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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.

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Nov 16, 2022

In this engaging discussion, Dannie Herzberg, a Partner at Sequoia Capital and former Head of Enterprise Sales at Slack, dives deep into effective sales onboarding strategies. He highlights the importance of structured processes, product knowledge, and customer engagement for new sales reps. Alongside insights from other experts, they tackle sales challenges in product-led environments and emphasize the necessity for proactive communication. The conversation underlines the shared responsibilities of leadership and new hires in creating a successful sales culture.

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ADVICE

Early-Stage Sales Onboarding

Prioritize product knowledge first for early-stage sales hires by exposing them to customer support tickets.
This helps them understand potential sales obstacles and the product's technical aspects.

ADVICE

Market Education for Sales

After product knowledge, focus on market education using fundraising decks.
This teaches the broader context and mission before detailed sales messaging.

ADVICE

Sales Training and Practice

For sales training, shadow founders, engage with top customers, and conduct mock demos.
This provides practical experience and simulates real sales scenarios.

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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?