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.
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.
How 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. To learn more: https://careers.toasttab.com/ai-in-hiring
Our Approach to Hybrid Working
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 hospitality community, regardless of location. Please visit the Locations page on our career site to learn more about our in-office expectations by region: https://careers.toasttab.com/locations-toast
Diversity, Equity, and Inclusion is Baked into our Recipe for Success
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.
Apply today!
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 [email protected].
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For roles in the United States, it is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.
Skills Required
- Progressive operations leadership experience managing managers in a high-volume, SLA-driven environment
- Proven ownership of significant operational or technology transformations with measurable outcomes
- Deep AI fluency with knowledge of LLMs, agentic workflows, and automation tooling (ability to evaluate trade-offs and prioritize use cases)
- Track record driving efficiency and quality improvements in financial services, fintech, or similarly regulated environments
- Strong executive presence and ability to present to senior leadership and influence cross-functional stakeholders
- Experience in financial services operations (banking, lending, payments) is strongly preferred
What the Team is Saying
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Toast Compensation & Benefits Highlights
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Parental & Family Support — Paid parental leave and family‑forming resources are highlighted as generous and inclusive. Backup child/adult care and caregiving supports further strengthen this area.
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Leave & Time Off Breadth — Flexible PTO, paid company holidays, and a paid sabbatical after extended tenure indicate broad time‑off options. Feedback suggests these policies compare well with peer tech employers.
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Wellbeing & Lifestyle Benefits — Access to no‑cost therapy/coaching, wellness stipends, and financial‑wellness resources is emphasized. These offerings extend support beyond core insurance into day‑to‑day wellbeing.
Toast Insights
What We Do
Toast is the all-in-one platform built for restaurants of all sizes. Toast provides a single platform of software as a service (SaaS) products and financial technology solutions that give restaurants everything they need to run their business, including point of sale, payments, supplier management, digital ordering and delivery, marketing and loyalty, and team management. By serving as the restaurant operating system across dine-in, takeout, and delivery channels, Toast helps restaurants increase revenue, streamline operations and deliver amazing guest experiences.
Why Work With Us
Our recipe for an awesome workplace: One splash of friendship A dollop of impact A sprinkle of no hierarchy & A heavy spoonful of individuality Mix these ingredients in a fast-paced and hardworking environment. Best paired with a side of interesting people who always bring their whole selves to work. *100% Sunday scary free
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Hybrid Workspace
Employees engage in a combination of remote and on-site work.
