Director of Product Management
Posted on: January 13, 2026 | Remote (Flexible)
Company Name: Hubstaff | Application Deadline: Open Until Filled
Team: Product | Reports To: Chief Product Officer (CFO)
Division: Product Management | Employment Type: Full-Time
Location: Remote (Global)
Schedule: Flexible Remote | Experience Level: 07+ Years
Company Overview
At Hubstaff, our mission transcends simply building software—we exist to illuminate and accelerate global work. We've built an industry-leading time tracking and workforce management platform that has become indispensable for remote and distributed teams worldwide. Our early belief in remote work wasn't just prescient; it was transformational. We've operated as a fully remote organization for over a decade, perfecting distributed collaboration long before it became a business imperative.
Today, more than 95,000 businesses across the globe rely on Hubstaff to run their daily operations. These organizations use our platform to track time and activity with precision, manage complex schedules and shifts across multiple timezones, generate accurate invoices that reflect actual work performed, and pay their global teams seamlessly regardless of geographic boundaries. Our platform has evolved from a simple time tracking tool into a comprehensive operational system that modern businesses cannot function without.
As remote and global work continue scaling exponentially, we believe Hubstaff will solidify its position as a core operational system for modern businesses—as fundamental as email, communication platforms, or project management tools. We're building deliberately toward that ambitious future, and we need exceptional product leadership to help us realize this vision.
This isn't just about incremental improvements to existing features. We're positioning Hubstaff to serve increasingly sophisticated organizations with complex operational needs, moving upmarket while maintaining the simplicity and usability that made us successful. This expansion requires strategic product thinking, disciplined execution, and leadership that can elevate our entire product organization.
Product Overview
Hubstaff serves small and medium-sized businesses as well as mid-market companies that hire globally and manage distributed, often client-facing teams across multiple continents and timezones. Our product ecosystem spans several critical operational domains: comprehensive time tracking with proof of work verification, sophisticated workforce management capabilities, actionable productivity insights that drive performance improvement, and integrated global payment systems.
Our product philosophy centers on three foundational principles: increasing transparency for teams so everyone understands how time is allocated and work is progressing; saving valuable time for managers and administrators by automating routine operational tasks; and helping organizations operate more effectively at scale as they grow from small teams to substantial distributed workforces.
Many customers depend on Hubstaff as a mission-critical system—their operations would halt without it. This dependency creates both opportunity and responsibility. We're committed to continuously raising the bar on product quality, usability, and tangible business impact. Our customers trust us with their most valuable resource—their people's time—and we take that responsibility seriously.
The Role
The Director of Product Management represents a senior leadership role with accountability for elevating product strategy, execution excellence, and people leadership across Hubstaff's core product areas. You will lead and develop a talented team of Product Managers while partnering closely with Engineering leadership and cross-functional stakeholders to deliver meaningful customer outcomes and measurable business results.
This role carries accountability for translating high-level company strategy into focused product investments, improving the quality of product decision-making across the organization, and ensuring teams consistently deliver high-impact work that moves critical business metrics. We're seeking a product leader with demonstrated strong judgment, an unwavering customer-first mindset, and proven ability to operate effectively in a growing, remote-first organization where asynchronous communication and distributed collaboration are the norm.
You'll operate at the intersection of strategy and execution, comfortable engaging in both big-picture strategic discussions about where Hubstaff should invest over the next three years and tactical conversations about specific feature prioritization decisions happening this quarter. You'll need to zoom in and zoom out fluidly, providing the right level of guidance and support for each situation.
Why This Role Exists
As Hubstaff continues scaling and moving upmarket to serve more sophisticated enterprise customers, the product surface area, customer needs, and strategic tradeoffs have become significantly more complex. Simple decisions that once took hours now require careful analysis of multiple stakeholder perspectives, market dynamics, and long-term strategic implications.
This role exists to address four critical organizational needs. First, raise the bar on product strategy and execution across multiple product areas, ensuring we're making smart bets that compound over time. Second, develop strong, outcome-oriented Product Managers who think strategically about customer problems rather than just executing feature requests. Third, ensure product investment is clearly tied to customer value and measurable business results, not just shipping features. Fourth, help Hubstaff evolve from a point solution into a comprehensive operational platform that global teams depend on for multiple critical workflows.
Without strong product leadership at this level, we risk fragmented strategy, inconsistent execution quality, and missed opportunities to serve our customers more comprehensively. This role provides the strategic oversight and tactical support needed to avoid those pitfalls.
What Success Looks Like
Success in this role manifests across several dimensions, each representing a critical transformation for our product organization.
Product Managers on your team will operate with clear ownership, strong discovery practices rooted in genuine customer insight, and consistently high-quality decision-making. They'll understand not just what to build but why it matters and how to measure impact. They'll proactively identify opportunities rather than waiting for direction.
Product roadmaps will be genuinely outcome-driven and clearly aligned to company priorities, with transparent traceability from individual features to strategic objectives. Stakeholders across the organization will understand why we're investing in specific initiatives and how success will be measured.
Hubstaff will show measurable improvement in core product metrics including activation rates for new users, engagement levels among existing customers, retention across various customer segments, and expansion revenue as customers adopt additional capabilities. These metrics will trend positively quarter over quarter, demonstrating that product improvements are translating into business results.
Cross-functional partners—Engineering, Design, Sales, Marketing, Customer Success—will view Product as a strategic driver that helps them succeed, not just a delivery function that builds what others request. Product will earn credibility through consistently good judgment and successful outcomes.
Finally, the product organization will scale smoothly as the company grows and serves increasingly sophisticated customers. We'll develop internal capabilities, processes, and frameworks that enable us to maintain quality and velocity even as complexity increases.
Responsibilities
Product Strategy & Vision
You'll help define and execute product strategy aligned with company goals, customer needs, and market opportunities. This involves synthesizing input from multiple sources—customer research, market analysis, competitive intelligence, business objectives—into coherent strategic direction that guides investment decisions.
Product Leadership
Lead, coach, and develop a team of Product Managers, setting clear expectations for ownership, judgment, and impact. You'll help team members grow their strategic thinking capabilities, improve their discovery practices, and strengthen their influence with cross-functional partners. Career development and performance management fall squarely within your accountability.
Customer-Centric Decision Making
Ensure teams deeply understand customer problems through rigorous discovery, qualitative research, and quantitative data analysis. Product decisions should be grounded in genuine customer insight, not assumptions or internal opinions. You'll model customer-first thinking and hold the team accountable to this standard.
Roadmap Ownership
Own and evolve product roadmaps that balance near-term impact with long-term strategic positioning. This requires making difficult tradeoff decisions about what not to build, sequencing initiatives for maximum learning and impact, and maintaining flexibility as market conditions evolve.
Business Outcomes
Drive product decisions explicitly tied to growth, retention, adoption, and expansion metrics. Every significant initiative should have clear success metrics defined upfront and regular measurement of actual results. You'll foster a culture of learning from both successes and failures.
Cross-Functional Collaboration
Partner closely with Engineering leadership, Design, Sales, Marketing, and Customer Success to align execution and priorities. These partnerships require building trust through consistent delivery, transparent communication, and genuine appreciation for different functional perspectives.
Market & Competitive Insight
Monitor industry trends, competitive landscape developments, and emerging opportunities to inform product direction. You'll maintain awareness of how the workforce management, productivity tools, and payments spaces are evolving and identify implications for Hubstaff's strategy.
Desired Skills & Experience
We're seeking candidates with substantial product management experience—specifically 7+ years in B2B SaaS environments, including direct ownership of complex products serving business customers. You've navigated the unique challenges of selling to businesses: longer sales cycles, multiple stakeholders, complex workflows, and demanding requirements around security, compliance, and integration.
At least 3+ years of experience leading and developing Product Managers is essential. You've hired, coached, and grown product talent. You understand how to provide strategic direction while empowering ownership. You've seen Product Managers develop under your leadership and can articulate your approach to talent development.
Proven ability to translate company strategy into focused product bets and measurable outcomes is critical. You've operated in environments where resources are finite and tradeoffs are real. You know how to say no strategically and articulate the reasoning clearly.
Strong product judgment represents perhaps your most important qualification—knowing when to explore new opportunities through experimentation, when to commit significant resources to proven opportunities, and when to say no to requests that don't align with strategy. This judgment comes from experience, reflection, and learning from both successes and failures.
Hands-on experience working closely with Engineering teams in Agile environments is required. You understand how product and engineering partnership works when it's healthy. You can engage in technical conversations without pretending to be an engineer. You respect engineering perspectives while advocating for customer needs.
A data-driven mindset with experience using both qualitative and quantitative insights to guide decisions is essential. You're comfortable with analytics tools, can interpret data correctly, and understand the limitations of data. You know when to trust the numbers and when to dig deeper.
Experience building products for SMB and/or mid-market customers provides valuable context. These segments have unique characteristics—budget constraints, fewer resources for complex implementations, need for immediate value—that influence product strategy.
Familiarity with workforce management, productivity tools, payments, HRIS-adjacent systems, or platform products represents a strong advantage. Domain knowledge accelerates your ability to contribute strategically and builds credibility with the team.
Finally, you must be comfortable operating in a fast-paced, high-ownership, remote-first environment. Remote work requires different communication skills, different leadership approaches, and different ways of building relationships and trust.
Why Join Hubstaff
This role offers the opportunity to shape product strategy at a scaled, profitable company with strong market position and ambitious growth objectives. You'll lead a talented team tackling meaningful problems for real customers who depend on our platform daily.
Our remote-first culture provides flexibility and autonomy while maintaining high standards for performance and impact. We've spent over a decade perfecting distributed collaboration, and we'll support your success in this environment.
You'll work on products that directly impact how modern businesses operate globally, touching critical workflows around time, work, and compensation. The scope and impact of your decisions will be substantial.
This is an opportunity to join a leadership team committed to building something enduring—not chasing short-term metrics at the expense of long-term value creation.
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