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 has a specific mandate to reorient 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 helps connect customer needs and market signals to product development. The position is remote, with travel required up to 15%.

Requirements

  • 5–7 years of product management experience in B2B SaaS or enterprise software, including 5+ years leading Product Managers or equivalent individual contributors.
  • Experience managing a complex domain such as payroll, HR, tax, or compliance, or a 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, including managing performance and supporting career growth.
  • Experience balancing roadmap strategy with hands-on delivery, including keeping features on schedule and within scope alongside Engineering.
  • Experience working day to day with Engineering, Customer Success/CX, 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 the judgment to tailor depth 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 across Greenshades’ product lines, grounded in customer and market signals.
  • Drive product strategy for the AI era by evaluating where AI/ML can improve efficiency and product experiences, and incorporate that perspective 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 in partnership with Engineering, ensuring features ship on time, within scope, and aligned with roadmap priorities.
  • Partner with Customer Experience to strengthen the flow of customer and market signals into intake, triage, and prioritization, and clarify how requests become roadmap decisions.
  • Serve as a key product escalation point for significant customer and internal issues, working with Support, TPE, and Engineering to resolve or route issues appropriately.
  • Partner with Product Marketing to align roadmap priorities, positioning, and launch timing.
  • Build and maintain working 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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