Director of Engineering

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Aiwyn

WebsiteLinkedInAll Job Openings

51 - 200 employees

Founded 2020

☁️ SaaS

💳 Fintech

🤝 B2B

💰 $113M Venture Round - Aiwyn on 2024-12

SaaS • Fintech • B2B

Aiwyn is a software platform for accounting firms that combines payments automation, practice management, a client experience portal, and a core tax system into a single, integrated solution. It helps firms accelerate payments, automate invoicing and reconciliation, modernize practice operations (time tracking, billing, project and resource management), and centralize client interactions and tax workflows. Aiwyn focuses on B2B partnerships with accounting firms and integrates with the wider accounting technology ecosystem; it recently acquired QuickFee’s U. S. payments business to strengthen its payments capabilities.

📋 Description

• 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.

🎯 Requirements

• 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 here's the tradeoff" 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.

🏖️ Benefits

• Competitive compensation and meaningful equity • 401(k) matching • Adventure Travel Stipend on each anniversary of your employment with Aiwyn