Director of Product

Role Summary The Director of Product leads Greenshades' product organization — owning roadmap strategy, delivery execution, and product experience quality across our payroll, HR, and tax compliance solutions. This role carries a specific mandate to reorient product strategy for the AI era: identifying where AI can reshape workflows, unlock new efficiencies, and differentiate the platform. This role manages a team of Product Managers and a Product Experience/UX designer, and partners closely with Engineering, Customer Experience, and Product Marketing to ensure the roadmap reflects real market and customer signal. As part of an integrated Product and Marketing organization, this role is central to tightening the loop between what customers need and what gets built. Responsibilities - Lead, mentor, and develop a team of Product Managers and the Product Experience/UX function; set clear priorities, coach on craft, and manage performance and growth. - Own and maintain a groomed, prioritized product roadmap that reflects the highest-value initiatives across Greenshades' product lines, grounded in customer and market signal. - Drive Greenshades' product strategy into the AI era — evaluating where AI/ML can create step-change efficiency and experience improvements across the product line, and ensuring roadmap prioritization reflects that lens going forward rather than treating AI as a bolt-on feature. - Own Product Experience: ensure usability, design consistency, and overall product quality are considered alongside feature delivery, not treated as an afterthought. - Drive day-to-day product delivery in close partnership with Engineering, ensuring features ship on time, within scope, and aligned with roadmap priorities. - Partner with Customer Experience to strengthen how customer and market signal flows into intake, triage, and prioritization — bringing structure and clarity to 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 ensure roadmap priorities, positioning, and launch timing are aligned and well-sequenced. - Build and maintain deep working knowledge of payroll, HR, and tax business processes, including how AI is reshaping those domains, through customer research, competitive analysis, and ongoing industry engagement. - Partner with the CMO on Product team budget, resourcing, and prioritization tradeoffs; report on progress against roadmap and team capacity. - Other duties as assigned. 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 ICs. - Experience managing a complex domain (payroll, HR, tax, compliance, or similar), or a track record of quickly mastering a new business domain, with a specific example you can describe. - Have shipped AI or ML-enabled capabilities in a B2B product, or led 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 in 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, including explaining product strategy and tradeoffs to both 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. Travel Required: Up to 15% Location: This is a remote position.