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