Careers

Help founders build in America.

Milestone is a team of immigration attorneys and engineers. We’re hiring people who care more about the filed petition than the hours behind it.

See open roles

How we work

A law practice rebuilt around the outcome.

Outcomes, not hours

We sell a filed petition at a fixed fee. Nobody here is measured on time billed.

AI does the groundwork

Evidence mapping, exhibits and first drafts are automated, so people spend their time on judgment.

Attorneys own the judgment

Strategy, advice and every signature stay with licensed attorneys. Engineering builds around that line.

New York, remote-friendly

We’re based in New York and work with people across the U.S.

Open roles

2 roles open now.

Legal

Immigration paralegal

Own cases from intake to filing, working alongside our attorneys and AI tools.

New York or remote (U.S.) · Full-time

Details

Your first 90 days

Run intake and evidence collection for O-1, EB-1A and EB-2 NIW cases.
Organize exhibits and check AI-prepared drafts for accuracy before attorney review.
Keep clients informed on every case you own, from first document to filing.
Help improve our checklists, templates and review steps.

What you bring

2+ years as an immigration paralegal, ideally in employment-based cases (O-1, EB-1, NIW, H-1B).
Precision with documents, USCIS forms and deadlines.
Clear, warm writing for clients who are new to the process.
Comfort with new software, including AI tools.

Nice to have

Experience with E-2 or consular processing.
A second language spoken by our clients.

Apply for this role

Engineering

Founding engineer, AI

Build the system that turns a founder’s record into a filed petition.

New York or remote (U.S.) · Full-time

Details

Your first 90 days

Ship improvements to the evidence-mapping and drafting pipeline used on live cases.
Build the tools attorneys use to review, correct and approve AI output.
Set up evaluation for accuracy and citations, so quality is measured, not assumed.
Work directly with attorneys and clients to decide what to build next.

What you bring

Strong TypeScript or Python, and LLM-based products shipped to real users.
Care for reliability, evaluation and privacy when handling sensitive personal data.
Product sense: you can talk to a user and turn what you hear into a plan.
Enjoyment of a small team where you own whole problems.

Nice to have

Experience in legal or another regulated domain.
Document processing or OCR.
Security and compliance work (for example, SOC 2).

Apply for this role

Visas

Building in America? So are we.

If you need a visa to join us, we’ll map out your path, the same way we do for our clients.

How hiring works

01
Intro call
30 minutes on what you want to do next and what we’re building.
02
Work sample
A short exercise close to the real job.
03
Meet the team
Conversations with the people you’d work with every day.
04
Offer
A written offer with the pay and terms spelled out.

Usually 2–3 weeks from first call to offer.

Apply

Tell us about yourself.

Don’t see your role? Choose “General application” and tell us what you’d bring.

Milestone is an equal opportunity employer. We welcome applicants of every background and don’t discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status or any other protected characteristic.