Engineering Manager, Tax

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 https://aiwyn.ai/ 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 https://github.com/column-tax/tax-calc-bench, 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 https://www.aiwyn.ai/resources/articles/aiwyn-claude-helping-firms-navigate-the-ai-future-of-tax/: 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