Director of Customer Success
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.
The Position
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.
What You’ll Do
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.
Requirements: What We’re Looking For
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
Why You Should Apply
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
Compensation & Benefits
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.
Average salary estimate
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