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 — Brought to you by: • CommandBar—AI-powered user assistance for modern products and impatient users: https://www.commandbar.com/lenny • Vanta—Automate compliance. Simplify security: https://vanta.com/lenny • LinkedIn Ads—Reach professionals and drive results for your business: https://www.linkedin.com/podlenny Find the transcript and references at: https://www.lennysnewsletter.com/p/building-a-world-class-sales-org Where to find Jason Lemkin: • X: https://twitter.com/jasonlk • LinkedIn: https://www.linkedin.com/in/jasonmlemkin/ • Website: https://www.saastr.com/ Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/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 Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Lenny may be an investor in the companies discussed.