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Staff Frontend Engineer

Who is Aiwyn and what do we do?


Aiwyn is the fastest-growing software company serving the accounting profession. Founded in 2020, we now work with 150+ of the largest CPA firms in the world. Our “Job to be done”: speed up cash flow, save Partner time, & deliver best-in-class client experiences. We do this by automating day-to-day firm operations with our Practice Automation solutions. Aiwyn is led by serial entrepreneurs with multiple exits and funded by top-tier investors (Bessemer, KKR, & Revolution). We're passionate about building a remarkable company with world-class people, processes, and technology.


To learn more, visit our website


About the role:

We’re building the future of tax software by leveraging AI to solve a massive problem: the tax industry is stuck with outdated legacy systems, while tax code complexity and CPA shortages keep increasing. This is a unique opportunity to build a truly innovative product from the ground up. The market is ripe for a better product, and recent AI advances have allowed us to build a better version of what exists. This means we can spend our time making our product as delightful as possible.


As a Frontend Engineer at Aiwyn, you’ll play a crucial role in building the user-facing aspects of our innovative tax platform. You'll be responsible for creating intuitive, efficient, and delightful experiences for CPAs, helping them navigate complex tax workflows with ease. We're looking for engineers who are product-minded and can think creatively to solve core and immediate problems, often in an ambiguous environment. You'll have a lot of responsibility and autonomy to make key technical decisions and own projects from conception to deployment.


Some of the challenges you might tackle include:

- Building a collaborative tax workbench that handles real-time updates across hundreds of interlinked forms and calculations – think Google Docs meets Bloomberg Terminal.

- Developing dynamic forms and workflows, bridging our database structure and desired user flows.

Managing complex client state transitions and dependencies, with multi-user collaboration and streaming updates.

- Collaborating closely with backend engineers, product managers, and designers to translate complex requirements into elegant and functional user interfaces.

- Ensuring our application is performant, accessible, and scalable to meet the needs of a growing user base.


Our tech stack includes Next.js, Typescript, Python (FastAPI, pyright, pydantic), Postgres, Cloud Run, CI/CD, and code reviews.


We’re seeking an experienced frontend specialist who is passionate about building exceptional user experiences. While we lean towards more senior candidates, we are very open to high-agency, earlier-career individuals who demonstrate a steep growth trajectory and a proactive, problem-solving mindset.


What We're Looking For
  • Proven experience in building complex, modern web applications, ideally with React and Next.js
  • Existing comfort deeply integrating AI tools into your workflows (Cursor, Windsurf, etc).
  • Strong proficiency in Typescript and a deep understanding of frontend best practices.
  • Product sense: an ability to think from the user’s perspective, contribute to product ideas, and understand product/engineering tradeoffs.
  • Excellent technical communication skills, especially in a remote, async-first environment. We value clear written and verbal communication.
  • A pragmatic approach to engineering; you value shipping and iteration but also care about code quality and thoughtful design.
  • Comfort with ambiguity and the ability to operate effectively with minimal guidance, seeing around corners.
  • Fluency with AI tools like coding assistants is a baseline requirement; we need engineers who have integrated them into their workflows.
  • You are focused on getting to the right outcome and are comfortable respectfully challenging others’ ideas and having your own challenged.
  • Comfort owning projects and working with high autonomy.


Why You Might Love It Here:
  • Impact: Your work will directly impact the efficiency and accuracy of tax preparation, aiming to deliver huge efficiency improvements for CPAs.
  • Autonomy & Ownership: We hire strong engineers and trust them. You'll own projects and make key technical decisions.
  • Technical Growth: You’ll have the freedom to work across our stack and tackle novel problems in a complex domain. We’re doing interesting AI applied to a legacy space.
  • Remote-First Culture: We protect deep work time, minimize recurring meetings, and communicate thoughtfully. You control your schedule and environment.
  • Solve Hard Problems: We're converting tax logic to code, building collaborative interfaces, and scaling computation engines.
  • Entrepreneurial Spirit: We’d be thrilled if many of our team members go on to found their own companies. We foster an environment of high responsibility and autonomy.


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.

Other benefits include:
  • Adventure travel stipend - you receive a $1,000 travel reimbursement on your work anniversary each year. We encourage our team to recharge and explore the world beyond their home office walls.
  • Remote, work-from-anywhere culture
  • Flexible PTO
  • World Class health benefits - we believe in fostering flourishing teams by providing benefits that go beyond the usual standards - Health, vision, dental, HSA/FSA, and mental health support.
  • Stock options - every Full Time Employee has ownership in Aiwyn's future and success.
  • 401(k) matching


Our Values:
  • Trust - We champion transparency, welcome differing perspectives, uphold accountability, and trust that others have good intentions
  • Courage - We have the courage to take calculated risks and embrace change, knowing what worked in the past won’t always work in the future
  • Impact - Rooted in determination and innovation, we chase extraordinary outcomes and impactful results
  • Relentlessness - We approach challenges with an unwavering resolve, never settling for mediocrity, and always striving to surpass expectations


Learn more about Aiwyn


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

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DATE POSTED
August 21, 2025
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