Founding AI Software Engineer — NYC (Hybrid)

Rollout; New York (NY); Hybrid; USD 120,000 - 180,000; Full time

Job summary

Rollout is seeking a Founding Software Engineer in NYC to join our first engineering hire, collaborating with the co-founders to build the product from the ground up and shape architecture, practices, and direction.

You’ll work on a modern AI product including a field mobile app for officers, an AI pipeline for reports, a laptop agent for forms, and secure infrastructure. This apprenticeship-style role offers hands-on ownership and close collaboration with senior engineers.

Qualifications

• Genuine fluency with modern AI coding tools and daily use.
• Solid CS fundamentals with a track record shipping software; internships or projects count.
• Fast learner who can understand unfamiliar codebases quickly.
• Strong written and verbal communication.

Responsibilities

• Be our in-house scout on AI-powered software development — track new models, agents, and coding tools as they ship, and bring back what’s actually worth adopting.
• Analyze our development workflows for opportunities to speed up development and improve testing.
• Sit with customers — in person, in Louisville and beyond — to understand how officers work, and translate that into technical decisions.
• Help evolve the engineering practices and standards the next ten engineers will inherit, working closely with the senior engineers setting them.
• Debug and resolve production issues, with support from the team on the gnarliest ones.
• Document technical decisions and communicate tradeoffs clearly.

Skills

AI tooling fluency

CS fundamentals

Fast learner

Strong communication

Curiosity and initiative

Ambiguity tolerance

Tools

Claude Code

Cursor

Copilot

Job description

Rollout is seeking a Founding Software Engineer in NYC to join our first engineering hire, collaborating with the co-founders to build the product from the ground up and shape architecture, practices, and direction.

You’ll work on a modern AI product including a field mobile app for officers, an AI pipeline for reports, a laptop agent for forms, and secure infrastructure. This apprenticeship-style role offers hands-on ownership and close collaboration with senior engineers.