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 earlystage 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 cofounder of EchoSign (later bought by Adobe), vice president at Adobe Systems, cofounder 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 hardtosell 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.