Director, Customer Success

SambaSafety; United States; Hybrid; USD 180,000 - 240,000; Full time

Benefits offered by this job

Flexible PTO

401k Employer Match

Generous Healthcare Benefits

Up to 12 weeks paid maternity leave

Wellness & Tuition Reimbursement

Flexible Work Arrangements

SambaSafety swag & events

Job summary

SambaSafety is seeking a Director of Customer Success for Workforce & Insurance to lead a 7-person team, own retention and expansion, and scale through AI-enabled tools. The role reports to the SVP of Customer Success and thrives in a fast-paced SaaS environment with strategiccustomer programs across enterprise accounts.

The position emphasizes executive communication, cross-functional collaboration, and proactive change management while driving measurable ROI and customer outcomes.

Qualifications

• 10+ years of senior Customer Success leadership experience in a fast-paced SaaS environment.
• 3–5 years managing a remote, geographically dispersed team.
• Bachelor’s degree in Business Administration or related field, or equivalent experience.
• Proven track record leading enterprise-wide strategic customer programs and complex initiatives.
• Strategic thinker with hands-on execution across priorities and change.
• Fluency with modern CS platforms and automation to scale insight.

Responsibilities

• Lead and develop a team of 7 CSMs serving enterprise, strategic, and SMB customers.
• Own retention and expansion goals, partnering with executives and cross-functional teams.
• Drive AI-enabled, data-driven customer outcomes and measurable ROI.
• Develop executive-level business reviews and strategic account plans for top customers.

Skills

Customer Success leadership

Remote team management

Executive communication

AI-enabled tools

Strategic account management

Education

Bachelor’s degree in Business Administration or related field

Tools

CRM platforms

AI-enabled automation

Job description

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 byThe Denver Post, Albuquerque Journal, Sacramento Bee, andBuilt In Colorado. And our employees rate SambaSafety as top-notch, with a rock solidTop 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.

Key Responsibilities:

Lead the team

• 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

Drive retention and growth

• 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

Optimize the customer journey

• 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

Be the executive customer partner

• 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

Required Qualifications:

• 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

Preferred Qualifications:

• 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

Benefits and Perks:

• Flexible and generous Paid Time Off and Paid Volunteer Days
• 401k Employer Match
• Generous Healthcare Benefits
• Up to 12 weeks paid time off for maternity leave based on tenure
• Wellness &Tuition Reimbursement
• Flexible Work Arrangements
• Lots of SambaSafety swag & SambaSafety Events

Our team of talented and committed safety professionals is exceptional. At SambaSafety we strive to foster an inclusive culture that supports, encourages and celebrates a wide array of diversity. We are committed to create a space where all employees can show up as their authentic selves every day, and we work to advance employee equality, diversity and inclusion.

SambaSafety provides equal employment opportunities to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, gender identity, and expression or genetics.

Come join us to find out for yourself what all the excitement is about!