
- 0:21SPEAKER_00: This is some of our earliest content from the early days.
- 0:24SPEAKER_00: It really took off.
- 0:26SPEAKER_00: And so I wanted to take a pause.
- 0:29SPEAKER_00: And think one of the 10 mistakes that founders are making today at 2024 when they
- 0:35SPEAKER_00: make the classic VP of sales higher.
- 0:39SPEAKER_00: And on the old days of SaaS where I made up a statistic, I said 70% of first VP of sales don't work out.
- 0:45SPEAKER_00: I think I surveyed 11 people and I think 7.8 of them said it.
- 0:49SPEAKER_00: So I think I coined 70%.
- 0:51SPEAKER_00: I've done surveys on LinkedIn for thousands of people.
- 0:53SPEAKER_00: They've confirmed it.
- 0:55SPEAKER_00: And you might think 12 years on, we would be getting better at this.
- 0:58SPEAKER_00: We would be getting better at making this critical hire right as founders.
- 1:03SPEAKER_00: But I can tell you across my portfolio, across CEOs I talked to, we're not.
- 1:06SPEAKER_00: We're just as bad as it, as ever.
- 1:10SPEAKER_00: And I'm going to walk through 10 mistakes founders are still making and some things we're getting worse.
- 1:15SPEAKER_00: My only hope is that one or two of these stick and you make less of a mistake.
- 1:20SPEAKER_00: But the meta point, it took me 11 years to figure out one thing on this.
- 1:25SPEAKER_00: 11 years, I'm embarrassed.
- 1:26SPEAKER_00: I knew a lot of this 12 years ago.
- 1:27SPEAKER_00: It took me 11 years to figure this out.
- 1:29SPEAKER_00: It might be one of the 10 points, so it might be redundant.
- 1:32SPEAKER_00: But if you make a critical hire and VP of sales or any role at your startup,
- 1:37SPEAKER_00: VP of anything,
- 1:38SPEAKER_00: it's your fault.
- 1:40SPEAKER_00: It's your fault.
- 1:42SPEAKER_00: I blamed my first mis-hire as VP of sales.
- 1:44SPEAKER_00: I blamed him for not doing the job,
- 1:47SPEAKER_00: for hiring terrible people,
- 1:49SPEAKER_00: for writing a letter to my board saying I was incompetent.
- 1:51SPEAKER_00: I blamed him for that, okay?
- 1:53SPEAKER_00: I did until about last year.
- 1:57SPEAKER_00: It took me 11 years or 12 years to realize it's my fault.
- 2:00SPEAKER_00: I hired him.
- 2:02SPEAKER_00: Your VPs, your executives, anyone on your team can never do enough due diligence.
- 2:07SPEAKER_00: They can never understand what your go-to-market motion is like,
- 2:10SPEAKER_00: what your metrics are like,
- 2:12SPEAKER_00: what your business is.
- 2:13SPEAKER_00: When I do investments,
- 2:14SPEAKER_00: I interview a lot of VPs for the founders at 1 million,
- 2:18SPEAKER_00: 10 million,
- 2:18SPEAKER_00: 20 million,
- 2:19SPEAKER_00: 60 million in ARR.
- 2:21SPEAKER_00: And I try to go last.
- 2:23SPEAKER_00: I try to be the last one for them to interview.
- 2:25SPEAKER_00: And I always ask them like a basic question.
- 2:27SPEAKER_00: I'm like,
- 2:28SPEAKER_00: Do you know how much revenue the company has?
- 2:30SPEAKER_00: Do you know how fast they're growing?
- 2:31SPEAKER_00: Do you know how many sales folks are on the sales team?
- 2:34SPEAKER_00: Nine out of 10 of the executives have no idea.
- 2:38SPEAKER_00: And we can mock them and we can say,
- 2:39SPEAKER_00: how could you have spent eight hours,
- 2:41SPEAKER_00: two hours with the CEO,
- 2:42SPEAKER_00: one with the CTO?
- 2:44SPEAKER_00: How could you not know these things?
- 2:45SPEAKER_00: And yeah, the best ones do know.
- 2:48SPEAKER_00: But all of a sudden it clicked on me.
- 2:49SPEAKER_00: We don't.
- 2:50SPEAKER_00: It's our fault.
- 2:52SPEAKER_00: We don't qualify candidates out enough.
- 2:55SPEAKER_00: We move too quickly.
- 2:56SPEAKER_00: We don't do reference checks since March, 2020.
- 2:58SPEAKER_00: We want to get it done.
- 3:01SPEAKER_00: And it's always our fault.
- 3:02SPEAKER_00: The candidate can never knew it up diligence.
- 3:04SPEAKER_00: So it's always your fault.
- 3:05SPEAKER_00: That's my meta learning that I want to talk through, but okay.
- 3:07SPEAKER_00: What are the 10 mistakes or 10 points now?
- 3:11SPEAKER_00: This one is newer.
- 3:12SPEAKER_00: This does become a vibe.
- 3:15SPEAKER_00: What did Paul Graham call it?
- 3:16SPEAKER_00: Founder mode.
- 3:16SPEAKER_00: Did anybody read this?
- 3:18SPEAKER_00: Anyone hear of this founder mode thing?
- 3:19SPEAKER_00: I think a few people saw it.
- 3:22SPEAKER_00: Great.
- 3:24SPEAKER_00: Be you.
- 3:25SPEAKER_00: Founder mode does not work for sales.
- 3:27SPEAKER_00: It does not work for inside sales.
- 3:28SPEAKER_00: It does not work for... There are elements of it that work, which we'll talk about.
- 3:33SPEAKER_00: There are elements that don't work, but you need a sales team to scale sales.
- 3:37SPEAKER_00: You do.
- 3:38SPEAKER_00: Founder mode in sales means not exiting sales, and we'll talk about that a bit.
- 3:44SPEAKER_00: Even if we don't, let me hit it.
- 3:45SPEAKER_00: The number one mistake that CEOs, founders make when they hire a VP of sales is they exit sales.
- 3:49SPEAKER_00: We've talked about this on Sastr.
- 3:51SPEAKER_00: They're tired,
- 3:52SPEAKER_00: they've been doing founder-led sales,
- 3:53SPEAKER_00: they hire Linda,
- 3:54SPEAKER_00: they hire Bob,
- 3:55SPEAKER_00: they hire Amelia,
- 3:56SPEAKER_00: they hire Jason,
- 3:57SPEAKER_00: and they're out of here.
- 3:58SPEAKER_00: They leave sales and they disappear for six months and sales goes in the toilet
- 4:03SPEAKER_00: because the VP of sales doesn't know the product.
- 4:05SPEAKER_00: They don't know the customers.
- 4:06SPEAKER_00: They don't know what happened.
- 4:07SPEAKER_00: They were never trading.
- 4:07SPEAKER_00: They were never onboarding.
- 4:09SPEAKER_00: Again and again, founders exit sales when they are VP of sales.
- 4:11SPEAKER_00: You cannot do that.
- 4:12SPEAKER_00: You have to spend just as much time in sales after you hire someone as you did before.
- 4:18SPEAKER_00: So your time should change.
- 4:19SPEAKER_00: You should be more of a middler.
- 4:21SPEAKER_00: A great VP of sales will grab you and bring you into 10 deals a month instead of
- 4:25SPEAKER_00: you having to do it,
- 4:26SPEAKER_00: but you'll never get the time back.
- 4:28SPEAKER_00: But when I see founders doing,
- 4:30SPEAKER_00: which is newer,
- 4:31SPEAKER_00: is they're either staying founder-led too long or they're reverting to founder-led.
- 4:37SPEAKER_00: They're reverting and...
- 4:40SPEAKER_00: Look,
- 4:40SPEAKER_00: if you've got,
- 4:41SPEAKER_00: you're closing million dollar deals and you have two reps working for you,
- 4:45SPEAKER_00: it's 500K,
- 4:45SPEAKER_00: 400K deals,
- 4:47SPEAKER_00: you could probably even get to eight to 10 million being founder-led,
- 4:50SPEAKER_00: you don't need that many people.
- 4:52SPEAKER_00: But even there, there's too much time, there's too much to do.
- 4:55SPEAKER_00: And so I see founders not even thinking about hiring a real VP of sales until eight,
- 5:01SPEAKER_00: 10,
- 5:01SPEAKER_00: 12 million ARR,
- 5:02SPEAKER_00: it's too late,
- 5:03SPEAKER_00: there's too many people.
- 5:05SPEAKER_00: And I see a new thing with some of the best founders I know who got burned.
- 5:10SPEAKER_00: They've had a miss hire for their first set of sales.
- 5:12SPEAKER_00: And then their second, sometimes their third.
- 5:14SPEAKER_00: And they're like, frack it, frack it.
- 5:16SPEAKER_00: I'm going back.
- 5:17SPEAKER_00: I'm rolling up my sleeves, like Paul Graham said, and we're going back to founder led.
- 5:21SPEAKER_00: We're at 17 millionaire.
- 5:22SPEAKER_00: I'm going to do it all myself.
- 5:24SPEAKER_00: I know we have four products and 80 people at the company and I got 11 VCs,
- 5:27SPEAKER_00: but I'm going to be the V I was never that good at it,
- 5:29SPEAKER_00: but I'm going to be the VP of sales now.
- 5:32SPEAKER_00: I tried to do that myself as a founder.
- 5:34SPEAKER_00: I lasted four days.
- 5:34SPEAKER_00: I couldn't handle the 12 folks on our team.
- 5:36SPEAKER_00: I couldn't handle it.
- 5:37SPEAKER_00: Maybe you can.
- 5:38SPEAKER_00: Okay.
- 5:38SPEAKER_00: But when you get big, it's too much.
- 5:40SPEAKER_00: You can't run outbound yourself.
- 5:41SPEAKER_00: You can't do, you can't spend your entire week doing an ABM strategy.
