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.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 [email protected].—Lenny may be an investor in the companies discussed. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe