Software Engineer, Strategic Initiatives

Aiwyn

1d•Remote

About The Position

Aiwyn is the first complete platform for modern Accounting Firms. Backed by top-tier investors like Bessemer, KKR, and Revolution, we're one of the fastest-growing scale-up SaaS companies in the world. We build category-defining technology, and we're doing it with world-class people, processes, and products. We work with the majority of the Top 500 firms in the country. We're modernizing the software accounting firms rely on every day, replacing decades-old systems and brittle integrations with tools they can actually trust, and we have rare product-market fit in an industry that's about to change permanently. The Software Engineer, Strategic Initiatives is one of the most important and high-leverage roles in Aiwyn engineering. This person operates as a force multiplier across the engineering organization — parachuting into the highest-priority bets and owning a portfolio of cross-cutting builds that don't always fit neatly on any single team's roadmap. This is the seat leadership reaches for when something hard, unscoped, and important needs to ship. The work that comes through this seat doesn't fit cleanly into an existing product team. These are the bets that need an owner who can find the angle, ship something real, and know when to push or when to kill it. The mandate is broad: own the high-leverage problems that need an owner but don't have one yet. You won't be told what to build in detail. You'll be trusted with a problem space, given a PM partner and the air cover of leadership, and expected to come back with something that actually works. You'll put your fingerprints on some of the most consequential things Aiwyn ships over the next few years, with impact visible across the company. This is a great role for engineers interested in technical leadership, zero-to-one builders, problem solvers, and future founders.

Requirements

Track record taking things from nothing to something real. You've owned the early-stage arc before — at a startup, on a side project, or inside a bigger company — and shipped it through to actual users. You can describe what it took.
Built agentic systems in production. Multi-step agents, tool use, retrieval, evals. You've shipped something real, you can talk about why your last system worked or didn't, and you know what you'd do differently next time.
Frontier-model fluency. You stay current on what the latest models can and can't do. You have informed opinions on prompt design, structured output, and where each generation breaks down.
Strong full-stack engineer. You can ship a backend service, glue it to a frontend, deploy it, and operate it. You won't be siloed by stack.
Product judgment. You know what "good" feels like when a user touches it. You don't ship demos disguised as products.
Willing to kill your own work. Not every bet pans out. The right answer is to write up what you learned and move on, not defend dead code.
Strong communicator. You can write a one-pager that lands with leadership and hand off a system to a product team without losing them.
Ambiguity is the norm. Many of the problems you'll own don't have clear owners, established processes, or obvious solutions. That's why they need you.
Context switching. You'll be moving between very different domains, sometimes in the same week.
The pace is fast. Aiwyn is growing quickly and the bar for output is high. This is not a role where you'll coast.

Nice To Haves

Experience working on platform products or shared infrastructure
Prior startup experience, especially at the Series A–C stage
Background that spans engineering and adjacent generalist functions (founding engineer, tech lead, solutions engineering)
Experience with fintech, accounting, or professional services software

Responsibilities

Take problems from concept to shipped. Discovery, prototyping, real-user validation, then a clean handoff or a clean shutdown. You own the full arc, with the PM and the team alongside you.
Build natively agentic workflows. Translate our Agent strategy into shipping product — multi-step agents, tool use, retrieval, and the evals to keep them honest.
Set up the loops. Evals, harnesses, sandboxes, MCP servers. The supporting infrastructure that lets the team move fast without giving up rigor. You'll often build these ahead of the actual work.
Run prototypes with real users. Whether internal or customer-facing, you're never building in a vacuum. You're getting feedback, iterating, and killing what's not working.
Partner widely. Product engineering, platform, GTM, customer-facing teams. They're your collaborators and eventually your handoff targets. You earn trust by execution.
Translate frontier-model capability into product. When new capabilities ship (bigger context, better tool use, native vision), you're the first one to ask "what does this make possible for us that wasn't possible before?"
You go from nothing to working in days, not sprints. A problem on Monday becomes something a real user is poking at by Friday. The first version is rough. The second one isn't.
You know when to push and when to stop. A bet either earns more investment or you kill it cleanly and write up what you learned. Things don't linger half-built.
Handoffs are constructive. When something is ready to live in a product team, you've made it easy for them to take it on. They feel handed a gift, not handed a problem.
What you build is reusable. The agents, evals, and tooling you ship aren't one-offs. They reuse the team's primitives and add new ones the rest of engineering reaches for.
The impact is legible. Anyone in the company can point to specific things in production at Aiwyn that exist because this seat existed.