Group Product Manager

The Role

We’re hiring a Group Product Manager to join our Entity Management team, reporting to the Head of Product. You’ll lead a small team of Product Managers and own a growing suite of products that help companies establish, manage, and maintain their business entities and payroll tax obligations.

Today, that includes

• Payroll Tax Registration Suite: Helping companies register, manage, and stay compliant with state payroll tax accounts throughout the full lifecycle.
• Business Formations: Helping companies form new business entities and manage the workflows required to get them up and running.

Our flagship product, State Payroll Tax Registration, established Middesk as a critical infrastructure partner for payroll providers like Gusto, Rippling, and Deel, helping their customers hire employees, run payroll, and stay compliant across the U.S.. The team is now building on that foundation in a few important ways: expanding beyond initial registration to support the full lifecycle of payroll tax account management, hardening and improving the platform to support its next horizon of scale, and bringing an entirely new Business Formations product suite to market.

You’ll be leading across products at very different stages of maturity. Some have meaningful scale and require continued investment in reliability, automation, operational efficiency, and platform capabilities. Others have only recently launched and require rapid iteration, customer discovery, and product-market fit work. Across the suite, we’re increasingly automating complex, multi-step compliance workflows through agentic systems that can act on behalf of our customers.

You’ll lead a small product team while staying close to the work yourself. You’ll help set priorities and coach PMs, while also owning the day-to-day execution of core parts of the roadmap. You’ll work directly with Engineering to shape requirements and ship on a fast, iterative cadence, talk with customers to validate problems and test solutions, and partner with leaders across Go-to-Market and Operations to grow these products through embedded partner distribution.

Location

We follow a hybrid work model, and for this role, there is an expectation of 2-3 days per week in our NYC office. Candidates should be based within a commutable distance, as we believe in the value of in-person collaboration and building strong team connections while also supporting flexibility where possible.

What You'll Do

• Lead a small product team while staying hands-on. Coach PMs, set priorities, and personally own meaningful parts of the roadmap from discovery through launch.
• Own the health of our flagship products, balancing reliability, efficiency, and new capabilities against metrics like SLA performance, retention, automation, and margins.
• Harden Payroll Tax Registration for its next stage of scale, improving reliability, reducing manual work, and strengthening the platform underneath it.
• Build and scale emerging products, including the broader payroll suite and Business Formations, from early launch through product-market fit.
• Use agentic workflows to automate complex compliance work, designing systems that safely reduce manual effort and improve over time.
• Stay close to customers and partners to identify problems, validate solutions, and shape the roadmap.
• Expand into new jurisdictions, capabilities, and distribution channels to grow the reach of the product suite.
• Support existing customers, helping resolve product issues and turning recurring pain points into product improvements.
• Partner tightly across Engineering, Operations, Legal/Compliance, and Go-to-Market to turn complex requirements into products that ship.

What We’re Looking For

• 5-7+ years of product management experience building and scaling B2B SaaS, automation, or complex workflow products.
• Experience building B2B products delivered through APIs or embedded partner ecosystems.
• A track record of owning products across different stages of maturity, from scaling established, revenue-generating products to developing and validating emerging product bets.
• Experience managing and developing a small team, while remaining comfortable staying close to the work and executing directly when needed.
• Strong systems and operational thinking, with an instinct for using metrics like completion rates, cost per action, automation rates, human intervention, and SLA performance to drive decisions.
• Comfort operating cross-functionally across Engineering, Operations, Legal/Compliance, and Go-to-Market teams.

Nice to Have

• Domain expertise in compliance, regulatory operations, payroll, fintech, or legal tech, with the credibility to challenge existing processes and translate complex regulatory requirements into scalable product and automation workflows.
• Experience operating in a high-growth startup environment, ideally at the Series B or C stage, with comfort moving quickly and iterating through ambiguity.