Director, FinTech Operations & AI Transformation

Toast creates technology to help restaurants and local businesses succeed in a digital world, helping business owners operate, increase sales, engage customers, and keep employees happy.   ABOUT THE ROLE We are looking for a transformational operator to lead the next chapter of our Financial Services Operations organization. This is not a steady-state management role. We are at an inflection point — transitioning from a human-led, high-touch model to a high-touch, agentic human-in-the-loop model — and we need a leader who can drive that transformation while simultaneously holding the line on the SLAs that underpin some of Toast's highest-NPS products. Reporting directly to the Head of Embedded Finance, the Director of Operations & AI Transformation will own end-to-end operational delivery across Embedded Finance - Banking, Lending, Collections, Leasing, Spend Management, and Financial Management. You will manage a team of 30+ managers and operators through an AI transformation roadmap, and redefine what "great" looks like in financial services operations.   WHAT YOU'LL OWN Operational Leadership & Performance - Own SLA performance and quality outcomes across all Embedded Fintech product verticals. - Build and maintain the operational dashboards, capacity models, and escalation frameworks needed to run a high-performing 30+ person organization. - Partner with Product and R&D to reduce the operational burden caused by gaps between applications and disparate systems — your goal is to eliminate the manual bridging work, not just manage it. - Champion a white-glove service standard: every customer interaction should feel intentional, expert, and high-trust.   AI Transformation & Automation - Lead the design and execution of an "Ops Engine" built on agentic protocols — AI-powered workflows that handle routine, repeatable tasks so your team can focus on high-complexity, high-value work. - Partner with R&D to identify where LLM-based tooling, intelligent routing, and automated decisioning can be embedded directly into operational workflows. - Define a phased AI transformation roadmap with clear milestones, risk controls, and measurable productivity outcomes. - Serve as the internal expert and advocate for agentic AI adoption in FinTech operations — educating the broader organization on what's possible and building the internal credibility to drive adoption.   Team Development & Culture - Directly manage a layer of operational managers; develop them into confident, data-driven leaders capable of running their verticals with increasing autonomy. - Build a coaching culture that prepares the broader team of operators for an AI-augmented future — upskilling, reskilling, and redeploying talent as the nature of the work evolves. - Navigate the human side of transformation with empathy and transparency: help the team understand what is changing, why it matters, and what their role looks like on the other side.   Strategic Influence - Synthesize operational performance data into executive-level insights; bring a clear point of view to senior leadership on where to invest, where to simplify, and where to automate. - Partner cross-functionally with Product, R&D, Risk, Compliance, and Finance to ensure operational requirements are reflected in product roadmaps and system architecture decisions. - Define the long-term organizational design for Operations — the right roles, structures, and skills for a high-touch, agentic team. - Turn Operations into a growth engine for Toast Embedded Finance.  Bringing the voice of the customer and a strong sense of hospitality to grow our products and deliver success for the customer.  WHAT WE'RE LOOKING FOR Requirements - Progressive operations leadership experience, with experience managing managers in a high-volume, SLA-driven environment. - Demonstrated experience leading teams through significant operational or technology transformation — not just participating in it, but owning the outcome. - Deep AI fluency: you understand the current landscape of LLMs, agentic workflows, and automation tooling well enough to evaluate trade-offs, prioritize use cases, and hold technical partners accountable. You don't need to build the models, but you need to know what they can and can't do. - Track record of driving measurable efficiency and quality improvements in financial services, fintech, or similarly complex regulated environments. - Strong executive presence: comfortable presenting to senior leadership, representing the team externally, and advocating for resources and priorities with data and conviction. - Experience in financial services operations — banking, lending, payments, or adjacent domains — is strongly preferred.   Leadership Profile - You lead through clarity: you can take a messy, multi-variable operational problem and distill it into a crisp framework your team can act on. - You are a coach first: you inves