Enrollment Technology Sales Executive

Strategic HR Business Advisors

Enrollment Technology Sales Executive driving partnerships across the benefits and HR tech space for T2B Solutions. Owning the sales cycle and presenting tailored solutions to clients.

Posted 5/2/2026full-timeRemote • Iowa • 🇺🇸 United StatesJuniorWebsite

About the role

Key responsibilities & impact

Drive new business and expand partnerships across the benefits and HR technology space.
Own the full sales cycle prospecting and opening doors with brokers, carriers, TPAs, and employer groups.
Lead discoveries to uncover enrollment and administration pain points.
Present tailored solutions that simplify implementation and improve the employee experience.
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.
Deliver clear, compelling value messaging that resonates with decision-makers.
Partner with internal teams to develop proposals, SOWs, and tailored solutions.

Requirements

What you’ll need

Bachelor's degree in business administration, marketing, or related field; preferred.
High school diploma or equivalent; required.
1-2+ years in inside sales, business development, or recruitment; preferred
Insurance or healthcare industry knowledge; preferred.
Experience in selling in the benefits, HR technology; preferred.
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.

Benefits

Comp & perks

Employees can work remotely

ATS Keywords

✓ Tailor your resume

Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools

sales cycleprospectingobjection handlingproject management

Soft Skills

communicationorganizationalleadership