About

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

I am a product and AI executive with sixteen years of experience across B2B SaaS and consumer products. I have led 6 global product teams with 6 direct reports, scaled a platform from 800 to 4,000 customers, and shipped products used by 100M+ people.

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, United States

The 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.

Then I build enough to find out whether I'm right. Sometimes the answer is a product, sometimes an agent or an automation, sometimes a single query, and sometimes it is stopping the work because it should not exist.

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 Transformation at honeycomb.io.

How 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.

What 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 →
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Recent writing

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Elsewhere

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.