VP, Digital Strategy & Enablement

The Role at a Glance

As the VP, Digital Strategy & Enablement, you will be responsible for defining and executing the digital vision and enablement agenda across Product, Marketing, and Customer Experience. You will set the multi-year vision for portal, mobile, text, and self-service channels; ensures AI and automation investments are aligned to business outcomes; and serves as the senior business voice in technology and product planning. You will own the strategy, roadmap, and performance outcomes for broker, plan sponsor employer and employee digital experiences (portals, self-service, and customer-facing applications).

What you'll be doing

• Define and lead the digital strategy across Customer Experience, Product, and Marketing, creating a multi-year vision and roadmap that supports business growth, customer needs, and enterprise priorities.  
• Transform customer, broker, and employer experiences by designing and optimizing seamless end-to-end digital journeys across onboarding, enrollment, service, claims, renewals, and self-service capabilities.  
• Drive innovation and modernization of digital platforms, web and mobile experiences, AI solutions, and automation capabilities to improve engagement, efficiency, accessibility, and speed to market.  
• Partner with senior leaders across the enterprise to embed digital capabilities into products, influence strategic investments, and enhance customer and advisor experiences.  
• Leverage customer insights, analytics, and Voice of the Customer (VOC) feedback to identify opportunities, prioritize improvements, and deliver measurable business and customer outcomes.  
• Establish and monitor experience standards and performance metrics, driving digital adoption, customer satisfaction, operational efficiency, and continuous improvement across all digital channels.  
• Lead large-scale transformation and change initiatives, optimizing processes, reducing friction, improving quality, and building scalable capabilities that support future growth.  
• Build, develop, and inspire a high-performing team, fostering a culture of innovation, accountability, collaboration, and continuous learning while attracting and retaining top talent.

What we’re looking for

Must-have experience (Required):

·    4 Year/Bachelor's degree or equivalent work experience (4 years of experience in lieu of Bachelor's) 
·    12+ Years experience in digital strategy, digital product management, customer experience, marketing technology, or transformation leadership
·    5+ years of managerial, supervisory and/or demonstrated leadership experience
·    Experience in strategic planning/execution
·    Strong presentation skills with demonstrated ability to influence at all levels of management through clear, informed and logical discussions/presentations
·    Excellent communication skills as well as ability to communicate knowledgeable and credibly with senior management and internal constituents

Nice-to have Experience (Preferred):

•    Working knowledge of Workplace solutions products including Group Benefits and retirement
•    Experience developing or informing multiyear digital roadmaps for client and broker facing experiences
•    Knowledge of AI and it’s current and projected impacts to client delivery

Application Deadline

Applications for this position will be accepted through August 28th, 2026 subject to earlier closure due to applicant volume