Director, Enrollment Strategy – Technology

The Hartford

Director of Enrollment Technology & Strategy responsible for driving premium growth through strategic enrollment solutions. Overseeing sales positioning and pre-sale support in a matrixed environment.

Posted 5/6/2026full-time🇺🇸 United StatesLead💰 $128,000 - $192,000 per yearWebsite

About the role

Key responsibilities & impact

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

What you’ll need

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

Comp & perks

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

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

enrollment strategytechnology solutionssales enablementemployee benefits enrollment platformsbenefits administration ecosystemsHR technologydata analysisRFP responsesconsultative sales supportchange management

Soft Skills

leadershipcoachingcollaborationinfluencecommunicationstrategic thinkingcustomer focusproblem-solvingteam developmentadaptability

Certifications

Bachelor’s degreerelevant technology certificationsproject management certificationHR certification