#startup #founder #entrepreneur #sales software sales, saas sales, startup founder tips, best startup founder podcast, sales hiring, Jason Lemkin
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.
#sales #salesperson #saas #startup #founder software sales, startup sales tips, tech sales, sales hiring tips, sales interview advice
Tomasz Tunguz, Partner at Redpoint Ventures and Jason Lemkin, Founder of SaaStr chat about the state of SaaS. IPOs, ICOs, M&A, and more!
Jason Lemkin is the founder of SaaStr, the world’s largest community for software founders, and a veteran SaaS investor who has deployed over $200 million into B2B startups. After his last salesperson quit, Jason made a radical decision: replace his entire go-to-market team with AI agents. What started as an experiment has transformed into a new operating model, where 20 AI agents managed by just 1.2 humans now do the work previously handled by a team of 10 SDRs and AEs. In this conversation, Jason shares his hands-on experience implementing AI to run his sales org, including what works, what doesn’t, and how the GTM landscape is quickly being transformed. *We discuss:* 1. How AI is fundamentally changing the sales function 2. Why most SDRs and BDRs will be “extinct” within a year 3. What Jason is observing across his portfolio about AI adoption in GTM 4. How to become “hyper-employable” in the age of AI 5. The specific AI tools and tactics he’s using that have been working best 6. Practical frameworks for integrating AI into your sales motion without losing what works 7. Jason’s 2026 predictions on where SaaS and GTM are heading next *Brought to you by:* DX—The developer intelligence platform designed by leading researchers: https://getdx.com/lenny Vercel—Your collaborative AI assistant to design, iterate, and scale full-stack applications for the web: https://vercel.com/lennyspodcast Datadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lenny *Transcript:* https://www.lennysnewsletter.com/p/we-replaced-our-sales-team-with-20-ai-agents *My biggest takeaways (for paid newsletter subscribers):* https://www.lennysnewsletter.com/i/182902716/my-biggest-takeaways-from-this-conversation *Where to find Jason Lemkin:* • X: https://x.com/jasonlk • LinkedIn: https://www.linkedin.com/in/jasonmlemkin • Website: https://www.saastr.com • Substack: https://substack.com/@cloud *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) Introduction to Jason Lemkin (04:36) What SaaStr does (07:13) AI’s impact on sales teams (10:11) How SaaStr's AI agents work and their performance (14:18) How go-to-market is changing in the AI era (19:19) The future of SDRs, BDRs, and AEs in sales (22:03) Why leadership roles are safe (23:43) How to be in the 20% who thrive in the AI sales future (28:40) Why you shouldn't build your own AI tools (30:10) Specific AI agents and their applications (36:40) Challenges and learnings in AI deployment (42:11) Making AI-generated emails good (not just acceptable) (47:31) When humans still beat AI in sales (52:39) An overview of SaaStr's org (53:50) The role of human oversight in AI operations (58:37) Advice for salespeople and founders in the AI era (01:05:40) Forward-deployed engineers (01:08:08) What's changing and what's staying the same in sales (01:16:21) Why AI is creating more work, not less (01:19:32) Why Jason says these are magical times (01:25:25) The "incognito mode test" for finding AI opportunities (01:27:19) The impact of AI on jobs (01:30:18) Lightning round and final thoughts *Referenced:* • Building a world-class sales org | Jason Lemkin (SaaStr): https://www.lennysnewsletter.com/p/building-a-world-class-sales-org • SaaStr Annual: https://www.saastrannual.com • Delphi: https://www.delphi.ai/saastr/talk • Amelia Lerutte on LinkedIn: https://www.linkedin.com/in/amelialerutte/ • Vercel: https://vercel.com • What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google): https://www.lennysnewsletter.com/p/what-the-best-gtm-teams-do-differently • Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch • Replit: https://replit.com • Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad • ElevenLabs: https://elevenlabs.io • The exact AI playbook (using MCPs, custom GPTs, Granola) that saved ElevenLabs $100k+ and helps them ship daily | Luke Harries (Head of Growth): https://www.lennysnewsletter.com/p/the-ai-marketing-stack ...References continued at: https://www.lennysnewsletter.com/p/we-replaced-our-sales-team-with-20-ai-agents _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.