Senior Technical Product Manager

Sidekick Labs | Senior Technical Product Manager | REMOTE (US Timezones) | Full-time | $170k to $230k Base + Equity + Health
Sidekick builds AI security software for enterprises. Our sensors observe AI behavior and use in situ. From those observations, our reasoning pipeline produces an application inventory and a risk picture, allowing us to provide real-time intervention and coaching right when it matters.
Compensation: base salary scaled to experience, meaningful early-stage equity, and 100% covered health insurance for you and your immediate family.
We are a highly senior team. Most of us have been founders or on early founding teams, so we operate with high ownership. The PM team is small, and everyone on it has a real, current AI-assisted practice: we design, prototype, and build with AI tools every day.
The role: You'll spend your time with customers and in the product.

You'll run discovery with CISOs and IT teams, guide pilots, and turn what you learn into clear direction for engineering. You'll also build: design and prototype with AI tools, make your own tools for research, analysis, and reporting, and open PRs against the product when that's the fastest way to get something done. On a small team, expect to take on whatever the company needs.
What we're looking for:
- 10+ years building B2B software, at least 5 of them as a PM
- Customer discovery and pilots you ran yourself, ideally with enterprise IT or security teams
- Things you built yourself that you can walk us through: prototypes, internal tools, or merged PRs
- Crisp, clear communication, written and spoken, with customers, engineers, and executives
- Security experience is a plus
To apply: Send an email to hiring@sidekicklabs.com with "Senior Technical Product Manager" in the subject.

Include a PDF of your resume, links to your LinkedIn and any GitHub or personal site, and a short description of something you built yourself (a prototype, a tool, a PR): what it does and why you built it. Include a link if you can share one.
I'm Paul, VP of Product: https://www.linkedin.com/in/paul-riegle/
https://jobs.sidekicklabs.com
https://sidekicklabs.com
[p.p. Eric (hn:mcintyem), VP Technology]