GTM Operator & Builder

I close revenue.
And am capable of building the systems behind it.

End-to-end: pipeline, conversion, expansion, retention — and the infrastructure that makes it repeatable.

Currently shipping Coop.ai — a personal CRM I built and use every day.
Matt Sterbenz

Revenue operator.
Systems architect.
Builder.

I've spent my career in founder-led SaaS environments where the expectation is full ownership — not just a number to hit.

This site is a living document — I've just started building it to tell the full story. It grows as I do.

I close complex SaaS deals and build the revenue infrastructure behind them. I'm most energized when I can own the full picture — pipeline through retention — and create systems that make good outcomes repeatable.

At Rep.ai (formerly ServiceBell), I helped grow active ARR from ~$150K to over $1M across 70+ logos while driving $3M+ in cumulative new ARR and $5M+ in total contracted revenue. ACV and commitment length grew 4×+. I sourced and operationalized strategic partnerships including Salesbricks, Arrows, Sybill, and ScreenSpace, to name a few. These became core revenue infrastructure. I also led the company's responsible wind-down in early 2026, owning customer transitions, offboarding, and difficult revenue conversations as the founder's trusted operator through the closing phase.

At Navless.ai (formerly Tourial), I closed ~40% of all new company ARR across a 10-person selling team and added 30 of ~70 new logos, helping scale ARR from ~$350K to $1.5M+.

I architect HubSpot-centric systems, structure deals at the executive level, and own the full revenue lifecycle from first call through renewal. And lately, I build tools — because understanding how things work is how I think.

Highlights

$3M+ New ARR
Drove $3M+ in cumulative new ARR and $5M+ in total contracted revenue across 70+ logos; ACV and commitment length grew 4×+ through executive negotiation and deal structuring.
Rep.ai
~40% of ARR
Closed ~40% of all new company ARR at Navless.ai across a 10-person selling team; added 30 of ~70 total new logos during tenure.
Navless.ai
4 Partnerships
Sourced, negotiated, and operationalized strategic partnerships (Salesbricks, Arrows, Sybill, ScreenSpace) that became core revenue infrastructure.
Rep.ai
Revenue Systems
Architected HubSpot-centric revenue systems integrating billing, onboarding, AI-driven insights, and lifecycle tracking into one operational layer.
Revenue Ops
Deal Execution
Closed complex technical SaaS deals via live product demos, executive-level negotiation, and structured contract design.
Sales
High Judgment
Led high-judgment customer transitions during a company wind-down — protecting relationships and managing revenue exposure with discipline.
Transitions

The Work in Detail

Revenue Leverage Systems Thinking End-to-End Ownership AI-Assisted Execution Pragmatic GTM Retention & Churn
HubSpot onboarding pipeline
Revenue Operations / GTM Infrastructure
Architecting the Full Customer Lifecycle System
Customer onboarding, lifecycle tracking, and revenue visibility were fragmented. Several million in ARR flowed through disconnected workflows, creating ambiguity in handoffs and limited retention insight.
Lifecycle ArchitectureHubSpotRevenue Systems
Read more →
Salesbricks case study
Revenue Operations / Rep.ai
GTM & Revenue Infrastructure Overhaul via Salesbricks
Rep.ai's sales process lacked professional billing and closing infrastructure. As ARR grew toward $1M+ across 70+ logos, the existing workflow couldn't support increasingly complex deal structures.
GTM OpsStrategic PartnershipDeal Architecture
Read more →
Interactive product tour
GTM Strategy / ServiceBell
Interactive Product Tour as a GTM Lever
Prospects struggled to quickly understand product value during early-stage sales conversations, slowing evaluation and deals.
Product GrowthInteractive DemoScreenSpace
Read more →
GTM Strategist
Quality-First GTM Conversion Strategy
Many SaaS teams default to maximizing lead volume — gating content, optimizing for downloads, and equating more leads with more growth.
GTM StrategyDemand QualityBuyer Experience
Read more →
Executive Operations
Customer & Revenue Stewardship During a Wind-Down
The company entered a wind-down phase with active customers, contractual commitments, and real revenue exposure. The environment required calm, high-judgment execution under financial and reputational constraint.
Executive JudgmentCustomer TrustRevenue Ownership
Read more →
What I'm building

Coop.ai. A personal CRM for the job search you're actually running.

A Chrome extension that auto-detects companies, scores roles against your preferences, and runs an AI advisor with real context about your pipeline. Built and used every day in my own search. In private beta.

Runs entirely in your browser. No backend, no data leaving your machine.
Live now · Coop.ai
Every email, meeting, and posting auto-attached to the right opportunity.
Stitches Gmail, Calendar, Granola, and the job site you're on into one workspace.
Helix Labs Solutions Architect $80MSeries B Sarah2h ago Tue 2pmintro call31 Q2 sync"GTM lean"g 8.4match JD$180K-$220K
7
integrations stitched
5 weeks
from idea to daily use

Operating Principles

Derived from an intrinsic motivators assessment I took a couple of years ago, synthesized and sanity-checked against real working patterns over time.

Powered by Attuned — Reiss Motivation Profile, completed a couple of years ago. Model-assisted synthesis, sanity-checked against real patterns.

  • Collective ownership. I'm motivated by teams that win together — shared outcomes, shared responsibility, low siloing.
  • Signal over activity. I prefer environments where impact is visible and decisions have consequences — not optics or process theater.
  • High standards, low ego. I value rational debate and strong opinions, but I'm aligned to the team goal, not personal credit.
  • Authority matched with accountability. Clear lanes, clear expectations, and 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 leverage, as long as the game is worth playing.

What I Am / What I Am 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-driven or quota-only
  • 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

What People Say

"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 Account Executive seat at the right company. I'm targeting roles that offer real ownership, autonomy, and fast feedback loops — environments where the work and the outcomes are directly connected.

I do my best work where sales is treated as a thinking function — where I'm expected to build, influence, and operate beyond just the number. Whether that's a leadership chair or an individual seat with real complexity, the bar is the same.

Get in Touch

Whether you're hiring, exploring a partnership, or just want to talk GTM — I'm open to the conversation.

Send a message