I’m Jeff Whiteside. I lead security at Chime and start companies on the side.
I started as an engineer at a small software company in suburban Chicago. Cybersecurity consulting pulled me in from there. Six years at Crowe as a risk consultant, doing everything: pentesting, vulnerability management, helping companies build programs that held up under pressure. Then Sutter Health, Credit Karma, and Chime in 2020. I’ve run security engineering, GRC, and now lead security at the senior director level. The company has grown substantially in that time and so has the scope of the work.
The security career is one track. The other is building. I built rifts.to because Mentimeter charges for something that should be free. Hey Coach is a subscription coaching app for men. I’m building HARDMODE, a fitness platform for trainers and clients. The same instinct drives all of it: find the real problem, build something that works, ship it.
I also serve on the board of the Financial Services AI Council.
I write here about business, technology, AI, marketing, and leadership. Not think pieces. Notes from inside the work.
Most of my work happens in parallel. I lead security at Chime full time. Nights and weekends go to rifts.to, Hey Coach, and HARDMODE. The discipline transfers both directions. Security sharpens your ability to scope tightly and fix what breaks fast. Building keeps you close to the real problems that matter.