- 5:45SPEAKER_00: You can't be in every single deal.
- 5:47SPEAKER_00: It doesn't work.
- 5:48SPEAKER_00: So if you make a misfire or two,
- 5:51SPEAKER_00: And you go back,
- 5:51SPEAKER_00: founder,
- 5:52SPEAKER_00: because you got no choice because it's your fault,
- 5:54SPEAKER_00: but you had to let Jason or Amelia go.
- 5:56SPEAKER_00: It's fine for a month,
- 5:57SPEAKER_00: a quarter,
- 5:58SPEAKER_00: but start recruiting the next day,
- 5:59SPEAKER_00: the next week when it doesn't work out.
- 6:01SPEAKER_00: You could not go without a head of sales for a year and get from 10 to 20 to 40 to 80.
- 6:06SPEAKER_00: There is too much human capital required.
- 6:09SPEAKER_00: Sales has no efficiencies whatsoever in it.
- 6:13SPEAKER_00: You need even more people the bigger you get.
- 6:15SPEAKER_00: It has dis-efficiencies of scale.
- 6:17SPEAKER_00: Software is wonderful.
- 6:19SPEAKER_00: In theory, you write it once, it can be read everywhere.
- 6:22SPEAKER_00: This has worked great since the days of floppy disks and DVD ROMs.
- 6:26SPEAKER_00: It has never worked in sales and never will.
- 6:28SPEAKER_00: You will need to hire headcount infinitely, linearly with revenue, and you can't do it without help.
- 6:33SPEAKER_00: So this is my advice.
- 6:35SPEAKER_00: Even if you're not sure,
- 6:37SPEAKER_00: buy two million in an era, be hiring your first set of sales, and we'll chat about the mistakes.
- 6:42SPEAKER_00: If it doesn't work out, hire another.
- 6:44SPEAKER_00: And if you go back to founder-led, don't stay, whatever you do, don't stay there.
- 6:48SPEAKER_00: Paul Graham may or may not,
- 6:50SPEAKER_00: he's much smarter than I am,
- 6:51SPEAKER_00: much richer,
- 6:52SPEAKER_00: much better investor,
- 6:53SPEAKER_00: but he never ran a founder-led sales company,
- 6:56SPEAKER_00: okay?
- 6:56SPEAKER_00: He didn't do it.
- 6:57SPEAKER_00: And he didn't mean founder,
- 6:58SPEAKER_00: maybe he did,
- 6:59SPEAKER_00: but in my mind,
- 7:00SPEAKER_00: he did not mean founder mode or whatever it's called to mean you be the VP of sales
- 7:04SPEAKER_00: of 23 million in an era,
- 7:05SPEAKER_00: or even six.
- 7:07SPEAKER_00: Don't go back.
- 7:07SPEAKER_00: This is a big mistake.
- 7:10SPEAKER_00: Okay, next one.
- 7:11SPEAKER_00: And this one is new too.
- 7:12SPEAKER_00: Maybe this was true before that little bug went around in 2020.
- 7:17SPEAKER_00: Maybe it was always true.
- 7:19SPEAKER_00: But frigging A, it is the truest thing in hiring any VP today.
- 7:26SPEAKER_00: Whether it was being locked up in our backyards for eight months,
- 7:29SPEAKER_00: whether it was the markets exploded in 2021,
- 7:32SPEAKER_00: coming down in 2022,
- 7:33SPEAKER_00: crashing in 2020,
- 7:34SPEAKER_00: there's been so much change in four years.
- 7:37SPEAKER_00: We are full of executives that are the jaded, the broken, and the done.
- 7:40SPEAKER_00: The jaded, the broken, and the done.
- 7:43SPEAKER_00: They need a job.
- 7:45SPEAKER_00: Okay,
- 7:45SPEAKER_00: that side hustle as a fractional CXO didn't work out,
- 7:49SPEAKER_00: their clients dried up,
- 7:50SPEAKER_00: they need a job again,
- 7:51SPEAKER_00: they're back out on the market.
- 7:53SPEAKER_00: Sometimes that can work, don't get me wrong.
- 7:55SPEAKER_00: Or the 11 side hustles they were running.
- 7:57SPEAKER_00: I don't know, but we've all been through so much.
- 8:00SPEAKER_00: Here's the issue.
- 8:02SPEAKER_00: When we started SaaSter, you couldn't find any VPs.
- 8:04SPEAKER_00: There weren't any VPs that had come out of Datadog or Mongo or Klaviyo or Bill that
- 8:09SPEAKER_00: are here,
- 8:10SPEAKER_00: the CEOs here,
- 8:11SPEAKER_00: any of these great companies.
- 8:12SPEAKER_00: They just, there were only so many executives when we started SaaSter.
- 8:15SPEAKER_00: Today,
- 8:16SPEAKER_00: there's a hundred public SaaS companies that are all turning over directors and VPs
- 8:21SPEAKER_00: and senior directors and senior managers,
- 8:23SPEAKER_00: hundreds of them every year.
- 8:24SPEAKER_00: And you will want to hire one of them.
- 8:26SPEAKER_00: Even folks that are here at Duplo Cloud and Notion, whoever.
- 8:29SPEAKER_00: We can read them here at G2, folks.
- 8:31SPEAKER_00: Great folks will leave G2 or whomever, and you'll want to hire some of them.
- 8:34SPEAKER_00: And these are great companies.
- 8:36SPEAKER_00: But you got to be careful.
- 8:37SPEAKER_00: Too many folks are jaded, broken, or done.
- 8:39SPEAKER_00: And I guess they're the same thing.
- 8:41SPEAKER_00: But I'll give you a few tells.
- 8:42SPEAKER_00: Don't hire these people.
- 8:44SPEAKER_00: We need pirates and romantics in your startup.
- 8:47SPEAKER_00: You need folks that want to go on this crazy journey with you,
- 8:50SPEAKER_00: not phone it in from home,
- 8:51SPEAKER_00: not phone it in working 18 hours at home and just managing people.
- 8:55SPEAKER_00: You don't need that.
- 8:56SPEAKER_00: So number one, don't hire the jaded.
- 8:59SPEAKER_00: The one literally four minutes in your interview,
- 9:02SPEAKER_00: they're telling you how the CEO or the VC screwed them over.
- 9:05SPEAKER_00: I can't tell you how many times I heard it.
- 9:07SPEAKER_00: I crushed it at my last startup that didn't make it and sales went down when I was there,
- 9:11SPEAKER_00: but it wasn't my fault.
- 9:13SPEAKER_00: It was that stupid CEO who didn't know sales, that dumb CEO, that idiotic meddling CEO.
- 9:18SPEAKER_00: I'm sure there's truth in that.
- 9:20SPEAKER_00: Anyone that says, I'm sure there's truth.
- 9:22SPEAKER_00: Don't hire them.
- 9:23SPEAKER_00: They're gonna think the same thing of you about three weeks in, okay?
- 9:25SPEAKER_00: They're gonna think the same thing of you, okay?
- 9:27SPEAKER_00: They may be right, but they're broken.
- 9:32SPEAKER_00: The next one, I crushed it, okay?
- 9:36SPEAKER_00: I took the company from 1 million to 800 million single-handedly myself,
- 9:41SPEAKER_00: but I made nothing because the VCs screwed me over.
- 9:43SPEAKER_00: The VCs screwed me over.
- 9:46SPEAKER_00: We raised 500 million and sold for 80 million.
- 9:48SPEAKER_00: Okay.
- 9:49SPEAKER_00: I don't think the VC has screwed you over.
- 9:50SPEAKER_00: Okay.
- 9:51SPEAKER_00: You sold.
- 9:52SPEAKER_00: This is called life.
- 9:53SPEAKER_00: I don't know if the Christoph got into this last presentation.
- 9:56SPEAKER_00: You sell for less than you raise.
- 9:57SPEAKER_00: No one makes any money.
- 9:59SPEAKER_00: Okay.
- 9:59SPEAKER_00: I'm sorry, Crimea River, but this isn't charity.
- 10:03SPEAKER_00: There are no best efforts points.
- 10:04SPEAKER_00: There's no participation points, folks.
- 10:07SPEAKER_00: This could be half the presentation.
- 10:08SPEAKER_00: There's no participation points in SaaS.
- 10:10SPEAKER_00: I'm sorry you busted your ass and the company sold for less than it raised and no one made any money.
- 10:16SPEAKER_00: That's life.
- 10:16SPEAKER_00: You didn't crush it, okay?
- 10:18SPEAKER_00: So anyone that tells you the VCs screwed them, it didn't work that way.
- 10:21SPEAKER_00: There is no magical deal out there where the VCs 10X their money and this great
- 10:27SPEAKER_00: executive you're meeting made nothing.
- 10:30SPEAKER_00: I can explain venture map, it doesn't work that way, okay?
- 10:33SPEAKER_00: There are times when the VCs get their money back 1X and employees make nothing, that does happen.
- 10:39SPEAKER_00: And maybe that's not fair at some level.
- 10:40SPEAKER_00: That's not crushing it.
- 10:41SPEAKER_00: Making one extra money in 10 years as a VC is not exactly crushing it, is it?
- 10:45SPEAKER_00: That's a 0% return.
- 10:47SPEAKER_00: Like IRR, it's not that great.
- 10:49SPEAKER_00: So you got to let these folks go.
- 10:52SPEAKER_00: Their related cousin is the broken.
- 10:54SPEAKER_00: They don't want to sell anymore.
- 10:56SPEAKER_00: So many sales leaders I talk to don't want to sell.
- 11:00SPEAKER_00: This is going to be a theme.
- 11:01SPEAKER_00: Don't confuse what they did and the beautiful PowerPoints they have and their
- 11:06SPEAKER_00: endless discussion of their brilliant process and how they do process and how great
- 11:09SPEAKER_00: they are at process and how great they are at managing process.
