Founding Software Engineer

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

Founding Software Engineer

You’ll be one of our first engineering hires, working directly with our co-founders to build the product from the ground up — and to shape the architecture, engineering practices, and product direction as we grow.

The work spans a modern AI product: a mobile app police officers use in the field; the AI pipeline that turns voice, photos, and notes into report-ready output; a laptop agent that fills report forms; and infrastructure secure enough for law enforcement data.

This role is an apprenticeship in building and thinking like an engineer at the frontier of AI-driven development. You’ll work shoulder-to-shoulder with our staff and senior engineers, absorb how they make architecture and product calls, and take on real ownership fast as you prove you’re ready for it.

About This Role

• In person, NYC. We work together in the New York City area, with hybrid flexibility. We believe the most effective and fun way to build a company is in a room together.

• In the field. Everyone on the team spends time with customers. Expect some travel to customer sites to watch officers use what you built, then fix what’s wrong.

• AI-native. The founding team ships with AI tools every day. We expect the same fluency in your workflow and look forward to learning from you.

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.

Qualifications

• Genuine fluency and excitement for modern AI coding tools (Claude Code, Cursor, Copilot, etc.) — you already build with them daily and want to stay ahead of how fast the landscape moves.

• Solid CS fundamentals and a track record of shipping working software — internships, coursework, personal projects, or open source all count; production experience isn’t required.

• Fast learner: you can go from an unfamiliar codebase or problem to a working solution with light guidance.

• Strong written and verbal communication skills.

• Curiosity and initiative — you go find the answer rather than wait to be handed one.

• Comfortable with ambiguity and confident asking good questions.

What Success Looks Like

Twelve months in:

• You’re the team’s go-to authority on AI-assisted development — everyone ships faster because of workflows you found or built.

• You can take a fuzzy problem and turn it into a shipped solution with minimal hand-holding.

• You’ve absorbed enough architecture and product context to start making calls of your own.

• Customers recognize you and trust what you’ve built.

• You’re ready for more ownership — and we’re ready to give it to you.