aiwyn - Engineering Manager, Tax
Requirements
• 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.
Benefits
• 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. • 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 • Stock options • 401(k) matching • Adventure Travel Stipend on each anniversary of your employment with Aiwyn • Relentless by Design • Owners not Renters • Trust at the Core
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