Director of Customer Success

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.

We are seeking an experienced Director of Customer Success to lead and scale our Customer Success function. This role will focus on enabling our customers to achieve their desired outcomes, building proactive success programs, and driving retention and expansion across the customer lifecycle. You will directly manage our team of Customer Success Managers (CSMs) and work closely with Sales, Product, and Support to improve the customer experience, drive GRR forward, and reduce churn.

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

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

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

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

• Define CS OKRs and manage key metrics like GRR, NRR, churn, and customer health scores.

• Collaborate cross-functionally with Sales, Product, Marketing, and RevOps to enhance the customer journey.

• Act as the main point of escalation for complex account issues and retention risks.

Must-Have Qualifications

• 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, proactive 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 tools

• Understanding of scaled CS models and automation workflows

• Comfortable 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 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.