Director, Customer Success & Delivery

ReSource Pro•Tampa, FL

4d•Remote

About The Position

As the Director, Customer Success & Delivery, for Propellint, a ReSource Pro company, you will be responsible for ensuring end-to-end excellence across delivery operations, client account management, workers' compensation solutions, and project governance. You will guide a matrixed team of Business Analysts, development resources, and cross-functional partners to deliver high-quality, scalable, and compliant solutions that meet ReSource Pro's organizational standards and client expectations. The Director, Customer Success & Delivery, will partner closely with Sales, Account Management, Product, Technology, and Executive Leadership to drive operational performance, strength client relationships, and expand ReSource Pro's presence and capabilities within the Technology Services ecosystem. We hire the best because we believe great people create exceptional experiences. That's why we hire individuals who not only bring talent and passion, but who thrive in our unique culture and live out our Core Values: Commitment to Community, Teamwork, Passion for Excellence, Service-Centric, and Best Self. All remote positions are based in the United States, and candidates must reside within the U.S. to be eligible for consideration.

Requirements

Bachelor's Degree in Business, Risk Management, Operations, or related field
10-15 years' experience in delivery management, operations, project leadership, or related functions
5-7 years' proven leadership experience overseeing high-performing teams in a matrixed or multi-disciplinary environment
Deep expertise in insurance, compliance, regulatory requirements, and industry standards
Proven ability to lead complex projects, develop governance structures, and drive operational improvements
Experience partnering with Sales on proposals, solution design, and RFP responses
Excellent communication, influencing, organizational, and analytical skills

Nice To Haves

Insurance designations (CPCU, CIC, etc.) and/or project management certifications (PMP, PgMP, Agile, etc.) strongly preferred

Responsibilities

Provide executive oversight of end-to-end delivery operations, ensuring consistent service quality, operational rigor, and alignment with organizational strategy and client commitments.
Establish, maintain, and continuously enhance delivery and project governance frameworks, standards, and controls that support scalable, compliant, and repeatable execution across the enterprise.
Lead and oversee complex, high-impact delivery initiatives and enterprise projects, ensuring cross-functional alignment, effective risk management, and successful execution within defined scope, timelines, and quality expectations.
Direct delivery planning and execution across teams, including resource allocation, capacity forecasting, dependency management, and prioritization of initiatives to support business objectives.
Monitor and analyze delivery and project performance metrics to identify trends, mitigate risks, remove operational bottlenecks, and drive continuous improvement in execution effectiveness.
Ensure organizational readiness for new initiatives, regulatory changes, and delivery model enhancements by proactively assessing impacts, coordinating stakeholders, and guiding implementation efforts.
Provide executive-level reporting, insights, and recommendations on delivery performance, project portfolios, and operational risks to senior leadership, supporting informed decision-making and strategic planning.
Define departmental goals, performance expectations, and capability development plans aligned with strategic priorities; Build team expertise in delivery best practices, workers’ compensation operations, and client-facing excellence; Promote knowledge sharing, cross-training, and continuous improvement across the department.
Develop, coach, and retain a high performing team by providing effective leadership, recruiting, coaching, training, and performance evaluation to team members. Participate in the knowledge management process by directing knowledge management activities and training resources to team members.
Evaluate account health indicators and collaborate with other leaders and internal team members to strengthen long-term client partnerships; Serve as an executive escalation point, providing strategic insight, issue resolution, and proactive risk management.
Participate in client and prospect meetings to provide expert-level credibility, thought leadership, and alignment on strategic initiatives.
Incorporate client feedback and industry trends into improvements to delivery processes and solutions; Oversee internal execution for key client accounts, ensuring service standards, SLAs, and delivery outcomes are consistently met.
Guide teams on complex claims topics, compliance requirements, regulatory interpretations, and operational impacts.