The Revenue Leadership Podcast with Kyle Norton

From Building Startups to Betting on Them with Jason Gelman of Primary Ventures

Feb 19, 2025

Jason Gelman, Operating Partner at Primary Ventures and co-founder of Jump, shares his journey from scaling Compass to supporting startups. He discusses the uncommon insight that not every startup needs venture funding. Gelman highlights the crucial go-to-market strategies for founders and the evolving role of AI in sales. He also sheds light on common scaling mistakes and the traits that distinguish exceptional Chief Revenue Officers (CROs) in today’s dynamic landscape.

01:22:22

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Episode guests

Jason Gelman

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Podcast summary created with Snipd AI

Quick takeaways

Jason Gelman emphasizes the importance of careful consideration regarding venture funding, advising that not all startups should pursue it for growth.

The role of an operating partner in venture capital is crucial for supporting startups, particularly in refining their customer acquisition and product-market fit strategies.

AI's rapid evolution is significantly transforming go-to-market approaches, pushing companies to innovate or risk falling behind in a competitive landscape.

Deep dives

Background and Career Transition

Jason Gelman shares his diverse career journey, starting as a lawyer before pivoting to the tech industry where he found his passion. After gaining extensive experience in business operations and revenue战略 at companies such as Compass, he transitioned to an operating partner role at Primary Ventures. This shift allowed him to leverage his operational expertise while supporting early-stage startups as they navigate growth challenges. His transition reflects a blend of personal ambition and a desire for a broader view of innovation across the tech landscape.

Intro

2min

Navigating the Shift: From Law to Tech and Venture Capital

11min

Optimizing Sales Meetings with a Unified Revenue Calendar

2min

Navigating the Shift to Venture Capital

20min

Navigating Challenges for Early-Stage Founders

2min

Navigating the VC Landscape

16min

Navigating VC Relationships

4min

Navigating AI in Sales and CRM Landscapes

22min

Navigating Career Transitions

4min

In this episode of the Revenue Leadership Podcast, host Kyle Norton sits down with Jason Gelman, Operating Partner at Primary Ventures and Co-Founder of Jump, to explore his transition from operator to VC and the lessons he’s learned along the way. Jason shares insights from scaling Compass from $100M to $6B in revenue, why not every startup should raise venture funding, and how founders can navigate the challenges of go-to-market strategy. They also cover the evolving role of AI in revenue leadership, the traits that separate great CROs from the rest, and the fundamental mistakes many startups make when trying to scale.

If you like what you heard from Kyle today, make sure to follow The Revenue Leadership Podcast by Pavilion for new episodes every Wednesday.

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Primary: https://www.primary.vc/

Jump: https://jumprevenue.com/

B&T Infra Newsletter: https://www.infranewsletter.com/

LinkedIn: https://www.linkedin.com/in/jasongelman/

Contact: Gelman@primary.vc

Key Chapters:

(00:00) - Introduction to Jason Gelman and Primary Ventures

(02:46) - The Role of an Operating Partner

(06:03) - Understanding Jump: A Revenue Calendar Tool

(08:53) - Navigating Venture Capital: When to Raise Funds

(12:05) - The Transition from Operator to VC

(15:02) - Lessons Learned as an Operating Partner

(17:53) - Identifying Product-Market Fit

(21:06) - The Importance of Talent in VC

(23:57) - Final Thoughts and Future Aspirations

(41:06) - Navigating Venture Capital Networks

(44:00) - Insights from Operating as a Non-Venture Backed Company

(49:40) - The 'God of Beliefs' Framework in Investment

(53:01) - Mastering VC Relationships

(56:27) - The Rapid Evolution of Go-To-Market Tech

(01:01:09) - The Future of CRM and AI Integration

(01:06:20) - The Challenge of Investing in AI Startups

(01:12:11) - Creating a Culture of AI Experimentation

(01:16:26) - Defining Greatness in Revenue Leadership

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The Revenue Leadership Podcast with Kyle Norton

From Building Startups to Betting on Them with Jason Gelman of Primary Ventures

Episode guests