Director of Payroll Operations

As the Director of Payroll Operations, you will own the end-to-end operational performance of Insure Pay’s payroll connectivity platform — driving strategy and execution across all payroll integrations, data workflows, and operational processes. You will sit at the intersection of operations, product, and payroll — ensuring that our payroll data pipelines, premium calculation engines, and disbursement processes run accurately, efficiently, and at scale.

You’ll be hands‑on with the systems, processes, and people that power our pay-as‑you‑go workers’ comp platform — overseeing everything from data ingestion and reconciliation to onboarding payroll providers and streamlining carrier workflows. If you thrive in a fast‑paced, high‑growth environment and want to modernize how insurance operations work, this role is for you.

• Own and continuously improve all payroll connectivity operations — including direct integrations, aggregator relationships, and services-based data flows
• Drive operational strategy and roadmap for payroll integrations, with a focus on accuracy, data quality, and straight‑through processing
• Lead operational discovery with carriers, payroll providers, agents, and internal stakeholders; translate insights into clear process requirements, acceptance criteria, and operational SOPs
• Partner with engineering and implementation teams to deliver API‑first capabilities across payroll data ingestion, premium calculation, and reconciliation
• Work alongside RPA Development to identify, design, and implement RPA solutions that automate repetitive operational workflows — reducing manual intervention, error rates, and processing time across the payroll and reconciliation lifecycle
• Establish and monitor operational KPIs — data quality, processing accuracy, automation coverage, exception rates, and onboarding timelines — and drive continuous improvement
• Ensure compliance, auditability, and controls are embedded in automated processes and product designs, with strong alignment to Info Sec and enterprise requirements
• Run effective Agile delivery rituals with your squad; maintain a healthy backlog; sequence delivery to maximize operational impact while unblocking go‑to‑market and onboarding
• Identify and prioritize payroll providers and platforms based on integration feasibility, operational complexity, and policyholder reach
• Lead onboarding and operational coordination with payroll providers, serving as Insure Pay’s primary point of contact for integration and workflow alignment
• 5+ years in operations management, product operations, or a combined product‑operations role within B2B SaaS or insurance technology
• At least 2+ years directly tied to workers’ comp, payroll data, or an adjacent domain (e.g., premium billing, reconciliation, audit)
• Demonstrated experience owning operational processes end‑to‑end — from intake and configuration through exception resolution and reporting
• Deep familiarity with API products, data integrations, and event‑driven architectures; comfortable reading API docs, mapping data flows, and translating technical constraints into operational decisions
• Working alongside engineering to automate high‑volume, rules‑based operational workflows
• Strong fluency in the workers’ comp/payroll ecosystem — payroll providers, policy/admin systems, audit dynamics, midterm endorsements, class codes, and exposure reporting
• A history of leveraging AI and automation to improve operational efficiency and streamline workflows
• A data‑driven mindset: defining operational metrics, identifying bottlenecks, and running process improvements to drive adoption, quality, and efficiency
• Exceptional written communication and structured thinking; credibility with…