About TailoredSim

We make working professionals genuinely good at AI.

Every company bought the AI tools. Very few people are actually good with them, because almost all AI training is videos about AI instead of practice with it. TailoredSim exists to close that gap: hands-on courses where you do realistic work from your actual job, an AI coach helps you through it, and an AI evaluator scores every exercise so the progress is real, and provable.

What we believe

Three convictions run through everything we build.

01

Practice beats videos

Nobody gets good at AI by watching someone else use it. Every TailoredSim course has you doing realistic work from the first minute, with an AI coach beside you when you get stuck.

02

Evidence beats completion

Finishing a course proves attendance. Our AI evaluator scores every exercise the way a demanding manager would, so learners know they are actually improving and employers can see it.

03

Real work beats toy examples

The exercises are the emails, reports, analyses, and workflows of an actual job, tailored to your role, because that is the only practice that transfers on Monday morning.

Who we are

Built by two people who have done this work for real.

Hiram Riddle

Hiram Riddle

Co-Founder

Former Bain and BCG consultant with an MIT MBA. Hiram has spent his career helping organizations decide where investments in people and technology actually pay off.

Mike Wing

Mike Wing

Co-Founder

Led business analytics for the Houston Rockets and built products from day one as a founding engineer, with an MIT MBA. Mike builds the platform and the systems behind it.

Alongside the platform, our services arm builds data and AI systems for businesses and trains the teams who run them. Learn about our consulting work.

See it for yourself.

The fastest way to understand TailoredSim is to take one lesson. It is free, and it is nothing like a video course.

Training for your team