Senior Manager, Customer Success

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Senior Manager, Customer Success based in the United States.

We are seeking an experienced Customer Success leader to manage and scale a high-performing team supporting a large mid-market customer portfolio. In this role, you will oversee customer retention, reduce churn, identify expansion opportunities, and maximize recurring revenue. You will lead a team of approximately eight Customer Success Managers responsible for more than 800 customers and a $16 million revenue portfolio. Combining strategic leadership with hands-on coaching, you will strengthen customer relationships and drive measurable business outcomes. You will also help modernize customer success operations through automation, AI-powered solutions, and proactive engagement strategies. This is an exciting opportunity to shape a growing customer success organization within a fast-paced, fully remote SaaS environment.

• Lead and manage a team of approximately eight Customer Success Managers responsible for supporting over 800 mid-market customers and a portfolio representing approximately $16 million in revenue.

• Recruit, develop, coach, and retain high-performing customer success professionals, fostering a culture of accountability, collaboration, and continuous improvement.

• Define and execute customer success strategies focused on product adoption, customer retention, churn reduction, and account expansion.

• Drive key business performance indicators, including Net Revenue Retention (NRR), Gross Revenue Retention (GRR), and customer churn targets.

• Partner with Sales, Product, Marketing, and other internal teams to improve the customer experience, strengthen relationships, and deliver measurable customer outcomes.

• Build strong communication and collaboration practices across a fully remote organization, ensuring alignment and effective execution across departments.

• Lead strategic projects and operational improvement initiatives that support the growth, scalability, and effectiveness of the customer success function.

• Organize team meetings, performance reviews, coaching sessions, and development initiatives to maintain high standards of execution and accountability.

• Leverage Planhat to monitor customer health, identify retention risks and expansion opportunities, and guide data-driven account management decisions.

• Develop and optimize customer success workflows within Planhat, including AI-powered and agentic workflows, automated processes, and proactive customer outreach initiatives.

• Participate in customer calls, support complex account discussions, and coach Customer Success Managers through call shadowing, feedback, and role-playing exercises.

• Lead the team through periods of rapid growth, organizational change, and evolving business priorities while maintaining engagement and operational consistency.

Requirements:

• At least 3 years of experience in Customer Success leadership, including direct management of teams of approximately 6–10 or more Customer Success Managers.

• Proven experience recruiting, developing, and managing high-performing teams, with strong people leadership and performance management capabilities.

• Demonstrated success driving customer retention, reducing churn, and achieving NRR and GRR objectives.

• Confidence managing customer pricing discussions, particularly in the context of contract renewals, negotiations, and account expansion opportunities.

• Experience collaborating cross-functionally with Sales, Product, Marketing, and other business functions to improve customer outcomes.

• Excellent communication and relationship-building skills, with the ability to influence stakeholders and foster collaboration across distributed teams.

• Proven ability to build engagement, accountability, and strong team culture in a fully remote working environment.

• Experience managing organizational change, leading teams through rapid growth, and adapting customer success strategies to evolving business needs.

• Comfortable participating in customer-facing discussions and coaching team members through call reviews, shadowing, and role-playing.

• Strong analytical capabilities, including developing customer health scores, defining performance metrics, analyzing retention trends, and building reporting dashboards.

• Expertise in customer success platforms and tools, with experience using Planhat considered an advantage.

• Practical experience implementing automation and AI-powered tools into customer success processes to improve productivity, engagement, and scalability.

• Strong strategic thinking, organizational skills, and the ability to balance operational priorities with long-term customer success objectives.

Additional assets:

• Previous experience in compliance-focused businesses, regulated industries, or vertical SaaS environments.

• Familiarity with Department of Transportation (DOT) compliance, fleet management, or transportation-related technology.

• Experience scaling customer success operations while managing large customer portfolios and recurring revenue targets.

• Knowledge of agentic AI workflows and automated customer engagement solutions.

Benefits:

• Competitive annual compensation ranging from $90,000 to $130,000 USD, depending on skills, experience, and location.

• Additional performance-based bonus opportunities.

• Fully remote working arrangement within eligible US states.

• Comprehensive medical, dental, and vision insurance coverage.

• 401(k) retirement plan with company matching contributions.

• Paid time off and company holidays.

• Wellness programs designed to support employee health and well-being.

• Employee Assistance Program (EAP) providing additional personal and professional support.

• Opportunities to shape and scale a growing Customer Success organization.

• Professional development opportunities through leadership responsibilities, team mentoring, and strategic initiatives.

• Occasional opportunities to visit company offices for team collaboration, training sessions, and company events.

We use an AI-powered matching process to ensure your application is reviewed quickly, objectively, and fairly against the role's core requirements. Our system identifies the top-fitting candidates, and this shortlist is then shared directly with the hiring company. The final decision and next steps (interviews, assessments) are managed by their internal team.

We appreciate your interest and wish you the best!

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