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 team working directly with customers to bring AI into real hiring workflows.

The Role

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

This is a high-ownership role focused on solving real problems fast. You’ll operate at the intersection of engineering, product, and customer needs, building end-to-end solutions that move the business forward.

What You’ll Do

• Work closely with sales and customers to understand real-world problems
• Build fast prototypes and iterate quickly under tight timelines
• Turn ambiguous requirements into working, end-to-end systems
• Ship across the stack and make pragmatic tradeoffs
• Help translate early solutions into production-ready systems
  
  

What We’re Looking For

• Ex-founders strongly preferred or similar startup experience
• Strong product sense and ability to make decisions without perfect information
• Comfortable working under pressure and hitting tight deadlines
• Deep understanding of software fundamentals (databases, systems, APIs)
• Strong full-stack or backend experience
• Heavy user of AI coding tools (Cursor, Claude Code, Codex, etc.)
• Knows how to use AI to move significantly faster than average engineers
• Able to break down business problems into creative technical solutions
• High ownership, scrappy, and execution-focused
  
  

Bonus

• Experience with LLMs, prompt engineering, or conversational AI
• Experience with real-time systems or voice/telephony
• Experience working with enterprise customers
  
  

Why join

• Competitive base salary bonuses
• Work on high-stakes, high-visibility problems with direct impact on company revenue
  
  

Build fast, ship often, and see immediate results