Director, Customer Success

SambaSafety• US,

7h•$120,000 - $150,000•Remote

About The Position

Who we are: 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. What You’ll Do: 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.

Requirements

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

Nice To Haves

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

Responsibilities

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