- 11:14SPEAKER_00: They don't want to sell anymore, but they need the job.
- 11:17SPEAKER_00: They don't want to do it.
- 11:18SPEAKER_00: Do they want to sell?
- 11:20SPEAKER_00: Ask, here's the simple way you can figure out if they're broken.
- 11:22SPEAKER_00: What do you want to do, Jason, your first two weeks on the job?
- 11:25SPEAKER_00: Amelia, what do you want to do your first two weeks on the job?
- 11:26SPEAKER_00: Brendan?
- 11:29SPEAKER_00: Oh, I need to set up processes.
- 11:30SPEAKER_00: Don't make the hire.
- 11:32SPEAKER_00: If they don't say go meet frigging customers the first two weeks, do not make the hire.
- 11:36SPEAKER_00: Anyone that wants to sell wants to be in deals the first day, the first week.
- 11:40SPEAKER_00: I want to go, I'm going to get on the road my first week and go meet your top 10 customers.
- 11:44SPEAKER_00: And then my second week, I'm going to start closing them.
- 11:46SPEAKER_00: That's what you want to hear.
- 11:48SPEAKER_00: That's what you want to hear, and it's probably true.
- 11:51SPEAKER_00: But too many folks worked from that ADU in their backyard,
- 11:54SPEAKER_00: got bitter,
- 11:56SPEAKER_00: stock went up,
- 11:57SPEAKER_00: stock went down,
- 11:57SPEAKER_00: thought they were millionaires,
- 11:58SPEAKER_00: were millionaires,
- 12:00SPEAKER_00: and now they just want to manage a team and not sell.
- 12:02SPEAKER_00: There's too many folks out there that just want to manage a team and not sell.
- 12:05SPEAKER_00: Do not hire them, they're broken.
- 12:07SPEAKER_00: And the last ones which were related to it, they're just done.
- 12:10SPEAKER_00: They're really nice.
- 12:12SPEAKER_00: They've been a fractional CRO for now four years.
- 12:14SPEAKER_00: They went fractional in June when it was easy.
- 12:17SPEAKER_00: Now we're in September.
- 12:18SPEAKER_00: They've been fractional for more than four years.
- 12:21SPEAKER_00: And they're nice.
- 12:22SPEAKER_00: And again, they have great strategy slides.
- 12:24SPEAKER_00: They have great triangles and squares and arrows going everywhere and how you
- 12:28SPEAKER_00: onboard 700 reps and their patented onboarding strategy.
- 12:32SPEAKER_00: But they're done.
- 12:33SPEAKER_00: They're done.
- 12:33SPEAKER_00: Again, simple test for all this.
- 12:35SPEAKER_00: What do you want to do your first two weeks, Christophe?
- 12:38SPEAKER_00: Jane, you don't hear them customers.
- 12:42SPEAKER_00: Don't.
- 12:42SPEAKER_00: Not even sell, but that's good.
- 12:44SPEAKER_00: You want to hear, I'm going to go meet customers.
- 12:45SPEAKER_00: I'm going to get on the road.
- 12:46SPEAKER_00: I'm going to go talk to prospects.
- 12:47SPEAKER_00: That's what you want to hear.
- 12:49SPEAKER_00: And I'm going to bring Brendan and Sam with me.
- 12:51SPEAKER_00: I'm going to bring these two guys with me.
- 12:53SPEAKER_00: But that used to be enough.
- 12:55SPEAKER_00: But there's too many folks that just want to manage and not work that think they
- 12:58SPEAKER_00: have a couple of folks to bring with them,
- 12:59SPEAKER_00: which we'll talk about.
- 13:00SPEAKER_00: It's not enough, but you want to hear, go meet customers.
- 13:03SPEAKER_00: Okay, we hit this one.
- 13:04SPEAKER_00: I'm not going to be redundant because I guess I got it, but I'm going to be redundant anyway.
- 13:09SPEAKER_00: Because you're all so many, this was not a mistake that I think we made before March 2020.
- 13:15SPEAKER_00: I got to say 80% of the VPs of sales candidates that founders that I know,
- 13:20SPEAKER_00: invest in,
- 13:20SPEAKER_00: work with,
- 13:21SPEAKER_00: ask me to meet 80%.
- 13:22SPEAKER_00: Bring me this guy, gal, whatever, no gender.
- 13:25SPEAKER_00: They won't do the sales themselves.
- 13:27SPEAKER_00: Again, process, slides.
- 13:29SPEAKER_00: Oh, I have my two weeks right here.
- 13:30SPEAKER_00: Process, not meeting customers.
- 13:32SPEAKER_00: Trust me, it's 80%.
- 13:33SPEAKER_00: You got to listen.
- 13:35SPEAKER_00: Just because they talk the talk about how it was so great at Datadog and how it was
- 13:39SPEAKER_00: so terrific does not mean they will do it anymore.
- 13:41SPEAKER_00: They got to do sales themselves.
- 13:44SPEAKER_00: How long?
- 13:45SPEAKER_00: Probably once you hit $200 million AR, they can get out of deals a little bit.
- 13:49SPEAKER_00: But I think most of you are under $200 million AR and maybe not.
- 13:53SPEAKER_00: Maybe not, right?
- 13:54SPEAKER_00: There's this classic story that I've told before,
- 13:56SPEAKER_00: if you're old OG Sasser,
- 13:58SPEAKER_00: and then there's a newer version of it.
- 13:59SPEAKER_00: But the classic story was one of our first 10 in the old days, biggest customers was Groupon.
- 14:05SPEAKER_00: When Groupon was exploding, they went from zero to 1,500 sales reps in a year and a half.
- 14:09SPEAKER_00: They're all using Adobe Sign Echo Sign.
- 14:12SPEAKER_00: Great, almost seven figure deal.
- 14:14SPEAKER_00: So we flew out there in the middle of a terrible Chicago winter.
- 14:17SPEAKER_00: It was like January or February.
- 14:18SPEAKER_00: I had a really thin like track sweatshirts that used to be in back then.
- 14:23SPEAKER_00: They're about a millimeter thick from Zazzle.
- 14:25SPEAKER_00: Wind was ripping through me at 20 degrees in Chicago.
- 14:28SPEAKER_00: Go up there, the group on hanging out, doing our pitch.
- 14:31SPEAKER_00: And next door is frigging Mark Benioff who flew in from Hawaii on his jet to meet
- 14:36SPEAKER_00: with then 24 year old Andrew Mason,
- 14:38SPEAKER_00: one of his,
- 14:39SPEAKER_00: a new $50 million a year customer.
- 14:40SPEAKER_00: Cause you gotta be in sales.
- 14:43SPEAKER_00: He's still doing it.
- 14:44SPEAKER_00: Mark Benioff said he still goes to Davos every year because he sits at the top of
- 14:47SPEAKER_00: one staircase there and he meets with 200 customers and prospects in Davos flying there.
- 14:51SPEAKER_00: Now, we can't all fly private.
- 14:53SPEAKER_00: It is convenient.
- 14:54SPEAKER_00: It is convenient.
- 14:55SPEAKER_00: But there's a point here, right?
- 14:57SPEAKER_00: You got to meet the customer.
- 14:58SPEAKER_00: So is it even at 200 million?
- 15:00SPEAKER_00: Salesforce is coming up on 30 billion and Mark Benioff is still out there hustling
- 15:03SPEAKER_00: and meeting with customers.
- 15:04SPEAKER_00: If you're a VP of sales and Gunnar or CRO, pass.
- 15:07SPEAKER_00: Don't matter what else you like them.
- 15:09SPEAKER_00: Okay, this one, a lot of you are gonna wanna give on.
- 15:14SPEAKER_00: You're gonna wanna challenge me on.
- 15:15SPEAKER_00: You're gonna wanna cut a quarter here.
- 15:18SPEAKER_00: You finally found someone that's actually willing to leave their home, okay?
- 15:22SPEAKER_00: That's willing to actually go meet a customer in person,
- 15:24SPEAKER_00: that's willing to actually sell and not just manage a team.
- 15:27SPEAKER_00: You finally found that, it takes you four months.
- 15:31SPEAKER_00: But it's not clear they really understand your product.
- 15:34SPEAKER_00: It's a little complicated.
- 15:35SPEAKER_00: It's environmental SaaS.
- 15:36SPEAKER_00: It's a deep type of compliance.
- 15:38SPEAKER_00: It's a new type of SOC 7 or 11 or 82.
- 15:41SPEAKER_00: And they've never really done security before.
- 15:44SPEAKER_00: But half these folks worked at a sales-led company, which they're salespeople.
- 15:50SPEAKER_00: Like, how hard is it to sell an e-signature or sales loft or outreach?
- 15:53SPEAKER_00: I'm not saying it's easy.
- 15:55SPEAKER_00: But if you've already used the tool for the last five years,
- 15:57SPEAKER_00: you probably have an intuitive sense of the product going into sell a complicated
- 16:02SPEAKER_00: piece of regulated software in a new industry.
- 16:05SPEAKER_00: Most people can't make the jump.
- 16:06SPEAKER_00: Okay.
- 16:07SPEAKER_00: That's an issue in and of itself.
- 16:10SPEAKER_00: Number one, most important thing, do not give on this.
- 16:12SPEAKER_00: Everyone is, this is, no one does reference checks since March, 2020.
- 16:15SPEAKER_00: No one asks sales reps to do demos before they hire them anymore.
- 16:19SPEAKER_00: Horrific error.
- 16:20SPEAKER_00: And everyone hires a VP of sales that never learns the product until after they start.
- 16:26SPEAKER_00: Never.
- 16:27SPEAKER_00: There's a company I invested in, I love this company.
- 16:31SPEAKER_00: They got to 10 million,
- 16:32SPEAKER_00: hired their third VP of sales,
- 16:35SPEAKER_00: great guy,
- 16:36SPEAKER_00: came in six months in,
- 16:37SPEAKER_00: sales were way down.
