Director, Enrollment Strategy and Technology

We’re determined to make a difference and are proud to be an insurance company that goes well beyond coverages and policies. Working here means having every opportunity to achieve your goals – and to help others accomplish theirs, too. Join our team as we help shape the future.   

The Director, Enrollment Technology & Growth Strategy is a senior leader responsible for driving enrollment-related premium growth through the strategic identification, design, assessment, and execution of enrollment technology solutions. This role sits at the intersection of sales, enrollment operations, technology, and customer experience, with accountability for advancing enrollment capabilities that improve win rates, customer satisfaction, and operational efficiency.

This leader oversees the evolution of enrollment sales positioning and presale support, including customer RFP responses, and partners closely with Sales, Relationship Management, Technology, and Priority Business teams to deliver scalable, technology-enabled enrollment solutions. The Director brings a strong external lens—understanding benefits administration partners, vendor capabilities, and market trends—and translates those insights into actionable strategies that help customers maximize their enrollment experience and outcomes.

Primary Job Duties

Enrollment Technology & Growth Strategy (30%)

• 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.

Sales Enablement & Presale Support (20%)

• 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.

Customer & Partner Enablement (15%)

• 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.

Platform Design & Execution (THPB) (15%)

• 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.

Technology Governance & Vendor Management (10%)

• 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.

Leadership & Cross-Functional Collaboration (10%)

• 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.

Qualifications

Basic Qualifications

• 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.

Preferred Qualifications

• 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.

Knowledge, Skills & Competencies

• Strategic thinker with a strong execution mindset.
• Ability to lead through influence and ambiguity.
• Excellent presentation, facilitation, and executive communication skills.
• Customer-centric approach with a deep appreciation for end-to-end enrollment experiences.
• Strong change management and stakeholder management capabilities.

*Open to all locations*

This role can have a Hybrid or Remote work arrangement.  Candidates who live near one of our office locations will have the expectation of working in an office 3 days a week (Tuesday through Thursday).   Candidates who do not live near an office will have a remote work arrangement, with the expectation of coming into an office only as business needs arise.

Compensation

The listed annualized base pay range is primarily based on analysis of similar positions in the external market. Actual base pay could vary and may be above or below the listed range based on factors including but not limited to performance, proficiency and demonstration of competencies required for the role. The base pay is just one component of The Hartford’s total compensation package for employees. Other rewards may include short-term or annual bonuses, long-term incentives, and on-the-spot recognition. The annualized base pay range for this role is:

Equal Opportunity Employer/Sex/Race/Color/Veterans/Disability/Sexual Orientation/Gender Identity or Expression/Religion/Age

About Us | Our Culture | What It’s Like to Work Here | Perks & Benefits