SendTax

Tax preparers spend the season chasing paper. Clients email a W-2 here, text a photo of a 1099 there, forget the third thing entirely, and ask “did you get it?” on repeat. The documents in question are some of the most sensitive a person owns. The process is somehow both insecure and exhausting.

SendTax replaces that with one secure place where a preparer and their client work from the same source of truth. It tells each client exactly which documents to upload, reads each one as it arrives, and keeps both sides in sync until everything is in.

We did not build this for a client. We built it ourselves: one designer and one engineer taking a regulated product from nothing to a live, secure system.

The product’s job is to make a stressful task feel handled. We build an accurate picture of each client’s situation from their prior-year return and a few simple questions, then tell them precisely what to upload: no blank box, no guessing. As documents land, the checklist fills itself in, and a clear “you’re done” closes the loop instead of a silent success.

Because trust is the whole game with tax data, we made it a visible part of the product, not fine print. A public Trust Center lays out, in plain language, how every document is handled and where the security program stands: modeled on SOC 2, and honest about what is in place today.

Holding it all together is one design system, shared across six front-end apps, so the filer app, the preparer app, the admin console, and the marketing site all feel like one product and stay consistent as they grow.

Maps to: Product design and direction·Service design·Design systems

Tax documents demand a backend that is cautious by design. Files are encrypted per document; access is enforced in the database itself, not only in application code; identity is multi-factor; and every read is logged and attributable to a person. None of this is a default we flipped on: each control is a deliberate choice, because with documents this sensitive the cost of getting it wrong is the whole business.

The pipeline that makes the product feel magic is real engineering: documents are classified and their data extracted by domain-specific models, then reconciled against what each client still owes the checklist. It runs asynchronously so the interface stays responsive while the work happens in the background.

The compliance program is automated wherever it can be: the logging, the scheduled reviews, and the reporting a real security posture has to keep producing. That is how two people sustain it without a compliance department.

Maps to: Engineering and infrastructure·AI products and domain models

The reason a two-person studio can ship a regulated product is that we removed the expensive parts of collaboration. We work in the same codebase: design decisions ship as real components, not specs handed across a wall. There is no project manager relaying messages between the person who designs it and the person who builds it, because that is the same conversation between the two of us.

None of that is magic, and it is not just the two of us getting along (although, we genuinely do!). We lean on AI for the repetitive parts of building software, so the two of us can spend our hours on what a model should not be trusted with: the security model, the data design, the content, and what the product should actually do.

We made our process a design problem too. We built the systems that let two people move fast without breaking things: conventions that keep our changes from colliding, security checks that run automatically on every commit so nothing sensitive slips through, and documentation that keeps the whole thing legible as it grows. That is the same lean, careful operating model we bring to client work.

Maps to: AI tooling and team enablement·Documentation·Systems

Our first early-access cohort launched and nobody signed up. Not one person. Rather than guess, we asked a few people directly, and the miss was obvious: we had taken security seriously from the first commit, but we were the only ones who knew it. We were asking people to hand over their most sensitive documents and giving them no reason to believe it was safe.

That is what produced the Trust Center and the written security program. It is the kind of judgment we think clients are really hiring for: noticing what a silent signal means, and turning it into the right work instead of more features.

SendTax is in private early access, with a public Trust Center, a working document pipeline, and a real, maintained compliance program. It is a complete, regulated product, built and run by two people.

If you are building something where the screen has someone’s paperwork, money, or attention on it, this is the level of care we bring, and the size of team it takes us to bring it.