Every argument clarity score on this site is built from rows on this page. Each
question and answer was assessed with names hidden, the host's own answers included, on
four things from 1 to 5:
directness (does it answer the question asked), coherence (do the ideas follow),
precision (concrete details and clear references), compression (says a lot per word). The weighted
mix (30/30/25/15) is the exchange score. A person's published score averages their exchange
scores on raw tape only, at least 8 of them, shrunk toward the cohort mean.
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Answered produced feed
D 5 · C 5 · P 4 · Cm 4 4.60
Q So this is a big question. Should founders do the first million dollars of sales themselves or should the founder? Yeah.
A 1000% founders need to do the first part of sales. Um, I don't know if it needs to be a number, like a million, like it depends on sort of what the, you know, they need to do it so they can understand the motion at the, at the early stage, right? It's the pre series a or series a level. So founders absolutely have to do it. What founders also have to do is they got to realize that their reps are never going to be able to close at their ratio in most cases, because they're the founder. They walk into the room and Nathan's like, this is the founder. I've got rapport with Nick. If something breaks, I'm calling Nick.
AI assessment note: “1000% founders need to do the first part of sales.”
Answered produced feed
D 5 · C 5 · P 4 · Cm 4 4.60
Q Yeah. Okay. That makes good sense. Now, when, um, Does that first sales hire always get promoted to essentially the head of sales, the VP of sales?
A No, I don't think you should. Um, let me rephrase that. I don't think that's what you're looking for. You're looking for the first sales person who wants to come in. You need to give them good equity, not, you know, bogus, you know, here's a thousand shares or 10,000 shares. You need to give that, that first rep equity. And you do need to have the conversation with them about, Do you want to be in leadership? Do you want to be in management? But it's certainly never a promise, right? What I do tell people to do is hire, um, the aspirational rep, hire the, you know, the director of sales who doesn't mind going down and building, right? Taking a step back and being a rep, but also has a chip on their shoulder to get promoted, to go and hire the VP of sales. And I see this all the time. If I go see people hire VPs of sales from places like Oracle, Or some other big company as their first rep, the biggest challenge, the biggest reason they don't work out is because they haven't actually built something from the bottom up. They haven't built the process from the bottom up. They've never built a sales playbook and a sales script. Like it's been so long since they've been in the trenches that that's what, that's often what I see happen. So I want you to go find the person and give them the shot they deserve because their current company has bought into some, you know, I don't know if …
AI assessment note: “No, I don't think you should... But it's certainly never a promise”
Answered produced feed
D 4 · C 4 · P 4 · Cm 3 3.85
Q So when do you usually get involved with SaaS companies? I mean, can you talk maybe about Gainsight? Like how early do you get involved typically?
A Gainsight is a really fun story. I'll give you the short version. I had one client in Austin. That was my first client. I was using a Yahoo email address. I'm flying back from Austin my first week. I sit down on the plane next to this guy, literally in suede shoes and jeans and a blazer. And it's Nick Maida from Gainsight. This is 11 years ago, 12 years, eight years ago, nine years ago. And they had 15 employees, right? He and I had this amazing conversation. We got shushed by the flight attendant twice. Um, and we were sober. We weren't drinking at all. We were just having a good time. And you know, You know, the biggest mistake I made in that deal is I, I should have taken options, but, uh, that's, so that is an instance where I got in really early to build. Right.
AI assessment note: “they had 15 employees... that is an instance where I got in really early”
Answered produced feed
D 3 · C 4 · P 3 · Cm 3 3.30
Q past reps were on LinkedIn. In other words, ones that were at Gainsight now are not at Gainsight anymore. There were 36. So there's a lot of sort of churn in the sales team. The annual quota target he told me was 800,000 dollars for those quota carrying reps. Write down this system for me. Where do you think it scales? Where does it break? Should other people copy this?
A Yeah. So I think that the answer to that is everything's an experiment the first two years in sales, right? There is no, here's the playbook for everybody. Right. Because you have to figure out what product market fit. You don't have product market fit or 10 or 20 customers. I just learned this yesterday from a, from a VC in Austin. Um, and, and I really thought it was interesting is that at 20 customers, you got a baseline. You got to get to 50 to really decide if you've got the right market fit. And he was talking in a very specific niche so that, you know, obviously there's a little bit of difference there. So what I think the key piece is bringing on that closer first. You need to bring in the closer who knows how to do it without the process being built. That's the question you're asking me. And yeah, you do want a sales process, but not super early on, not with your first, second, or third rep. Maybe by the time you get to your second or third, you start to figure out what your first process is. And even then I call it a process hypothesis because it's going to change. I can assure you that what Nick put together Uh, way back when, when I was there and we talked about creating the stages is probably very different than what it is now. And as an early stage founder and even a mid stage or even Nick, you should be looking to break it. What did we, what did, what do we need …
AI assessment note: “everything's an experiment the first two years in sales, right? There is no, here's the playbook”
