aiwyn - Engineering Manager, Payments
Requirements
• 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.
Responsibilities
• 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.
Benefits
• 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. • 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 • Stock options • 401(k) matching • Adventure Travel Stipend on each anniversary of your employment with Aiwyn • Relentless by Design • Owners not Renters • Trust at the Core
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