Senior Customer Success Manager

Job Type

Full-time

Houston, Texas preferred, Remote Potential

Chief Customer Officer

Some travel necessary for in-person strategic customer meetings & internal events

With almost 30 years of proven reliability, PCS Software, Inc., is the all-in-one Transportation Management System trusted by more than 1,000 carriers and brokers is a leading provider of transportation management solutions. PCS is dedicated to empowering carriers, brokers, and shippers to streamline operations, improve efficiency, and maximize profitability. With a suite of advanced software tools, PCS supports the entire freight lifecycle from planning and execution to compliance and analytics.

With Cortex AI embedded, PCS TMS turns data into decisions — helping customers work smarter, faster, and more profitably every day.

As a Senior Customer Success Manager at PCS Software, you will serve as a strategic partner and trusted advisor to our Enterprise-tier customers. You will manage a portfolio of approximately 25+ high-value accounts and be responsible for driving customer success, maximizing value realization, and ensuring long-term retention and growth. This is a high-touch, relationship-driven role requiring executive presence, strategic thinking, and deep industry expertise in the transportation and logistics sector.

You will conduct monthly operational meetings, semi-annual in-person Quarterly Business Reviews, proactive renewal management, and custom success planning. Your ability to build executive-level relationships and deliver measurable business outcomes will be critical to success in this role.

• Function as a strategic business advisor and trusted partner to C-level and VP-level stakeholders within your assigned Enterprise accounts.
• Set strategic direction for customer's use of PCS Software to address business challenges via best practices and a consultative approach.
• Build and maintain deep, long-term relationships with key decision-makers and influencers across the customer organization.
• Facilitate setting measurable business outcomes and success criteria with customers aligned to their operational and financial goals.
• Hold customer and PCS accountable to delivering against goals and measurements of success through regular tracking and reporting.

• Conduct monthly operational health check meetings (12 per year) to monitor platform adoption, usage trends, and customer satisfaction.
• Deliver two comprehensive Quarterly Business Reviews (QBRs) annually—one at 8 months before renewal and one at 2 months before renewal—preferably in-person at customer sites.
• Present data-driven insights, ROI analysis, and strategic recommendations during business reviews to demonstrate value and identify expansion opportunities.
• Participate in monthly internal health reviews with the Customer Success team to proactively identify risks and opportunities across your portfolio.

• Own and manage the renewal process for all Enterprise accounts with proactive negotiation and contract management.
• Achieve annual retention targets of greater than 95% for Enterprise accounts and contribute to Net Revenue Retention (NRR) targets of greater than 105%.
• Identify and drive expansion revenue opportunities through upsells and cross-sells aligned to customer business needs.
• Develop and execute detailed account management plans to achieve revenue targets and maximize customer lifetime value.

• Proactively identify opportunities and risks within customer organizations and present recommendations and solutions to mitigate churn.
• Escalate at‑risk customers to leadership and collaborate cross‑functionally to resolve complex issues in a timely manner.
• Serve as the escalation point for critical customer concerns, ensuring white‑glove service and rapid resolution.
• Monitor customer health scores and proactively intervene when health drops or usage trends indicate potential risk.

• Remain an expert on PCS Software TMS product…