Skip to content

How I got here

Background

A career spent untangling complexity.

I started in payments, learned firsthand how complex systems shape the client experience in wealth management, and went to business school to get closer to the decisions behind them. Since then, I’ve kept moving toward the intersection of product, strategy, and execution — following the same question wherever I go: how can this work better?

A hand-drawn map of the United States.
Miami University
Northern Trust Fiserv
Northern Trust University of Texas
American Express
Six milestones, one throughline. Hover, tap, or focus a dot to see where I studied and worked.

The path

A few roles, one throughline

  1. Master of Business Administration

    Texas McCombs

    Austin, TX

    Where I pulled the threads together — economics, operations, product — and pointed them on purpose at strategy and product work. Less a new field than a name for what I had been circling all along.

  2. Business Strategy Manager, MBA Intern

    American Express

    Sunrise, FL

    A strategy summer between MBA years, and my step closer to product: I mapped a sprawling servicing operation end to end, then handed senior leadership and the product team a prioritized short list of bets worth making.

  3. Associate Wealth Advisor — Second Vice President

    Northern Trust

    Austin, TX

    Relocated to Austin to help grow an employer-sponsored wealth advisory program — shaping the offering, the customer journey, and the operating model behind it. My first real taste of building something new instead of running something built.

  4. Senior Associate, Wealth Strategies — Officer

    Northern Trust

    Chicago, IL

    Two years inside the machinery of a private bank — serving ultra-high-net-worth families and business owners across a dozen teams, on work that rarely looked the same twice. I learned to move through ambiguity and built the playbooks that made the messy parts repeatable.

  5. Sales Analyst, Payment Solutions

    Fiserv

    Chicago, IL

    My first look inside financial services — and an early lesson in how fast an industry can change. Talking with partners about what they were trying to solve, I learned the best answers start by listening for the problem behind the ask.

  6. B.S. in Business Economics, Minor in Spanish

    Miami University, Farmer School of Business

    Oxford, OH

    Economics is where I got hooked on why systems behave the way they do — incentives, tradeoffs, and the gap between how a thing should work and how it actually does.

By the numbers

What the work adds up to

A few figures from the work behind the story — the scale, the growth, and the kind of complexity I like to sit with.

$1.2B

Assets onboarded across 26 complex ultra-high-net-worth relationships.

Northern Trust

36K+

Servicing agents in the ecosystem I mapped to inform a cloud transformation.

American Express

12 → 26

Employer partnerships scaled through a financial-wellness program I helped shape.

Northern Trust

Team revenue growth as that program expanded (~$500K → $1.5M).

Northern Trust

6 → 1

Legacy servicing systems assessed toward a single cloud experience.

American Express

How I work

Different roles. Same instincts.

Make the messy visible

I start by mapping what’s actually happening — systems, handoffs, customer journeys, and the dependencies between teams — until the real problem is on the table.

Make it simpler

Then I look for what can be removed, standardized, or automated. Real leverage comes as often from taking things away as from adding them.

Make it work in real life

The best strategy isn’t the cleverest slide. It’s the one customers understand and teams can actually run.

That’s the background.
Here’s what I’ve built with it.

Selected projects across product strategy, AI-enabled tools, and systems I’ve built to make work a little easier.

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.

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.