About

Hi. I'm Katy. I ask a lot of questions.

I have spent most of my career walking into complicated systems and wanting to understand why they work the way they do.

Portrait of Katy Simmons
Katy Simmons, Little Rock, AR
01The short version

I am genuinely curious about people's work. Show me the spreadsheet you hate. Show me the process nobody understands. Tell me what you do every Friday because the system cannot. Tell me which part makes absolutely no sense but everyone stopped questioning three years ago. That's usually where things get interesting.

I'm a connector and a systems thinker. While someone is explaining a problem, I'm usually already connecting it to three other things I've heard and starting to sketch what could change. Sometimes that produces a big operating model. Sometimes I spend two hours investigating and the solution is embarrassingly simple. Both are good outcomes.

The through-line: Apptegy to 4,000 customers, support rebuilt as a product at The Weather Company, a company-wide AI operating model at SoundCloud, and now AI Operations at honeycomb.io.

02How I work
I listen first
I listen before I prescribe. The request is rarely the problem.
I think out loud
I share half-formed thinking because collaboration improves it.
I want disagreement early
Late agreement costs more than early friction.
I am not attached to my idea
I care more about whether something works than whether my original idea survives.
I like people who tell me what they hate
Show me the spreadsheet you cannot stand. That is where the work is.
I ask why
I will absolutely ask why we are doing something everyone else has accepted as normal.

Where I'm at my best

  • Ambiguous mandates where the scope has to be invented before it can be delivered.
  • Cross-functional work spanning product, engineering, legal, and operations.
  • Organizations adopting AI who want results, not a demo.
  • Teams that would rather be told the truth early than reassured late.

Where I'm not the right fit

  • Roles that need a caretaker of an already-optimized system.
  • Environments where governance is theater and the answer is decided before the research.
  • Work with no access to the people actually doing the job.
03Outside the work

I co-founded Arkansas Women's Outreach, a nonprofit improving access to period supplies and women's health resources in the homeless community. I have mentored founders through a FinTech accelerator, and I have spent more of my career than my titles suggest developing product people whose careers eventually outgrew mine. That is still the part I am proudest of.

Based in Little Rock, AR · Globally Available.

Katy Simmons leaning across an Arkansas Women's Outreach information table, mid conversation with a visitor picking up a flyer
Newspaper clipping headlined about outreach targeting the needs of homeless women in Little Rock, with a photo of volunteers packing supplies
Arkansas Women's Outreach

Arkansas Women's Outreach: the booth, not the board deck.

Katy Simmons on a Girls Who Code panel, microphone in hand, facing a room of seated students with their hands raised

Girls Who Code

Panel, questions, no slides.

Most of what I know about developing people, I learned in rooms like this one: answer the question actually being asked.

Katy Simmons riding in a tight criterium pack wearing number 151, cornering low on a closed street course
Criterium racing

Reading the field, committing before it's safe.

Black and white studio portrait of Katy Simmons, arms folded, looking directly at the camera

Off the clock

Two sons, a bike, and a nonprofit. The parts of my life that keep the work honest, and that taught me most of what I know about ambiguous mandates.

  • Katy Simmons seated at a restaurant table with her two sons, all leaning in for the photo
    Home crew. The original ambiguous mandate.
  • Katy Simmons outdoors on a cool race morning with two family members, race numbers pinned on
    Race morning, three generations deep.
  • Katy Simmons in a cycling kit and helmet, straddling a road bike before the start of a race
    Bike racing: a hobby that rewards early, imperfect decisions.
04What people say
She consistently cut through the noise, evaluating opportunities and pressure-testing their potential.
Maria Von Watzdorf, VP, Product at SoundCloudMaria Von WatzdorfVP, Product at SoundCloudRead in full →
She set the tone for the product team and laid the foundations for the majority of the products that are growing today in Apptegy.
Guillermo Araiza, Staff Product Manager at CrunchyrollGuillermo AraizaStaff Product Manager at CrunchyrollRead in full →
She has strong convictions and ideas, and backs both up through methodical research and validation.
Kathleen Conley, Product Manager at ApptegyKathleen ConleyProduct Manager at ApptegyRead in full →
All reviews →
05Elsewhere

Contact

Let's get into it.

Ambiguous problem, AI adoption that stalled, an operating model that stopped scaling, a support function that should be a product. That is the conversation I want.