The short version

We are building software that companies can trust with the written answers they give their customers, where a wrong answer is a broken commitment. You will be the engineer who makes sure it deserves that trust: helping shape the first release as it is built, proving it against its promises, and carrying it into our first clients' own environments. Few roles let one engineer see a product from the first checkpoint to live use, and leave their mark on both.

Why this role exists now

Our product is specified in detail, and its first full release is being built now. You come in before the build's first checkpoint, as the engineer who reads what is built, tells us whether it does what the specification promises, and then carries it into our first clients and stands behind it there. Your judgment shapes how we run the build, and every installation after it.

What we do

We build verification-first document software for United States mid-market companies in compliance-heavy industries, where a written answer to a customer is a commitment. The software runs inside each client's own cloud account. Client content stays within environments the client controls, the software sends nothing out on its own, and a named person at the client reviews every answer before it goes out. The venture is founded by two experienced operators and is in stealth.

What you will do

During the build

- Work day to day with the build team: answer technical questions, keep one running log of open questions, decisions, defects and risks, and make sure every technical clarification is written down. Anything touching scope or schedule goes to a founder.
- At each checkpoint, read the code, tests and architecture in our repository, and check them against the specification and against criteria written in advance. Flag what is missing or does not behave as promised.
- Run our evaluation and acceptance tests at each checkpoint and report the results with evidence.
- Turn every defect into a reproducible case built on synthetic data, so no client material is ever needed to fix it.
- Recommend acceptance or rejection at each checkpoint. A founder decides.

With our first clients

- Run a rehearsal installation in a clean environment: install, upgrade and roll back, and get the installation guide fixed wherever it is wrong.
- Install at each client alongside their information technology staff, under access they grant for the session: permissions, networking, sign-in through their identity provider, and the connections the product needs.
- Inside each client's environment, prepare their approved content with them and tune the system against our evaluation tool.




- Draft the technical sections of the security questionnaires our buyers send us (where data lives, who can access it, encryption, backup and incident response) for a founder's sign-off.

Once clients are live

- Run scheduled quality sessions with each client's team, under access they grant for the session. Explain in plain language why the system produced what it did, and propose what should change.
- Diagnose problems from logs that by design contain no client content, run the regression check on every release, and guide each client through the upgrades they start.
- Bring what you learn at clients back as proposals for what goes into each release.

Where this role can go The first release is the beginning, not the job. We are building a company that finds where compliance-heavy companies spend their best people's time on written work, and builds products that do that work faster, to a standard those companies can put their name to. Our first product is one of several we plan for the same clients. As the company grows, this role can grow with it, for the person who shows they are ready:

- Find the next problem. Every installation shows you how a company really works. Spot where that work could be done better, and help shape what we build next.
- Build, not only check. Take a growing hand in how each new product is designed and built, from the first architecture choices onward.
- Bring the frontier in. Track what is current in AI, judge what is genuinely ready for companies that cannot afford a wrong answer, and bring the best of it into our products.
- Lead. Grow into the company's technical authority alongside the founders: the voice our clients' technical teams trust, a trusted partner to the founders on the decisions that shape the company, and a leader in how our engineering grows.

None of this is promised on day one. It is the direction we hope the right person grows into, and it is why we call this a founding role. And because your stock option grant is a founding grant, you share in every product we build after the first.

Who this fits

What we need

- You have held software you did not write to a specification, and you can describe a release you sent back and why.
- You read application code, ideally Python, well enough to check a system you did not write against what it promises,



and you can run its build and test suite yourself.
- You have installed, upgraded and supported software inside environments you did not control, such as customer cloud accounts or regulated enterprise environments, and you can describe a rollback you performed. Amazon Web Services experience matters most.
- You write defect reports, installation guides and questionnaire answers that a reader outside your team can follow cold, in plain language without unexplained jargon.
- You are obsessed about client success, your own learning & development, and contributing to winning

Strong pluses

- You have measured the output of a search or language model system with test sets and thresholds, rather than judging it by eye.
- You have answered security questionnaires for a product you supported, or worked with clients in a regulated industry.
- You use AI coding tools daily and check what they produce.
- Fluency in English is a must, fluency in Korean is a nice-to-have

You might be a forward-deployed or solutions engineer at a company that deploys into customer cloud accounts, a senior engineer who has moved into delivery, or an independent consultant who has led builds and owned the code review and the installation guide.

How you are paid

This is built for someone who wants to own part of what they build. You receive a significant founding stock option grant, the kind usually reserved for a company's first technical person, vesting over time with acceleration at each milestone. During the build, cash is paid for each checkpoint review you complete, whatever its outcome, and at each client installation that goes live.

Once our first clients are live, cash moves to a market day rate. It will not compete with a salary during the build; it is designed to compete on what you own in three years. This is an independent contract engagement to begin with, and the grant is made once our option plan is adopted, subject to board approval.

We are hoping you can help grow this role into a full-time position.

How we select A first conversation. Shortlisted candidates then read part of the specification under a non-disclosure agreement, and the second conversation includes a short practical session: we look together at a small piece of code and ask whether it keeps one of the product's promises, and we talk through what could go wrong at a first installation. Nothing in the process asks for unpaid written work.

Candidates must be legally able to provide services in the United States or Canada. We welcome applicants of every background and consider all qualified candidates without regard to any characteristic protected by law.

📌 Founding Engineer, Build and Deployment (Toronto)
🏢 Rainharbor
📍 Toronto