Director, FinTech Operations & AI Transformation

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.

Responsibilities

• 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.
• Bring the voice of the customer and a strong sense of hospitality to grow our products and deliver success for the customer.

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.
• 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.

Qualifications

Base salary range for this role is listed below. The starting salary will be determined based on skills, experience, and geographic location. In addition to base salary, our total rewards components include cash compensation (overtime, bonus/commissions if eligible), equity, and benefits. You can learn more about how we align pay with local labor markets in our Geographic Pay Zone Philosophy.

• Zone A: $155,000—$248,000 USD
• Zone B: $135,000—$216,000 USD
• Zone C: $122,000—$195,000 USD

Skills

Progressive operations leadership experience, deep AI fluency, track record of driving efficiency and quality improvements, strong executive presence, and experience in financial services operations.

Benefits

Our total rewards components include cash compensation (overtime, bonus/commissions if eligible), equity, and benefits. You can learn more about how we align pay with local labor markets in our Geographic Pay Zone Philosophy.

• Zone A: $155,000—$248,000 USD
• Zone B: $135,000—$216,000 USD
• Zone C: $122,000—$195,000 USD

Pay

The base salary range for this role is listed below. The starting salary will be determined based on skills, experience, and geographic location. In addition to base salary, our total rewards components include cash compensation (overtime, bonus/commissions if eligible), equity, and benefits. You can learn more about how we align pay with local labor markets in our Geographic Pay Zone Philosophy.

• Zone A: $155,000—$248,000 USD
• Zone B: $135,000—$216,000 USD
• Zone C: $122,000—$195,000 USD

Schedule

Our approach to hybrid working 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, regardless of location.

Toast Uses AI In Its Hiring Process

Throughout the hiring process, our goal is to get to know you. We use AI tools to support our recruiters and interviewers with tasks like note-taking, summarization, and documentation of interviews to ensure they can be fully focused on your conversation. All hiring decisions are made by people.

Equal Opportunity Employer

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.