I turn operational chaos into seamless systems

Our healthcare customers used our phone- and text-enabled AI workflows to coordinate patient care, so shutting them off to make updates was not an option. With the rapid changes in the AI market, though, we needed to stay on top of new chat and voice models and ensure that they'd follow directions. When new AI models came out, I tested each one against existing workflows before we made any changes, then led migrations across our entire client base.

The result: Zero downtime, more accurate responses, and stronger adherence to safety guardrails.

Over the years, product teams at the company had each built their own payment flows, and none of them talked to each other. Many ran on outdated APIs that needed upgrading to stay compliant and use Stripe's newer features. Some accounts even belonged to abandoned products or those whose owners had left the company years ago. I worked with our partners at Stripe and our Finance and Accounting teams to take stock of everything. I tracked down account owners and closed what we didn't need. Then I worked with our payments engineers to upgrade the accounts we kept.

The result: 50+ accounts streamlined into just a few, with up-to-date APIs, the latest features, and new opportunities for better pricing from our partners.

Trademark enforcement had slipped down the Legal team's priority list, which left our IP exposed, so I built a system for it. I drafted enforcement letter templates for our in-house counsel to review and approve, set up a database of our trademarks and their filing status, and made a kanban board to track violations. Then I automated sending the letters, so the team could focus on judgment calls rather than paperwork.

The result: We more than doubled our IP enforcement capacity.

Answering each chargeback took about six minutes. We could handle it until we couldn't. Our transaction volume got too big, and our team of three couldn't keep up. Chargebacks were going unanswered, eating into our revenue. We tried the representment tools on the market, but they were expensive and didn't fit how we worked. So I designed our own, then refined the scope so our payments engineers could build it in less than a month.

The result: Response time dropped from 6 minutes to under 30 seconds, and we started recovering $200K+ in additional revenue every year.

We had no real way to tell how our Fraud and Risk team was doing or what to improve as the company grew. I outlined the KPIs that mattered, then led a multi-year data project to collect the metrics behind them. As the team scaled up, I wrote our escalation procedures and training materials, and I onboarded and mentored new team members.

The result: Year-over-year improvements and a team that grew to cover fraud and chargebacks for every Automattic product, including the WooCommerce marketplace with over $5B in merchant volume.