Who is Aiwyn and what do we do? 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. To learn more, visit our website 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 role 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.
What you'll do You'll have a diverse portfolio encompassing some of the highest priority initiatives at the company. Some of the things you will work on could include: 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?" What good looks like 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.
What we're looking for Must haves: 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. Nice-to-haves (not required): 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 What to expect 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. Interview process We'll share a detailed interview plan with you on the intro call. The loop is designed to mirror the actual job: real artifacts to react to, conversations that look like the conversations you'd have on
the team, and reference checks taken seriously. We'll move quickly when there's mutual fit.
Why Work at Aiwyn? The big-picture value proposition of this role is simple: join us, and you'll be paid competitively to have freedom in solving worthwhile, challenging problems alongside other A-players at a fast-growing SaaS startup led by an experienced and successful team with industry experience AI-by-Default - you'll have access to best-in-class AI tools and work in an environment that embraces an AI-by-default mindset, where curiosity and experimentation are part of how we operate Remote-first organization Competitive
compensation and
benefits Stock options 401(k) matching Adventure Travel Stipend on each anniversary of your employment with Aiwyn Our Values: Relentless by Design Owners not Renters Trust at the Core Aiwyn is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to age, ancestry, color, family or medical care leave, gender identity or expression, genetic information, marital status, medical condition, national origin, physical or mental disability, political affiliation, protected veteran status, race, religion, sex (including pregnancy), sexual orientation, or any other characteristic protected by applicable laws, regulations and ordinances. Candidate information will be treated in accordance with our CCPA privacy notice which can be found here: https://www.aiwyn.ai/ccpa
