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Hi, I’m Maddy.

I turn “that’s just how we’ve always done it” into “why didn’t we do this sooner?”

I’ve spent my career simplifying complex customer experiences across payments, wealth management, and product strategy—connecting teams, building systems, and creating AI-enabled tools that help people work better together.

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Résumé

My experience spans building and scaling new offerings, shaping product strategy for complex transformations, and creating digital tools from scratch.

Across each, I’ve gravitated toward the same kind of work: making sense of complicated problems, connecting teams and customer needs, and turning ideas into products and systems that work in the real world. It’s the work I’m looking to do next, at the intersection of product, strategy, and operations.

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PDF · 259 KB · Last updated August 2026

How I See It

Boring is a feature

The best system is the one nobody notices; if a process needs a hero every week, it’s broken, not resilient.

Simplify before you scale

Automating a bad process just gets you more of it, faster — I fix the workflow before adding a single tool.

Name the tolerated problem

Every team has a broken thing everyone quietly works around; saying it out loud is the first real step toward fixing it.

Clarity beats cleverness

If I can’t explain the fix on a whiteboard in two minutes, it’s too complicated to trust or to maintain.

Translate, don’t relay

My job at the seam of operations and product is turning each side’s shorthand into something the other can actually act on.

Currently

  • 01 — Listening

    Lenny’s Podcast and Morning Brew on repeat.

  • 02 — Building

    Building an AI second brain in Claude Code — because one brain isn’t keeping up anymore.

  • 03 — Thinking

    Thinking about how much more useful I can be now that the line between “I have an idea” and “I can build a version of it” is disappearing.

  • 04 — Learning

    Getting sharp enough with SQL to answer my own questions before I bug the data team.

  • 05 — Enjoying

    Trying to find the best Chicken Caesar wrap in Austin.

Updated August 2026

Contact

Let’s connect.

Whether it’s a role, a referral, or just a good conversation about building things — I’d genuinely love to hear from you.

About

Hi — I’m Maddy.

I didn’t always know I wanted to work in product. I did know that I was unusually bothered by things that were harder than they needed to be.

Early in my career, I kept finding myself more interested in the system around the work than the task itself — why a process took seven steps instead of three, why important information lived in five different places, or why the people closest to a problem rarely seemed to be the ones designing the solution.

Eventually, I realized that was the work I wanted to be doing.

I went to business school to get closer to the decisions behind the products and systems I had spent years working inside. Since then, I’ve gravitated toward the space between product, strategy, and operations: understanding what people actually need, making sense of messy problems, and turning that ambiguity into something a team can build, improve, or act on.

I’m especially interested in what happens between a good idea and something that actually works — the tradeoffs, handoffs, processes, and tiny decisions that determine whether a product makes someone’s day easier or just gives them another tab to open.

Long term, I want to keep getting better at that: learning enough about customers, technology, and the business to connect the dots between them — and helping build things that make people wonder why they ever did it the old way.

Maddy McEnery outdoors in a garden, wearing a green floral dress.

A few true things

  • Based in Austin — by way of the Chicago suburbs.
  • Can happily lose an afternoon thrifting for furniture I don’t need.
  • Will reorganize a shared doc whether or not you asked.
  • Charcuterie board enthusiast; die-hard Chicago Blackhawks fan.