This week on The Revenue Leadership Podcast, I spoke with Jason Gelman, Operating Partner at Primary Ventures and co-founder of Jump. Our conversation explored the valuable perspectives gained from viewing revenue leadership through both operational and investment lenses. Jason's journey from successful operator running strategy and operations at Compass from $100M to $6B ARR to venture capital at Primary offers insights that could transform your approach to leading revenue teams and navigating today's rapidly evolving tech landscape.
Listen to Jason's episode on Apple and Spotify.
The Operating Partner: More Than Just a Talking Head
Many revenue leaders view the transition to venture capital as a retreat from the frontlines and as "hanging up your guns," as Jason puts it. His mentors warned him of becoming "just a frameworks guy" with limited impact. Jason discovered that operating partners at early-stage firms like Primary can have tremendous influence by working deeply with founders at critical inflection points.
"I told myself I would never be the frameworks and storytelling and big idea guy," Jason explains. "If I do this and I don't feel like I'm solving problems and I'm just saying generic frameworks and inapplicable stories... I just can't be that person."
This distinction highlights a critical insight about venture roles: impact varies dramatically depending on the firm's priorities. While some operating partners primarily support diligence and LP reporting, Primary's model invests heavily in direct founder support.
Five Key Takeaways for Revenue Leaders
1. Building Credibility with Executive Teams Requires Financial Fluency
What separates good CROs from great ones? According to Jason, it's analytical fluency.
"The hardest skill set to find in a CRO is someone who is deeply analytically fluent and P&L fluent," Jason notes. "The best CROs have pretty rich analytical fluency about the numbers and mechanics of the business."
This aligns with research from SBI, which found that top-performing CROs spend 20% more time analyzing business performance data than their peers. The ability to translate sales activities into financial outcomes is what elevates a tactical sales leader to a strategic business executive. Revenue leaders can build financial acumen by partnering closely with your finance team, and participating in financial planning sessions.
2. VC Networks Are More Powerful Than Most Realize
Jason revealed how venture capital's information asymmetry provides advantages that most operators don't fully appreciate.
"The amount of access we have to getting back channels and answers and private information is astounding... Send me a company that you're interested in, and I guarantee you we can find some information that would not be publicly available."
This network effect extends to talent placement as well. VCs have powerful incentives to place talent in their portfolio companies, creating extraordinary opportunities for operators who actively engage with these networks.
The opportunity here is for revenue leaders to actively engage with venture capital networks even when you're not job searching. Offer to help with diligence calls, provide references, and attend events. These relationship investments can lead to value connections, expert information and career opportunities down the road.
3. The "Gotta Believe" Framework for Evaluating Opportunities
One of the most insightful frameworks Jason shared is Primary's "Gotta Believe" approach to evaluating investments:
"We have an investment thesis... But the 'Gotta Believe' are the unanswered questions, the risks. If this business is going to be successful, you gotta believe that X will happen, Y will happen. These are the real decision points in each investment."
This framework forces explicit acknowledgment of the bets and risks in any significant decision - whether investing in a company or joining one as an executive.
This is a fantastic way for revenue leaders to weigh their next career move or major strategic initiative through. Explicitly list what "must be true" for success. This might include assumptions about product evolution, competitive dynamics, or talent availability. Making these assumptions explicit can help quantify risk and identify the most critical variables to test.
4. Brute-Forcing Growth Without Product-Market Fit Is a Recipe for Burnout
Both Jason and I shared painful experiences of scaling revenue organizations without true product-market fit. As Jason described:
"Anyone who's seen a 'scale up before you're ready' story knows it's really painful. We were able to get this company to over 50 million ARR without perfect product market fit."
This pattern appears repeatedly in venture-backed companies that prioritize growth metrics over customer outcomes and sustainable unit economics. The psychological toll on revenue teams forced to sell products with marginal fit is substantial and leads to burnout.
This is a great reminder for revenue leaders to rigorously validate product-market fit before scaling your revenue team. Look beyond surface metrics like growth rate to customer retention, implementation success, and willingness to serve as references. Push back on pressure to scale prematurely, as the long-term costs typically outweigh short-term gains.
5. AI Will Fundamentally Reshape the Go-to-Market Tech Stack
On the rapidly evolving GTM tech landscape, Jason shared a provocative prediction:
"I would not be surprised if one mega GTM tool emerges at some point that basically eats tons and tons of the other workflows and apps."
This disruption goes beyond incremental improvement to question fundamental assumptions about how CRM and related tools function. As Jason notes, "If you ever wanted to unseat Salesforce, this is the only time I've ever seen where there's this window where it could possibly happen."
The challenge for operators is determining which tools to adopt now versus which to wait on. Jason recommends creating a "sales lab" model where select team members experiment with emerging technologies and report findings to the broader organization.
Managing VC Relationships: The Fundamentals Matter
For founders and CROs working with investors, Jason's advice is refreshingly straightforward:
"If I was the CEO of a business reporting to a board, I would be very transparent. I would be very communicative, no surprises, consistent updates, all of that." This might seem obvious, but the reality is that pressure and emotion often override these fundamentals. The relationship deteriorates when founders withhold challenging information or delay critical updates.
Jason's recommendation to venture partners is to frame their advice from the perspective of "If I were the CEO of your business, here's what I would do" provides a useful model for advisors. This approach shifts the discussion from abstract advice to concrete action, while maintaining respect for the founder's ultimate decision-making authority.
Creating Optionality in Your Career Path
For revenue leaders considering their next move, Jason's experience suggests value in creating optionality through strategic role selection. His move to Primary opened three potential paths: joining a portfolio company as COO, founding a startup with Primary's backing, or transitioning into investing. This optionality-focused approach to career planning creates more resilience in uncertain markets.
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The transition from operator to investor provides a unique vantage point on how businesses succeed and fail. While Jason's journey is still unfolding, his perspective offers valuable insights for revenue leaders navigating today's rapidly evolving landscape.
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