Enrollment Technology Sales Executive

Clark Schaefer Strategic HR

Enrollment Technology Sales Executive at T2B Solutions driving sales and partnerships in HR tech and employee benefits. Managing full sales cycle and building relationships.

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

About the role

Key responsibilities & impact

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.

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

Health insurance
401(k) matching
Flexible work hours
Paid time off

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

business developmentinside salesproject managementdata managementbenefits administration outsourcingoutbound outreach campaignsqualifying prospectsscheduling meetingsvalue messagingenrollment technology

Soft Skills

communication skillsorganizational skillsrelationship buildingobjection handlingprioritizationworkload management

Certifications

Bachelor's degreeHigh school diploma