Director of Engineering

The role Platform owns the parts of Aiwyn that everything else is built on: our build and cloud infrastructure, our core IP data ingestion and normalization pipeline, our tax engine, our implementations engineering, and the productivity group elevating how the whole company works in the AI era. You’ll lead five teams and roughly thirty engineers today, with engineering managers on each team and a peer product leader you’ll partner with closely. Headcount will grow. This is a platform role with a lot of product work in it. The ingestion and normalization pipeline and our tax engine are core IP, and the work to make them best in class comes straight from your organization. You won’t just be enabling other people’s products. You’ll be building some of the most important ones at Aiwyn. What the Platform Delivers Product teams ship on top of platform without thinking about it. Our internal APIs, primitives, and golden paths are well defined enough that other engineers reach for them by default. They don’t fight infrastructure, they don’t reinvent integrations, and they don’t get blocked waiting on us. Our ingestion pipeline and tax engine are best in class. Firms trust us with the data and calculations their entire practice depends on. The platform team is delivering accuracy, performance, and breadth that legacy providers can’t match. Implementations land cleanly. New customers get to value fast. Engineering, product, and the customer team have a shared view of what’s happening, and the same bug doesn’t surface twice. Production is boring. Deploys are daily, incidents get diagnosed at the root, and the team takes infrastructure, change management, observability, and on‑call seriously enough that surprises are rare. The whole company moves faster because of how this team works. The productivity team is shipping leverage that compounds across engineering, product, and operations. AI isn’t a side initiative, it’s the default way work happens. The team is legible. Anyone in the company can see what platform is working on, why, and how it’s going. Day to day Lead the leaders. Coach and develop EMs across infrastructure, foundations, tax engine, implementations, and productivity. Hire when the bar requires it, performance manage when it doesn’t, and build a leadership team that can scale. Own the operating model. Define the rhythms, metrics, and standards that make the org legible and accountable, including cycle planning, change management, design review, incident response, and on‑call quality. Set technical direction. Partner with your engineers, EMs, and anyone else with strong opinions on the multi‑year evolution of the tax engine, the ingestion and normalization pipeline, and our core infrastructure on GCP. Hold the bar on operational excellence. Get us to daily deploys. Push incident response toward root cause. Build the metrics and forums that make execution legible and force the right conversations. Partner across the company. Work shoulder to shoulder with your peer product leader on platform, with the product engineering org, with support, and with GTM. Earn trust by execution and by making other teams demonstrably better. Qualifications Manager of managers, ideally for 2+ years. You’ve led multi‑team engineering organizations of 20+ and grown leaders inside them. Operational excellence in your blood. You’ve operated high‑availability services and you have a high floor for what’s table stakes. 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 it didn’t hold. You can describe the timeline of the last person you managed out and what you learned from it. Taste and judgment that doesn’t get replaced by AI. You have strong opinions about what good looks like in code, in systems, and in operating cadences, and you can defend them. You also know when to disagree and commit. AI‑native fluency. You use AI tooling daily, you’ve actively pushed your team to adopt it, and you have a clear point of view on where it helps and where it creates noise. If you’re earlier on this curve, you’re catching up fast and obviously. Strong communicator and partner. You write clearly, hold the room without dominating it, and can turn “no” into “yes, and there’s the trade‑off” when you’re talking up. Bonus: B2B SaaS or regulated environments where reliability, predictability, and trust matter more than novelty. Fintech, accounting, payments, or similar are a strong plus. What We Offer The chance to lead the platform underneath one of the most consequential vertical SaaS companies of the next decade, in an industry that’s about to change permanently. A direct, reflective peer leadership team that actively welcomes challenge and debate. Real autonomy. Freedom to restructure, hire, and set the standard, with founders who are receptive and supportive. Competitive compensation and meaningful equity. 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: #J-18808-Ljbffr