Head of Engineering

About Beemo

Building custom software used to be a privilege of scale. Only enterprises could justify it, so everyone else rented what a vendor decided to build. AI has collapsed that cost, and we believe the firms that own their technology will outcompete the ones renting it.

Beemo Automation makes that achievable for wealth management firms. We build custom AI systems inside each client's own cloud environment, so the firm owns the infrastructure outright while we build and operate it for them. Our clients are independent RIAs and multi-family offices representing more than $100B in combined assets.

This is not a thesis we're testing. It's a business: bootstrapped, profitable, and having served more than 50 firms in the last two years. Our headquarters is in downtown Chicago, where most of our team is based.

About the Role

We are hiring our first Head of Engineering to own how we architect and deliver client systems. We have a delivery team shipping client work today, and you will lead them technically: defining our standards, leading our most complex engagements, and representing Beemo in client architecture and security reviews.

You will also own the platform that makes our delivery model work. The internal tooling, AI-assisted development workflows, evaluation harnesses, and review gates that let a small team ship production software into regulated environments safely and repeatedly. Making that system trustworthy is as central to this role as any single client build.

We are open to remote candidates anywhere in the US. We have a strong preference for people in Chicago who want to work hybrid out of our downtown office, and either way you should expect periodic travel to client sites.

What You'll Do

Design the architecture for AI systems that run inside client cloud environments: identity, access, data boundaries, and the agent patterns built on top of them.
Lead our hardest client engagements from first whiteboard to production.
Own the room in client architecture and security reviews, with CTOs and information security teams on the other side of the table.
Build the delivery platform that makes our model work: AI-assisted development workflows, evaluation harnesses, CI, and review gates that make speed safe in regulated environments.
Set the engineering standards the rest of the team builds inside.
Make the technical case for Beemo in the proposals and architecture documents that decide whether we win.

What You'll Bring

Must-haves

10+ years of software engineering experience, including ownership of production systems.
Deep Microsoft Azure expertise across compute and integration (Functions, Container Apps, Logic Apps), AI services (AI Foundry, Copilot Studio), and data storage (Blob/ADLS, Azure SQL, AI Search).
Strong command of Azure identity and governance (Entra ID, RBAC, Key Vault) in tenants you don't control.
Experience deploying and operating systems within a client's cloud environment and governance model.
A track record of passing enterprise security review in a regulated industry such as financial services, insurance, or healthcare.
Ability to lead technical discussions independently with client CTOs and information security teams.
Hands-on experience with AI-assisted development tools and workflows.
Strong written communication skills.

Nice to have

Consulting, professional services, or embedded engineering experience.
Background in wealth management, financial services, or fintech.
Experience building internal developer tooling or platform standards.

Compensation and Benefits

$190,000 to $240,000 base salary, commensurate with experience.
Performance bonus tied to delivery performance, paid quarterly.
Meaningful equity participation.
Health coverage via ICHRA.
Unlimited paid time off.
Hardware and home office setup.
Remote-friendly, with a hybrid schedule available for Chicago-based team members.