Senior Manager, Customer Success

The Senior Manager, Mid-Market Customer Success will lead a growing team responsible for ensuring customer retention, driving expansion opportunities, reducing churn, and maximizing net revenue retention (NRR) and gross revenue retention (GRR). This role is central to the company’s mission of delivering measurable value to our customers while building a world-class customer success function. Joining during an exciting period of growth, this leader will have the opportunity to shape how the team operates, including enabling agentic workflows and proactive customer outreach.

WHAT YOU'LL DO

• Lead and manage a team of ~8 Customer Success Managers serving 800+ mid-market customers, representing $16MM in revenue.

• Recruit, develop, and retain top CS talent while fostering a high-performance culture.

• Drive adoption, retention, and expansion strategies to achieve NRR, GRR, and churn retention targets.

• Partner cross-functionally with Sales, Product, Marketing, and other teams to improve the customer experience and deliver business outcomes.

• Collaborate interdepartmentally in a fully remote environment, building strong working relationships and clear communication across teams.

• Provide leadership on special projects, operational improvements, and strategic initiatives to scale the CS function.

• Lead team meetings, performance management, and coaching to ensure accountability and results.

• Utilize Planhat to monitor customer health, identify risks/opportunities, and guide data-driven decisions.

• Help build and refine workflows within Planhat, including agentic workflows and proactive customer outreach, as the CS function scales.

WHO YOU ARE

• 3+ years of experience in Customer Success leadership, including leading teams of 6–10+ Customer Success Managers.

• Strong people management skills with experience hiring and building high-performing teams.

• Proven track record of driving retention, reducing churn, and achieving NRR and GRR goals.

• Confident handling pricing conversations with customers, including during renewals and expansions.

• Experience working cross-functionally with Product, Sales, and Marketing.

• Strong cross-collaborative communication skills.

• Proven record of building engagement and accountability on a fully remote team.

• Experience leading teams through rapid growth and reorganization, with strong change management skills.

• Comfortable joining and leading customer calls, and coaching CSMs through call shadowing and role-playing.

• Strong analytical skills, including designing customer health scores, defining CS metrics, and building dashboards.

• Expertise in customer success platforms; experience with Planhat is a plus.

• Hands-on experience bringing automation and AI tools into Customer Success workflows.

• Experience in compliance, regulated-industry, or vertical SaaS is strongly preferred.

• Experience in a DOT compliance or fleet management environment is a plus.

Location: This role is primarily remote (US based), with the expectation of occasional visits to our offices for team collaboration, training, or company events.

This role may be based remotely out of the following states: Arizona, California, Colorado, Connecticut, Florida, Georgia, Illinois, Indiana, Kansas, Massachusetts, Maryland, Michigan, Missouri, Nebraska, New Hampshire, New Jersey, New York, North Carolina, Pennsylvania, Rhode Island, South Carolina, Tennessee, Texas, Virginia, Wisconsin

ABOUT US

At the company, we’re reimagining how safety-sensitive industries hire, stay compliant, and manage risk. We’ve evolved into a modern SaaS company with an all-in-one, AI-ready platform that helps transportation, construction, distribution, and utility businesses operate faster, smarter, and safer.

As we continue to grow, we’re looking for curious, strategic thinkers who thrive in complexity, are motivated by making an impact, and want to join a team that’s passionate about building great products and supporting customers. Our core values — Teammateship, Grit, and Innovation — guide everything we do. Whether we’re collaborating internally or helping customers, we approach every challenge with optimism, humor, and a shared commitment to success.

Benefits

The company offers a comprehensive benefits package that includes medical, dental, and vision coverage, a 401(k) with company match, paid time off and holidays, wellness programs, and an employee assistance program.

Equal Employment Opportunity

The company is an Equal Opportunity Employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity or expression, national origin, age, disability, protected veteran status, or any other legally protected characteristic.

Reasonable Accommodations

If you require a reasonable accommodation during the application or interview process, please contact us at [link for members]

Employment Status

Employment with the company is on an at-will basis. Nothing in this job posting or in future communications should be construed as a contract of employment.

Massachusetts Applicants: It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.

Privacy Policy: Please see our Applicant Privacy Policy [link for members] for more information on how the company processes your personal information during the recruitment process and, if applicable based on your location, how you can exercise any privacy rights.