Enrollment Technology Sales Executive

Job Opportunity: Enrollment Technology Sales Executive with T2B Solutions - Remote

We are seeking an Enrollment Technology Sales Executive to drive new business and expand partnerships across the benefits and HR technology space. In this role, you’ll own the full sales cycle prospecting and opening doors with brokers, carriers, TPAs, and employer groups; leading discoveries to uncover enrollment and administration pain points; and presenting tailored solutions that simplify implementation, improve the employee experience, and deliver measurable value.

Responsibilities include:

• Build and grow a targeted pipeline of insurance carriers, brokers, TPAs, and HR tech partners.
• Research executive contacts using Linked In, Zoom Info, Salesforce, and other prospecting tools.
• Run outbound outreach campaigns that drive engagement and generate responses.
• Qualify prospects, handle objections, and schedule high-value meetings.
• Lead discovery calls that uncover needs, pain points, and decision criteria.
• Position T2B’s HR/benefit technology expertise, including Employee Navigator, bswift, UKG, benefits administration outsourcing, data management, and consolidated self-billing services.
• Deliver clear, compelling value messaging that resonates with decision-makers.
• Partner with internal teams to develop proposals, SOWs, and tailored solutions.
• Build relationships with leaders across the employee benefits technology ecosystem.
• Become the go-to expert on enrollment technology, point solutions, and modern file management.

Skill Requirements:

• Bachelor's degree in business administration, marketing, or related field; preferred.
• High school diploma or equivalent; required.
• Insurance or healthcare industry knowledge; required.
• 1–2+ years in inside sales, business development, or recruitment; required.
• Experience in selling in the benefits, HR technology; required.
• Excellent communication and organizational skills.
• Strong project management skills with the ability to prioritize and manage workload.
• Proficiency in Microsoft Word, Excel, and PowerPoint.
• Experience in SaaS, Employee Navigator, bswift, Plan Source, UKG, ADP, or similar platforms; preferred.