GTM Operator & Builder

I close revenue
and build the
systems behind it.

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

Matt Sterbenz
$1M+ ARR grown at Rep.ai

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, I helped grow ARR from ~$150K to over $1M across 70+ logos while increasing ACV and commitment length ~3x. I sourced and operationalized strategic partnerships — Salesbricks, Arrows, Sybill, ScreenSpace — that became core revenue infrastructure.

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

$150K → $1M+
Helped grow Rep.ai ARR across 70+ logos; increased ACV and commitment length ~3x 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
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 →
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 →
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 →

Situation

Action

Outcome

Tools & Projects

I build tools that solve problems I actually have. This section grows as projects ship.

Live
Personal Career Site
This site. Built to tell the story behind the resume — case studies, operating principles, proof of work.
You're here →
In Progress
AI Writing Assistant (Chrome Extension)
A personal Grammarly alternative built on the Claude API. Grammar, tone suggestions, and email polish — tailored to how I actually write. Works in Gmail and LinkedIn.
Shipping soon
Planned
More coming
Building is how I think. More tools in the pipeline — this section updates as things ship.
Watch this space

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

I'm targeting roles that offer true ownership, autonomy, and fast feedback loops. Environments where the work and the outcomes are directly connected.

Explicitly not looking for quota-only AE roles.

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