Group Product Manager
Middesk
Group Product Manager
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.
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.
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