Director of Product

Greenshades Software•Jacksonville, FL
•Remote

About The Position

The Director of Product leads Greenshades' product organization, owning roadmap strategy, delivery execution, and product experience quality across payroll, HR, and tax compliance solutions. The role is responsible for reorienting product strategy for the AI era by identifying where AI can reshape workflows, unlock efficiencies, and differentiate the platform. The Director manages Product Managers and a Product Experience/UX designer and partners closely with Engineering, Customer Experience, and Product Marketing. As part of an integrated Product and Marketing organization, the role connects customer needs with product development. The Director owns product strategy and delivery, leads and develops the product team, and ensures usability and design quality are considered alongside feature delivery. The role also partners with the CMO on budget, resourcing, and prioritization, and reports on roadmap progress and team capacity. This is a remote position with travel required up to 15%.

Requirements

  • 5–7 years of product management experience in B2B SaaS or enterprise software, including 5+ years leading a team of Product Managers or equivalent individual contributors.
  • Experience managing a complex domain such as payroll, HR, tax, or compliance, or a demonstrated track record of quickly mastering a new business domain with a specific example.
  • Experience shipping AI- or ML-enabled capabilities in a B2B product, or leading a roadmap shift toward AI.
  • Experience hiring, coaching, and developing product talent, managing performance, and supporting career growth.
  • Experience balancing roadmap strategy with hands-on delivery and keeping features on schedule and within scope alongside Engineering.
  • Experience working day to day with Engineering, Customer Success/Customer Experience, and Marketing to align product decisions with business priorities.
  • Strong written and verbal communication skills, including explaining product strategy and tradeoffs to technical and non-technical audiences.
  • Experience presenting product strategy, roadmap progress, and resourcing tradeoffs to executive leadership, with judgment to tailor content and framing for an ELT audience.

Responsibilities

  • Lead, mentor, and develop Product Managers and the Product Experience/UX function; set priorities, coach on craft, and manage performance and growth.
  • Own and maintain a groomed, prioritized product roadmap reflecting high-value initiatives across Greenshades' product lines and customer and market signals.
  • Drive product strategy for the AI era by evaluating where AI/ML can improve efficiency and user experience, and incorporating those opportunities into roadmap prioritization.
  • Own Product Experience, ensuring usability, design consistency, and overall product quality are considered alongside feature delivery.
  • Drive day-to-day product delivery with Engineering, ensuring features ship on time, within scope, and in alignment with roadmap priorities.
  • Partner with Customer Experience to strengthen customer and market signal intake, triage, and prioritization, and clarify how requests become roadmap decisions.
  • Serve as a product escalation point for significant customer and internal issues, working with Support, TPE, and Engineering to resolve or route them appropriately.
  • Partner with Product Marketing to align roadmap priorities, positioning, and launch timing.
  • Build and maintain knowledge of payroll, HR, and tax business processes and how AI is reshaping those domains through customer research, competitive analysis, and industry engagement.
  • Partner with the CMO on Product team budget, resourcing, and prioritization tradeoffs; report on roadmap progress and team capacity.
  • Perform other duties as assigned.
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