Director, Customer Success – Delivery

Role Overview

• 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.

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

Tech Stack

• PMP

Benefits

• Generous PTO plan with paid holidays + floating holidays
• 100% paid Employee Healthcare on Day 1
• Eligible for all medical, dental, and vision benefits on Day 1
• 401k with employer match, vested on Day 1
• Opportunity to work for a growing, global organization.
• Ability to engage with clients and internal partners to make an impact.
• Organization-wide focus on growth and development