20 Sales: Asana’s Former CRO, Oliver Jay on How To Create and Execute a World-Class Sales Playbook, Why You Should Do Both PLG and Enterprise Sales at the Same Time, Three Non-Obvious Qualities the Best Sales Reps Have & The Four Steps To Sales Team Onboarding

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.

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?