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

- 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.

- 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.

- 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.

- 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. 

- 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.

- 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.

At Toast, our employees are our secret ingredient—when they thrive, we thrive. The restaurant industry is one of the most diverse, and we embrace that diversity with authenticity, inclusivity, respect, and humility. By embedding these principles into our culture and design, we create equitable opportunities for all and raise the bar in delivering exceptional experiences.

We Thrive Together

We embrace a hybrid work model that fosters in-person collaboration while valuing individual needs. Our goal is to build a strong culture of connection as we work together to empower the restaurant community. To learn more about how we work globally and regionally, check out: https://careers.toasttab.com/locations-toast.

Toast is committed to creating an accessible and inclusive hiring process. As part of this commitment, we strive to provide reasonable accommodations for persons with disabilities to enable them to access the hiring process. If you need an accommodation to access the job application or interview process, please contact candidateaccommodations@toasttab.com.

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