- 16:39SPEAKER_00: But honest,
- 16:40SPEAKER_00: most honest guy in the world gets up in the board meeting and he says,
- 16:42SPEAKER_00: I gotta be honest,
- 16:44SPEAKER_00: I didn't actually learn the product.
- 16:46SPEAKER_00: When I started, I thought I could do it.
- 16:48SPEAKER_00: I thought I could do it.
- 16:48SPEAKER_00: I thought the simple tagline of this company, which is great.
- 16:51SPEAKER_00: The tagline is great.
- 16:52SPEAKER_00: It turns out you go in, the customers just cut his head off.
- 16:55SPEAKER_00: They wanted to know the deep ways that's integrated with 28 leaders,
- 16:58SPEAKER_00: how the workflows work,
- 17:00SPEAKER_00: why,
- 17:00SPEAKER_00: and importantly for sales today,
- 17:02SPEAKER_00: why you would win when they have 10 competitors.
- 17:04SPEAKER_00: You cannot walk into a meeting in this world when it is,
- 17:08SPEAKER_00: when some areas are in a downturn,
- 17:10SPEAKER_00: I don't believe we're overall in a downturn,
- 17:11SPEAKER_00: but everything's harder.
- 17:13SPEAKER_00: You can walk in there and think you're going to be a people person when whomever,
- 17:18SPEAKER_00: Duplo Cloud or Drada or JustWorks walks in there and they know the frigging market cold.
- 17:22SPEAKER_00: They know when you're weak, they know how to fix, they know how to solve your problem as a customer.
- 17:26SPEAKER_00: And Mr. Backslabbing Lunch Guy comes in and just wants to talk about, where do your kids go to school?
- 17:31SPEAKER_00: Oh, really?
- 17:32SPEAKER_00: My kids go to Nueva, which is right over there.
- 17:34SPEAKER_00: That's great.
- 17:35SPEAKER_00: Next.
- 17:36SPEAKER_00: Okay.
- 17:37SPEAKER_00: I got 99 problems to solve and us talking about sports or the Olympics or the tour
- 17:42SPEAKER_00: to Italy ain't solving one of my problems.
- 17:44SPEAKER_00: And it just does not work.
- 17:46SPEAKER_00: I see folks just get slaughtered in sales when they're not product experts from the
- 17:51SPEAKER_00: bottom to the top,
- 17:52SPEAKER_00: from the bottom to the top.
- 17:53SPEAKER_00: We are all such, we are all every year.
- 17:55SPEAKER_00: We are smarter buyers, all of us up and down the stack.
- 17:59SPEAKER_00: And you cannot go into that meeting and not know the product.
- 18:02SPEAKER_00: It is embarrassing.
- 18:04SPEAKER_00: It is embarrassing.
- 18:05SPEAKER_00: Whatever you do, you can't hire a VP of sales that is not willing.
- 18:08SPEAKER_00: And I know many will challenge me on this, sales leaders.
- 18:12SPEAKER_00: They'll think about this and then they're gonna come back to me three or four
- 18:14SPEAKER_00: months later and say,
- 18:15SPEAKER_00: you're right.
- 18:15SPEAKER_00: I wouldn't let them start until they know the product fold.
- 18:19SPEAKER_00: I wouldn't let them start.
- 18:20SPEAKER_00: Now,
- 18:21SPEAKER_00: best of all is literally give them the,
- 18:23SPEAKER_00: if you really think they're so great,
- 18:25SPEAKER_00: give them the offer,
- 18:25SPEAKER_00: agree on the comp,
- 18:26SPEAKER_00: agree on the equity and say,
- 18:28SPEAKER_00: you know what?
- 18:29SPEAKER_00: Now take a month before you even show up and go learn the pro- I don't even want you starting.
- 18:33SPEAKER_00: Go to all of our webinars, go do it, do it every UBU.
- 18:37SPEAKER_00: You show up October, a Halloween, not tomorrow, and you show up an expert, right?
- 18:43SPEAKER_00: And a related point,
- 18:44SPEAKER_00: I remember in the early days of Gusto,
- 18:45SPEAKER_00: Josh Reeves,
- 18:47SPEAKER_00: a very distinctive CEO,
- 18:48SPEAKER_00: but I remember he had this thing that at the time I thought was crazy,
- 18:51SPEAKER_00: which is when Josh would hire a new executive,
- 18:53SPEAKER_00: I think he wouldn't let him work for 60 days.
- 18:55SPEAKER_00: And I think at this time we can ask them,
- 18:57SPEAKER_00: I think we more wanted to make sure they knew the gusto culture.
- 19:00SPEAKER_00: Like you have to wear slippers in the office, not shoes.
- 19:02SPEAKER_00: And there's a certain way of doing business.
- 19:04SPEAKER_00: And maybe that was the goal,
- 19:06SPEAKER_00: but there's something to really knowing the company and the product as a leader
- 19:10SPEAKER_00: before you start.
- 19:11SPEAKER_00: And I just see train wrecks.
- 19:13SPEAKER_00: You come into a complicated space and you don't know the product.
- 19:19SPEAKER_00: One of my favorite companies I've ever invested in,
- 19:21SPEAKER_00: they just broke up with their second VP of sales after over a year.
- 19:25SPEAKER_00: And they closed their first seven figure deal the other day, seven figure deal a year.
- 19:30SPEAKER_00: The VP of sales allegedly was an expert in the industry.
- 19:34SPEAKER_00: He had worked at a competitive company before,
- 19:37SPEAKER_00: but always had a team of SEs,
- 19:38SPEAKER_00: sales engineers and solution architects with him.
- 19:41SPEAKER_00: Never learned the product in a year for this seven figure deal, they left him outside in the lobby.
- 19:46SPEAKER_00: They left him outside because the last big deal, he embarrassed them.
- 19:50SPEAKER_00: Not because he's not smart or a good person,
- 19:53SPEAKER_00: but he could not go in front of a Fortune 500 CTO and talk API and security with
- 19:59SPEAKER_00: the Fortune.
- 19:59SPEAKER_00: He embarrassed them.
- 20:00SPEAKER_00: He embarrassed the founders.
- 20:02SPEAKER_00: So for the next seven-figure deal, they left him in the lobby.
- 20:05SPEAKER_00: They flew out and they left him in the lobby.
- 20:07SPEAKER_00: And that was the right call because he never learned.
- 20:10SPEAKER_00: Maybe you can make this work with 10,000 SEs, but most of us don't have enough around.
- 20:14SPEAKER_00: So,
- 20:15SPEAKER_00: I, this is just me.
- 20:18SPEAKER_00: Maybe you could wing this pre 2020.
- 20:20SPEAKER_00: Maybe you can wing it in 2021 when people would buy anything with a pulse in some categories.
- 20:25SPEAKER_00: Okay.
- 20:25SPEAKER_00: Maybe you literally could.
- 20:26SPEAKER_00: I don't think this works today.
- 20:28SPEAKER_00: Either make sure they're a product expert before I start force them to do a demo
- 20:31SPEAKER_00: that you believe that you would hire or give them a vacation until they start,
- 20:35SPEAKER_00: but don't let them start up thinking that they will learn your product on day one.
- 20:38SPEAKER_00: We don't have that.
- 20:39SPEAKER_00: They'll close nothing.
- 20:41SPEAKER_00: Okay.
- 20:41SPEAKER_00: Related point.
- 20:43SPEAKER_00: This one seems so obvious.
- 20:46SPEAKER_00: my friends, but it's maybe the most important.
- 20:51SPEAKER_00: I know I put it on five, not one or 10, but it's probably the most important point in here.
- 20:56SPEAKER_00: Whenever a VP of sales doesn't work out with,
- 20:59SPEAKER_00: and I talked to the CEO and I talked to the founders,
- 21:01SPEAKER_00: the other four things are true.
- 21:02SPEAKER_00: Were they a product expert?
- 21:03SPEAKER_00: No.
- 21:04SPEAKER_00: Okay.
- 21:04SPEAKER_00: Did they really want to sell?
- 21:05SPEAKER_00: Nah.
- 21:06SPEAKER_00: Well, all these issues came up.
- 21:07SPEAKER_00: Were they checked out?
- 21:08SPEAKER_00: Yeah.
- 21:09SPEAKER_00: Did they bash their last?
- 21:10SPEAKER_00: Did they blame the VCs?
- 21:11SPEAKER_00: Sure.
- 21:11SPEAKER_00: Yeah.
- 21:11SPEAKER_00: All these things.
- 21:12SPEAKER_00: Then I asked them at the very end, did you 100% believe in Jason?
- 21:18SPEAKER_00: Did you know in your heart and soul that she or he would be successful?
- 21:22SPEAKER_00: And they always say, no, I never.
- 21:23SPEAKER_00: I got tired.
- 21:24SPEAKER_00: I'd been looking for six months.
- 21:26SPEAKER_00: I needed an answer.
- 21:28SPEAKER_00: Lemkin was the best one I could find.
- 21:29SPEAKER_00: And we all have to settle at some level.
- 21:32SPEAKER_00: Like Mr. Perfect, Ms.
- 21:33SPEAKER_00: Dashboards is not the right call.
- 21:35SPEAKER_00: But they never believed.
- 21:37SPEAKER_00: They never believed.
- 21:38SPEAKER_00: And the ones that fly...
- 21:40SPEAKER_00: When I hired Brendan Cassidy,
- 21:42SPEAKER_00: who we've talked about,
- 21:43SPEAKER_00: he's probably here,
- 21:45SPEAKER_00: who had been the first head of sales at LinkedIn.
- 21:47SPEAKER_00: I had a disagreement with one of my VCs who thought he wanted someone more senior or whatever.
- 21:51SPEAKER_00: This was years ago.
