Director, Enrollment Strategy – Technology

Role Overview

• Set and execute a clear vision for enrollment growth enabled by technology across market segments
• Identify, evaluate, and recommend buy/build/vendor solutions to support enrollment effectiveness, scalability, and straight-through processing
• Establish a forward-looking enrollment technology roadmap aligned to business strategy, customer needs, and premium growth objectives
• Monitor performance against growth, customer satisfaction, and operational KPIs to inform investment and prioritization decisions
• Oversee the evolution of enrollment-related sales positioning, value propositions, and go-to-market messaging
• Lead enrollment components of pre-sale responses, including customer RFPs, finalist presentations, and solution design
• Partner with Sales and Underwriting to ensure enrollment capabilities are clearly articulated, differentiated, and aligned to customer needs and pricing strategies
• Support field teams with tools, insights, and guidance to improve close rates and enrollment outcomes
• Develop deep expertise in how benefits administration partners deliver the enrollment experience, including platform capabilities, limitations, and emerging enhancements
• Guide teams in advising customers on how to best leverage benadmin partners to maximize employee engagement, participation, and satisfaction
• Collaborate with external partners and internal stakeholders to influence roadmap alignment and integration opportunities
• Lead the design and evolution of Priority Business’s THPB enrollment materials platform and related straight-through-processing workflows
• Partner with Technology, Operations, and Product teams to ensure solutions are scalable, compliant, and operationally sound
• Ensure enrollment materials and execution processes are efficient, accurate, and aligned to customer and regulatory requirements
• Own ongoing assessment, selection, and management of enrollment-related technology vendors and tools
• Establish governance standards for enrollment technology usage, integration, and performance
• Identify opportunities to retire, enhance, or consolidate tools to reduce complexity and improve outcomes
• Lead, coach, and develop a team of enrollment and technology-focused professionals
• Influence across a highly matrixed environment, partnering with Sales, Relationship Management, Technology, Operations, Legal, and Marketing
• Drive change management and adoption for new enrollment capabilities across internal teams and customers.

Requirements

• Bachelor’s degree or equivalent experience
• 8+ years of experience in employee benefits, enrollment strategy, sales enablement, technology, or related fields
• 5+ years of leadership experience, including leading managers or senior individual contributors
• Demonstrated experience evaluating and implementing technology solutions in a complex, matrixed organization
• Experience with employee benefits enrollment platforms, benefits administration ecosystems, or HR technology
• Proven success driving premium growth, improving win rates, or enhancing customer experience through enrollment strategies
• Strong understanding of pre-sale processes, RFP responses, and consultative sales support
• Experience partnering with technology, product, and operations teams to deliver scalable solutions
• Data-driven mindset with the ability to translate insights into strategy and execution.

Benefits

• Health insurance
• 401(k) matching
• Flexible work hours
• Paid time off
• Professional development opportunities
• Short-term or annual bonuses
• Long-term incentives
• On-the-spot recognition