Jason Lemkin created and runs SaaStr, the world’s largest community for B2B/SaaS founders, and is the managing director of SaaStr Fund, a $90 million venture capital firm specializing in early-stage enterprise investments. He is also the mastermind behind two major tech conferences each year—one in the Bay Area, drawing in over 15,000 people, and another in Europe, with a crowd of more than 3,000 SaaS executives, founders, and entrepreneurs. Before SaaStr, Jason wore many hats: CEO and co-founder of EchoSign (later bought by Adobe), vice president at Adobe Systems, co-founder and president of NanoGram Devices Corp., vice president of NeoPhotonics, and a senior director at BabyCenter. In our conversation, we discuss:
• How far you should go without a salesperson
• Signs it’s time to hire salespeople
• Why you need to hire two salespeople
• How to compensate your salespeople
• How to interview salespeople
• When to hire a VP of Sales
• How to prevent their flaming out
• How to scale your sales org
• How to improve the relationship between your sales and product teams
• Much more

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Find the transcript and references at: https://www.lennysnewsletter.com/p/bu...


Where to find Jason Lemkin:
• X:   / jasonlk  
• LinkedIn:   / jasonmlemkin  
• Website: https://www.saastr.com/


Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X:   / lennysan  
• LinkedIn:   / lennyrachitsky  


In this episode, we cover:
(00:00) Jason’s background
(06:18) The importance of sales in B2B businesses
(11:23) Signs that you should start hiring salespeople
(14:19) Attributes to look for in early sales reps
(19:08) Hiring a VP of Sales
(26:43) The role of a VP of Sales
(30:06) Interviewing salespeople
(45:16) Determining sales compensation and quota
(53:34) Transitioning from 100% commission to a smaller percentage
(56:58) Indicators of a hard-to-sell product
(59:39) Scaling the sales organization
(01:05:26) Understanding sales roles and titles
(01:10:02) Product involvement in sales, and vice versa
(01:20:32) Thoughts on product teams taking on P&L responsibilities
(01:27:23) One thing founders can do to become better at sales
(01:31:02) The ideal trial length for a free trial sales team
(01:39:50) Closing thoughts
(01:41:43) Lightning round


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Lenny may be an investor in the companies discussed.