Executive Director, IT Digital Delivery

Trustmark • Lake Forest, IL

21d

About The Position

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 Responsible for driving the end-to-end delivery of digital first, frictionless experience across broker, employer, employee, and internal service journeys. Challenges System Integration partners, reviews and validates solution designs, and ensures all digital platforms are architected for performance, scalability, and long-term extensibility. Infuses intelligent workflows, generative AI, and emerging protocols such as Model Context Protocol (MCP) into next-generation digital experiences. Collaborates with Enterprise Architecture, Enterprise Integrations, Experience Design, Infrastructure, Data, Security, and SI partners to deliver scalable, high-quality digital capabilities that advance the modernization strategy.

Requirements

• Bachelor’s degree in Computer Science, Engineering, Information Systems, or related field.
• 12+ years of leadership experience in digital delivery, engineering, or enterprise transformation.
• Experience delivering in value-stream–aligned or scaled agile environments.
• Demonstrated success managing and holding SI partners accountable for design, delivery, and quality.
• Strong understanding of modern digital platforms, cloud-native engineering, and automation/AI capabilities.
• Strong delivery leadership combined with deep expertise in modern digital engineering, Experience Design (XD), and AI-enabled platforms that power large-scale digital transformation.
• Technically fluent in modern frameworks (i.e.. React, MUI, micro frontends, design systems), mobile-responsive architectures, digital content platforms, chatbots, event-driven services, and API-first integrations.
• Experienced people management leader.
• Exceptional leadership and communication skills, with ability to influence at executive levels.
• Proven ability to manage complex, large-scale delivery portfolios with multiple interdependencies.
• Strong vendor management and negotiation capabilities, with accountability for partner performance.
• Deep understanding of agile-at-scale delivery methods and modern digital solution delivery.
• Ability to lead through ambiguity and drive modernization across technology and business teams.
• Strong technical judgment and ability to guide decision-making in complex, multi-platform environments.

Nice To Haves

• Master’s degree.
• Certifications in Agile/SAFe, PMP, or equivalent are desirable.

Responsibilities

• Lead end-to-end digital delivery across value streams, ensuring predictable execution, transparency, and alignment to business outcomes.
• Oversee delivery of modern digital omni-channel experiences across portals, enrollment workflows, mobile-responsive interfaces, and servicing tools
• Serve as an escalation point for delivery risks, dependencies, and issues, driving proactive mitigation and course correction.
• Review and approve solution designs, XD flows, journey maps, wireframes, architecture diagrams, and integration patterns.
• Serve as the technical authority for digital delivery, ensuring solutions meet expectations for performance, security, scalability, accessibility, and maintainability.
• Champion modern engineering practices including micro frontends, reusable components, API-first patterns, cloud-native architectures, DevOps, CI/CD automation, and observability
• Partner with Experience Design to embed user-centered, journey-aligned design and consistent use of enterprise design systems.
• Adopt an AI- and automation-first approach, integrating chatbots, guided workflows, personalization engines, OCR, RPA, and AI-driven validation, and leveraging emerging technologies such as Model Context Protocol (MCP) to enable intelligent and context-aware digital experiences.
• Provide strong oversight of SI partners, holding them accountable for quality, reusable asset development, standards compliance, and delivery timelines.

Benefits

• Trustmark benefits include health/dental/vision, life insurance, FSA and HSA, 401(k) plan, Employee Assistant Program, Back-up Care for Children, Adults and Elders and many health and wellness initiatives.
• We also offer a 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: Executive
• Number of Employees: 5,001-10,000 employees