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

Lenny's Podcast: Product | Growth | Career

Feb 18 2024 • 2 hrs 1 min

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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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


• Marc Benioff on LinkedIn:

• Snowflake:

• Yamini Rangan on LinkedIn:

• Salesforce:

• HubSpot:

• Twilio:

• Cloudflare:

• GitHub:


• What is Davos and why is it important? Your guide to the World Economic Forum’s annual meeting:

• Adobe:

• Satya Nadella on LinkedIn:

Glengarry Glen Ross on Prime Video:

The Wolf of Wall Street on Prime Video:

• A step-by-step guide to crafting a sales pitch that wins | April Dunford (author of Obviously Awesome and Sales Pitch):

• Pipedrive:

• Sam Blond on LinkedIn:

• Gong:

• Zendesk:

• ZoomInfo:

• Apollo:

• Daniel Chait on LinkedIn:

• SAP:

• Lessons on building product sense, navigating AI, optimizing the first mile, and making it through the messy middle | Scott Belsky (Adobe, Behance):

• VistaPrint:

• Procore:

• Matt Mullenweg on LinkedIn:

• Wordpress:

• SaaStr University:

From Impossible to Inevitable: How SaaS and Other Hyper-Growth Companies Create Predictable Revenue:

• Pavilion:

• Top 10 Learnings about Free Trials with Tomasz Tunguz:

The Terminal List on Prime Video:

Top Gun: Maverick on Paramount:

• OpusClip app:

• OnePlus Open smartphone:

• SaaStr conferences:

• Marketo:

• Zoomtopia:

• Money20/20:

• Shoptalk:

• Jeff Lawson on LinkedIn:

• Eric Kwan on LinkedIn:

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