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 replacing 40-year-old tax engines and brittle integrations with software accounting firms can actually trust, and we have rare product-market fit in an industry that's about to change permanently. We're hiring an Engineering Manager to lead the team that owns our tax engine: the calculation core that's already filed over a million returns and is now the wedge that lets us own the entire return end to end.

The role

The tax engine is one of the most strategic pieces of IP at Aiwyn. Owning it is the difference between running the entire return pipeline (preparation, calculation, e-file, delivery) and playing nice with the incumbents forever. It's also the foundation we're opening up to AI labs and modern firms who want a tax engine they can actually build on top of.

You'll lead the engineering team behind this work. A team of engineers today, headcount growing, partnering closely with a PM and a deeply tenured group of CPAs and tax experts on this team who set the bar for what "correct" means.

Day-to-day

When this team is doing its job, two things should be true:

• The engine is best in the industry, and increasingly open. We built TaxCalcBench, which has become how the AI labs measure their frontier models on tax calculation, and the takeaway is that even the best ones can't calculate a return reliably on their own. That's why Anthropic came to us to ship Aiwyn Tax as a Claude Connector: Claude provides the intelligence, we provide the correctness. The work ahead is making that pattern the default across every major lab and every modern accounting startup that wants a tax engine they can build on top of.

• Coverage grows at AI-pace, accuracy stays at 100%. The next milestone is full 1040 coverage for every American filer, and from there we keep going into other forms. The hard part isn't speed (AI gives us speed); it's that the IRS doesn't let you be wrong, so the iteration loop has to get faster every cycle without giving up an inch of correctness.

Day-to-day

• Manage and grow the team. Coach engineers, run real 1:1s, set the bar, hire when it requires it, and performance manage when it doesn't.

• Own the tax engine roadmap with your PM and tax leads. Sequence what gets built and when, decide what "done" means in partnership with the tax experts, and translate strategic priorities (new jurisdictions, new APIs, AI lab partner asks) into tractable engineering work.

• Build the system that builds the engine. Your team owns the agent tooling, the test infrastructure, and the confidence metrics that let the engine grow at speed without sacrificing accuracy. Make the loop faster every cycle.

• Work in the trenches with the tax experts. They've been doing this for decades. They're your closest collaborators and your toughest users. They build and verify coverage, own what "correct" means, and are on the hook when something isn't right. Spend real time with them, understand what it actually takes to file across federal and state jurisdictions, and translate that depth into the systems your team builds.

• Operate cleanly. Cycle planning, change management, on-call, incident response, and the operating cadences that make execution legible across the org.

What we're looking for

• Engineering manager for 2+ years, leading teams of 5+. You've coached engineers, set the bar on a team, and grown people on it. You can name the people you've developed and describe how.

• Manager-first. You can't get by here on being the strongest IC in the room. The value you deliver is through the team. If your default is to grab the keyboard when things get hard, this isn't the role.

• Hands-on technical history in complex domains. Before you managed, you shipped real systems where correctness, edge cases, and domain depth mattered. You can talk credibly about architecture with the engineers on your team and earn their trust on the technical merits.

• Demonstrated ability to bridge engineering and a non-engineering domain. Engineers and tax experts (or doctors, or lawyers, or any deep domain expert) think wildly differently. You've worked closely with non-engineering experts before, taken their judgment seriously, and built shared language and shared artifacts that let both sides do their best work. We've watched smart people struggle here, and this is the part of the job we look at hardest.

• Operational excellence in your blood. You can describe the metrics your last team ran by, what was broken about them when you got there, and what specifically you did to move them.

• Lived experience holding people accountable. You've built teams up by setting a real bar and managed people out when they didn't hold it. You can describe the timeline of the last person you managed out and what you learned.

• AI-native fluency. AI tooling is woven into how you work and how your team ships, and you have a clear point of view on where it helps and where it creates noise.

• Bonus: experience building or leading a rules engine, calculation engine, or comparable system. Tax, payroll, billing, pricing, underwriting, claims adjudication, compliance, benefits. Anywhere correctness is non-negotiable, the rules come from a domain outside engineering, and the system has to compose hundreds or thousands of those rules into an answer you can defend.

• Bonus: tax industry experience. Direct work on a tax engine or in tax technology is a strong plus, but not required.

What we offer

• The chance to lead the team that owns one of the most consequential pieces of IP at Aiwyn, in an industry that's about to change permanently.

• A direct, reflective leadership team that actively welcomes challenge and debate.

• Real autonomy. Freedom to shape your team, your process, and your bar.

• Competitive compensation and meaningful equity.

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