Senior Director, Change Management

Trustmark’s mission is to improve wellbeing – for everyone. It is a mission grounded in a belief in equality and born from our caring culture. It is a culture we can only realize by building trust. Trust established by ensuring associates feel respected, valued and heard. At Trustmark, you’ll work collaboratively to transform lives and help people, communities and businesses thrive. Flourish in a culture of diversity and inclusion where appreciation, mutual respect and trust are constants, not just for our customers but for ourselves. At Trustmark, we have a commitment to welcoming people, no matter their background, identity or experience, to a workplace where they feel safe being their whole, authentic selves. A workplace made up of diverse, empowered individuals that allows ideas to thrive and enables us to bring the best to our colleagues, clients and communities.

About the role

We are looking for a Senior Director, Change Management at Trustmark.

Leads organizational change for a multiyear transformation that modernizes Voluntary Benefit’s (VB) product, distribution, service, and technology ecosystem. Partners with business and IT to design and execute people centered change strategies for platform adoption, process redesign, data/integration shifts, and new digital experiences for brokers, employers, and employees. Anchors change plans to business outcomes, OKRs including engagement, and readiness metrics; ensure transparent communication, targeted training, and post go live reinforcement to drive measurable adoption.

Key Accountabilities:

• Change Strategy & Roadmap - Build a comprehensive change strategy spanning front and back-office capabilities (policy admin, claims, billing, distribution), data/integration, identity/security, and digital channels; sequence OCM activities alongside the program delivery plan.
• Stakeholder Engagement & Journeys - Map stakeholder journeys (broker, employer, employee, VB, IT), define impacts, and tailor engagement for each segment; maintain “parking lot” and ownership for unresolved change issues.
• Communications & Enablement - Deliver plainspoken, timely communications that explain the “why,” the decisions (e.g., platform first alignment), and upcoming changes; create concise narratives that frame complex roadmaps and architecture for nontechnical audiences.
• Training & Adoption - Design role-based training and support plans for new processes and tools; enable brokers/employers/employees and internal teams to use new digital channels and workflows; establish a community of practice to scale change techniques.
• Readiness, Metrics & OKRs - Define readiness heatmaps, adoption OKRs, and reinforcement plans; report progress against OKRs and business outcomes.
• Agile Ways of Working - Embed OCM into agile ceremonies, sprint reviews, and release planning; coach product and delivery teams on people-first practices and role clarity.
• Cutover & Post-Go-Live Reinforcement - Coordinate cutover communications, hyper care, and reinforcement activities; manage change risk during migration phases and early adoption, with feedback loops to improve experience.
• Partner & Vendor Alignment - Align OCM plans with Service Integrator/consulting partners; ensure messaging and training reflect ecosystem decisions and distribution/broker lifecycle impacts.
• Governance & Operating Model - Contribute to transformation governance, roles, and decision rights; ensure OCM accountabilities are clear across business and IT functions.

Minimum Requirements:

• Bachelor’s degree; 6+ years of OCM experience, including 4+ years leading complex, multi-workstream transformations.
• Demonstrated expertise in change management principles and methods (e.g., impact analysis, stakeholder journeys, communications, training, reinforcement, measurement).
• Proven ability to translate technology architecture and delivery roadmaps into simple, audience-appropriate narratives and training.
• Strong collaboration skills with cross-functional leaders; confidence presenting to and engaging with executive audiences.
• Familiarity with agile delivery and product-centric operating models; comfortable working within sprint-based plans and ceremonies.
• · Proficiency with collaboration and portfolio tools (e.g., Teams/SharePoint; portfolio planning such as OnePlan for resource alignment).

Preferred:

• Transformation experience in insurance or other highly regulated industries, especially programs touching policy administration, claims, billing, and distribution/broker enablement.
• Experience aligning OCM with ecosystem modernization (platform-first min