Hubstaff is hiring a Director of Customer Success

Hubstaff is looking for a Director of Customer Success to lead and scale our Customer Success function. You’ll focus on enabling customers to achieve their desired outcomes, building proactive success programs, and driving retention and expansion across the entire customer lifecycle.

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 for renewals, upsells, and health check-ins.
• 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.

What We're Looking For

• 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 Have

• 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.

Technical Stack

• Vitally
• Gainsight
• HubSpot

Team & Environment

You will lead and directly manage the team of Customer Success Managers (CSMs), working closely with Sales, Product, and Support.

Benefits & Compensation

• $130,000–$135,000 USD base salary (80%) + commissions (20%).
• 30 days of PTO per year.
• Private health insurance + 401(k) (US only).
• Annual team retreats.
• Yearly stipend for home office and training.
• Generous parental leave.

Work Mode

This is a global position. Hubstaff is a remote-first team with an async-first culture, high trust, and low turnover, on a mission to help distributed teams work smarter.

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.