Director of Product Management

Hubstaff•Toronto, OH

10h•Remote

About The Position

Hubstaff helps organizations around the world optimize productivity and workforce operations. Trusted by 95,000+ businesses, our platform powers time tracking, team management, project insights, and payroll automation. We’ve been a remote-first company for over a decade — and we’re on a mission to help distributed teams work smarter, not harder. Product Overview Hubstaff serves SMB and mid-market companies that hire globally and manage distributed, often client-facing teams. Our product spans time tracking and proof of work, workforce management, productivity insights, and payments. Many customers rely on Hubstaff as a mission-critical system. We focus on transparency, operational efficiency, and meaningful business impact while continuously raising the bar on product quality and usability. The Role The Director of Product Management is a senior leadership role responsible for elevating product strategy, execution, and people leadership across Hubstaff’s core product areas. You will lead and develop a team of Product Managers and partner closely with Engineering, Design, and cross-functional leaders to deliver high-impact customer and business outcomes. This role is accountable for turning company strategy into focused product bets, strengthening product decision-making, and ensuring consistent execution. Why This Role Exists As Hubstaff continues to scale and move upmarket, product complexity and strategic tradeoffs are increasing. This role exists to: Raise the bar on product strategy and execution across multiple product areas Develop strong, outcome-oriented Product Managers Ensure product investment is clearly tied to customer value and business results Support Hubstaff’s evolution into a more comprehensive operational platform for global teams What Success Looks Like In this role, success means: Product Managers operate with clear ownership, strong discovery practices, and sound judgment Product roadmaps are outcome-driven and aligned with company priorities Measurable improvement in activation, engagement, retention, and expansion Cross-functional partners see Product as a strategic driver, not just a delivery function The product organization scales smoothly as the company grows

Requirements

7+ years of product management experience in B2B SaaS
3+ years leading and developing Product Managers
Proven ability to translate company strategy into focused product bets
Strong product judgment and decision-making skills
Hands-on experience working closely with Engineering teams in an Agile environment
Data-driven mindset using qualitative and quantitative insights
Experience building products for SMB and/or mid-market customers
Comfortable operating in a high-ownership, remote-first environment

Nice To Haves

Familiarity with workforce management, productivity, or platform products is a plus

Responsibilities

Define and execute product strategy aligned with company goals and customer needs
Lead, coach, and develop a team of Product Managers
Ensure deep customer understanding through discovery, research, and data
Own and evolve outcome-driven product roadmaps
Drive decisions tied to growth, adoption, retention, and expansion
Partner closely with Engineering, Design, Sales, Marketing, and Customer Success
Monitor market trends and competitive dynamics to inform product direction

Benefits

Competitive executive-level compensation, aligned with U.S. and Canadian SaaS market benchmarks
Performance-based bonus and equity opportunities
Fully remote role with high autonomy and ownership
Comprehensive benefits and retirement plans (where applicable)
Generous paid time off
Annual work-life balance stipend (equipment, learning, wellness, or travel)
Annual compensation and performance reviews
Annual in-person company retreats

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