Cassie Young is a General Partner at Primary Venture Partners, a $1B AUM early-stage firm in New York backing category-defining SaaS, fintech, and vertical software companies. Before investing, she spent 15 years as a GTM operator, serving as Chief Revenue Officer at Sailthru and later Chief Customer & Commercial Officer at Marigold (Campaign Monitor, Sailthru, and other martech brands), where she scaled global sales, marketing, and customer success organizations.

Today, Cassie leads investments while also running Primary’s Impact program, giving founders access to a 30-person team across talent, GTM, and strategic finance, and she continues to teach operators through programs like Pavilion and Duke’s Innovation & Entrepreneurship board.

Discussed in this episode:

• How Cassie “accidentally” became a VC after 15 years in GTM leadership.
• The career advice Bill Gurley gave her that changed her trajectory.
• Why Primary refuses to say “platform” and instead built a 30-person Impact team.
• How she actually sources pre-seed/seed founders before they leave their jobs.
• Primary’s 5-part Founder Outcomes Framework (vision, talent, JDCE, and more).
• The difference between real traction vs. “happy ears” and fake design partners.
• Why she’s picky on GTM/AI tools and looks for step-change, not incremental gains.
• How operators can actually break into VC (hint: it’s all about doing the work).

Episode highlights

00:35 — Clay, usage-based pricing, and the $100M ARR rocketship

09:10 — The real story on AISDR: where AI reps actually work (and where they really don’t)

14:02 — Inside “The Gross Retention Apocalypse” and why AI experimental budgets are a ticking time bomb

22:46 — How Cassie accidentally became a VC and the Bill Gurley advice that changed her career path

27:17 — Why Primary hates the word “platform” and how Cassie built a 30-person Impact team for founders

36:10 — Cassie breaks down her 5-part founder outcomes framework (including “jaw-dropping customer experience”)

46:01 — Avoiding “happy ears”: how founders should really use design partners and MedPick-style rigor

57:48 — Time to value as the new north star and why nailing a tight wedge beats peanut-buttering features

1:01:29 — So you want to be a VC: Cassie’s playbook for operators to break into venture (without delusion)

Brought to you by: AngelList

How did we build the GTMfund back office? Easy!

We leveraged AngelList’s Rolling Fund product for Fund I, which was the perfect vehicle to scale up GTMfund in its first iteration. This structure allowed us to build our network, and add revenue leaders while we raised and deployed capital simultaneously, which was crucial for getting early points on the board and building relationships with founders.

For Fund II, we transitioned to a traditional closed-end fund structure through AngelList. This time with institutional investor support. This model allowed us to be more intentional about our portfolio construction. We worked closely with the AngelList team throughout this process, and they were incredible — always there to support us and our LPs every step of the way.

If you’re raising a fund or are looking to migrate your fund, we highly recommend you check them out. You can do so at www.angellist.com/gtmfund.

The GTMnow Podcast
The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.

Visit gtmnow.com for more episodes and other interesting content.

Dave Boyce is a go-to-market–focused technology executive, author of Freemium, and longtime SaaS operator and board member. Over two decades leading and advising B2B companies, he’s helped founders navigate the shift from sales-led to product-led, from gut-driven to instrumented, and now from manual GTM to AI-assisted systems. Today, Dave teaches revenue architecture and PLG through Winning by Design’s Growth Institute, works with leadership teams on Bow Tie–based growth models, and is all-in on how AI will reshape GTM as a true engineered system.

Discussed in this episode

• Why classic sales & marketing playbooks haven’t caught up to how modern buyers actually buy.
• How the Bowtie model exposes the real levers of growth that funnels hide.
• Why PLG-style thinking is now essential even for sales-led and enterprise motions.
• The 3 first principles of freemium: empathy, generosity, and metrics.
• Where AI can reliably outperform humans across the customer journey, and where it absolutely shouldn’t.
• How to design hybrid human + AI workflows using a clear data model, not vibes.
• What RevOps should own in a modern revenue architecture (and why it can’t just serve the CRO narrative).
• Hard-earned founder lessons from Fundly on reinvention, calling bets early, and letting go of old branches.

