Jul 27, 2022 · 32m · 20vc
20VC: The Memo: What is a Sales Playbook? Does the Founder Need to Create It? Should the First Sales Hire Be a Leader or a Rep?
compilation · excluded from per-person scoring
Harry Stebbings · 10m spoken Sam Taylor · 4m spoken Oliver Jay · 3m spoken Zhenya Loginov · 2m spoken Carl Parrish · 2m spoken Jordan Van Horn · 2m spoken Jeanne DeWitt Grosser · 1m spoken Mitch Tarica · 1m spoken Dannie Herzberg · 1m spoken
0:00 / 0:00
gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
This episode of 20VC featuring top revenue leaders explores whether early-stage founders should personally build their startup's initial sales playbook and whether their first sales hire should be an executive leader or frontline account executives. The experts present contrasting go-to-market strategies based on product complexity, market category dynamics, and founder bandwidth.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 33.4% of the talking time here. How this is scored →
Harry as informed peer 3.0 Guest teaching 3.8 Guest disagreement 2.0 Harry pushing back 2.5
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 22:23 Sam Taylor calls bullshit on non-founder playbook creation
Sam Taylor forcefully rejects Zhenya Logvinov's premise that founders shouldn't create sales frameworks, calling bullshit and arguing that fundraising itself proves founder sales ability.
Hardest push from Harry ▶ 15:20 Harry Stebbings openly disagrees on founder sales playbook creationHarry directly pushes back against Zhenya Logvinov's position, stating bluntly that he disagrees and arguing that founders must build the initial sales playbook.
Biggest teaching moment ▶ 6:18 Oliver Jay reframes playbook definitionsOliver Jay corrects Harry's definition of a sales playbook as merely a repeatable process, categorizing that as a secondary step and educating him on the primary persona discovery playbook.
Harry holds his own ▶ 9:28 Harry Stebbings cites Zoom CRO Mitch Tarika to challenge guestHarry demonstrates deep domain knowledge across his guest network by citing contrasting views from Zoom's Mitch Tarika to challenge Oliver Jay on whether to hire reps or a head of sales first.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Jordan Van Horn on Sales Playbook Foundations | 0 | 4 | 1 | 0 | Jordan Van Horn presents a monologue laying out the 5 core functions of a sales playbook and distinguishing V0 from V20 playbooks. The host does not interact directly with the guest during this snippet, keeping host expertise and pushback at 0. | |
| Oliver Jay on Agility and Category Dynamics | 4 | 5 | 2 | 3 | Oliver Jay reframes Harry's definition of a playbook, explaining that repeatable processes are secondary to persona discovery. Harry demonstrates host expertise by referencing prior interview insights from Zoom CRO Mitch Tarika to push back on hiring order. | |
| Danny Herzberg on Founder-Led Sales and Player-Coach Hiring | 5 | 4 | 3 | 6 | Harry directly pushes back against Zhenya Logvinov's claim that founders shouldn't create playbooks, bluntly stating his disagreement. Zhenya defends his stance by emphasizing sales as a specialized discipline and arguing that early heads of sales provide leverage. | |
| Carl Parrish on Repeatable Processes and Leadership Weight | 3 | 3 | 1 | 2 | Carl Parrish explains why founder sales are not scalable and how playbook creation signals repeatability. Harry guides the conversation by framing the dilemma of hiring a sales leader versus frontline reps first. | |
| Sam Taylor on Sales Frameworks and Dual Metrics | 4 | 4 | 4 | 3 | Sam Taylor forcefully rejects Zhenya Logvinov's earlier premise by calling bullshit on the idea that founders cannot build frameworks. He also dismisses Harry's binary hiring question by offering a third path focused on dual ARR and insight metrics. | |
| Jeanne DeWitt Grosser on Sales as Skill and Hiring Timing | 2 | 3 | 1 | 1 | Jeanne DeWitt Grosser highlights sales as a technical skill comparable to coding, while Mitch Tarika outlines four pillars of sales leadership. Harry facilitates with standard follow-up questions without significant pushback. |
Statements from this episode (18)
Jordan Van Horn: Founders are 100% accountable for creating the V0 sales playbook
“I think a hundred percent, a leader of an organization, a founder is accountable for that V zero of that playbook.”
