Director of Product Management

Company Overview

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

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

Desired Skills & Experience

• 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

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

• Comfortable operating in a high-ownership, remote-first environment

Compensation & 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