Oliver Jay: How To Create and Execute a World-Class Sales Playbook | 20VC #889

ℹ️ EPISODE INFO

Released

May 25, 2022

Duration

54m

Channel

The Twenty Minute VC

Watch on YouTube

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📝 EPISODE DESCRIPTION

Oliver Jay (OJ) is one of the most successful sales leaders of the last decade. Most recently, OJ spent 6 years at Asana where he was hired as the company’s first revenue leader. As CRO, OJ was responsible for product-led and sales-led revenue and grew the team from less than 20 to over 450. Before Asana, OJ spent 4 years at Dropbox in a period of hyper-scaling for the business where OJ was Head of APAC and LATAM. At Dropbox, OJ scaled the sales team from 0 to 50 while tripling ARR. If that was not enough, OJ is also an independent board member at Grab, the leading Super app in Southeast Asia. ------------------------------------------ Timestamps: 0:00 Entry into Sales 4:35 The Playbook 12:23 The Hiring Process 27:50 Sales Compensation 32:09 Sales Onboarding 43:55 Head of Sales relationship with the CEO 45:46 Postmortem Reviews 49:33 Oliver Jay: AMA ------------------------------------------ In Today’s Episode with Oliver Jay You Will Learn: 1.) Entry into Sales: How did OJ make his way into sales with Dropbox? If OJ were to choose 1-2 lessons from his time at Dropbox and Asana that have stayed with him, what would they be? How did they impact his mindset? What were some of the non-obvious but crucial things Asana and Dropbox did in sales that led to success? 2.) The Playbook: Why does OG disagree with so many definitions of “the sales playbook”? What is the sales playbook to OJ? What are the different chapters? Should the founder be the one to create the sales playbook? What are the signs that the founder has a repeatable and scalable playbook? When is the right time to hire the first sales rep? Should it be a Head of Sales or Sales Rep? How does the first hire depend on whether you are PLG or enterprise sales led? 3.) The Hiring Process: How does OJ structure the hiring process? How does OJ know the qualities that he wants to uncover in each candidate? What questions does OJ ask to unpack whether the candidate has those qualities? How does this differ when hiring sales reps vs sales leaders? How does OJ use the sales demo to test the quality of a candidate? What does he want to see? Who does OJ bring into the interview process? When do they get involved? What are two questions that will immediately tell whether someone is a good manager? 4.) Sales Onboarding: How does OJ segment sales onboarding into 3 crucial steps? Chapter 1: Support: Why does OJ believe it is so important for reps to spend their first week with support? What should they look to learn? What questions should they be asking? Chapter 2: Market Knowledge: How can sales leaders teach and educate new reps on market landscape, dynamics and competition? Why does this have to come before sales training? Chapter 3: Sales Training: In the final step, what does the sales training process? What does OJ look for in the final sales demo? When does OJ let reps speak to customers? How does this differ when comparing enterprise to PLG? ------------------------------------------ #OliverJay #20VC #20SALES #HarryStebbings #Sales #SalesTips #VentureCapital #FounderLife #InterviewQuestions

🎤 SPEAKERS

• Oliver Jay

  guest

• Harry Stebbings

  host

• Narrator

  other

🧾 EPISODE SUMMARY

In this episode of The Twenty Minute VC, featuring Oliver Jay and Harry Stebbings, Oliver Jay: How To Create and Execute a World-Class Sales Playbook | 20VC #889 explores oliver Jay Explains Building Agile Sales Playbooks For Product-Led Startups Oliver Jay (OJ), former sales leader at Dropbox and Asana, explains how to build and scale a world-class sales motion, especially in product-led growth (PLG) companies. He distinguishes between two ‘playbooks’: the early discovery playbook (who to sell to, how, and why it matters) and the later repeatable process playbook, which only becomes real once you have significant AE scale. OJ argues founders must be deeply involved in the first playbook, hire customer-facing people early for learning (not just revenue), and prioritize agility and insights over premature process. He also dives into hiring, onboarding, compensation, and the critical CEO–head of sales partnership, emphasizing that sales should be seen as a strategic problem‑solving function, not a second-class citizen to product.

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