Director of Customer Success

\u003ch2\u003e\u003cstrong\u003eCompany Overview\u003c/strong\u003e\u003c/h2\u003e\u003cp style=\"min-height:1.5em\"\u003eAt 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.\u003c/p\u003e\u003cp style=\"min-height:1.5em\"\u003eWe’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.\u003c/p\u003e\u003cp style=\"min-height:1.5em\"\u003eWe’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.\u003c/p\u003e\u003cp style=\"min-height:1.5em\"\u003c/p\u003e\u003ch2\u003e\u003cstrong\u003eThe Position\u003c/strong\u003e\u003c/h2\u003e\u003cp style=\"min-height:1.5em\"\u003eWe are seeking an experienced \u003cstrong\u003eDirector of Customer Success\u003c/strong\u003e to lead and scale our Customer Success function.\u003c/p\u003e\u003cp style=\"min-height:1.5em\"\u003eThis 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.\u003c/p\u003e\u003cp style=\"min-height:1.5em\"\u003eThis is a high-visibility leadership role with direct impact on company growth and customer outcomes.\u003c/p\u003e\u003cp style=\"min-height:1.5em\"\u003c/p\u003e\u003ch2\u003e\u003cstrong\u003eWhat You’ll Do\u003c/strong\u003e\u003c/h2\u003e\u003cul style=\"min-height:1.5em\"\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eLead, support, and grow a high-performing Customer Success team.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eDesign and scale programs that improve onboarding, retention, and expansion.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eServe as a strategic partner to top accounts, ensuring value delivery and long-term growth.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eDevelop and optimize lifecycle playbooks (renewals, upsells, health check-ins, etc.).\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eDefine CS OKRs and manage key metrics (GRR, NRR, churn, customer health).\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003ePartner with Sales, Product, Marketing, and RevOps to enhance the customer journey.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eAct as the main escalation point for complex accounts and retention risks.\u003c/p\u003e\u003c/li\u003e\u003c/ul\u003e\u003ch2\u003e\u003cstrong\u003eRequirements: What We’re Looking For\u003c/strong\u003e\u003c/h2\u003e\u003cp style=\"min-height:1.5em\"\u003e\u003cstrong\u003eMust-Have Qualifications\u003c/strong\u003e\u003c/p\u003e\u003cul style=\"min-height:1.5em\"\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eYou embody our core values.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003e7+ years in Customer Success at a B2B SaaS company, including 3+ years in a leadership role.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eProven success designing and scaling CS programs that drive retention and expansion.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eStrong grasp of customer health scoring, churn drivers, and GRR/NRR metrics.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eExcellent leadership and coaching skills, especially with remote and distributed teams.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eAnalytical and data-driven, with the ability to turn insights into strategy.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eClear communicator with strong cross-functional collaboration skills.\u003c/p\u003e\u003c/li\u003e\u003c/ul\u003e\u003cp style=\"min-height:1.5em\"\u003e\u003cstrong\u003eNice-to-Haves\u003c/strong\u003e\u003c/p\u003e\u003cul style=\"min-height:1.5em\"\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eExperience as the first or founding CS leader in a startup.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eFamiliarity with both SMB and mid-market/enterprise customer motions.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eHands-on experience with Vitally, Gainsight, HubSpot, or similar CS tools.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eUnderstanding of scaled CS models and automation workflows.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eComfort in fast-paced, async-first environments.\u003c/p\u003e\u003c/li\u003e\u003c/ul\u003e\u003cp style=\"min-height:1.5em\"\u003e\u003c/p\u003e\u003ch2\u003e\u003cstrong\u003eWhy You Should Apply\u003c/strong\u003e\u003c/h2\u003e\u003cul style=\"min-height:1.5em\"\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eOwn and scale a high-impact Customer Success function in a growing SaaS company.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eMake a direct impact on retention, expansion, and customer satisfaction.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eJoin a remote-first team with strong values, high trust, and low turnover.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eCollaborate closely with our CEO and leadership team to shape company-wide strategy.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eEnjoy autonomy, flexibility, and the chance to build something meaningful.\u003c/p\u003e\u003c/li\u003e\u003c/ul\u003e\u003cp style=\"min-height:1.5em\"\u003e\u003c/p\u003e\u003ch2\u003e\u003cstrong\u003eCompensation \u0026 Benefits\u003c/strong\u003e\u003c/h2\u003e\u003cp style=\"min-height:1.5em\"\u003e\u003cstrong\u003eSalary \u0026amp; Type\u003c/strong\u003e\u003c/p\u003e\u003cul style=\"min-height:1.5em\"\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003e$130,000–$135,000 USD base (80%) + commissions (20%)\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eOn-target earnings (OTE): ~$160,000 USD\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eFull-time employee role (US)\u003c/p\u003e\u003c/li\u003e\u003c/ul\u003e\u003cp style=\"min-height:1.5em\"\u003e\u003cstrong\u003eWork Setup\u003c/strong\u003e\u003c/p\u003e\u003cul style=\"min-height:1.5em\"\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003e100% remote — async-first culture with flexible hours\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eFT Job: Approx. 40 hours/week\u003c/p\u003e\u003c/li\u003e\u003c/ul\u003e\u003cp style=\"min-height:1.5em\"\u003e\u003cstrong\u003eBenefits\u003c/strong\u003e\u003c/p\u003e\u003cul style=\"min-height:1.5em\"\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003e30 days of PTO per year\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003ePrivate health insurance + 401(k) (US only)\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eAnnual team retreats (past locations: Costa Rica, Ibiza, Mexico)\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eYearly stipend (home office, training)\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eGenerous parental leave\u003c/p\u003e\u003c/li\u003e\u003c/ul\u003e\u003cp style=\"min-height:1.5em\"\u003e\u003cem\u003e\u003cstrong\u003eInclusion at Hubstaff\u003c/strong\u003e\u003cem/\u003e\u003c/p\u003e\u003cp style=\"min-height:1.5em\"\u003e\u003cem\u003eHubstaff 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.\u003c/em\u003e\u003c/p\u003e\u003cp style=\"min-height:1.5em\"\u003e\u003c/p\u003e