In this episode of GTM by the Numbers, host Brandon Redlinger sits down with Cassie Young, General Partner at Primary Venture Partners, SaaS operator turned investor, and longtime GTM leader. Cassie brings a rare perspective at the intersection of operating and investing, having led Sailthru through a turnaround and acquisition before advising and backing today’s fastest-growing SaaS companies.

Together, Brandon and Cassie unpack what it really takes to level up from functional leader to true GM, and why mastering the numbers is the most underrated skill for anyone aiming at the C-suite. Cassie shares stories from her career—turnarounds, acquisitions, scaling, and boardroom conversations—and delivers hard-won lessons on how GTM leaders can sharpen their edge in today’s fast-moving market.

What you’ll hear in this episode:

Why P&L fluency is the biggest barrier to the C-suite (and how to develop it)
How to build strong partnerships with your CFO and finance team
The truth about moats in the AI era and why speed may be the only sustainable advantage
Why customer success is on the brink of a renaissance
How to keep a real pulse on the market (hint: it starts with reading the news and ends with listening to customers)
The difference between good and great GTM leaders, and the concept of “first team”

This episode is for GTM executives who want to think like operators, act like board members, and stay one step ahead in a rapidly changing SaaS landscape.

Resources mentioned in this episode:

Clouded Judgment (Altimeter Capital) – Weekly SaaS/Cloud newsletter with Wall Street comps + commentary.

https://cloudedjudgement.substack.com/

Mostly Metrics – Finance-oriented SaaS newsletter by CJ Gustafson, focused on metrics, benchmarks, and CFO perspective.

https://www.mostlymetrics.com/

Axios Pro Rata – Daily newsletter on deals, fundraising, and venture capital.

https://www.axios.com/newsletters/pro-rata

StrictlyVC – Daily newsletter on venture capital news and trends.

https://strictlyvc.com/

Iconiq Capital – Compass – Interactive SaaS benchmarking tool by Iconiq.

https://growth.compass.iconiqcapital.com/

The Five Dysfunctions of a Team by Patrick Lencioni

https://www.amazon.com/Five-Dysfunctions-Team-Leadership-Fable/dp/0787960756

The Advantage by Patrick Lencioni

https://www.amazon.com/Advantage-Organizational-Health-Everything-Business/dp/0470941529

The First 90 Days by Michael Watkins

https://www.amazon.com/First-90-Days-Strategies-Expanded/dp/1422188612

Pavilion CRO School – Executive education program where Cassie teaches on GTM and P&L fluency.

https://www.joinpavilion.com/pavilion-university/cro-school

Connect with Cassie on LinkedIn: https://www.linkedin.com/in/cassyoung

Connect with Brandon on linkedin.com/in/brandonredlinger

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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