- 21:52SPEAKER_00: I knew a hundred fricking percent in my heart, he was the guy.
- 21:56SPEAKER_00: I knew it for a couple of reasons.
- 21:57SPEAKER_00: I knew because I'd done a reference check with him about a year prior and he gave
- 22:01SPEAKER_00: me the best insights of any sales leader I'd ever talked to just in a reference
- 22:04SPEAKER_00: check for you at recruiting.
- 22:05SPEAKER_00: I knew I wanted him, but most importantly, even if I was wrong, I knew I want him.
- 22:10SPEAKER_00: So I backed him on anything, wherever he needed help.
- 22:12SPEAKER_00: And most importantly, your job as leaders with your VPs is not to tell them what to do,
- 22:18SPEAKER_00: It's to backfill them.
- 22:19SPEAKER_00: This is where the founder mode comes in,
- 22:21SPEAKER_00: not to do their job,
- 22:22SPEAKER_00: but to back,
- 22:22SPEAKER_00: not everyone can be great at everything.
- 22:24SPEAKER_00: So you've got to backfill them.
- 22:25SPEAKER_00: If you 100% believe in them and they need you in Chicago,
- 22:29SPEAKER_00: a Groupon in the middle of the winter with a jacket on,
- 22:31SPEAKER_00: you're going to be there.
- 22:31SPEAKER_00: If you don't believe in them,
- 22:33SPEAKER_00: They're going to give up on them.
- 22:34SPEAKER_00: They're going to fail.
- 22:35SPEAKER_00: Don't hire any VP that you don't 100% believe in.
- 22:38SPEAKER_00: It doesn't mean you need to be 100% right, but you have to say in my gut, I love Jason.
- 22:43SPEAKER_00: I love Amelia.
- 22:44SPEAKER_00: I love Brendan.
- 22:44SPEAKER_00: I love Sam.
- 22:45SPEAKER_00: No matter what anyone,
- 22:46SPEAKER_00: no matter when anyone on my board or any of my,
- 22:48SPEAKER_00: even the rest of my team,
- 22:49SPEAKER_00: the best ones often your team will be split on because they may be a threat to the
- 22:52SPEAKER_00: way things are,
- 22:53SPEAKER_00: the way things are.
- 22:54SPEAKER_00: But this is the number one, I always have to do to really believe in them.
- 22:57SPEAKER_00: No, founders know we have that spider sense.
- 23:00SPEAKER_00: of even if we haven't made the hire,
- 23:02SPEAKER_00: we know who we think is that your jaw drops the best of the best and don't make the hire.
- 23:06SPEAKER_00: It's not going to work out if you don't believe.
- 23:09SPEAKER_00: Okay.
- 23:09SPEAKER_00: Point six, this seems minor, but again, this is a new one over the last couple of years.
- 23:17SPEAKER_00: This mythical full-stack salesperson.
- 23:20SPEAKER_00: Mythical full-stack.
- 23:22SPEAKER_00: We talked a lot about this with Sam Buon,
- 23:23SPEAKER_00: who was Xero of Brex in our Miami meetup earlier this year,
- 23:26SPEAKER_00: and I'm going to come back to that in a second.
- 23:29SPEAKER_00: This does exist, but it's rare, and it has to exist at birth, okay?
- 23:34SPEAKER_00: And what do I mean is,
- 23:36SPEAKER_00: Today everyone wants,
- 23:37SPEAKER_00: there's this meme,
- 23:38SPEAKER_00: there's this myth,
- 23:38SPEAKER_00: there's founder mode,
- 23:39SPEAKER_00: but there's also this full stack AE and full stack BP of sales and zero where you
- 23:43SPEAKER_00: know how to do everything.
- 23:44SPEAKER_00: You're graded out.
- 23:45SPEAKER_00: I do my own outbound.
- 23:46SPEAKER_00: I do my own qualification.
- 23:47SPEAKER_00: I do, I do my own training.
- 23:50SPEAKER_00: I do my own onboarding on my own SC.
- 23:52SPEAKER_00: I close everything.
- 23:53SPEAKER_00: I go from SDR to close to everything.
- 23:55SPEAKER_00: And I get what these walk this.
- 23:56SPEAKER_00: There's nothing more frustrating than a founder than when half your sales team just
- 24:00SPEAKER_00: waits for the inbound lead to come.
- 24:02SPEAKER_00: And that's all they do.
- 24:03SPEAKER_00: They just want the inbound lead to come in and say,
- 24:04SPEAKER_00: I want to buy today and then send them a document to e-signature.
- 24:07SPEAKER_00: That's half of sales and SaaS.
- 24:09SPEAKER_00: And I'll share data on this tomorrow.
- 24:11SPEAKER_00: I'm not making it up.
- 24:12SPEAKER_00: And it drives us nuts when we want this.
- 24:13SPEAKER_00: And we think we want this full stack person.
- 24:16SPEAKER_00: But they're really rare.
- 24:17SPEAKER_00: Folks that haven't done outbound, they can't learn on your dime.
- 24:21SPEAKER_00: Folks that haven't done partnerships,
- 24:22SPEAKER_00: channels,
- 24:22SPEAKER_00: technical buyers,
- 24:23SPEAKER_00: in-person price point,
- 24:24SPEAKER_00: the points I put at.
- 24:26SPEAKER_00: And it doesn't exist for a sales rep unless you trade them from day zero, in which case it's possible.
- 24:30SPEAKER_00: But you have to only hire folks that have been full stack,
- 24:33SPEAKER_00: that have earned their own soup,
- 24:35SPEAKER_00: that have earned their own keep.
- 24:37SPEAKER_00: Most importantly for VPs of sales, do not expect a full stack VP of sales or CRO to magically happen.
- 24:44SPEAKER_00: Ask them.
- 24:45SPEAKER_00: If outbound, here's a perfect example.
- 24:47SPEAKER_00: This is my real point.
- 24:48SPEAKER_00: And I can give you so many stories.
- 24:49SPEAKER_00: If outbound is not part of your model,
- 24:51SPEAKER_00: if it's 100% inbound,
- 24:52SPEAKER_00: then you don't need an outbound expert today.
- 24:54SPEAKER_00: Maybe you want to add it, okay?
- 24:55SPEAKER_00: If your model is like 20%, 50%, 80% outbound and you want it to go up,
- 25:00SPEAKER_00: And you love this head of sales, but they've only done inbound 0% chance of success.
- 25:06SPEAKER_00: What are they going to spend a year learning outbound?
- 25:08SPEAKER_00: They're going to go buy nooks or some other tool here and magically turn it on.
- 25:11SPEAKER_00: These are great products.
- 25:12SPEAKER_00: That alone is not enough.
- 25:13SPEAKER_00: If you've never done it before.
- 25:15SPEAKER_00: Another huge flag.
- 25:18SPEAKER_00: is direct versus indirect revenue.
- 25:20SPEAKER_00: How much revenue you get direct or versus partners.
- 25:23SPEAKER_00: I just talked with a VP of sales I've known for over a decade that flamed out at a
- 25:27SPEAKER_00: SaaS company at 40 million,
- 25:29SPEAKER_00: got fired,
- 25:29SPEAKER_00: okay,
- 25:30SPEAKER_00: at 40 million.
- 25:31SPEAKER_00: And I said, what happened to this guy?
- 25:33SPEAKER_00: It took me a year to realize half our revenue came from partners in the channel.
- 25:37SPEAKER_00: I'd never done that before, he said.
- 25:38SPEAKER_00: So not only did it take him a year to figure something out,
- 25:40SPEAKER_00: he should have figured it out the first week,
- 25:42SPEAKER_00: but he never leaned in on this indirect selling because he was only a direct
- 25:46SPEAKER_00: selling guy.
- 25:47SPEAKER_00: Okay, he didn't get, he couldn't be full stack.
- 25:49SPEAKER_00: Partnerships, channels, can they sell to a technical buyer?
- 25:52SPEAKER_00: Like we talked about where they left the VP of sales in the lobby, right?
- 25:56SPEAKER_00: Are they willing to sell in person or only on the phone?
- 25:58SPEAKER_00: This sounds, this was a big, this was still a big deal before 2020.
- 26:01SPEAKER_00: Today, it's a huge deal.
- 26:03SPEAKER_00: If you've only sold,
- 26:04SPEAKER_00: again,
- 26:05SPEAKER_00: from your ADU or from home,
- 26:06SPEAKER_00: and your motion,
- 26:07SPEAKER_00: and you sell more when you go visit customers,
- 26:10SPEAKER_00: and it's true of 96.842% of us,
- 26:13SPEAKER_00: and they're not willing to travel,
- 26:15SPEAKER_00: they're not gonna start traveling when they magically join you.
- 26:18SPEAKER_00: I interviewed almost 40 VPs of sales last year, early last year.
- 26:23SPEAKER_00: Only two were actually willing to travel.
- 26:26SPEAKER_00: You can laugh, only two out of 40.
- 26:28SPEAKER_00: My point,
- 26:28SPEAKER_00: there's a lot to read into that,
- 26:30SPEAKER_00: but my point is don't expect your VP of sales to do these things,
- 26:34SPEAKER_00: outbound,
- 26:35SPEAKER_00: partnership,
- 26:35SPEAKER_00: indirect,
- 26:36SPEAKER_00: technical selling,
- 26:36SPEAKER_00: travel,
- 26:38SPEAKER_00: that if you know you need them,
- 26:39SPEAKER_00: if they're already part of your motion,
- 26:41SPEAKER_00: ask if they've done it before,
- 26:42SPEAKER_00: just be kind.
- 26:43SPEAKER_00: How much outbound have you done?
- 26:44SPEAKER_00: How much partnership sales have you done?
- 26:45SPEAKER_00: How much channel sales have you done?
- 26:47SPEAKER_00: How much traveling did you do at your last job?
- 26:49SPEAKER_00: Do you mind?
