Jason Miller is the VP of Sales at Unify, a signal-based selling platform helping go-to-market teams connect buyer intent to personalized outreach at scale.

Before Unify, Jason spent just over seven years at Monday.com, joining as one of the first 12 US sales hires when the company was almost entirely PLG and didn't even believe it needed a sales team. He helped build the outbound motion from the ground up, moved into sales leadership, and scaled the company through hypergrowth to IPO.

Prior to Monday.com, Jason was at Convey (now project44), where he took over the founder-led sales playbook and built out the SDR and AE teams in the scrappiest of environments where you either learn fast or you don't last.

He came up reading Predictable Revenue, built his career on the belief that inputs always drive outputs, and carries a clear philosophy into every org he joins: hire slow, keep the bar high, and don't confuse quota attainment with talent.

Timestamps

(00:00) Cold open: the Mount Rushmore of GTM signals(02:28) Jason's background: falling into sales and finding SaaS(05:30) What makes the Israeli tech scene different from SF and New York(09:35) Crossing the PLG chasm: why he left Monday for a sales-led company(10:19) Why he almost didn't join a go-to-market company (and what changed)(12:07) How to evaluate founders in an interview process(14:14) The dating analogy: finding the right sales culture fit(14:50) The hiring mistake that taught him never to lower the bar(16:52) How to prevent "shiny object" bias in an interview loop(18:56) What top candidates actually do differently (the follow-up problem)(20:24) Asking better questions: layers, active listening, and interview-as-discovery(22:23) The $1M growth hire and the future of the sales team(25:52) The sales tech landscape in 2026: how to cut through the noise(29:04) Ideal stack for a Series B AI-native: CRM, CI, sequencer, signals(30:53) Clay vs. Unify: how to think about using both(33:24) PLG vs. SLG: what really changes when the inbound stops(38:17) The three metrics every AE should track(39:46) Why quota attainment can be misleading(45:13) Cold outbound isn't dead (it just has to be better)(47:45) Roleplay, reps, and why HyperBound might be the most underrated tool(50:05) Methodologies that actually matter: MEDIC, MEDDPICC, Spiced

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/

Evan Cassidy’s Background

Evan Cassidy is the VP of Sales at Decagon, the leading AI-native customer support platform. He joined as the company's first sales hire when it was doing less than $2M in ARR. Now? Decagon is valued at $4.5B, and Evan has been instrumental to scaling the GTM org along the way from a team of ten through Series A, B, C, and D.

Before Decagon, Evan held sales leadership roles at Drift and Dropbox (after getting rejected the first time and doing a 10-month stint at Yelp to build his foundation) before reapplying and landing the role.

Before getting into tech, Evan was a competitive rower: captain of Columbia's heavyweight team, two-time US Under-23 National Team member, and spent time at the Olympic Training Center in Oklahoma City.

Evan had an unconventional start to his career after not starting full-time work until 25 that included driving across the country to San Francisco with no job, no plan, and not much money.

His career has been a study in reinvention and in knowing when to throw yourself in the deep end.

Timestamps

(00:00) Intro & Evan's story: from rowing to Oklahoma City to San Francisco

(06:16) Columbia's 100-year rebuild in 2 years and how that shapes Evan’s approach to team building today

(11:22) What traits replace "former athlete" for candidates who didn't play college sports

(15:17) Breaking into tech in 2013 and why Dropbox was the target

(20:06) Getting rejected, going to Yelp, and coming back to get the job 10 months later

(25:12) Why most people ruin their job search by skipping the inner work

(28:45) The Never Search Alone approach and the feedback that redirected his career

(33:00) What "feeling stuck" actually feels like and how one moment with an exec coach shifted things completely

(40:50) Joining Decagon with a 2- and 3-year-old and under $2M in revenue

(46:11) The AI bifurcation and why salespeople need to move now

(51:37) What Decagon's GTM culture looks like and who is actually a good cultural fit

(57:15) Building a magnetic organization: what it means, why it matters(01:01:30) Where customer support automation goes from here

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/

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/