Episode highlights

00:00 — GTM is still running 20-year-old playbooks

01:29 — “Sales, marketing, CS… the last unengineered engine”

03:20 — The myth of “just add more heads”

05:50 — The Fundly story: reinvention, too late

08:30 — Why Freemium had to be written

11:01 — Three first principles of freemium

15:25 — Mapping AI across the entire customer journey

19:29 — “Automate the predictable, humanize the exceptional”

25:18 — What the Bowtie exposes that funnels hide

27:25 — Building a “minimum viable Bowtie

This episode is brought to you by our sponsor: ZoomInfo

ZoomInfo is the GTM Intelligence Platform built for sales, marketing, and RevOps.

By unifying data, workflows, and insights into a single system, ZoomInfo helps revenue teams find and engage the right buyers, launch go-to-market plays faster, and drive predictable growth. With industry-leading accuracy and depth of data, it gives your team the intelligence advantage to win in competitive markets.

It’s trusted by the fastest-growing companies and has become the category leader in GTM Intelligence.

Learn more at zoominfo.com.

Follow Dave Boyce (Guest)

• LinkedIn: https://www.linkedin.com/in/boycedave
• Substack: https://daveboyce.substack.com

Where to Find GTMnow

• Website: https://gtmnow.com
• LinkedIn: https://www.linkedin.com/company/gtmnow
• X (Twitter): https://x.com/GTMnow_
• YouTube: https://www.youtube.com/@GTM_now
• Podcast Directory: https://gtmnow.com/tag/podcast

The GTMnow Podcast
The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.

Visit gtmnow.com for more episodes and other interesting content.

Brian Weinberger is the Chief Revenue Officer at Sisense, a leading analytics platform helping companies embed intelligence into every product experience. With over 30 years in sales leadership across New York’s tech scene, Brian has built and scaled go-to-market teams at every stage—from early-stage startups to category-defining giants like Yext, Segment, and Salesforce.

Discussed in this episode

• The evolution of partner selling — from VARs to SIs to ecosystems
• How to know if partner selling fits your GTM model
• The delivery-first mindset that drives retention
• Direct vs. partner motion: Microsoft vs. Salesforce
• Why enablement is the #1 green flag for partner success
• Partner marketing: how to make resellers self-sustaining
• Using AI to power future-ready GTM models
• The case for hybrid work in high-performance sales cultures

Episode Highlights

00:00 — The “year four” moment when partners are selling for you

01:07 — 30 years of selling through partners in New York

03:22 — Start partner strategy with delivery, not distribution

06:32 — Why partner selling creates “superhuman” sellers

09:59 — Salesforce vs. Microsoft: direct vs. reseller — and why the future is hybrid

12:13 — The startup hack: sell delivery on your paper, subcontract partners

17:16 — A 90-day playbook for integration partnerships

21:39 — Hiring the right people to build a partner business

27:18 — How Sisense runs delivery partners and an Australian reseller

29:55 — White-labeling Snowflake: using resell to get the giant’s attention

This episode is brought to you by our sponsor: BoomPop

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Follow Brian Weinberger

• LinkedIn:https://www.linkedin.com/in/brianweinberger

Recommended Books

• What Great Salespeople Do by Michael Bosworth & Ben Zoldan — The power of storytelling in sales
• The Power of Nice by Linda Kaplan Thaler & Robin Koval — Why kindness compounds in business
• Sacred Hoops by Phil Jackson — Coaching and leadership lessons from the Bulls dynasty

Referenced

• Sisense: https://www.sisense.com
• Snowflake: https://www.snowflake.com
• AWS: https://aws.amazon.com
• Salesforce: https://www.salesforce.com
• Microsoft: https://www.microsoft.com
• Accenture (SI example): https://www.accenture.com

The GTMnow Podcast
The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.

Visit gtmnow.com for more episodes and other interesting content.