Founding Engineer

About LegalOS

LegalOS is building the AI-native immigration law firm for the world’s top talent and the companies that hire them.

Today, high-stakes immigration cases — O-1s, EB-1s, L-1s, H-1Bs, and other employment-based visas — are still handled through slow, expensive, manual law firm workflows. Companies can pay $10K–$35K and wait weeks or months for a process that should be dramatically faster, more transparent, and more software-driven.

LegalOS combines AI agents trained on decades of immigration case data with licensed attorney oversight to prepare USCIS-ready work visa petitions dramatically faster than traditional firms.

We have deep founder-market fit. Matthew, our CEO, previously founded Legal Bullet, an immigration software company recognized by Forbes 30 Under 30. Matthew and Rachel, our COO, are siblings who grew up around immigration law through their father’s 40+ year immigration practice. Claire, our CTO, rounds out the founding team with engineering experience building AI and compliance systems at scale.

This is a market we know firsthand: we have grown up around thousands of immigration cases, seen decades of attorney judgment up close, and understand the operational pain companies face when trying to hire and retain global talent.

About the role

We are hiring a Founding Engineer to help build the core product and AI workflows that make LegalOS scalable.

You will work directly with Claire, our CTO, and Matthew, our CEO, to turn complex immigration workflows into intuitive, reliable software used by clients, attorneys, and our internal case operations team.

You will own major product surfaces across our Next.js/TypeScript app, Supabase/Postgres backend, AI workflow orchestration, document generation system, and internal review tools.

This is not a normal full-stack role. Your job is to help turn LegalOS from a services-assisted workflow into a scalable, self-serve immigration platform.

The right person is part product engineer, part systems thinker, part AI workflow builder, and part founder. You should be excited to own the messy middle between “this workflow works manually” and “this is now a reliable product system that scales.”

What you’ll do

• Build customer-facing case intake and evidence collection workflows
• Build AI-assisted document analysis, case drafting, evidence mapping, and follow-up question generation
• Build internal case operations tools for tracking active matters, missing documents, deadlines, and filing status
• Build attorney review dashboards that make AI-generated petitions easier to verify and improve
• Improve document generation, source attribution, versioning, and export workflows
• Create product experiences that make LegalOS increasingly self-serve for both clients and attorneys
• Build systems that improve case quality, reduce review time, and let us process more visas without scaling headcount linearly
• Work with the CTO and CEO to define technical strategy across system design, data modeling, service boundaries, and infrastructure choices

What success looks like in your first 90 days

In your first 30 days, you will learn the LegalOS product, case workflow, AI pipeline, and attorney review process. You will ship improvements to an existing product surface, understand where founder/operator/attorney time is being spent, and identify the highest-leverage automation opportunities.

In your first 60 days, you will own and ship a meaningful product workflow end-to-end — for example, improving case intake, evidence mapping, attorney review, document generation, or AI follow-up question generation.

In your first 90 days, you will have made LegalOS materially more scalable: reducing manual review time, improving case packet quality, or making a core workflow more self-serve for clients, attorneys, or internal operators.

The goal is not to ramp slowly. The goal is for you to become one of the people who defines how LegalOS is built.

What we’re looking for

• 3+ years building production web apps, or equivalent evidence of exceptional product engineering ability
• Excellent with TypeScript, React, and full-stack product development
• Strong frontend taste — your work makes other engineers want to copy it
• Comfortable working across frontend, backend, database, AI APIs, and internal tooling
• Strong judgment around system design, database architecture, and scaling product systems
• Experience with modern AI product patterns: agentic workflows, tool calling, streaming, structured outputs, evals, and AI workflow orchestration
• Familiarity with AI frameworks and infrastructure such as Vercel AI SDK, Mastra, MCP, workspaces/filesystems, and sandboxes for agents
• Able to take an ambiguous workflow and independently turn it into a shipped product
• Move fast, communicate clearly, and care about quality
• Excited by legal tech, immigration, and automating expert-services workflows
• Want to join early enough to have real product, technical, and cultural influence

Bonus points

• Shipped AI/LLM products to production
• Experience with document-heavy workflows
• Experience in legal tech, fintech, healthcare, HR tech, compliance, or other regulated industries
• Early-stage startup background
• Major OSS contributions

This is a high-ownership founding engineering role. You should be comfortable talking to users, attorneys, and operators; understanding messy workflows; and building the product systems that make them 10x better.

If you want to help rebuild one of the most important legal infrastructure markets from first principles, we’d love to talk.

Interview Process

Our process is designed to be fast, practical, and focused on how you think and build.

1. Intro call with Matthew, CEO, and Claire, CTO — 30 minutes  

We’ll discuss LegalOS, your background, what you’ve built, and what kind of role you’re looking for.

2. Technical/product conversation with Claire, CTO — 60 minutes  

We’ll go deep on your past projects, technical judgment, product instincts, and how you approach ambiguous engineering problems.

3. Paid 2–3 day work trial + founder working session  

We’ll give you a small, realistic product/engineering project based on a simplified LegalOS workflow. The goal is to see how you build, communicate, make tradeoffs, and turn ambiguity into product.

4. Final conversation with the founding team — 30 minutes  

We’ll discuss role scope, compensation, equity, working style, references, and mutual fit.