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