20 Sales: The Ultimate Guide to Sales Onboarding for New Sales Reps and Sales Leaders, The Biggest Red Flags in the First 30 Days & What Can Be Done to Set Them Up for Success with Leaders from Figma, Dropbox, Miro and more.
Oliver Jay (OJ) is one of the most successful sales leaders of the last decade. Most recently, OJ spent 6 years as CRO @ Asana and grew the team from 20 to over 450, becoming a master in sales onboarding in the process. Before Asana, OJ spent 4 years at Dropbox, where OJ was Head of APAC & LATAM.
Jordan Van Horn is a Revenue Leader @ Monte Carlo. Prior to this role, Jordan spent 4 years at Segment as VP of Sales, leading a sales team of 50+ Account Executives. Before Segment, Jordan was at Dropbox for 4 years leading enterprise sales for Dropbox Business.
Dannie Herzberg is a Partner @ Sequoia Capital and before Sequoia, Dannie spent 4 years at Slack as their Head of Enterprise Sales, growing the business from $100M – $1B in revenue. Before Slack, Dannie spent over 5 years at Hubspot building sales teams.
Zhenya Loginov is the CRO @ Miro. At Miro, Zhenya runs the go-to-market team of 700+ people across. Prior to Miro, Zhenya was the COO @ Segment where he built and ran the global go-to-market team of 200+ people. Pre-Segment, Zhenya led a 100-person team at Dropbox across different functional areas.
Lauren Schwartz is VP of Enterprise Sales at Fivetran, where she has scaled the team to nearly 100, while more than tripling enterprise revenues. Previously, Lauren spent close to 4 years at Segment where she started as the first female AE and ultimately built and led sales teams in enterprise and growth.
Kyle Parrish is VP Sales @ Figma, where he built the sales engine from scratch to today, with over 100 in sales. Before Figma, Kyle spent over 5 years at Dropbox in numerous different roles including Head of Sales, and Global Partnerships lead, responsible for growing Dropbox's partner ecosystem.
In Todays Episode on Sales Onboarding We Discuss:
1.) How should the onboarding process for all new sales reps be structured?
2.) How should the onboarding process for a new sales leader be structured?
3.) What specific things can leaders do to set both reps and leaders best up for success?
4.) What are the single biggest red flags in the first 30 days that a rep is not going to work out?
5.) What tools and software can be used to improve this process of ramping new reps?
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?
Today we deconstruct the canonical question in early-stage sales. Does the founder need to create the sales playbook? Then secondly, if not, should the first sales hires be reps or a sales leader? Today we are joined by 7 of the best sales leaders to share their thoughts.
Jordan Van Horn is a Revenue Leader @ Montecarlo. Previously Jordan spent 4 years with Segment and before that spent another 4 years at Dropbox.
Oliver Jay (OJ) most recently spent 6 years at Asana where he was hired as the company's first revenue leader. Before Asana, OJ spent 4 years at Dropbox where he scaled the sales team from 0 to 50 while tripling ARR.
Dannie Herzberg is a Partner @ Sequoia Capital and previously spent 4 years at Slack as their Head of Enterprise Sales. Before Slack, Dannie spent 5 years at Hubspot building sales, opening an SF office, and then joining product to launch CRM & platform.
Zhenya Loginov is the CRO @ Miro, where he runs the go-to-market team of 700+ people across 11 global offices. Prior to Miro, Zhenya was the COO @ Segment. Finally, before Segment, Zhenya led a 100-person team at Dropbox across numerous different functional areas.
Kyle Parrish is VP Sales @ Figma, where he has scaled the sales team from 0 to over 100 people in sales. Before Figma, Kyle spent over 5 years at Dropbox in numerous different roles including Head of Sales, where he scaled the Austin, Texas office from 3 to over 80 people.
Sam Taylor is the VP of Sales and Customer Success @ Loom, at Loom Sam leads Revenue Org including: Direct Sales, Customer Success, Self-Serve Revenue Growth/Assist. Prior to Loom, Sam spent over 4 years at Salesforce, following their acquisition of Quip, where he was the first sales leader. Before Salesforce and Quip, Sam spent over 3 years at Dropbox as a mid-market sales leader.
Jeanne DeWitt Grosser is Head of Americas Revenue & Growth @ Stripe. Pre-Stripe, Jeanne was CRO @ Dialpad and also spent many years at Google in numerous different roles including most recently as Director of GSuite SMB & Mid-Market Sales, North America and LATAM.
Mitch Tarica is Head of North America Sales at Zoom Video Communications. Before Zoom, Mitch spent over 5 years at RingCentral and before RingCentral, Mitch was at Oracle for over 7 years in numerous different sales roles.
In Today's Discussion on Sales Playbooks We Learn:
1.) What is the right definition for a "sales playbook"?
2.) When is the right time to change your "sales playbook"?
3.) What are the biggest mistakes or misnomers made around the "sales playbook"?
4.) Should the founder be the one to create the first sales playbook or can it be a sales leader?
5.) When is the right time for founders to hire their first sales leaders?
6.) For the first sales hire, should founders hire sales reps or a sales leader?
7.) When should you hire a rep vs a sales leader? What are the nuances?
20 Sales: 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 with Oliver Jay, Former CRO
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?
Head of Revenue and BD at Asana, Oliver Jay: The Cutting Edge of Product-Led Growth
When Oliver Jay worked for venture capital firm New Enterprise Associates in the late 2000s, he found that the most rewarding aspect for him was working with portfolio companies and watching the beginnings of sales operations.
“But as an associate, let’s be honest, I was there to crunch numbers, and write memos, and source deals,” Oliver said. “That’s why I decided to leave. Even though I loved the job intellectually, I just wanted a piece of the action.”
Soon after, Oliver earned an MBA from Harvard Business School, and flexed his sales knowledge at companies like Dropbox. Now, Oliver works as Head of Global Revenue and Business Development at Asana, a company developing a work management platform.
On this episode of Go to Market Grit, Joubin and Oliver talk about Oliver’s upbringing, the benefits of implementing “checks and balances” into the hiring process, and how to blend product-led growth and value enterprise sales.
In this episode, we cover:
How Oliver educated himself about go-to-market operations by embarking on a 'campaign' to meet and learn from successful sales leaders. (3:03)
'I learned a ton': Oliver's thoughts on the value of business school. (9:04)
Oliver's experience as an immigrant in the United States — and how he wants to teach authenticity and grit to his children. (12:18)
How Oliver learned that he had an eye for identifying talent — and how he motivates and inspires teams with long term goals. (17:31)
Building 'checks and balances' into the hiring process. (21:56)
Uber vs. Grab: Oliver's firsthand experience on the board of Grab as it competed with Uber for the Asian rideshare market. (24:19)
'Seed, land, and expand': What Oliver's experience working at Dropbox taught him about structuring sales organizations at product-led companies. (28:06)
Oliver's current business, Asana, its work management platform — and building a ‘balanced’ company culture. (38:28)
Uncovering whether a job candidate understands excellence during an interview — and the value of helping people grow and develop. (41:28)
What the word grit means to Oliver. (44:41)
Links:
Connect with Oliverhttps://asana.com
Connect with JoubinTwitter
LinkedIn
Email: gtmg@kleinerperkins.com
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