Investing challenges in go-to tech

Jason Gelman’s Background

Jason Gelman is a Go-to-Market Operating Partner at Primary Venture Partners, one of the largest early-stage VC firm that just closed its $625 million Fund V (the largest to date) a few days ago, bringing total AUM to ~$1.6B.

Before Primary, Jason led Revenue Strategy & Operations at Compass, helping scale the company from ~$100M ARR to $6B through their IPO. He got his start in the New York tech scene after attending law school, where he quickly realized the meritocracy of tech was a better fit for him than the rigid hierarchies of the legal world. He’s never looked back.

At Primary, Jason has built out two core programs for portfolio companies: a Market Development team (centralized BD outreach on behalf of founders) and a Go-to-Market Engineering program (tech stack buildout and systems architecture). He's also leading the development of the firm's investment thesis around go-to-market tech.

Discussed In This Episode

• How Primary's portfolio support model actually works and why "advice-giving" doesn’t cut it

• The Market Dev team's unfair advantage: why outreach from Primary converts better than any vendor pitch

• The Go-to-Market Architect role: why it's different from a GTM Engineer (and why Clay's definition falls short)

• Why a profile with deep experience in legacy SaaS tools + fluency in modern AI will easily earn $500K to $1M+/year

•How to find the rare 3-in-30: RevOps chops + AI fluency + business acumen

• The Full Stack GTM person: one role replacing marketer + SDR + AE

• How the PNL test should filter every sales tech investment and why the old "time savings" ROI story is dead

• Where Salesforce is headed in the next 10 years and why its pricing leverage is finally at risk

• Why Slack might be Salesforce's best asset going forward

• Small teams doing massive revenue: what $1M+ IRR per employee actually looks like

• How to break into VC from a go-to-market background

Timestamps

(00:00) Intro & Jason's Background: From Law School to NYC Tech

(07:15) The Go-to-Market Operating Partner Role: What It Is (and Isn't)

(11:38) How Primary's Portfolio Support Programs Were Built

(16:42) The Market Development Team: Primary's Unfair BD Advantage

(21:26) Go-to-Market Engineering: Building the Stack for Founders

(25:43) The GTM Architect vs. GTM Engineer and Why the Distinction Matters

(30:09) Why This Profile Will Earn $500K–$1M+ and How to Find One

(34:21) The Full Stack GTM Role: One Person Replacing Three

(37:07) Primary's Investment Thesis: The PNL Test for Sales Tech

(42:30) Where Salesforce Is Headed and Why Its Grip Is Finally Slipping

(49:04) Small Teams, Massive Revenue: GTM Efficiency Benchmarks

(55:35) How to Break Into VC from a Sales/GTM Background

About The Vibescaling Podcast

The Vibescaling podcast interviews GTM leaders and investors at top AI startups and early-stage companies.

Every week, host Chris Balestras, partner @ Vibescaling (an advisory, recruiting, investing, & media firm for seed through series C AI-natives) sits down with GTM operators from the fastest-growing AI natives and SaaS companies to break down what's actually working in go-to-market today.

No fluff, no theory - just honest, tactical insights from people in the trenches building the next generation of AI breakouts.

About Vibescaling

Vibescaling is an advisory, recruiting, investing, & media firm for seed through series C AI-natives & fast-growing SaaS startups.

Where to Find Vibescaling

LinkedIn: https://www.linkedin.com/company/vibescaling/

YouTube: https://www.youtube.com/channel/UC-rcm2qdgF22H2th_Khrlxg

Newsletter: https://www.vibescaling.blog/

Website: https://www.vibescaling.ai/