- 26:50SPEAKER_00: Oh, I love it.
- 26:50SPEAKER_00: Like I can't stand being at home.
- 26:52SPEAKER_00: My husband drives me nuts.
- 26:53SPEAKER_00: Great.
- 26:54SPEAKER_00: Okay.
- 26:54SPEAKER_00: But you got to ask this.
- 26:55SPEAKER_00: Don't just smite.
- 26:56SPEAKER_00: The meta point is don't assume they will do all of it.
- 26:59SPEAKER_00: Most VPs of sales zeros either won't have it or don't want to.
- 27:05SPEAKER_00: Okay.
- 27:05SPEAKER_00: The next couple ones, and then we can take questions with our remaining time.
- 27:09SPEAKER_00: This one's an oldie.
- 27:11SPEAKER_00: This one hasn't changed.
- 27:13SPEAKER_00: Some of this stuff is, I think, new vibes since 2020, especially since 2023.
- 27:17SPEAKER_00: This one slide, I think I wrote in 2012, 2013, 2014, 2024, 2025.
- 27:19SPEAKER_00: But man, this is brutal, my friends.
- 27:20SPEAKER_00: This is brutal.
- 27:29SPEAKER_00: A mishire in a VP of sales sets you back a year.
- 27:33SPEAKER_00: The only thing that's changed in my learning as we started it is it's your fault, not theirs.
- 27:38SPEAKER_00: It is your fault if you make a mishire.
- 27:40SPEAKER_00: You did not do enough diligence.
- 27:41SPEAKER_00: You did not spend enough time in person.
- 27:43SPEAKER_00: You did it over Zoom.
- 27:44SPEAKER_00: You did not understand that actually they've never done channel sales.
- 27:47SPEAKER_00: They've actually never done outbound.
- 27:49SPEAKER_00: You did not understand that they are not
- 27:51SPEAKER_00: They've never sold to a technical buyer before.
- 27:53SPEAKER_00: They've never sold in your industry before.
- 27:55SPEAKER_00: You skip too many steps.
- 27:56SPEAKER_00: It's your fault, but it will set you back a year.
- 27:59SPEAKER_00: Why?
- 28:00SPEAKER_00: A couple of things.
- 28:02SPEAKER_00: The first one is when you make a true miss hire sales always goes down.
- 28:05SPEAKER_00: It happened to me.
- 28:06SPEAKER_00: It happened to half the people here this week or more.
- 28:09SPEAKER_00: You go in in the product led stage.
- 28:11SPEAKER_00: You're not a great seller.
- 28:12SPEAKER_00: You're not a perfect closer.
- 28:13SPEAKER_00: The product cold, the customers love you.
- 28:15SPEAKER_00: And then you disappear from sales and you bring in someone that doesn't know your product.
- 28:18SPEAKER_00: What do you think happens?
- 28:20SPEAKER_00: Sales goes down, those deals don't close.
- 28:22SPEAKER_00: Even worse, she brings in or he brings in two reps that don't know the product either.
- 28:26SPEAKER_00: Now you've got three new sellers on your team that don't know the product or the industry,
- 28:30SPEAKER_00: throwing them at deals where if just you and Linda did it together,
- 28:33SPEAKER_00: they all would have closed.
- 28:34SPEAKER_00: They all would have closed.
- 28:36SPEAKER_00: So it gets worse and then they hire three and then they hire 10 and all your money's gone.
- 28:42SPEAKER_00: Okay.
- 28:43SPEAKER_00: And then what,
- 28:43SPEAKER_00: after a month and then Saster says only give them 30 days,
- 28:47SPEAKER_00: but no one believes it,
- 28:48SPEAKER_00: even though I wrote that post and you give them 60 days and 90 days.
- 28:51SPEAKER_00: And then you're in, if you have any investors, they say Jim's a nice guy.
- 28:55SPEAKER_00: He's pretty good.
- 28:56SPEAKER_00: They're bored.
- 28:57SPEAKER_00: Who's talked to him twice.
- 28:58SPEAKER_00: Give Jim another quarter.
- 29:00SPEAKER_00: So now you're six months in seven months in,
- 29:02SPEAKER_00: and then you go to let Jim go a month,
- 29:03SPEAKER_00: seven,
- 29:04SPEAKER_00: and he changes your mind.
- 29:05SPEAKER_00: Cause he's a good sales guy and it's nine months and he's hired 10 people.
- 29:09SPEAKER_00: And then you finally move on from Jim and it, and you start your search for six months.
- 29:12SPEAKER_00: You've lost a year and millions of dollars.
- 29:15SPEAKER_00: This avoidable story is again and again.
- 29:18SPEAKER_00: So look,
- 29:20SPEAKER_00: there are certain miss hires or,
- 29:22SPEAKER_00: or mistakes you're going to make that are very,
- 29:24SPEAKER_00: there's the old saying push down or do the mistakes that are reversible,
- 29:27SPEAKER_00: slow down the big ones that are irreversible.
- 29:29SPEAKER_00: This one's in the middle.
- 29:31SPEAKER_00: It's not irreversible, but boy, it's damaging.
- 29:34SPEAKER_00: So when you're tired,
- 29:35SPEAKER_00: when you've been looking for six months,
- 29:37SPEAKER_00: when you've honestly interviewed 30,
- 29:39SPEAKER_00: you're not pretending you've interviewed 30 candidates like we do,
- 29:42SPEAKER_00: but you've really interviewed 30 and you meet with Jason and you're not 100% all in,
- 29:47SPEAKER_00: just realize,
- 29:50SPEAKER_00: Push on and find someone you love in life, in hiring, as a co-founder.
- 29:55SPEAKER_00: Find the one you love because you're going to lose a year when you settle.
- 29:57SPEAKER_00: It's not worth it.
- 29:59SPEAKER_00: You think settling is good.
- 30:00SPEAKER_00: You think, look, I know I'm tired.
- 30:03SPEAKER_00: I know Jason's not the greatest VP of sales, but at least I'll have somebody
- 30:07SPEAKER_00: There is a little bit of rarefied air between very good and great.
- 30:10SPEAKER_00: Don't get me wrong.
- 30:11SPEAKER_00: That's taking risk.
- 30:12SPEAKER_00: But when you settle, sales will go down.
- 30:14SPEAKER_00: All the money will be gone and they'll hire 10 terrible reps.
- 30:16SPEAKER_00: It's not worth it to buy yourself two weeks of mental relief of having made the hire.
- 30:21SPEAKER_00: It's not worth it.
- 30:22SPEAKER_00: You'll lose a year.
- 30:24SPEAKER_00: Okay.
- 30:25SPEAKER_00: And these ones are updated versions of older points, but I got to tie it all together.
- 30:28SPEAKER_00: So we've all done it.
- 30:31SPEAKER_00: This mistake we actually,
- 30:32SPEAKER_00: we used to make in the early days of SaaS for all time because we didn't have all
- 30:35SPEAKER_00: the veterans.
- 30:36SPEAKER_00: We didn't have all the folks that had come out of Mongo and Salesforce.
- 30:39SPEAKER_00: And actually we had folks from Salesforce who started SaaS, but there wasn't enough others.
- 30:43SPEAKER_00: Now, again, there's a hundred public SaaS companies to recruit from.
- 30:46SPEAKER_00: So in the old days, we would hire folks that were too junior to do the role.
- 30:50SPEAKER_00: Now we're hiring hundreds of folks that are broke and burnt.
- 30:53SPEAKER_00: but certainly have the title on their LinkedIn.
- 30:55SPEAKER_00: But still, what are you going to do?
- 30:57SPEAKER_00: So you can't hire the SVP from Salesforce or Mongo or Trulio that doesn't want to sell anymore.
- 31:02SPEAKER_00: You can't make that hire.
- 31:04SPEAKER_00: So you can go for that perfect Goldilocks person that has everything at the right
- 31:08SPEAKER_00: moment in time and the right hour in their career.
- 31:10SPEAKER_00: And yeah,
- 31:11SPEAKER_00: they have an offer from OpenAI and Cohere and Glean and Notion,
- 31:14SPEAKER_00: but they still want to join your startup they've never heard of.
- 31:17SPEAKER_00: Of course they do.
- 31:18SPEAKER_00: Of course they do, because you're such a great founder.
- 31:21SPEAKER_00: But so that Goldilocks person probably doesn't exist.
- 31:24SPEAKER_00: So when you decided the SUV from Datadog is wrong, they got fired because he never left the ADU.
- 31:29SPEAKER_00: And you decided Mr. Goldilocks doesn't exist.
- 31:31SPEAKER_00: And you realize you got to hire a stretch.
- 31:33SPEAKER_00: You got to hire a kid.
- 31:34SPEAKER_00: Now, this kid may be 60 or maybe 26.
- 31:36SPEAKER_00: I don't know.
- 31:38SPEAKER_00: But what I mean is you got to hire someone on their journey with energy that's
- 31:40SPEAKER_00: going on the way up because this is their shot to be your head of sales.
- 31:43SPEAKER_00: Of course you do.
- 31:44SPEAKER_00: Of course you need a stretch hire.
- 31:46SPEAKER_00: But there's just one thing you have to do when you're stretch hire.
- 31:48SPEAKER_00: They're not going to have the full package.
- 31:50SPEAKER_00: They may not have worked at the right place.
- 31:52SPEAKER_00: They probably even got fired once if they're a pyrodramatic and passionate.
- 31:55SPEAKER_00: It's okay.
- 31:56SPEAKER_00: Getting fired from every job in sales is probably bad.
- 31:58SPEAKER_00: Getting fired just once, a good sign, just once.
- 32:01SPEAKER_00: But you cannot, the whole point, going back to the first point of
- 32:06SPEAKER_00: why you can't stay in founder-led.
