Matt Ryan · Chicago

Revenue is an engineering problem. I've spent a career treating it like one.

I build the teams that get AI adopted inside complex enterprises: forward deployed engineering, professional services, and post-sales. I started as a software engineer and still think like one.

Built at
Matt Ryan
VP, Global Solutions & Customer SuccessG2 · 2024 to now
01About

The most technical voice in the executive room.

I started as a software engineer. I still think like one: how software gets built, how it breaks, and what it takes to get it adopted inside a large enterprise.

At IBM, I led multi-year ERP deployments in regulated industries across nearly 40 countries. Sales teams pulled me into deals because I could tell a CIO, honestly, what their investment would produce. I was the person who made the quota carrier credible.

At Alight, under private equity ownership, I scaled a Workday practice from a $10M acquisition to a business approaching $200M. The board did not care about effort. It cared whether the business was getting more valuable, and I still run every decision through retention, margin, and the investor story.

At Slack, I built a team of 65+ forward deployed technical architects through the IPO and the $27B Salesforce acquisition. Then came Upwork and G2, where everything converged: one operating model with AI running across the customer lifecycle.

02Lessons earned

I treat every error as a blueprint.

Early in my career, one misplaced semicolon cut a DELETE statement off before its WHERE clause. Instead of two rows, it wiped more than 400,000 production employment records. We recovered everything. Then my manager pulled me aside.

Since then, I design organizations to engineer mistakes out, not just fix them.

You won't be remembered for the mistakes you make, only for the ones you make twice.
My manager, roughly 400,000 records later
Resilience

Systems that hold under real load, with failure modes designed for in advance.

Repeatability

Delivery that works no matter who is in the room.

Accountability

Named owners, measured outcomes, and postmortems that change the design.

03Expertise

What teams bring me in to solve.

01

Forward deployed engineering and services

Technical teams that work beside customers and turn what recurs into product. Built at Slack and G2.

02

AI across the customer lifecycle

Prediction, agents, and the data underneath them, running from onboarding to renewal.

03

Post-sales architecture

Onboarding, retention, and expansion designed so revenue compounds.

04

Technical pre-sales

Honest answers to what an investment will produce, so delivery never inherits a promise it cannot keep.

04Selected work

Built, shipped, and measured.

G2 · 2024 to now

Professional services from inception

I arrived to no implementation function and retention near 50%. I built the services business, pricing, and a delivery model across three regions.

Slack / Salesforce · 2020 to 2022

Forward deployed engineering, $100K to $11M

Grew a pilot into an $11M annual business and a team of 65+ forward deployed architects on three continents. At Rivian, every vehicle on the production line had its own Slack channel wired to real-time alerts.

Alight / Strada · 2012 to 2020

Workday practice, $10M to ~$200M

Built the delivery framework and go-to-market from a 60-person acquisition. Clients included UPS, Goldman Sachs, and Home Depot.

G2 · 2025

Repositioning G2 for the agent economy

Co-launched G2's commercial MCP strategy, opening G2's data to AI agents as buyers.

ai.g2.com ↗
05Things I build myself

Things I build myself.

I lead teams that build with AI, and I build with it myself.

Personal project

Infiniti

An app that preserves a person's stories, voice, and values so the people they love can keep hearing from them. I'm building it for my son. React, deployed on Vercel.

06Career

Engineer to operator to executive.

2024 to NOWG2 · VP, Global Solutions & Customer SuccessArchitected the AI GTM Operating System; built professional services from inception across three regions; co-launched G2's commercial MCP strategy.
2022 to 2024Upwork · VP, Enterprise SolutionsBuilt the enterprise solutions and post-sales model and contributed to 37% enterprise growth.
2020 to 2022Slack (Salesforce) · Professional Services LeaderBuilt customer delivery, customer experience, and a team of 65+ forward deployed technical architects. Through the IPO and the $27B Salesforce acquisition. Named Slack Leader of the Year, 2022.
2012 to 2020Alight / Strada · VP, Professional ServicesScaled a Workday HCM practice from a $10M acquisition with 60 consultants toward a business approaching $200M, through an Aon spin-off and Blackstone acquisition.
2007 to 2012IBM · Managing Consultant, Global Business ServicesMulti-year ERP and service model deployments for financial services, utilities, and heavily regulated industries. Lived in India over a year, built delivery teams in Poland and the Philippines, worked in nearly 40 countries.
2000 to 2007Baxter International · Software Engineer to Technology Project ManagerBuilt enterprise HR and finance tools in Java and PeopleSoft. Technical lead on a PeopleSoft rollout across 55 countries.
Let's build it

Let's talk about AI in the enterprise.

I speak and write about what it actually takes to get AI adopted inside complex organizations.