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

ℹ️ EPISODE INFO

Released

February 18, 2024

Duration

2h 1m

Channel

Lenny's Podcast

Watch on YouTube

▶ Open ↗

📝 EPISODE DESCRIPTION

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.

🎤 SPEAKERS

• Jason Lemkin

  guest

• Lenny Rachitsky

  host

🧾 EPISODE SUMMARY

In this episode of Lenny's Podcast, featuring Jason Lemkin and Lenny Rachitsky, Building a world-class sales org | Jason Lemkin (SaaStr) explores jason Lemkin’s playbook for building and scaling B2B sales teams Jason Lemkin lays out a practical, often counterintuitive blueprint for when and how to build a B2B sales organization, starting with founders closing the first 10 customers themselves. He explains why your first two sales hires must be people you’d personally buy from, why you should delay hiring a VP of Sales until at least two reps are reliably hitting quota, and how to structure compensation so reps are accretive rather than a cash drain. The conversation dives into the critical (and tense) relationship between product and sales—how product leaders should engage in sales cycles, handle feature requests, and think about free trials and pricing. Jason also touches on event strategy, arguing that small, high‑quality customer gatherings are often more valuable than mid‑tier conferences, and urges product leaders to make this “the year of the customer.”

🔗 RELATED EPISODES

How to build a company that withstands any era | Eric Ries, Lean Startup author

Head of Claude Code: What happens after coding is solved | Boris Cherny

Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead)

Building a world-class data org | Jessica Lachs (VP of Analytics and Data Science at DoorDash)

What most people miss about marketing | Rory Sutherland (Vice Chairman of Ogilvy UK, author)

5 essential questions to craft a winning strategy | Roger Martin (author, advisor, speaker)