Product Manager, Middesk

• 5-7+ years of experience in product management, technical consulting, or operational leadership, with a focus on building and deploying enterprise focused products, automation platforms, or complex workflow systems
• History of managing B2B SaaS solutions delivered through API integrations or within embedded partnership ecosystems
• Demonstrated success managing established, profitable solutions beyond initial launch phases. You excel at scaling and stabilizing high-volume offerings by maintaining consistent reliability for current users while deploying strategic roadmap expansions and delivering quantifiable gains in operational efficiency and product margins
• A proven track record owning mature, revenue-generating product lines; you know how to scale and harden products while balancing reliability for existing users with the delivery of strategic expansion features and measurable margin improvements
• An operator with a mindset rooted in systems thinking, with an obsession for tracking KPIs like task completion rates, cost-per-action, human-in-the-loop intervention rates, and strict SLA adherence

Desirable

• We're hiring a Product Manager to join our Entity Management team, reporting to the Director of Entity Management
• This team owns our Payroll Solutions suite of products — helping companies register, manage, and stay compliant on state payroll tax accounts — and is bringing new products to market that help companies form, maintain, and manage business entities throughout their lifecycle
• These products automate complex, multi-step compliance workflows through agentic systems that act on behalf of our customers
• You'll own the day-to-day execution of the roadmap for a core piece of this suite — writing specs, running sprints with engineering, and shipping features on a fast, iterative cadence
• You'll talk directly with customers to validate problems and test solutions, and partner with a small, cross-functional group of leads spanning Engineering, Go-to-Market, and Operations to grow these products through embedded partner distribution
• You'll also work closely with legal and compliance SMEs to translate regulatory complexity into clear, buildable requirements
• Drive the health of our flagship product lines, ensuring a strategic balance between operational stability, efficiency, and the introduction of new capabilities while remaining accountable for core metrics like SLA performance, retention, and per-account margins
• Scale our reach by expanding jurisdictional coverage and launching adjacent compliance products that span the business lifecycle - from formation to dissolution - while optimizing for distribution through our embedded partner network
• Scope pre-deployment workflows, conduct prompt and policy engineering, manage rigorous offline evaluations, and orchestrate safe rollouts. Post-deployment, establish continuous improvement loops by analyzing production results to refine agent/system behavior, improve resolution rates, reduce escalation frequency, and compound efficiency gains across the product line
• Write clear, buildable specs, run sprints with engineering, and ship features on a fast, iterative cadence. Act as the central node between Operations, Engineering, Legal/Compliance, and Go-to-Market teams to ensure alignment on roadmap execution and embedded partner distribution