Director of Engineering

Aiwyn

Director of Engineering to oversee platform development at Aiwyn, a fast-growing SaaS company. Leading multi-team engineering efforts to build essential infrastructure and solutions.

Posted 6/22/2026full-timeRemote • 🇺🇸 United StatesLeadWebsite

Tech Stack

Tools & technologies

Google Cloud Platform

About the role

Key responsibilities & impact

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

What you’ll need

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

Comp & perks

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

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

operational excellencehigh-availability servicesmetrics developmentincident responsechange managementdesign reviewGCPAI toolingperformance managementteam leadership

Soft Skills

coachingcommunicationaccountabilityjudgmenttrust buildingcollaborationproblem-solvingdecision-makingadaptabilityleadership