Cracked Software Engineer - Special Projects

HeyMilo•San Francisco, CA

About The Position

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. 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.

Requirements

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

Nice To Haves

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

Responsibilities

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

Benefits

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

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