The Role:

We're hiring a Manager, Product Operations to lead a critical part of the operational infrastructure behind Middesk's products reporting to our Head of Product.

Middesk operates products that turn complicated, fragmented real-world processes into simple customer experiences. Behind those experiences is significant operational complexity. Registering a company for payroll taxes may require navigating different requirements, systems, and government agencies across all 50 states. Business formations introduce another set of jurisdiction-specific workflows. Across our Business Verification and Credit products, complex cases, data issues, and exceptions require careful investigation and judgment.

Our Product Operations teams sit at the center of that complexity. They help ensure our products deliver accurate, reliable outcomes for customers, own the workflows required when automation cannot complete the job, investigate complex cases and product issues, manage quality and remediation programs, and turn what they learn from operating the product into better processes and better products.

This role will initially lead our Entity Operations team, a team of approximately 5-7 people supporting our Payroll Tax and emerging Business Formations products, with the opportunity to expand over time to oversee Product Operations across Middesk more broadly.

You will be responsible for building an operation that can scale alongside the products it supports. That means developing the team, establishing strong operating rhythms and quality programs, improving measurement and visibility into product health, managing our BPO partners, and systematically reducing unnecessary manual work through better processes, tooling, automation, and AI.

Just as importantly, this is not a team that simply executes processes handed to it. Product Operations is an important feedback loop into the product itself. You and your team will develop deep expertise in government requirements and operational edge cases, identify where workflows break down, and work closely with Product and Engineering to turn that knowledge into more reliable and scalable systems.

What You'll Do:

• Lead and develop a high-performing operations team. Set clear expectations, coach team members, and build strong operating rhythms.
• Own the operational health of our Entity Management products. Ensure Payroll Tax Registration, Business Formations, and adjacent products deliver accurate, timely, and reliable outcomes.
• Build scalable operations across complex government workflows. Improve how we manage work spanning all 50 states local agencies.
• Establish strong quality programs. Build the metrics, controls, audits, and remediation processes needed to continuously improve performance.
• Make operations more efficient. Improve processes, tooling, automation, and AI-enabled workflows to reduce manual work while preserving appropriate human judgment.
• Turn operational knowledge into better products. Partner closely with Product and Engineering to surface recurring issues, document requirements, and improve workflows and automation.
• Own our BPO and external operations model. Manage training, quality, capacity, performance, and escalations across internal and external teams.
• Build visibility into performance. Develop the dashboards and measurement systems needed to understand throughput, quality, turnaround times, automation, and capacity.

What We're Looking For:

• 5-7+ years of experience in operations, product operations, compliance operations, regulatory operations, or another function involving complex workflows.
• Experience leading and developing an operations team.
• Experience managing outsourced or external operations teams, including BPOs, vendors, or offshore partners.
• Strong systems and process thinking, with a track record of improving operations through process design, tooling, automation, AI, and measurement.
• Strong analytical instincts and comfort using operational metrics to identify bottlenecks and improve performance.
• Experience partnering closely with Product and Engineering to turn operational problems into better systems.
• A high degree of ownership and comfort operating in a fast-moving, ambiguous environment.
• Clear communication and sound judgment when working through complex or sensitive issues.

Nice to Have:

• Experience in payroll, business formation, government registrations, tax operations, compliance, fintech, or legal tech.
• Experience operating workflows across multiple jurisdictions or government agencies.
• Experience operating in a high-growth startup environment, ideally at the Series B or C stage, with comfort moving quickly and iterating through ambiguity.