Hi, I'm Taylor Riley

I'm a technical leader who thrives at the intersection of complex systems and real human impact. I don't just manage — I build.

Growing up in Dubuque, Iowa, I learned the value of hard work early — excelling in tennis at Hempstead High School, then earning dual degrees in Accounting and Finance at the University of Iowa. Working through college in restaurants taught me how to handle pressure, read people, and stay calm when things go sideways.

My career started in the TaxAct call center during the 2008 financial crisis — answering calls from people genuinely struggling. That experience shaped everything. I discovered that the technical side of tax software, mixed with real problem-solving, was exactly where I belonged. I could architect systems and understand the human beings they serve.

I moved quickly — Tax Analyst I, II, Senior, Principal — then relocated with my family to Northern Virginia when my wife Emily received a great opportunity. I became one of TaxAct's first fully remote employees, later helping pave the way for the company's smooth transition to remote work during COVID. When Cinven acquired TaxAct and Drake Tax, I stepped into management to tackle the challenge of merging two very different tax software companies into one.

Then the AI wave arrived, and I did what I always do — I built. Instead of waiting for tooling to show up, I wrote a code intelligence MCP server that indexes 63 repositories into a searchable knowledge graph, and an anti-fabrication documentation system that stops language models inventing DSL syntax that doesn't exist. That work is why I'm now the AI ambassador for our tax development department — the person the org routes AI evaluation and adoption through. Getting a model to be useful is easy; getting it to be trustworthy when the output becomes someone's filed tax return is the actual problem, and it's the one I find genuinely interesting.