Director, FinTech Operations & AI Transformation

Toast•Boston, MA

3d•$122,000 - $248,000•Hybrid

About The Position

Toast is seeking a transformational leader to head their Financial Services Operations organization. This role involves leading the transition from a high-touch, human-led model to a high-touch, agentic human-in-the-loop model, driving AI transformation while maintaining service level agreements (SLAs) for key products. The Director will oversee end-to-end operational delivery for Embedded Finance products, including Banking, Lending, Collections, Leasing, Spend Management, and Financial Management. The position involves managing a team of over 30 managers and operators, redefining operational excellence in financial services.

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, owning the outcome.
Deep AI fluency: understanding of LLMs, agentic workflows, and automation tooling 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.
Ability to lead through clarity, distilling complex problems into actionable frameworks.
Coaching-first leadership style, investing in the development of direct reports.
Direct and data-driven approach, backing up points of view with evidence.
Ability to maintain operational excellence in the present while building for the future.

Responsibilities

Own SLA performance and quality outcomes across all Embedded Fintech product verticals.
Build and maintain operational dashboards, capacity models, and escalation frameworks for a 30+ person organization.
Partner with Product and R&D to reduce operational burden by eliminating manual bridging work between applications and systems.
Champion a white-glove service standard for all customer interactions.
Lead the design and execution of an 'Ops Engine' using agentic protocols and AI-powered workflows.
Partner with R&D to embed LLM-based tooling, intelligent routing, and automated decisioning into operational workflows.
Define and execute a phased AI transformation roadmap with clear milestones, risk controls, and measurable outcomes.
Serve as the internal expert and advocate for agentic AI adoption in FinTech operations.
Directly manage operational managers, developing them into data-driven leaders.
Build a coaching culture to upskill, reskill, and redeploy talent for an AI-augmented future.
Navigate the human aspects of transformation with empathy and transparency.
Synthesize operational performance data into executive-level insights for senior leadership.
Partner cross-functionally with Product, R&D, Risk, Compliance, and Finance to ensure operational requirements are integrated into roadmaps and system architecture.
Define the long-term organizational design for Operations, including roles, structures, and skills for an agentic team.
Transform Operations into a growth engine for Toast Embedded Finance by incorporating customer feedback and a hospitality approach.