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.

In this episode of GTM by the Numbers, Brandon Redlinger chats with Jon Miller to rethink how marketing and revenue teams should operate when AI is at the core—not bolted on. Jon breaks down where AI is already working (inbound agents, agentic workflows that compress prep/follow-up) and where it isn’t (spray-and-pray outbound “personalization” without human oversight). He explains why to avoid multi-year vendor lock-in during this transition, how “AI-curated playlists” will replace rigid nurture streams, the emerging shape of GTM orgs (fewer SDR bodies, rise of GTM engineers), and how to measure AI’s impact through efficiency and effectiveness with pipeline and revenue still as the gate.

In this episode, we break down:

• Why bolting AI onto 15–25-year-old, rules-based systems is “lipstick on a pig”, and what it looks like when reasoning replaces rules.
• The “AI DJ” model: 1:1 orchestration that curates a personalized playlist of actions for every contact (goodbye, one-size-fits-all nurtures).
• Agentic AE workflows that auto-build account plans, research, and follow-ups so reps spend less time prepping and more time selling.
• AI SDRs: why inbound agents shine (speed + always-up-to-date) and why outbound still needs real human oversight.
• Measuring AI with hard ROI on efficiency (time saved) vs. harder-to-measure effectiveness (synthetic panels, engagement lift, pipeline).
• How AI will disintermediate your marketing (search today, inbox tomorrow) and what survives (experiences, relationships and craftsmanship)

Resources mentioned in this episode:

Claude (Anthropic): Jon and Brandon reference using Claude for building and experimenting with AI workflows and prototypes.

https://www.anthropic.com/claude

Lovable: “Vibe-coding” tool Jon and Brandon discuss for quickly prototyping apps/sites to convey product vision.

https://lovable.dev/

Clay + HubSpot integration: Used by Brandon to automate research, notes, and follow-ups in GTM workflows.

https://www.clay.com/university/guide/hubspot-integration-overview

All-In Podcast: One of Jon’s go-to listens to understand diverse viewpoints.

https://allin.com/

Christopher S. Penn / Trust Insights: Jon’s recommended source for staying current on marketing AI.

https://www.trustinsights.ai/blog/

From Impossible to Inevitable (Aaron Ross & Jason Lemkin): Quoted during the selling-time discussion.

https://fromimpossible.com/

Connect with Jon at LinkedIn: https://www.linkedin.com/in/jonmiller2

Connect with Brandon at 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.

In this episode of GTM by the Numbers, host Brandon Redlinger chats with Jacco van der Kooij, founder of Winning by Design, to unpack why most GTM efficiency metrics are dead wrong—and what CROs should be tracking instead. They dive into the Bow Tie model, the rising cost of acquisition, and the untapped power of customer-led growth. If you're leading a SaaS revenue team and questioning whether your metrics actually reflect success, this conversation will give you the clarity, and the playbook, you need.

What you’ll hear in this episode:

• Why most SaaS GTM teams are addicted to acquisition
• How to calculate GTM efficiency and what "good" really looks like
• The impact of operational debt on growth
• How to create customer-led campaigns that scale
• Why post-sale motions are underfunded (and how to fix it)
• When expansion should drive more growth than acquisition
• Why modern sales trips should feel like “Lollapaloozas”
• The rise of HLG (Human-Led Growth) and what to do about it

Resources mentioned in this episode:

Winning by Design AI – “Talk to Jack”: An AI-powered assistant on the Winning by Design site that answers GTM questions and includes hidden “Easter eggs” for curious users.

Link: https://www.winningbydesign.com/ai

Pavilion: A community platform for reps and leaders to leverage for peer-based networking and customer engagement during sales trips.

Link: https://bit.ly/pavilion-membership

David Spitz Reports on SaaS GTM Efficiency: Mentioned as a leading source for analyzing GTM efficiency across public SaaS companies, especially in relation to CAC trends.

Link: https://benchsights.com/

Connect with Jacco

• LinkedIn: https://www.linkedin.com/in/jaccovanderkooij/
• Winning By Design: https://winningbydesign.com/

Connect with Brandon

• LinkedIn: 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.