Matt Sterbenz - revenue and GTM operator

I close revenue. And I build the systems behind it.

Closing is the foundation - founding AE to Head of Revenue at an AI SaaS startup. Then I built Coop, an AI career CRM, solo.

Matt Sterbenz
$3M+ cumulative new ARR closed at Rep.ai. $5M+ total contracted.
70+ logos managed - $1M+ active ARR, grown from ~$150K.
~40% of all new company ARR at Navless.ai, on a 10-person selling team.
3rd of 1,300+ Medicare Advantage sellers nationwide, first sales seat at Willis Towers Watson.
About

Account executive at heart. Operator by demand.

This site is a living document - it grows as the work does.

I'm an account executive at heart who grew into broader commercial and GTM leadership because the environment demanded it. Closing is the foundation. Everything else got built on top of it.

At Rep.ai (formerly ServiceBell) I went from founding AE to Head of Revenue & GTM Operations: revenue P&L, GTM infrastructure, pricing, lifecycle, and the SDRs, AEs, and CSMs running it. Active ARR grew from ~$150K to $1M+ across 70+ logos. $3M+ in cumulative new ARR, $5M+ in total contracted revenue. ACV and commitment length grew 4x+. Partnerships I sourced - Salesbricks, Arrows, Sybill, ScreenSpace - became core revenue infrastructure.

When Rep.ai wound down in early 2026, the founder trusted me to run it responsibly. I protected the customer relationships, met the contractual commitments, and closed every account out cleanly.

Before that, at Navless.ai (formerly Tourial), I closed ~40% of all new company ARR across a 10-person selling team - 30 of ~70 new logos - while ARR scaled from ~$350K to $1.5M+.

My first sales seat: 3rd-most Medicare Advantage sales nationwide out of 1,300+ at Willis Towers Watson.

Lately I build the tools too. Understanding how things work is how I think.

Selected work

The work in detail

Situation

Action

Outcome

What I'm building

Coop.ai. A job-search partner that actually knows you.

A Chrome extension plus a local MCP companion, powered by my own Claude. Built solo - five weeks from idea to daily use. Coop runs my search every day. In private beta.

78 MCP tools · 5 weeks to daily use · 0 API keys needed

No backend. Coop sends nothing anywhere - only my own Claude talks to Anthropic.

Three verbs on every opportunity

Re-reads new signal - meetings, emails, elapsed time - then re-runs the research and scores.

The real thing lives at coopmcp.com ↗

How I work

Operating principles

  • Collective ownership. Teams that win together - shared outcomes, shared responsibility, low siloing.
  • Signal over activity. Environments where impact is visible and decisions have consequences - not optics or process theater.
  • High standards, low ego. Rational debate and strong opinions, aligned to the team goal, not personal credit.
  • Authority matched with accountability. Clear lanes, clear expectations, accountability without micromanagement.
  • Fast feedback loops. I do best when iteration cycles are short and learning compounds in the open.
  • Upside-oriented, not comfort-oriented. I'll trade predictability for real upside, as long as the game is worth playing.

What I am / what I'm not

What I am

  • +Revenue closer and architect
  • +Big-picture and conscientious
  • +Deeply curious, energized by learning
  • +Fluid thinker, strong opinions loosely held
  • +Relationship builder through candor and consistency
  • +High-judgment under ambiguity
  • +Kind of intense - I care and follow through

What I'm not

  • ×A sales bro
  • ×A deck-and-dash seller
  • ×Activity for activity's sake
  • ×Manipulative or games-playing
  • ×Performative or optics-first
  • ×Comfortable with shallow thinking

Where I fit best

Good fit

  • +High-trust teams, clear decision owners
  • +Direct connection: work → business outcomes
  • +Rational, candid communication
  • +Short learning loops, iteration valued

Poor fit

  • ×Consensus-heavy, diluted responsibility
  • ×Activity metrics over impact
  • ×Politics or performative process
  • ×Low-autonomy, high-oversight roles
See my Reiss Motivation Profile

Powered by Attuned - a Reiss Motivation Profile I completed a couple of years ago, sanity-checked against real working patterns since.

What people say

On the record

"A rare strategic partner I've retained across three separate companies. Matt operates less like a vendor and more like a strategic consultant. He bridges sales, customer success, and product with executive presence and integrity. Matt has my highest recommendation."

Ken Jackson VP of Marketing

"Matt showed up as a true design partner during our implementation of Rep.ai. He aligned on clear success criteria, welcomed candid product feedback, and collaborated closely as we refined real-world use cases. He is responsive, clear in communication, and stays engaged in the details while maintaining strategic alignment."

Jennifer McNamara Chief Marketing Officer

"Matt combines tactical execution with strong strategic judgment. From a quote-to-cash and GTM operations perspective, he handled a complex setup seamlessly - integrating Salesbricks, Stripe, subscription management, and reporting. He balances big-picture thinking with operational detail."

Jordan Davis Director of Sales Engineering

What I'm looking for

GTM leadership, or a strategic AE seat at the right seed or Series A B2B SaaS or AI company. Real ownership, autonomy, and fast feedback loops - work and outcomes directly connected.

I do my best work where sales is treated as a thinking function. Leadership chair or an individual seat with real complexity - the bar is the same.

Contact

Get in touch

Hiring GTM leadership or a strategic AE - or you just want to talk revenue. Either way, the calendar is open.