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 We work with 800+ of the top 1,000 accounting firms in the country on payments. It's our core business and the front door to everything else on the platform. We process billions of dollars a year through it, and the volume is growing fast. We're hiring an Engineering Manager to lead
the team that owns this surface: the AR automation engine that connects directly to the practice management systems firms run their business on, ingests invoices, collects through ACH, card, and digital wallet, and posts the result back to the ledger.
The role Payments is how Aiwyn lands, how Aiwyn expands, and the system every other product on the platform eventually depends on.
The team you'll lead owns the engine that runs it. Invoice ingest, the firm-branded client portal, payment authorization and automation, collections, reconciliation, and the integrations into payment processors, partners, and the practice management systems firms already use. You'll lead the engineering team behind this work. A team of engineers today, headcount growing, partnering closely with a PM and the operators across the business who depend on this system being correct, fast, and visible. What good looks like When this team is doing its job, two things should be true: Firms trust the platform with their money. Money movement at this scale doesn't get to be wrong. Firms can see the full lifecycle of every payment, audit trails are clean, and when something fails the system explains itself. Compliance posture is airtight. The platform behaves the way you'd expect a system handling billions of dollars to behave. Volume grows, automation grows, and the rails hold. Today, most clients of our customers still pay manually, and most firms still review every collections touchpoint by hand. There's enormous headroom to bring that work onto the platform. The job is to make automation easy enough that firms actually adopt it, while uptime, latency, and correctness keep improving as volume scales. 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 payments roadmap with your PM. Sequence what gets built and when, decide what "done" means, and translate strategic priorities into tractable engineering work. Build the system that runs the engine. Your team owns the payment rails, the integrations, the authorization and audit layer, the reconciliation pipeline, and the operational tooling that makes all of it legible. Make the loop faster every cycle without giving up correctness. Work in the trenches with the operators. Finance, support, compliance, customer success, and the firms themselves are your closest collaborators and your toughest users. They live with the consequences when the system is wrong. Spend real time with them, understand what it actually takes to run AR for a top accounting firm, 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. Payments has no tolerance for outages.
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 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, concurrency, and integration depth mattered. You can talk credibly about architecture with the engineers on your team and earn their trust on the technical merits. Payments or fintech experience. You've worked on a payments platform, a processor, an AR or billing system, or another money-movement system. You know what ACH, card networks, settlement, chargebacks, NACHA, and PCI mean in practice, and you have opinions about how to do this work well. 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. Uptime, latency, error budgets, incident response. This is a system that runs around the clock with billions of dollars moving through it, and
the team has to operate that way. 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: integration-heavy platforms. Experience leading teams whose work lives or dies by the quality of integrations into systems you don't control is a strong signal. What we offer The chance to lead
the team behind Aiwyn's core business, 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. 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
