May 25, 2022 · 54m · news
Oliver Jay: How To Create and Execute a World-Class Sales Playbook | 20VC #889 · 20VC with Harry Stebbings
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of 20VC, tech operating veteran Oliver Jay shares high-growth sales strategies, detailing how early-stage founders can successfully build agile sales playbooks, align hiring and onboarding with product mastery, and navigate the transition from PLG to enterprise and outbound sales.
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 18.7% of the talking time here. How this is scored →
Harry as informed peer 3.2 Guest teaching 4.8 Guest disagreement 2.3 Harry pushing back 2.8
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 14:34 Oliver rejects Jason Lemkin's hiring advice
When Harry cites Jason Lemkin's tactic of pitting two reps against each other Hunger Games style, Oliver directly rejects the framing, stating that if you rely on cohort competition you hired the wrong people.
Hardest push from Harry ▶ 9:46 Harry pushes Oliver on VC playbook adviceHarry directly challenges Oliver's dynamic playbook concept by citing VC advice and pointing out that reps churn and morale suffers when founders fail to provide a structured playbook early on.
Biggest teaching moment ▶ 7:07 Oliver redefines the 20-AE playbook thresholdOliver dismantles the standard industry usage of the word playbook, educating Harry that a repeatable sales playbook cannot be formally declared until a company has at least 20 ramped AEs.
Harry holds his own ▶ 9:46 Harry articulates rep failure modes from a VC perspectiveHarry demonstrates domain knowledge by detailing the exact mechanics of rep churn and toxic team dynamics that occur when junior hires lack a structured sales process.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Oliver Jay's Path from Finance to Scaling Sales | 2 | 3 | 1 | 2 | Harry sets up the interview asking about Oliver's career path from finance to sales at Dropbox and Asana. Oliver explains the evolution from BYOD to BYOA and product-led growth dynamics. The dynamic is polite and conversational with minimal friction. | |
| Demystifying and Structuring the Sales Playbook | 5 | 6 | 4 | 5 | Oliver immediately pushes back on the common definition of a sales playbook, reframing it around persona discovery rather than scalable processes. Harry presses back with VC perspective, asking how his usual advice to founders is wrong when lack of a playbook leads to rep churn. Oliver explains that repeatable playbooks shouldn't be locked down until a company has at least 20 ramped AEs. | |
| Deciding When and Whom to Hire First | 4 | 5 | 4 | 3 | Harry quotes Jason Lemkin's advice to hire two sales reps simultaneously and pit them against each other 'Hunger Games style.' Oliver explicitly disagrees with this premise, arguing that early stage reps need a culture of collaboration rather than manufactured internal competition. | |
| Designing the Interview Process and Compensation for Early Sales | 3 | 5 | 2 | 2 | Oliver breaks down hiring traits like reverence for product and making others better, sharing concrete interviewing techniques. He also warns against setting up traditional commission plans too early before target metrics are validated. | |
| Structuring an Effective Sales Onboarding Program | 2 | 5 | 1 | 2 | Oliver outlines a three-step onboarding framework starting with support and product exposure, followed by market knowledge, and ending with sales tactics. Harry acts as an active listener, asking tactical follow-up questions to clarify timelines and customer touchpoints. | |
| Transitioning to Outbound Sales and the CRO-CEO Partnership | 3 | 5 | 2 | 3 | Oliver warns against treating outbound cold emailing as a quick fix for plateauing PLG metrics. Harry asks how CEOs should manage CRO partnerships and handle rep excuses like bad timing using Toyota's Five Whys framework. |
Statements from this episode (14)
In tech, you either build or sell product; everything else is support
“And if you're going to operate, you either build product or you sell product. Everything else is supporting one of those two.”
Dropbox pioneered the enterprise bring-your-own-application movement
“Dropbox was the company that shattered and started the BYOA move.”
Software companies can run PLG and enterprise sales simultaneously
“When I first joined Asana, and even today, when I talk to a lot of people, I think there is this predominant view of that. You can, you have to pick one or the other. And at Asana, we pioneered and we try to do both at the same time. And I think the results we…”
Pure self-serve works in developer tools because developers avoid sales calls
“There are some categories where you can get really far with a self-serve only model. I'm thinking about Atlassian and how far they went in the sort of in that DevOps world. It makes total sense, right? No developer really wants to get on a phone or get cold ca…”
Non-developer PLG startups miss significant growth without sales teams
“Almost every other persona. Sales make sense, right? To compliment, not to say that you have to lead with sales, but sales can really help you move up and get to the larger, more strategic conversations. So I think it depends on your product. But generally spe…”
Wait for 20 ramped AEs before building a repeatable sales playbook
“I don't think you create that playbook until you have at least 20 ramped AEs.”
Early sales teams need collaboration over manufactured internal competition
“I think if you really need to rely on sort of like having people with the same cohort to drive competition, I think you may have hired the wrong people in my opinion, right? Because in that early stage, I'm actually trying to foster more than anything, a cultu…”
Startups should hire product-passionate reps over generic playbook followers
“PLG is on the rise. You want this, I want this person to convey this passion and this love for the product to their customers, as opposed to just following some playbook.”
Sequence sales onboarding: product first, market second, sales methodology last
“I would sequence product knowledge first, and then sales knowledge, right, you know, kind of like, and then, oh, so I would do product first, market first, second, and sales last.”
Asana reached $20M in self-serve revenue without a sales deck
“When I joined Asana, we had twenty million in revenue, mainly driven from our self-serve business, right? And there was no, we didn't have a sales deck.”
Outbound sales requires distinct buyers, messaging, and larger deal sizes
“For outbound to be successful, generally speaking, you're selling to a different buyer. Probably a more senior persona. You're probably selling a different value. And so therefore you need different messaging. In terms of the sales process, absolutely, you'll …”
Cold outbound fails without company-wide marketing and product alignment
“If what you mean by going outbound is you're just going to get some salespeople to go buy some lists and just start cold emailing, LinkedIn bombing people. It won't gonna work because your entire conversion process is designed around a different buyer, articul…”
Asana adopted Toyota's Five Whys process for lost sales post-mortems
“At Asana, we had a practice called Five Whys, it was adopted from Toyota, that I think is very effective.”
The best tech companies put sales on equal footing with product
“A lot of times in tech, frankly, I think sales people are second class citizens. Because they're not building a product and all that, and I think I would love to change that, because I think the best companies are the ones where sales, collecting customer feed…”
Shorts cut from this episode
▶ The Best Interview Question (when hiring for management) · 2 (@23:57)
▶ How To Test New Salespeople? 🤔 #shorts · 20VC with Harry St (@37:49)
▶ HIRING TIP: Look for this ONE TRAIT when interviewing Sales (@20:30)
▶ Top 3 things every Sales Playbook needs · 20VC with Harry St (@5:31)
▶ Best interview question when hiring for management · 20VC wi (@23:57)
▶ Email Marketing is DEAD · 20VC with Harry Stebbings (@50:11)