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.lennyspodcast.com/building-a-world-class-sales-org-jason-lemkin-saastr/ — 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.linkedin.com/in/sam-blond-791026b/ • Gong: https://www.gong.io/ • Zendesk: https://www.zendesk.com/ • ZoomInfo: https://www.zoominfo.com/ • Apollo: https://www.apollo.io/ • Daniel Chait on LinkedIn: https://www.linkedin.com/in/dhchait/ • SAP: https://www.sap.com/ • Lessons on building product sense, navigating AI, optimizing the first mile, and making it through the messy middle | Scott Belsky (Adobe, Behance): https://www.lennyspodcast.com/lessons-on-building-product-sense-navigating-ai-optimizing-the-first-mile-and-making-it-through-t/ • VistaPrint: https://www.vistaprint.com/ • Procore: https://www.procore.com/ • Matt Mullenweg on LinkedIn: https://www.linkedin.com/in/mattm/ • Wordpress: https://wordpress.com/ • SaaStr University: https://app.saastruniversity.com/collections/20252 • From Impossible to Inevitable: How SaaS and Other Hyper-Growth Companies Create Predictable Revenue: https://www.amazon.com/Impossible-Inevitable-Hyper-Growth-Companies-Predictable/dp/1119531691 • Pavilion: https://www.joinpavilion.com/ • Top 10 Learnings about Free Trials with Tomasz Tunguz: https://www.youtube.com/watch?v=tfQNJpnxmMw • The Terminal List on Prime Video: https://www.amazon.com/The-Terminal-List-Season-1/dp/B09HYNH8TK • Top Gun: Maverick on Paramount: https://www.paramountmovies.com/movies/top-gun-maverick • OpusClip app: https://www.opus.pro/ • OnePlus Open smartphone: https://www.amazon.com/OnePlus-Dual-SIM-Unlocked-Smartphone-Hasselblad/dp/B0CHN7M531/ • SaaStr conferences: https://www.saastr.com/events/ • Marketo: https://go.marketo.com/about-marketo-landingpage-emea.html • Zoomtopia: https://zoomtopia.com/ • Money20/20: https://us.money2020.com/ • Shoptalk: https://shoptalk.com/ • Jeff Lawson on LinkedIn: https://www.linkedin.com/in/jeffiel/ • Eric Kwan on LinkedIn: https://www.linkedin.com/in/erickwan/ — 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. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe