Director of Customer Success

At Hubstaff, our mission is to empower people to have their most productive workday. We do this by providing the industry-leading workforce analytics and time tracking platform for remote and distributed teams.

We’ve been fully remote for over a decade—long before it became a trend—and we continue to believe that remote work represents the most significant shift in the modern workplace since the advent of the PC. Our platform helps more than 95,000 businesses track time, manage schedules, and automate payments with transparency and accountability at its core.

We’re a product-led company with a winning culture, strong momentum, and a long-term vision: to become an essential part of every remote company’s tech stack. And we’re just getting started.

We are seeking an experienced Director of Customer Success to lead and scale our Customer Success function.

This role will focus on enabling customers to achieve their desired outcomes, building proactive success programs, and driving retention and expansion across the lifecycle. You will directly manage our team of Customer Success Managers (CSMs) and collaborate closely with Sales, Product, and Support to improve the customer experience, advance GRR, and reduce churn.

This is a high-visibility leadership role with direct impact on company growth and customer outcomes.

• Lead, support, and grow a high-performing Customer Success team.

• Design and scale programs that improve onboarding, retention, and expansion.

• Serve as a strategic partner to top accounts, ensuring value delivery and long-term growth.

• Develop and optimize lifecycle playbooks (renewals, upsells, health check-ins, etc.).

• Define CS OKRs and manage key metrics (GRR, NRR, churn, customer health).

• Partner with Sales, Product, Marketing, and RevOps to enhance the customer journey.

• Act as the main escalation point for complex accounts and retention risks.

Must-Have Qualifications

• You embody our core values.

• 7+ years in Customer Success at a B2B SaaS company, including 3+ years in a leadership role.

• Proven success designing and scaling CS programs that drive retention and expansion.

• Strong grasp of customer health scoring, churn drivers, and GRR/NRR metrics.

• Excellent leadership and coaching skills, especially with remote and distributed teams.

• Analytical and data-driven, with the ability to turn insights into strategy.

• Clear communicator with strong cross-functional collaboration skills.

Nice-to-Haves

• Experience as the first or founding CS leader in a startup.

• Familiarity with both SMB and mid-market/enterprise customer motions.

• Hands-on experience with Vitally, Gainsight, HubSpot, or similar CS tools.

• Understanding of scaled CS models and automation workflows.

• Comfort in fast-paced, async-first environments.

• Own and scale a high-impact Customer Success function in a growing SaaS company.

• Make a direct impact on retention, expansion, and customer satisfaction.

• Join a remote-first team with strong values, high trust, and low turnover.

• Collaborate closely with our CEO and leadership team to shape company-wide strategy.

• Enjoy autonomy, flexibility, and the chance to build something meaningful.

Salary & Type

• $130,000–$135,000 USD base (80%) + commissions (20%)

• On-target earnings (OTE): ~$160,000 USD

• Full-time employee role (US)

Work Setup

• 100% remote — async-first culture with flexible hours

• FT Job: Approx. 40 hours/week

Benefits

• 30 days of PTO per year

• Private health insurance + 401(k) (US only)

• Annual team retreats (past locations: Costa Rica, Ibiza, Mexico)

• Yearly stipend (home office, training)

• Generous parental leave

Inclusion at Hubstaff

Hubstaff is proud to be an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all team members, regardless of background, identity, or lived experience.