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.

Accountabilities
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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.

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

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

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

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

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

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

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

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

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

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

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

Requirements:

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

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

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

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

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

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

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

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

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

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

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

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

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

Additional assets:

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

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

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

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Knowledge of agentic AI workflows and automated customer engagement solutions.

Benefits:

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

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Additional performance-based bonus opportunities.

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Fully remote working arrangement within eligible US states.

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Comprehensive medical, dental, and vision insurance coverage.

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401(k) retirement plan with company matching contributions.

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Paid time off and company holidays.

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

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

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Opportunities to shape and scale a growing Customer Success organization.

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

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