Jordan Van Horn: Founders must explicitly document who NOT to sell to
“Also, by the way, it's really important for that founder to document who you're not trying to solve the problem for, because that's going to be a direction of how you actually focus the sales team that you go and hire.”
Jordan Van Horn: Top founders own go-to-market positioning in perpetuity
“I'd argue that no matter how successful a company is, the best founders in the world are accountable to answering those three questions in perpetuity, not at just at seed stage, but at series A, series B, series C as a public company.”
Oliver Jay: Founders must drive sales until the initial playbook exists
“If that playbook hasn't been written, founder must be involved. You have to talk to the customer to hear the feedback firsthand so that you can then incorporate it into your product and eventually get the product market fit.”
Oliver Jay: Repeatable sales playbooks require at least 20 ramped AEs
“I don't think you create that playbook until you have at least 20 ramped AEs, where you have the right to say this is a playbook.”
Oliver Jay: Startups in existing categories should hire a sales leader first
“If your product and your business is going after an existing category, and you're just a much better version of it, so there's already, sometimes already budget, but certainly it's pretty clear who the buyer is and what are you solving? I would lean towards a …”
Oliver Jay: Category-creating startups should hire frontline reps before a sales leader
“On the other hand, if you're trying to actually create a new category, what you're selling is fundamentally the first piece of that kind of software solving that admit problem at a company. I think you're better off with hiring some hungry and smart customer f…”
Herzberg: Closing initial deals builds sales empathy and informs product
“And after selling the first 10, 20 customers. The founder will, number one, have a really good sense of empathy for the first official salespeople that he or she brings on, and number two, will learn that selling is one of the most important input mechanisms f…”
Herzberg: First sales hire should be a player-coach, not executive VP
“The next one could be a Player coach who can roll up his or her sleeves, do the selling while simultaneously taking the lead on hiring the next four account executives. And often we see that we look for someone who has led a team before. So they are thinking c…”
Logvinov: Founders shouldn't write initial sales playbooks for hires
“I think if the founder sort of hires salespeople who he gives the playbook to that the founder developed, it's going to be less effective and less efficient than if Founder brings in the person and lets them create something that they would feel ownership over…”
Logvinov: Hire a head of sales at $1M revenue or initial deals
“After you close to either several deals, or maybe you are up to maybe one million in revenue, it is time to hire your first head of sales.”
Logvinov: Hiring a sales leader frees bandwidth, junior reps consume it
“The junior rep will consume bandwidth from the founder, and the founder will need to spend time on those first few reps to enable them, to support them, to show them what to do. And the head of sales will instead create bandwidth that the founder can use to go…”
Parrish: Hire a head of sales when building out 3+ reps
“When you've got some conviction that, Hey, this is a motion that's going to require a sales team. I know that we've got capacity to hire at least let's call it three salespeople go and get that head of sales, go and get that frontline sales manager.”
Sam Taylor: Startup founders who raise capital have already proven sales ability
“I'd kind of call bullshit on the founder can't create it. Like, if you raised money, you started a company, and you have the capital to hire it, you're in sales. So you've already created that sales pitch.”
Sam Taylor: Early sales teams must deliver customer insights alongside ARR
“With these early hires, and I still repeat this, and my team, if they listen at some point, they're going to go, oh man, there he is saying it again, but I really view that our team is on the hook for two things, ARR and Insights. And the insights are almost a…”
Grosser: Founders wait too long to hire dedicated sales reps
“Sales is a skill, just like writing code is a skill. And so they often, I think, maybe hang on to that role as the initial salesperson, maybe a little bit too long before thinking about perhaps I want to bring in somebody who has good sales skills in this area…”
Grosser: Early startups should hire individual sellers before a Head of Sales
“I think you don't have to get your head of sales in at that moment. You know, you want to get probably a seller who's done it before, who has some amount, you know, enough experience that they can sort of be self-driven on this But I think it's hard sometimes …”
Tarika: Zoom CEO Eric Yuan Still Joins Customer Sales Meetings
“Eric has led by example. From the minute he started at Zoom up until I was on customer meetings with Eric as we closed the quarter, I've had the pleasure to work for some founders throughout most of my career. They have all been very, very involved from the on…”