Cracked Software Engineer - Special Projects

About HeyMilo

HeyMilo is building AI interviewers that run real conversations with candidates. We help companies screen faster and make better hiring decisions using conversational AI.

We’re a small, fast-moving team working directly with customers on real problems.

The Role

We’re hiring a cracked software engineer to work on special projects.

This is a high-ownership role where you’ll solve ambiguous, real-world problems and ship quickly. You’ll operate across product and engineering, building end-to-end solutions that actually get used.

What You’ll Do

* Build and ship full-stack solutions quickly

* Prototype new AI-driven features and workflows

* Turn ambiguous requirements into working systems

* Iterate fast based on real usage and feedback

* Make pragmatic tradeoffs to move fast

What We’re Looking For

* Strong full-stack or backend experience (Python, TypeScript, etc.)

* Experience with LLMs and prompt engineering

* Heavy user of AI coding tools (Cursor, Claude Code, Codex, etc.)

* Strong fundamentals (databases, APIs, system design)

* Ability to break down complex problems into simple solutions

* High ownership, scrappy, and execution-focused

* Comfortable working under pressure and hitting tight deadlines

Bonus

* Experience with conversational AI or telephony systems

* Experience building production AI systems

Why join

* High ownership and fast iteration

* Work on real problems with real users

* Small team, no bureaucracy

* Work on high-impact problems across customers and product

* Competitive pay, benefits, and RRSP match