Hi, I’m Steve Cahill.

I turn AI’s potential into practical changes in how work gets done, with measurable business outcomes and a humanist focus.

My experience spans Enterprise AI, Business Systems, and Enterprise Architecture. I connect strategy to the systems, teams, and everyday workflows that make it real.

Building Enterprise AI at Udemy

I led Enterprise AI strategy and adoption, bringing together practical applications, governance, and employee enablement. Our work reached across all company functions, from engineering to sales, finance, legal, HR, and IT, connecting AI investment to the workflows and outcomes that mattered to each team.

One example: Prepper, one of many agents we built inside the four walls of Udemy, brings together customer information, sales content, and a variety of other signals to assist customer-facing roles with preparation for informed conversations. We measured a clear increase in funnel conversion rates and a straight line to increased revenue.

Leading the Technology Behind the Business

At United Talent Agency, I built the enterprise architecture function, consolidating scores of legacy systems obtained through years of M&A. At GrowGeneration, I led digital transformation across supply chain, retail, e-commerce, and finance. At PagerDuty, I built the finance systems team and advanced automation across core enterprise platforms. As a technology consultant, I guided organizations through the decisions, implementations, and changes necessary for lasting transformation.

Those experiences shaped how I approach change: understand the business, make ownership clear, and build something people can operate and improve.

My Philosophy

Start with work worth improving.

Understand where employees lose time, where decisions stall, and where customers experience friction. Choose opportunities with clear owners and meaningful measures of success.

Let humans be human.

People set direction, exercise judgment, and remain accountable. Build evaluation, feedback, and oversight into workflows so that responsibility stays clear as automation grows.

Tech is only part of the story.

Pair useful solutions with hands-on learning, practical governance, and ongoing support. Help employees recognize opportunities and develop the confidence to pursue them. Celebrate loudly.