Cracked Software Engineer - Special Projects

HeyMilo AI

$80K — $120K *
Enterprise Technology
Less than 5 years of experience
Job Overview by Ladders

Qualifications

  • 5-7 years of strong full-stack or backend experience (Python, TypeScript, etc.)
  • Familiarity with LLMs and prompt engineering
  • Extensive experience using AI coding tools (Cursor, Claude Code, Codex, etc.)
  • Strong fundamentals in databases, APIs, and system design
  • Ability to deconstruct complex problems into straightforward solutions
  • Demonstrated high ownership and execution focus
  • Comfortable working under pressure with tight deadlines

Responsibilities

  • Build and ship full-stack solutions quickly
  • Prototype new AI-driven features and workflows
  • Translate ambiguous requirements into functional systems
  • Iterate rapidly based on user feedback and real usage
  • Make pragmatic decisions to enhance speed and efficiency

Benefits

  • High ownership and fast-paced iteration
  • Opportunity to tackle real problems faced by real users
  • Small team environment with minimal bureaucracy
  • Engagement with high-impact challenges across customers and products
  • Competitive pay and comprehensive benefits, including RRSP matching
Full Job Description
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

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