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?
20 Sales: Three Reasons Why Sales People Fail | The Two Things That Matter When Hiring Sales Leaders | Why Revenue, Discounting and Price Do Not Matter in the Early Days with Jordan Van Horn, Revenue Leader @ Monte Carlo
Jordan Van Horn is a Revenue Leader @ Monte Carlo, the world's first data observability company. Prior to this role, Jordan spent an incredible 4 years in sales at Segment including as VP of Sales leading a sales team of 50+ Account Executives and leading the first international expansion for the company into Dublin. Before Segment, Jordan was at Dropbox for 4 years leading enterprise sales for Dropbox Business in California.
In Today's Episode with Jordan Van Horn We Discuss:
1.) Entry into the World of Sales:
How did Jordan make his way into the world of sales first with a vineyard?
What are 1-2 of the biggest takeaways for Jordan from seeing the scaling sales teams at both Segment and Dropbox? How did seeing that impact his mindset?
What does Jordan know now that he wishes he had known when he entered sales?
2.) The Sales Playbook:
How does Jordan define "the sales playbook"? What is it not?
What five core things should the sales playbook help you accomplish?
Should the founder be responsible for the sales playbook? Can it be created by a Head of Sales?
How does Jordan advise founders on three signals that now is the right time to bring in a sales hire?
How does Jordan advise founders on whether the first sales hire should be a rep or a leader?
3.) The Secrets to Pricing and Discounting:
Why does Jordan not care what price customers pay in the early days? If it is not about ARR, what should teams be optimizing for?
When does price discipline become important in a company journey? What are the dangers of not having price discipline?
What two tools do sales leaders have to use in order to create urgency in a deal closing process?
How should sales leaders think about building multiple champions within a potential customer? At what price point is it worth it?
4.) The Hiring Process:
How does Jordan structure the hiring process for all new sales hires?
What are the must-ask questions that Jordan asks all new candidates? What does he want to see in those answers?
Who else does he bring into the hiring process? At what stage do they get involved? What are they testing for?
Does Jordan use case studies with candidates? What makes the best? What makes the worst?
5.) The Onboarding:
What is the ideal onboarding process for new sales reps?
What should founders do and prep for when onboarding their first sales hires? What materials and recordings should they have ready?
What are some early signs that a new hire is not working out? How do we measure their impact?
For enterprise sales, it takes a long time to close new deals, how can one determine effectiveness of new reps when the sales cycle is so long?
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?