- 32:08SPEAKER_00: At the end of the day,
- 32:09SPEAKER_00: if you can actually sell and you can learn the product,
- 32:11SPEAKER_00: you can get on the run,
- 32:11SPEAKER_00: you can talk to customers,
- 32:12SPEAKER_00: you can do the sales process yourself as a VP of sales,
- 32:15SPEAKER_00: not skip it because you want to be a manager,
- 32:16SPEAKER_00: but do it yourself.
- 32:18SPEAKER_00: Then it all becomes about human capital.
- 32:20SPEAKER_00: I've got to grow the sales team from two to four to eight to 16,
- 32:22SPEAKER_00: 32,
- 32:22SPEAKER_00: 64,
- 32:22SPEAKER_00: 128,
- 32:24SPEAKER_00: because our revenue is doubling each year.
- 32:26SPEAKER_00: Whenever it's growing, you have to roughly grow headcount with your revenue and sales.
- 32:31SPEAKER_00: You can't avoid it.
- 32:32SPEAKER_00: 500K quota, 800K, 400K, it doesn't matter.
- 32:34SPEAKER_00: You can't increase it to 4 million.
- 32:36SPEAKER_00: It don't work that way.
- 32:37SPEAKER_00: So if your yielded quotas for an 80 is 500,000 and you want to add 5 million to bookings,
- 32:43SPEAKER_00: you need 10 scaled reps.
- 32:44SPEAKER_00: And if you want to add 50 million, you need 100.
- 32:46SPEAKER_00: You can't get around the math.
- 32:47SPEAKER_00: So at the end of the day,
- 32:50SPEAKER_00: if they know the product and they can sell,
- 32:51SPEAKER_00: the most important thing is recruiting.
- 32:53SPEAKER_00: VPs of sales are the best recruiters on your management team because they're constantly recruiting.
- 32:58SPEAKER_00: So make sure, even in a stretch candidate,
- 33:01SPEAKER_00: that they have hired two to three salespeople that hit quota before.
- 33:06SPEAKER_00: Not 20, not 200, but it's not enough if they inherited a team.
- 33:10SPEAKER_00: It's not enough if they were on a sales team.
- 33:12SPEAKER_00: It's not enough if they were an SDR that got promoted to manager but never hired
- 33:16SPEAKER_00: any of the SDRs that reported to her.
- 33:18SPEAKER_00: They have to have hired two people and made them successful.
- 33:21SPEAKER_00: If they can figure out how the hell to find two people in this crazy world
- 33:26SPEAKER_00: where everyone really wants to work 10 hours a week from home.
- 33:28SPEAKER_00: If they can find two people that can get quoted,
- 33:30SPEAKER_00: they can eventually find 200 for you,
- 33:31SPEAKER_00: because it's hard to find two.
- 33:33SPEAKER_00: So ask them who the two are nicely, and then say, hey, can I go talk with Pooey and Robbie?
- 33:39SPEAKER_00: Just ask.
- 33:40SPEAKER_00: And if they're any good, they'll connect you
- 33:43SPEAKER_00: on the meeting and you call them up and just ask the question, how was it working?
- 33:47SPEAKER_00: How was it working with Brendan?
- 33:48SPEAKER_00: What was it like?
- 33:49SPEAKER_00: How did he find you?
- 33:50SPEAKER_00: Oh, he hunted me down, right?
- 33:52SPEAKER_00: He hunted me down at this event.
- 33:53SPEAKER_00: Here are those great thing.
- 33:54SPEAKER_00: He lured me out of this company and I closed 600 K with him the next, in the next 12 months.
- 33:59SPEAKER_00: Great story.
- 34:00SPEAKER_00: How'd you do it with Robbie?
- 34:01SPEAKER_00: Here are those stories.
- 34:03SPEAKER_00: No one does this anymore.
- 34:05SPEAKER_00: You don't want to do this because you want to believe that LinkedIn is going to
- 34:08SPEAKER_00: work out because you're tired.
- 34:09SPEAKER_00: You don't want to do this because you're worried what you're going to hear.
- 34:12SPEAKER_00: You're worried that they'd never really hired two reps before,
- 34:15SPEAKER_00: that they don't actually know how to recruit.
- 34:17SPEAKER_00: Because the folks that don't, you know what they do?
- 34:19SPEAKER_00: They show up.
- 34:20SPEAKER_00: First, they work on their process slides for a couple of weeks.
- 34:24SPEAKER_00: Then they tell you they're going to spool up a few recruiters they worked with
- 34:27SPEAKER_00: before that they never really worked with before.
- 34:30SPEAKER_00: And so three,
- 34:30SPEAKER_00: four months later,
- 34:31SPEAKER_00: they've hired two bottom of the barrel reps from some recruiter they don't know.
- 34:36SPEAKER_00: Great.
- 34:36SPEAKER_00: That gets you nowhere.
- 34:39SPEAKER_00: I've said it before, but it's worth saying again.
- 34:41SPEAKER_00: Any great sales leader always has a couple folks ready to go with her the next day.
- 34:45SPEAKER_00: And I know you gotta be careful with this word this day, but it's true, this word.
- 34:48SPEAKER_00: They groom them.
- 34:49SPEAKER_00: They groom them.
- 34:50SPEAKER_00: The best sales leaders are meeting with tons of folks up and down from SDR to AE to senior.
- 34:56SPEAKER_00: And they're asking, I wanna work with them.
- 34:59SPEAKER_00: I wanna work with them again.
- 35:00SPEAKER_00: Or they're meeting with VPs of sales that leave a hot startup.
- 35:03SPEAKER_00: Who is the best person on your team?
- 35:04SPEAKER_00: Linda, Amelia, and Stacey.
- 35:06SPEAKER_00: And they go meet with them.
- 35:07SPEAKER_00: Because it's half the job at scale.
- 35:09SPEAKER_00: Half the job is recruiting.
- 35:10SPEAKER_00: So if they can't bring two good people with them, they'll never do it.
- 35:14SPEAKER_00: And just go talk to them.
- 35:17SPEAKER_00: I ask so many CEOs this question.
- 35:20SPEAKER_00: Okay, you hired Jim.
- 35:22SPEAKER_00: Does he have any to bring with him?
- 35:23SPEAKER_00: Yeah, Jim's got a couple of great folks to bring with him.
- 35:25SPEAKER_00: Did you talk to them?
- 35:26SPEAKER_00: No.
- 35:27SPEAKER_00: 80% chance those folks aren't coming with Jim or they don't exist or...
- 35:32SPEAKER_00: They were somebody worked with, it's not true.
- 35:34SPEAKER_00: You gotta talk to the two.
- 35:35SPEAKER_00: If they can hire two great folks, they can hire 200.
- 35:38SPEAKER_00: Think about it, it's true.
- 35:40SPEAKER_00: Okay, an ultimate point.
- 35:42SPEAKER_00: I'm forgetting what the ultimate point is, but this one's so important.
- 35:46SPEAKER_00: This one is so important.
- 35:47SPEAKER_00: If you guys have investors, they're, listen, they're right on many things.
- 35:53SPEAKER_00: They're almost always wrong on a VP of sales.
- 35:57SPEAKER_00: I can't tell you how many boards I've been on,
- 35:58SPEAKER_00: how many startups I've been on where every single VC is wrong.
- 36:02SPEAKER_00: They're all wrong.
- 36:03SPEAKER_00: All of them.
- 36:04SPEAKER_00: They're all wrong.
- 36:05SPEAKER_00: They all love the handsome six foot four paratrooper that talks the talk in a deep
- 36:10SPEAKER_00: voice and looks good in a button down.
- 36:12SPEAKER_00: They love them.
- 36:14SPEAKER_00: And he talks quota attainment and quota metrics and funnel management and
- 36:20SPEAKER_00: And he talks the talk, and he's got a, I don't know what a baritone is, but he talks all the great.
- 36:25SPEAKER_00: I had 111.6%, and I was at 11 president circles.
- 36:29SPEAKER_00: I was at the, and I love them.
- 36:30SPEAKER_00: And I was at, I knew Reed back when at LinkedIn, and I knew whoever.
- 36:34SPEAKER_00: I knew them all.
- 36:35SPEAKER_00: I knew Tiago at TalkDesk, and I knew them all.
- 36:37SPEAKER_00: Then your board falls in love with the name dropper, paratrooper.
- 36:40SPEAKER_00: They love them.
- 36:41SPEAKER_00: They don't know.
- 36:41SPEAKER_00: They don't know.
- 36:44SPEAKER_00: And why?
- 36:44SPEAKER_00: One, most of VCs have never done sales.
- 36:47SPEAKER_00: They've never done it and they don't know.
- 36:48SPEAKER_00: So they give you terrible advice.
- 36:50SPEAKER_00: The subtler one is,
- 36:53SPEAKER_00: There's more and more VCs that were CEOs and were founders back in the day, and those are great.
- 36:57SPEAKER_00: All things being equal, pick one of them.
- 37:00SPEAKER_00: Not that big a deal,
- 37:01SPEAKER_00: we could talk about it,
- 37:02SPEAKER_00: but it's nice to have a VC who was a founder,
- 37:04SPEAKER_00: a successful founder.
- 37:06SPEAKER_00: There's a lot of reasons that's comforting.
- 37:08SPEAKER_00: There's only so many slices of your cap table you can give up.
- 37:11SPEAKER_00: It's nice to have a successful CEO.
- 37:12SPEAKER_00: The problem is the company they founded 12 years ago with a million dollar ACV in a
- 37:16SPEAKER_00: different industry is not yours.
- 37:18SPEAKER_00: It's not the same product as selling to restaurants at 2K a year.
- 37:23SPEAKER_00: It's not the same.
- 37:24SPEAKER_00: And just because they know sales doesn't mean they know your sales.
- 37:26SPEAKER_00: So they give you bad advice too.
- 37:28SPEAKER_00: They're mapping it.
- 37:29SPEAKER_00: That's so common.
