Software Engineer, Experience

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 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 brittle, decades-old accounting practice management systems 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 a senior software engineer to join the Experience team, which owns Engagement Letters and the Client Experience Portal.

The role

Aiwyn Experience connects accounting firms with their clients through Engagement Letters and the Client Experience Portal. We help firms create, send, track, and renew engagement letters, and give their clients a shared place to review and sign agreements and interact with their firm.

You'll be a senior engineer on the team behind this work, partnering closely with a deeply tenured group of accounting and firm operations experts who set the bar for what "correct" means.

Day-to-day

• Build the systems firms run their business on. Own the services, infrastructure, and confidence metrics that let practice management grow at speed without sacrificing accuracy or trust. Make the iteration loop faster every cycle.
• Work in the trenches with the domain experts. They've been doing this for decades. They're your closest collaborators and your toughest users. Spend real time with them, understand how accounting firms run and translate that depth into the systems you build.
• Build and extend the APIs that Aiwyn, firms, and partners build on top of. Integrations are the wedge. Make connecting firm systems, data sources, and downstream tools seamless, and the surface area something engineers actually want to use.
• Take projects from spec to ship to scale. Own the work end to end, including the parts outside your comfort zone.

What we're looking for

• 5+ years of professional software engineering experience, with a track record of taking full ownership of the projects you take on.
• Hands-on technical depth in domains where correctness matters. You've shipped real systems where edge cases, accuracy, and domain depth were non-negotiable.
• Experience in project management and/or fintech software. This is the domain you'd be building in, so experience here is what we're looking for — though it's not a hard requirement. You understand why getting these systems right is non-negotiable.
• Demonstrated ability to bridge engineering and a non-engineering domain. Engineers and finance/accounting 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.
• AI-native fluency. AI tooling is woven into how you work and ship, and you have a clear point of view on where it helps and where it creates noise.
• Comfortable across the stack. Backend, frontend, or infrastructure — you can reason about whatever the problem actually requires.
• Bonus: experience building or contributing to a billing, ledger, workflow, role based access control (RBAC), authentication, or comparable system. Practice management, billing, pricing, underwriting, claims adjudication, compliance, benefits. Anywhere correctness is non-negotiable and the system has to compose hundreds or thousands of rules into an answer you can defend.

What we offer

• The chance to build on one of the most consequential parts of the Aiwyn platform, in an industry that's about to change permanently.
• A direct, reflective leadership team that actively welcomes challenge and debate.
• Real autonomy and ownership over the systems you build.
• 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