Harry Stebbings + Jason Lemkin TOGETHER on 20VC!

A little while ago Harry and Jason did a deep dive both on best practices in building a sales and revenue org, and what’s going on in the venture industry.

It’s now up on 20VC and it’s super fun to watch us get back together again!!  Take a listen!!

20VC: Why the Traditional Seed Fund Model No Longer Works, Why Multi-Stage Funds Investing at Seed Bring Signaling Risk but also Less Pressure, The One Criteria All Potential Sales Hires Need to Have and The Clear Signs of 10x Sales Hires with Jason Lemkin @ SaaStr

Jason Lemkin is the Founder and Managing Partner @ SaaStr, a social community of 500,000+ SaaS founders and a $100M venture fund. In the past, Jason has made investments in the likes of Algolia, Talkdesk, Pipedrive, Salesloft, and RevenueCat to name a few. Prior to SaaStr, Jason was the Co-Founder and CEO @ Echosign, backed by Emergence Capital, Echosign was bought by Adobe and is Adobe Sign as we know it today.

In Today’s Episode with Jason Lemkin You Will Learn:

1.) Origins into Venture:

  • How Jason made his way into the world of venture having sold EchoSign?
  • What were some of Jason’s biggest lessons from his first 4 investments being unicorns?

2.) The Importance of Ownership & Multi-Stage Funds

  • How does Jason assess the importance of ownership today?
  • If companies can be $20BN, does ownership really matter?
  • How does Jason advise founders who have offers from multi-stage funds at seed?
  • Why does taking multi-stage money at seed result in less pressure for founders?
  • Does Jason believe that signaling risk from large funds is real, when investing at seed?

3.) Building Your Sales Team

  • Does the founder have to be the one to create the sales playbook? What are the nuances?
  • Should you hire a Head of Sales or sales reps first? What should you expect from each?
  • What are the one criteria that you must look for when hiring your first sales reps?
  • What are the signals that a sales rep or leader is a 10x hire?
  • What works when hiring sales reps, 80% of the time?

4.) Boards and VC Value Add:

  • Why has Jason changed his mind when it comes to boards? Why are some inefficient and some very efficient?
  • How do the best founders manage their board? How do they bring in their exec team?
  • What is the right documentation to prepare for board meetings? Why does Jason prefer slide decks over Notion and Coda?
  • How can leaders use board meetings to direct and goal set with functional leads?

Published on May 6, 2022

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