Weekend Software Developer Ai Trainer Jobs in Boston, MA

OnRamp transforms B2B customer onboarding into a revenue driver. Our platform automates workflows, streamlines playbooks, and accelerates time-to-value, helping enterprises reduce onboarding time by up to 70%. Backed by leading investors (we just raised our $15M Series A) and trusted by Fortune 15 companies, we’re redefining how companies bring new customers online.

We’ve built the system of record for post-sale workflows, powering onboarding and expansion for enterprise customers including Fortune 15 companies. Now we’re evolving that foundation into something much bigger: an intelligent system that actually does the work.

We’re building an agentic platform that eliminates friction in the B2B customer relationship.

We’re hiring a software engineer who has figured out what most engineers are still catching up to: how to use AI to build enterprise-grade software dramatically faster — without sacrificing quality.

To be clear about what this is and isn’t: this is not an ML research role, and it’s not a prompt-engineering role. It’s a software engineering role for someone with real fundamentals who has made AI a core part of how they build — someone who directs coding agents, runs parallel workstreams, and ships in a week what used to take a team a quarter.

This is a high-impact individual contributor role on a small, elite team, reporting directly to our Head of Engineering. Our whole engineering organization is being built around AI leverage — you won’t be the odd one out fighting for tooling budget. You’ll be a founding example of how we work.

We’re deliberately not posting a checklist of frameworks and years of experience. We care about what you can build and how fast you learn, not what your last title was — we’ll calibrate level, scope, and compensation to you.

• Ship enterprise‑grade features end to end — from ambiguous product problem to production — at a pace that surprises people, with AI in the loop at every step

• Direct coding agents (Claude Code, Cursor, Codex, or whatever wins next) as a force multiplier: parallel workstreams, asynchronous agents finishing work while you sleep, and your judgment steering all of it

• Own the quality bar that makes speed sustainable: architecture, code review, testing, and guardrails that keep AI‑generated code enterprise‑ready — our customers include Fortune 15 companies

• Work across the full stack of a modern web platform on AWS, including the agentic AI features inside our product

• Help write the playbook for AI‑augmented development at OnRamp — the workflows, tooling, and standards that make every engineer here faster

• Partner tightly with Product and talk directly with customers, so what you build maps to real value

• A software engineer first. You have strong fundamentals — system design, data modeling, APIs, debugging, testing — because AI amplifies judgment; it doesn’t replace it

• You’ve fully integrated AI into how you build. Not autocomplete — agents doing real, delegated work. You can describe your workflow in detail and it’s clearly ahead of the curve

• You have proof. You can point to production software you shipped with AI leverage — solo output that used to require a team — and explain exactly how you did it

• You know where AI fails. You’ve developed the review discipline, testing habits, and skepticism to catch what agents get wrong before customers do

• Enterprise‑minded: you understand that reliability, security, and data integrity are features, and you build like people’s businesses depend on your code — because they will

• High ownership and product‑minded — you run toward ambiguity, make calls, and measure yourself on outcomes, not tickets

• The entire company is built around this way of working — AI leverage is the engineering strategy, not a side experiment

• A lean team shipping at the impact of a much larger organization, on a real product with real enterprise customers

• You’ll help define what AI‑native engineering looks like — and build a career story very few engineers can tell yet

We’re a Boston‑centered engineering culture — our home base is a top‑floor office in Fort Point, and we do our best work when we can get in a room together. We prefer candidates local to Boston who want to be in the office a couple of days a week. That said, for the right person, we’re open to remote.

• Build a category‑defining agentic platform used by enterprise and mid‑market clients, including Fortune 15 companies

• Join a high‑growth AI‑first company that just raised its $15M Series A led by top investors

• Small team, huge surface area — high ownership, low bureaucracy, and your work ships to real customers fast

• An AI stipend for tools, subscriptions, and experiments that help you work smarter

• Highly competitive cash compensation, equity with real upside at our stage, and comprehensive benefits: health, dental, and vision; unlimited PTO; paid parental leave; 401(k); and education and wellness stipends

OnRamp is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic. OnRamp considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. OnRamp is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. If you need assistance or an accommodation due to a disability, please don’t hesitate to let us know.