Director, Customer Success

Hi, we’re SambaSafety and we offer the industry’s most comprehensive driver monitoring software. Our mission is promoting safer communities by reducing risk through data insights. Companies trust SambaSafety to keep their employees safe on the roads, price and reduce risk, help protect their brand, their bottom line, and our global community. 

We’ve built an inclusive, supportive, and exceptional culture where every employee is empowered in their role. Don’t take our word for it; we’ve been recognized as a Top Workplace by The Denver Post, Albuquerque Journal, Sacramento Bee, and Built In Colorado. And our employees rate SambaSafety as top-notch, with a rock solid Top Rating on Glassdoor.

The Director, Customer Success – Workforce & Insurance owns execution of SambaSafety’s Customer Success strategy for our direct Workforce and Insurance customers, including our growing captive insurance programs. Reporting to the SVP of Customer Success, you’ll lead a team of 7 CSMs, deepen enterprise customer relationships, own retention and expansion, and champion AI-enabled tools that scale the team’s efficiency while leading transparently through change.

• Manage and develop 7 CSMs serving enterprise, strategic, and SMB customers, driving success through clear KPIs, systems, and processes
• Recruit, onboard, and coach a capable, self-sufficient team, setting clear expectations and building individual career growth plans
• Communicate priorities and organizational change early and often, keeping the team aligned and steady
• Advocate for the team and customers with executives and cross-functional partners, keeping Customer Success in strategic decisions

• Own and report net revenue retention (NRR) for the enterprise book, and set the targets the team is measured against
• Identify and execute opportunities to grow revenue through retention, upselling, and improved customer experience
• Drive measurable customer outcomes and ROI rather than activity metrics, and minimize churn across products
• Leverage AI-enabled tools, automation, and data to scale customer insight and team efficiency

• Map the customer journey and standardize interventions across adoption, growth, and renewal
• Define customer segmentation (Enterprise, Strategic, Mid-Market) and tailor strategies to each
• Capture and report Voice of the Customer, and partner with Onboarding, Implementation, and Technical Services to keep customers at the center of our processes
• Analyze customer and industry data to inform strategy across SambaSafety, and translate key trends into actionable plays for the team

• Maintain relationships with top customers and serve as the executive stakeholder and escalation point for key or at-risk accounts
• Set and hold the standard for executive business reviews (QBRs/EBRs) built around each customer’s goals and metrics
• Own a structured Sales-to-CS handoff and a standing operating rhythm with Sales, including joint at-risk account reviews
• Develop strategic account plans for our largest customers in partnership with Sales to guide retention, growth, and executive engagement

• 10+ years of senior Customer Success leadership experience, ideally in a fast-paced, mission-critical SaaS environment at a high-growth company
• 3–5 years managing a remote, geographically dispersed team
• Bachelor’s degree in Business Administration or a related field, or equivalent experience
• Proven track record leading enterprise-wide strategic customer programs and complex initiatives across the business
• Strategic thinker who balances long-term vision with hands-on, operational execution across competing priorities
• Fluency with modern Customer Success platforms, with demonstrated comfort using AI-enabled tools and automation to scale customer insight and team efficiency
• Demonstrated ability to communicate and present effectively to senior executives, evidenced by leading executive business reviews or comparable high-stakes presentations
• Genuine curiosity about customers’ businesses and industries, with a relentless focus on customer experience
• Proven ability to lead through organizational change with steadiness, and to coach and develop a growing, distributed team

• Industry experience in fleet management, driver safety, risk management, telematics, or insurance
• 5+ years of experience in driver safety, fleet management, insurance (including captive programs), and/or Gig-economy companies
• Intermediate command of API integrations