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Jason Lemkin created and runs SaaStr, the world\u2019s 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\u2014one 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:

\u2022 How far you should go without a salesperson

\u2022 Signs it\u2019s time to hire salespeople

\u2022 Why you need to hire two salespeople

\u2022 How to compensate your salespeople

\u2022 How to interview salespeople

\u2022 When to hire a VP of Sales

\u2022 How to prevent their flaming out

\u2022 How to scale your sales org

\u2022 How to improve the relationship between your sales and product teams

\u2022 Much more

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Find the full transcript at: https://www.lennysnewsletter.com/p/building-a-world-class-sales-org

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Where to find Jason Lemkin:

\u2022 X: https://twitter.com/jasonlk

\u2022 LinkedIn: https://www.linkedin.com/in/jasonmlemkin/

\u2022 Website: https://www.saastr.com/

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Where to find Lenny:

\u2022 Newsletter: https://www.lennysnewsletter.com

\u2022 X: https://twitter.com/lennysan

\u2022 LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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In this episode, we cover:

(00:00) Jason\u2019s 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

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Referenced:

\u2022 Marc Benioff on LinkedIn: https://www.linkedin.com/in/marcbenioff/

\u2022 Snowflake: https://www.snowflake.com/en/

\u2022 Yamini Rangan on LinkedIn: https://www.linkedin.com/in/yaminirangan/

\u2022 Salesforce: https://www.salesforce.com/

\u2022 HubSpot: https://www.hubspot.com/

\u2022 Twilio: https://www.twilio.com/

\u2022 Cloudflare: https://www.cloudflare.com/

\u2022 GitHub: https://github.com/

\u2022 Columbo: https://www.imdb.com/title/tt1466074/

\u2022 What is Davos and why is it important? Your guide to the World Economic Forum\u2019s 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

\u2022 Adobe: https://www.adobe.com/

\u2022 Satya Nadella on LinkedIn: https://www.linkedin.com/in/satyanadella/

\u2022 Glengarry Glen Ross on Prime Video: https://www.amazon.com/Glengarry-Glen-Ross-James-Foley/dp/B002NN5F7A

\u2022 The Wolf of Wall Street on Prime Video: https://www.amazon.com/Wolf-Wall-Street-Leonardo-DiCaprio/dp/B00IIU9FQY

\u2022 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/

\u2022 Pipedrive: https://www.pipedrive.com/

\u2022 Sam Blond on LinkedIn: https://www.linkedin.com/in/sam-blond-791026b/

\u2022 Gong: https://www.gong.io/

\u2022 Zendesk: https://www.zendesk.com/

\u2022 ZoomInfo: https://www.zoominfo.com/

\u2022 Apollo: https://www.apollo.io/

\u2022 Daniel Chait on LinkedIn: https://www.linkedin.com/in/dhchait/

\u2022 SAP: https://www.sap.com/

\u2022 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/

\u2022 VistaPrint: https://www.vistaprint.com/

\u2022 Procore: https://www.procore.com/

\u2022 Matt Mullenweg on LinkedIn: https://www.linkedin.com/in/mattm/

\u2022 Wordpress: https://wordpress.com/

\u2022 SaaStr University: https://app.saastruniversity.com/collections/20252

\u2022 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

\u2022 Pavilion: https://www.joinpavilion.com/

\u2022 Top 10 Learnings about Free Trials with Tomasz Tunguz: https://www.youtube.com/watch?v=tfQNJpnxmMw

\u2022 The Terminal List on Prime Video: https://www.amazon.com/The-Terminal-List-Season-1/dp/B09HYNH8TK

\u2022 Top Gun: Maverick on Paramount: https://www.paramountmovies.com/movies/top-gun-maverick

\u2022 OpusClip app: https://www.opus.pro/

\u2022 OnePlus Open smartphone: https://www.amazon.com/OnePlus-Dual-SIM-Unlocked-Smartphone-Hasselblad/dp/B0CHN7M531/

\u2022 SaaStr conferences: https://www.saastr.com/events/

\u2022 Marketo: https://go.marketo.com/about-marketo-landingpage-emea.html

\u2022 Zoomtopia: https://zoomtopia.com/

\u2022 Money20/20: https://us.money2020.com/

\u2022 Shoptalk: https://shoptalk.com/

\u2022 Jeff Lawson on LinkedIn: https://www.linkedin.com/in/jeffiel/

\u2022 Eric Kwan on LinkedIn: https://www.linkedin.com/in/erickwan/

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

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Lenny may be an investor in the companies discussed.