AI Transformation + Product LeadershipKaty Simmons

Turning AI strategy into products, operating models, and measurable results.

For more than 16 years, I've worked across product leadership, business strategy, software development, entrepreneurship, and AI transformation. I've built products, grown businesses, designed systems, and helped organizations solve problems they didn't always realize they had.

Illustrated portrait of Katy Simmons, drawn in blue ink on a pale background. She faces the viewer with long wavy hair and a wide smile.

I figure out what needs to be built, why it matters, and make it happen.

Companies I've worked with

  • The Weather Company
  • The Weather Channel
  • Weather Underground
  • Storm Radar
  • SoundCloud
  • Honeycomb
  • Apptegy
  • The Venture Center

AI transformation

89%
of contracts reconciled automatically end to end
700K/day
tracks scanned in production
6
functions on one AI operating model
Capability
AI evaluation, autonomy, and governance

Product leadership

$20M
ARR the flagship platform reached
800 → 4,000
customers on the flagship
2 → 436
customers on a 0 to 1 product
6
product teams led

Problems I'm brought in to solve

  • Possible ≠ useful.

    The trap

    Just because AI can do something does not mean it should.

    What I do

    I start with the problem, consider the available options, and decide what makes sense. Sometimes that is an AI system. Sometimes it is a report, a rule, a better process, or a clearer way to use the systems you already have.

  • Automated ≠ improved.

    The trap

    If a process is broken, automating it does not make it better.

    What I do

    I follow the work, understand the decisions, find the exceptions, and identify what needs to change before deciding what technology belongs there.

  • A prototype ≠ proof.

    The trap

    A convincing demonstration does not tell you whether something will work in your business.

    What I do

    I look for evidence in real data, real workflows, and the experience of the people who will use or be affected by the system. We want to know where it fails, too. Especially where it fails.

  • Output ≠ outcome.

    The trap

    An AI system can complete a task without solving the problem.

    What I do

    Did the customer get an answer? Did the employee save time? Did someone have to redo the work? Did the organization get the result it needed?

    That is what matters.

  • Usage ≠ capability.

    The trap

    Giving people access to AI does not mean they know how to use it. Completing a course does not mean anything changed.

    What I do

    I care about what people can do, the judgment they apply, and whether their work improves.

  • Activity ≠ progress.

    The trap

    A full backlog, a polished demo, and a green status report do not prove that a project is ready to advance.

    What I do

    Progress requires evidence against agreed outcomes, clear treatment of risk, and honest decisions about what happens next.

How I Approach It →

What All of This Has Produced

I've been fortunate to work on some genuinely interesting problems.

Some were obvious opportunities to build something new.

Others were buried inside processes, assumptions, organizational habits, or technologies that weren't doing what people expected.

Here are a few examples of what happened when we figured out the real problem and did something about it.

01 / BBA Corp

From a bookstore website to a software business.

A request to sell textbooks online revealed an opportunity to own the on-campus experience that larger competitors couldn't easily replicate.

I helped turn that opportunity into an e-commerce business generating approximately $1 million in its first year, then expanded it into a multi-campus platform and built the teams to support its growth.

The important decision wasn't simply to build a website. It was recognizing which part of the customer experience was worth owning.

02 / Apptegy

From an urgent communication problem to a new product line.

When COVID closed school buildings, I conceived Rooms to connect individual classrooms with families.

The product opportunity was clear, but the commercial assumptions weren't. We needed to prove that school districts would pay for a product with a different buyer and budget from our flagship offering.

I held the broader launch until we had that evidence.

Rooms grew from two design partners to 436 customers in two years.

03 / SoundCloud

From AI detection to decisions the platform could actually trust.

Detecting AI-generated music was a technical challenge.

Determining what to do with the results was a product challenge.

I worked on the decision layer connecting model predictions to labeling, review, monetization, and appeals, with particular attention to false positives and their consequences for artists.

I also helped bring approximately 30 AI pilots across six functions into a more coherent roadmap and shared approach.

04 / The Weather Company

From closing tickets faster to reducing the need for tickets.

The original request was a support bot.

I wanted to understand why customers needed support in the first place.

I analyzed redacted support email across three brands, developed a shared taxonomy, and used the findings to help turn support into a product with clear ownership, metrics, and a roadmap.

The opportunity wasn't simply faster responses.

It was improving the experiences that generated the requests.

05 / Honeycomb

From AI experimentation to measurable operational change.

I led discovery across 36 conversations, identifying more than 100 workflows and 400 tasks.

We evaluated 23 AI experiments and prioritized four based on value, feasibility, risk, and ownership.

One opportunity involved Finance reconciliation, where critical rules and information were scattered across contracts, spreadsheets, and institutional knowledge.

I built a system that used AI for contract interpretation, deterministic code for financial calculations, and human judgment for exceptions.

The automated run now takes less than five minutes, compared with a previous process that took roughly a week, with Finance continuing to review exceptions.

The point wasn't to automate everything.

It was to make the process faster, more reliable, and easier for Finance to control.

All case studies →

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 SoundCloud

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.