Enrollment Technology Sales Executive

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 LinkedIn, ZoomInfo, 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.

The T2B Solutions Team is experienced, technical and dedicated – making us an effective partner. With separate specialists in Implementation, Account Management, Electronic Data Interchange (EDI), Custom File Feeds, and Ongoing Case Support, we have the depth of resources to provide precise and valuable service or advice.

​T2B uses its decades of experience in employee benefits, benefits technology and human resources to help clients maximize the use of benefits enrollment technology. We provide expertise for clients on the initial system implementation, data migration, plan set-up, communication, self-service open enrollment, ongoing new hire and life event processing. By understanding our clients’ needs, we craft strategic solutions for Benefit/HR technology that make sense for our clients.

Apply online today!

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