Navigating Free Trials and Customer Engagement

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

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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:

• X: https://twitter.com/jasonlk

• LinkedIn: https://www.linkedin.com/in/jasonmlemkin/

• Website: https://www.saastr.com/

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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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

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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/

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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.

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