Senior Director, Change Management

Trustmark • Lake Forest, IL

7d • $107,546 - $160,583

About The Position

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.

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).

Nice To Haves

• 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 mindset, data/integration runway, identity/security).
• Partner/Service Integrator collaboration and vendor-led workshops/demos.

Responsibilities

• 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.
• 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.
• 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.
• 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.
• Define readiness heatmaps, adoption OKRs, and reinforcement plans; report progress against OKRs and business outcomes.
• Embed OCM into agile ceremonies, sprint reviews, and release planning; coach product and delivery teams on people-first practices and role clarity.
• Coordinate cutover communications, hyper care, and reinforcement activities; manage change risk during migration phases and early adoption, with feedback loops to improve experience.
• Align OCM plans with Service Integrator/consulting partners; ensure messaging and training reflect ecosystem decisions and distribution/broker lifecycle impacts.
• Contribute to transformation governance, roles, and decision rights; ensure OCM accountabilities are clear across business and IT functions.

Benefits

• Health/dental/vision
• life insurance
• FSA and HSA
• 401(k) plan
• Employee Assistant Program
• Back-up Care for Children, Adults and Elders
• many health and wellness initiatives
• Wellness program that enables employees to participate in health initiatives to reduce their insurance premiums.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior