Engineering Manager, Tax

Aiwyn

27d•Remote

About The Position

Aiwyn is seeking an Engineering Manager to lead the team responsible for their tax engine, a critical component of their modern Accounting Firm platform. This role is pivotal in replacing outdated tax software with reliable technology and is central to Aiwyn's strategy of owning the entire tax return process. The tax engine is also the foundation for integrating AI capabilities and serving modern firms. The tax engine is a strategic asset for Aiwyn, enabling end-to-end control of the tax return pipeline (preparation, calculation, e-file, delivery) and serving as a platform for AI labs and other firms. The Engineering Manager will lead a growing team of engineers, collaborating closely with a Product Manager and experienced CPAs and tax experts who define accuracy standards. The team's focus is on ensuring the tax engine is best-in-industry and increasingly open, evidenced by the development of TaxCalcBench and the integration with AI models like Claude. The goal is to achieve full 1040 coverage for all American filers and expand to other forms, maintaining 100% accuracy while accelerating iteration cycles.

Requirements

2+ years of experience as an Engineering Manager, leading teams of 5 or more.
Proven ability to coach engineers, set team standards, and develop individuals.
Manager-first approach, prioritizing team enablement over individual technical contribution.
Hands-on technical background in complex domains where correctness and edge cases are critical.
Demonstrated ability to collaborate effectively with non-engineering domain experts (e.g., tax experts).
Strong operational skills, including experience with team metrics and driving improvements.
Experience holding individuals accountable and managing performance.
Proficiency with AI tooling and a clear understanding of its application in software development.

Nice To Haves

Experience building or leading a rules engine, calculation engine, or similar system (e.g., tax, payroll, billing, pricing, underwriting, claims adjudication, compliance, benefits).
Experience in the tax industry, specifically working on a tax engine or in tax technology.

Responsibilities

Manage and grow the engineering team, including coaching, performance management, and hiring.
Own the tax engine roadmap in collaboration with the Product Manager and tax leads, translating strategic priorities into engineering tasks.
Oversee the development of agent tooling, test infrastructure, and confidence metrics to enable rapid, accurate engine growth.
Work closely with tax experts to understand the intricacies of federal and state tax filing and translate this knowledge into system design.
Ensure operational excellence through effective cycle planning, change management, on-call rotations, and incident response.