Trustmark · 1 month ago
Executive Director, IT Digital Delivery
Greater Chicago Area
Full-time
Onsite
Lead/Staff, Director/Executive
$132K/yr - $245K/yr
12+ years expTrustmark is dedicated to improving wellbeing for everyone through a culture of trust and inclusion. The Executive Director, IT Digital Delivery will be responsible for driving end-to-end digital delivery and ensuring the development of high-quality digital capabilities that align with the company’s modernization strategy.
FitnessHealth Care
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
Qualification
Required
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
Preferred
Master's degree
Certifications in Agile/SAFe, PMP, or equivalent are desirable
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
Company
Trustmark
Trustmark is a national employee benefits company.
1001-5000 employees
H1B Sponsorship
Trustmark has a track record of offering H1B sponsorships. Please note that this does not
guarantee sponsorship for this specific role. Below presents additional info for your
reference. (Data Powered by US Department of Labor)
Distribution of Different Job Fields Receiving Sponsorship
Represents job field similar to this job
Trends of Total Sponsorships
2025 (6)
2024 (4)
2023 (5)
2022 (9)
2021 (5)
2020 (2)
Funding
Current Stage
Late StageLeadership Team
D
Daniel Hanke
Senior Vice President, Chief Information Officer (CIO)
Erich Sternberg
Chief Strategy Officer and President, Voluntary Benefits
Recent News
2025-11-18
Company data provided by crunchbase