Building a world-class sales org | Jason Lemkin (SaaStr)

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 • Vanta—Automate compliance. Simplify security. • LinkedIn Ads—Reach professionals and drive results for your business — Find the full transcript 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 — Referenced: • Marc Benioff on LinkedIn: https://www.linkedin.com/in/marcbenioff/ • Snowflake: https://www.snowflake.com/en/ • Yamini Rangan on LinkedIn: https://www.linkedin.com/in/yaminirangan/ • Salesforce: https://www.salesforce.com/ • HubSpot: https://www.hubspot.com/ • Twilio: https://www.twilio.com/ • Cloudflare: https://www.cloudflare.com/ • GitHub: https://github.com/ • Columbo: https://www.imdb.com/title/tt1466074/ • What is Davos and why is it important? Your guide to the World Economic Forum’s annual meeting: https://www.euronews.com/next/2024/01/15/what-is-davos-and-why-is-it-important-your-guide-to-the-world-economic-forums-annual-meeti • Adobe: https://www.adobe.com/ • Satya Nadella on LinkedIn: https://www.linkedin.com/in/satyanadella/ • Glengarry Glen Ross on Prime Video: https://www.amazon.com/Glengarry-Glen-Ross-James-Foley/dp/B002NN5F7A • The Wolf of Wall Street on Prime Video: https://www.amazon.com/Wolf-Wall-Street-Leonardo-DiCaprio/dp/B00IIU9FQY • A step-by-step guide to crafting a sales pitch that wins | April Dunford (author of Obviously Awesome and Sales Pitch): https://www.lennyspodcast.com/a-step-by-step-guide-to-crafting-a-sales-pitch-that-wins-april-dunford-author-of-obviously-awesom/ • Pipedrive: https://www.pipedrive.com/ • Sam Blond on LinkedIn: https://www.