Senior Director, Business Operations (BizOps)
Chexy
Sales & Business Development, Operations
Toronto, ON, Canada
Posted on Dec 10, 2025
At Chexy, we’re reshaping the way money moves—making payments smarter, faster, and more rewarding.
We started by being the first in Canada to let people pay their biggest and most painful bills with credit cards and earn rewards on money they had to spend anyway. Now, we’re on a much bigger mission: to build a super app that acts as your co-pilot for all your money—helping you get more value from every dollar you spend.
As a high-growth fintech startup, we’re at the forefront of payments innovation, and we’re looking for hungry, ambitious people to help us scale. If you thrive in a fast-moving, high-energy environment and want to be part of something big, we’d love to work with you.
About the role
Chexy is hiring a Senior Director of Business Operations to unify and scale our front-line and back-office operations across Customer Support, Fraud Operations, and Payment Operations into a single, high-performing org. This leader will own operational readiness for major product/feature launches, build an AI-first operations model, and develop the systems, controls, and talent required to scale efficiently.
This role will report directly into the CEO and is designed to grow into a COO seat over time, making it ideal for an operator who can both run today’s ops flawlessly and architect tomorrow’s operating model.
What you’ll do
Build and lead a unified Operations org
- Consolidate Customer Support, Fraud Ops, and Payment Ops into one aligned operating model with clear ownership, shared goals, and consistent tooling.
- Hire, develop, and lead managers/leads across functions; set team structure, capacity planning, career ladders, and performance management.
- Establish operating cadence: weekly metrics, incident reviews, QA programs, SOPs, training, and continuous improvement loops.
Own launch readiness and cross-functional execution
- Partner with Product, Engineering, Risk/Compliance, Finance, and Data to ensure operational readiness for new products/features.
- Create a repeatable Launch Readiness framework: staffing, tooling, training, workflows, escalation paths, and go-live checklists.
- Drive post-launch retros and ensure learnings translate into durable process and product improvements.
Become an AI-first ops organization
- Define the strategy and roadmap to scale operations with AI: self-serve support, agent assist, intelligent triage, automated investigations, and reconciliation support.
- Identify high-ROI workflows to automate; implement guardrails and QA to ensure accuracy, compliance, and customer trust.
- Use data to measure impact (handle time, resolution rates, fraud loss, dispute outcomes, cost to serve) and continuously optimize.
Own payments operations and daily reconciliation oversight
- Ensure end-to-end payments operations run smoothly: exceptions, escalations, disputes/chargebacks (as applicable), and vendor/partner coordination.
- Oversee daily reconciliation and ensure the team has the tooling and controls to catch, resolve, and prevent variances (execution may be done by a hire on your team).
- Partner closely with Finance to strengthen controls, reporting, and auditability.
Drive operational excellence through metrics and system
- Define and own KPIs/OKRs across support, fraud, and payments; build dashboards and enforce accountability.
- Improve quality and reduce cost-to-serve via workflow redesign, tooling, knowledge management, and smart deflection.
- Establish escalation and incident management processes that are fast, customer-centered, and blameless.
What we are looking for (required)
- 10+ years (or 8+ with exceptional fit) in BizOps / Operations leadership within complex, high-volume B2C environments—ideally with payments and risk/fraud components.
- Proven experience leading multi-function operations teams (e.g., Support + Risk/Fraud + Payments/FinOps) and scaling them through growth.
- Strong working knowledge of payments operations concepts (e.g., settlement flows, exceptions handling, disputes, reconciliation controls) and how to operationalize them.
- Demonstrated ability to partner cross-functionally with Product/Eng to operationalize launches and influence roadmap prioritization.
- Track record of using automation and AI to improve efficiency and quality (from experimentation to rollout and governance).
- Data-driven operator: comfortable defining metrics, building operating rhythms, and driving measurable improvements.
- Exceptional ownership, judgment, and calm execution in ambiguous, high-stakes situations.
Nice to have
- Experience in fintech, payments platforms, marketplaces, or other high-throughput transaction businesses.
- Experience implementing modern support stacks (CRM, ticketing, QA tooling, knowledge base, workforce management).
- Familiarity with compliance/risk frameworks relevant to payments (you won’t need to be the compliance officer, but you should partner effectively).
- Experience building shared services or “ops platform” functions that serve multiple product lines
Why this role is special
- You’ll own three mission-critical teams and turn them into a single, scaled operating engine.
- You’ll help define what AI-first operations looks like in a real payments + risk environment.
- The role has a clear growth path to COO for a leader who can build durable systems and drive company-wide execution.