mcintyem

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 [email protected] 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]

Sidekick Labs | Senior SWE, R&D Engineer, Intelligence Engineer | 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. We expect you to have a real, current AI-assisted development practice. Our system spans several languages, and we expect you to use AI tools to quickly navigate unfamiliar parts of the codebase so you can comfortably own problems end-to-end across a broad stack.

We are hiring for three roles:

- Senior Software Engineer: You will work across our event-driven architecture. You'll write Go and Python backend services and touch endpoint-deployed browser and desktop components. You need to be comfortable developing in a multi-tenant, microservice-driven SaaS architecture and understand typical scale and security implications for such products.

- R&D Engineer: This is not an open-ended research function. You will take ambiguous feasibility questions tied to our roadmap and return defensible answers inside a week. You'll build handoff-ready prototypes, then shift into engineering mode to personally drive them through to production. You will also define operational envelopes and degradation boundaries, and rigorously deprecate infeasible ideas with documented rationale to avoid future re-litigation.

- Intelligence and Data Processing Engineer: This role is for someone who loves real browser and desktop forensics. You'll use dev tools and debuggers as your primary instruments. Expect to be reading minified code to find where state lives and analyzing network logs to understand undocumented APIs. You will figure out how AI products work and build the prototyping and automation to maintain our software inventory.

To apply: Send an email to [email protected] with the role in the subject. Include a PDF of your resume, a quick sentence or two about a tough technical problem you've solved recently, and links to your GitHub, personal site, and/or LinkedIn.

I'm Eric, VP of Technology, and I will personally read every email sent to the HN subaddress. You can view my background here: https://www.linkedin.com/in/three-two-one

https://sidekicklabs.com

Author here. My wife gave me a dead ~1996 Ernest D3 coin payphone for my birthday; the original board was toast, so I gutted it and rebuilt the internals with a Raspberry Pi Zero 2W, with PoE, audio, and custom HATs + an open-source SIP stack and kept it genuinely coin-operated (escrow, rate plans, intercept tones, and a hidden hold-# refund trick).

Two highlights: the call-progress tones come from the codec's hardware tone generator (it's like IQ had this in mind?) and the software is multiprocess behind a board HAL (including a mock backend so the phone logic is unit-testable without the hardware). Repo has the PCB/BOM/parts too, plus a 3-part write-up. Happy to answer anything.

Write-up: http://blog.1in1e6.com/2026/06/payphone-part-1-new-old-phone...

(for the AI crowd - I architected it, but used Claude Code to fill it in; that's part 3 of the write-up.)