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 invest in the managers who report to you and hold a high bar for their development.

- You are direct and data-driven: you bring a point of view to every conversation and back it up with evidence.

- You can hold the tension between today and tomorrow — maintaining operational excellence in the present while building the foundation for a fundamentally different future.

WHY THIS ROLE

- Direct impact: You will define the operational model for financial products used by hundreds of thousands of restaurants and their guests.

- Transformational mandate: You have explicit executive sponsorship and R&D partnership to reimagine how this team works — this is a rare opportunity to build something genuinely new inside a scaled organization.

- High visibility: The financial products you support deliver some of the highest NPS scores at Toast. Your work is seen, measured, and valued.

- Team: You are joining a leadership team that is investing heavily in this space and wants a peer who will push the thinking, not just execute the plan.