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