- 37:30SPEAKER_00: So again, just listen to your VC's investors.
- 37:34SPEAKER_00: And it's not that they won't have a few good, but I just think 87.2% of the time,
- 37:40SPEAKER_00: They just give you the wrong advice for VPSO zero.
- 37:43SPEAKER_00: So be nice, nod your head, say thank you.
- 37:46SPEAKER_00: But if your gut is, if your gut isn't a hundred percent, don't make the hire.
- 37:49SPEAKER_00: And again, if your gut is a hundred percent, they tell you it's the wrong hire.
- 37:52SPEAKER_00: Tell them, thank you.
- 37:54SPEAKER_00: I'd still make the hire.
- 37:55SPEAKER_00: Okay.
- 37:56SPEAKER_00: Last one.
- 37:58SPEAKER_00: And then with whatever time we have left, I think we have time.
- 38:00SPEAKER_00: I'll take any questions you guys want.
- 38:04SPEAKER_00: This is new.
- 38:06SPEAKER_00: It's old.
- 38:07SPEAKER_00: This is old.
- 38:08SPEAKER_00: but it's new because in that earlier slide,
- 38:11SPEAKER_00: I talked to so many founders have given up and gone back to founder led sales.
- 38:15SPEAKER_00: They've given up.
- 38:16SPEAKER_00: They've given up.
- 38:17SPEAKER_00: It's not just, they made one bad VP of sales hire.
- 38:19SPEAKER_00: They made two and they're burned and they're tired and they lost,
- 38:22SPEAKER_00: they burned half the money and they lost a year and they did it twice.
- 38:26SPEAKER_00: And they realized, shoot, I'll just do the million dollar deal myself.
- 38:29SPEAKER_00: I'll just go up to the customer and close it myself.
- 38:31SPEAKER_00: I've been doing this for five years.
- 38:32SPEAKER_00: I'm tired of it.
- 38:35SPEAKER_00: Was just emailing with the CEO I invested in this morning.
- 38:39SPEAKER_00: got the company to 20 million, 2015, 2020.
- 38:44SPEAKER_00: So from 2015 to 2020, he got it to 20 million, and then he went to 20 million, and then 20 million.
- 38:51SPEAKER_00: Went through three,
- 38:53SPEAKER_00: then went to founder,
- 38:53SPEAKER_00: and finally found his guy,
- 38:56SPEAKER_00: got back to 40% growth,
- 38:57SPEAKER_00: not 100%,
- 38:57SPEAKER_00: but back to 40% growth,
- 38:59SPEAKER_00: and sold his company for 300 million.
- 39:00SPEAKER_00: He was that third VP of sales.
- 39:03SPEAKER_00: Gave up for a couple of years.
- 39:04SPEAKER_00: Gave up.
- 39:04SPEAKER_00: Went into founder-led sales at 20 million in the desert.
- 39:08SPEAKER_00: Did it all himself.
- 39:09SPEAKER_00: But there was churn and there were industry issues.
- 39:11SPEAKER_00: So for every new customer he brought in, he lost one.
- 39:13SPEAKER_00: And he was bailing out the boat, but he didn't have the help.
- 39:15SPEAKER_00: And he couldn't... Those two bad VPs of sales and the terrible COO, he couldn't get over it.
- 39:21SPEAKER_00: And then he finally found the one he loved.
- 39:24SPEAKER_00: And going from zero to 40% and having a company that had no value to 300 million, pretty big change.
- 39:31SPEAKER_00: So...
- 39:33SPEAKER_00: My point is she is out there.
- 39:37SPEAKER_00: She is out there.
- 39:38SPEAKER_00: There are, even in today's world, there are ambitious folks, sales,
- 39:42SPEAKER_00: Doesn't breed ambition the way it did before March 2020, but it still breeds ambition.
- 39:46SPEAKER_00: It's competitive.
- 39:47SPEAKER_00: The best folks want in sales, want their shot.
- 39:51SPEAKER_00: They want their chance.
- 39:52SPEAKER_00: They want the chance.
- 39:53SPEAKER_00: They want the bar.
- 39:54SPEAKER_00: They want the big equity.
- 39:55SPEAKER_00: They want the chance to put that VP of sales on their resume.
- 39:58SPEAKER_00: They want their shots, time in the sun, especially if they worked under a great one.
- 40:02SPEAKER_00: What you'll find is the really charismatic, successful VPs of sales
- 40:07SPEAKER_00: Like on my own team,
- 40:08SPEAKER_00: Sam Blahn,
- 40:08SPEAKER_00: Brendan Cassidy,
- 40:09SPEAKER_00: why are those folks the heads of revenue at Rippling and Brex and so many other companies?
- 40:13SPEAKER_00: They're all our team and so many leaders.
- 40:16SPEAKER_00: Gong, why did our team?
- 40:18SPEAKER_00: Yeah, they were great.
- 40:19SPEAKER_00: They were very good, but they also were breeded to want to be Brendan or Sam.
- 40:23SPEAKER_00: They wanted it and they went out and they've become the CROs at 10 iconic leaders
- 40:27SPEAKER_00: from Rippling to Gong to Brex and others.
- 40:30SPEAKER_00: They wanted it.
- 40:31SPEAKER_00: So these ambitious folks are out there
- 40:34SPEAKER_00: Even if, and give them their shot, keep interviewing a hundred and
- 40:40SPEAKER_00: If you don't think there's a great VP of sales out there, it's because you've never worked with one.
- 40:46SPEAKER_00: This is maybe the last point I'll make and take a break.
- 40:48SPEAKER_00: This was an old,
- 40:49SPEAKER_00: maybe one of the best blog posts I ever read in my entire life was years ago,
- 40:54SPEAKER_00: a guy named Joe Kraus,
- 40:55SPEAKER_00: who you won't know,
- 40:56SPEAKER_00: but he founded Excite,
- 40:57SPEAKER_00: which was an early Google competitor that got bought for billions.
- 41:00SPEAKER_00: And then he founded an early collaboration company bought by Google.
- 41:04SPEAKER_00: And one of the first things he wrote when he was at Google is,
- 41:07SPEAKER_00: If you don't think you need a great general counsel, it's because you've never worked with one.
- 41:11SPEAKER_00: You think legal is stupid.
- 41:12SPEAKER_00: You don't see the point.
- 41:12SPEAKER_00: It's wasting your time.
- 41:14SPEAKER_00: But when you've worked with a great,
- 41:15SPEAKER_00: when you're growing and you have a million contracts and risks and you've worked
- 41:17SPEAKER_00: with a great lawyer,
- 41:18SPEAKER_00: you're like,
- 41:19SPEAKER_00: Jesus,
- 41:19SPEAKER_00: that's great.
- 41:21SPEAKER_00: Turns out, I've rewritten this for us.
- 41:23SPEAKER_00: It's true of everything.
- 41:25SPEAKER_00: So many great CTOs today think they don't need a VP of engineering.
- 41:28SPEAKER_00: I'm tired.
- 41:28SPEAKER_00: I don't want, I don't want someone that just does process and wears a blazer.
- 41:32SPEAKER_00: You don't need that.
- 41:33SPEAKER_00: But if you've worked with someone that is amazing,
- 41:35SPEAKER_00: you will never go back when you've worked with a great VP of engineering,
- 41:38SPEAKER_00: you will never go back.
- 41:39SPEAKER_00: So many folks today are like, oh, I'll be the VP of product forever.
- 41:42SPEAKER_00: I don't need someone that like is working on a pixel in Gmail.
- 41:47SPEAKER_00: Understood.
- 41:49SPEAKER_00: Have you ever worked with a great VP of product that could walk into an enterprise
- 41:52SPEAKER_00: customer and make that workflow work and close that six-figure deal with you?
- 41:56SPEAKER_00: Once you have, you've worked with an amazing one.
- 41:57SPEAKER_00: Have you worked with a VP of product that went out and in his first two weeks met
- 42:00SPEAKER_00: with 50 customers and came back with 10 insights you didn't know about your customers?
- 42:05SPEAKER_00: You probably have and I have.
- 42:06SPEAKER_00: Then you'll want that VP of product.
- 42:08SPEAKER_00: Same with marketing and it is true with VP of sales.
- 42:10SPEAKER_00: If you are burnt,
- 42:12SPEAKER_00: if you made two mishires and you're a little bit broken like Andy in that story,
- 42:15SPEAKER_00: like many of us are,
- 42:16SPEAKER_00: And you don't want to, you don't want to get off the floor and you want to stay in founder mode.
- 42:19SPEAKER_00: Trust me, there are the ambitions out there.
- 42:21SPEAKER_00: Go find them.
- 42:22SPEAKER_00: You will find them.
- 42:23SPEAKER_00: There are the ambitious.
- 42:24SPEAKER_00: Your product.
- 42:25SPEAKER_00: Yeah.
- 42:26SPEAKER_00: Okay.
- 42:26SPEAKER_00: Maybe you do some weird regulatory thing for wastewater management,
- 42:31SPEAKER_00: or maybe you do some weird,
- 42:33SPEAKER_00: really weird part of,
- 42:34SPEAKER_00: of defense security or really weird part of the tech stack that people aren't interested.
- 42:38SPEAKER_00: Maybe you're doing advanced Fortran integrations and you think you can't find anybody to do this.
- 42:42SPEAKER_00: You will find somebody.
- 42:43SPEAKER_00: You will find somebody if you're tenacious that loves it.
- 42:46SPEAKER_00: Your product is, you're not that special.
- 42:48SPEAKER_00: Your product isn't that special.
- 42:49SPEAKER_00: Your moment, the way you're bringing these elements together, very few things in software are new.
- 42:53SPEAKER_00: You will find your person, keep hunting.
- 42:55SPEAKER_00: So those are my 10.
- 42:56SPEAKER_00: Thank you.
- 42:57SPEAKER_00: Appreciate it.