Enrollment Technology Sales Executive

Clark Schaefer Strategic HR

Enrollment Technology Sales Executive at T2B Solutions driving new business and expanding partnerships across benefits and HR technology.

Posted 6/29/2026full-timeRemote • Iowa • 🇺🇸 United StatesJuniorMid-LevelWebsite

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.
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.

Benefits

Comp & perks

🌐 Worldwide ❌ Jobs You've Hidden ⭐️ Saved Jobs ✅ Applied Jobs ✉️ Email Alerts 👤 Account Clark Schaefer Strategic HR Website LinkedIn All Job Openings 11 - 50 employees We are Clark Schaefer Strategic HR, proud members of the Clark Schaefer Hackett family of brands. We can partner with you to develop, strengthen, augment, or manage your human resources function. We give you the benefits of having experienced HR professionals without adding headcount. We save you time by tackling your HR challenges – no matter how big or small – allowing you to focus on what you do best. Enrollment Technology Sales Executive Job not on LinkedIn 🔥 6 minutes ago 🌾 Iowa – Remote ⏰ Full Time 🟢 Junior 🟡 Mid-level 👨‍💼 Chief Technology Officer (CTO) Apply Now Find Hiring Managers Customize resume + cover letter Report problem ☆ Save ☑️ Mark as applied ❌ Hide 📋 Description
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
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. Apply Now 📊 Check your resume score for this job Improve your chances of getting an interview by checking your resume score before you apply. Check Resume Score Similar Jobs Field CTO 🕒 June 22 Cursor 51 - 200 🤖 Artificial Intelligence ☁️ SaaS 🤝 B2B Website LinkedIn All Job Openings Field CTO engaging with senior technical leaders at sophisticated companies to shape AI adoption strategies. Collaborating with sales, engineering, and product teams to influence executive stakeholders. 🇺🇸 United States – Remote ⏰ Full Time 🟡 Mid-level 🟠 Senior 👨‍💼 Chief Technology Officer (CTO) Co-Founder, CTO – AI PropTech for Municipal Approvals 🕒 June 4 FutureSight 11 - 50 🤖 Artificial Intelligence 🤝 B2B Website LinkedIn All Job Openings Co-Founder & CTO leading technical direction for innovative AI PropTech startup in municipal approvals. Oversee system architecture and build founding engineering team. 🇺🇸 United States – Remote ⏰ Full Time 🟡 Mid-level 🟠 Senior 👨‍💼 Chief Technology Officer (CTO) Co-Founder, CTO – AI PropTech for Municipal Approvals 🕒 June 4 FutureSight 11 - 50 🤖 Artificial Intelligence 🤝 B2B Website LinkedIn All Job Openings Technical Co-Founder & CTO shaping product vision and technical architecture for an AI PropTech startup. Building workflow intelligence software for development and infrastructure teams. 🇺🇸 United States – Remote ⏰ Full Time 🟡 Mid-level 🟠 Senior 👨‍💼 Chief Technology Officer (CTO) Co-Founder – CTO, AI PropTech for Municipal Approvals 🕒 June 4 FutureSight 11 - 50 🤖 Artificial Intelligence 🤝 B2B Website LinkedIn All Job Openings Co-Founder & CTO at VentureLandera building workflow intelligence software for municipal approvals. Leading technical direction and architecture with meaningful ownership and strategic influence. 🇺🇸 United States – Remote ⏰ Full Time 🟡 Mid-level 🟠 Senior 👨‍💼 Chief Technology Officer (CTO) Co-Founder – CTO, AI PropTech for Municipal Approvals 🕒 June 4 FutureSight 11 - 50 🤖 Artificial Intelligence 🤝 B2B Website LinkedIn All Job Openings Co-Founder & CTO defining AI-driven workflow solutions for fragmented development and infrastructure processes. Leading technical direction and forming the founding engineering team in a startup environment. 🇺🇸 United States – Remote ⏰ Full Time 🟡 Mid-level 🟠 Senior 👨‍💼 Chief Technology Officer (CTO) View More Chief Technology Officer Jobs 🌐 Worldwide Built by Lior Neu-ner. I'd love to hear your feedback — Get in touch via DM or support@remoterocketship.com Search Search Jobs by country Search jobs by city Search jobs by job title Search entry-level jobs Search junior-level jobs Search senior-level jobs Search jobs by tech stack Search jobs by contract type Search remote internships Search remote part-time jobs Remote jobs Anywhere in the World Companies Hiring Anywhere in the World Companies Hiring Sales People Anywhere in the World Companies Hiring Software Engineers Anywhere in the World Resources Advice Tips for finding remote jobs Interview questions and answers Resume examples Cover letter examples Post a job Affiliates Privacy policy Terms of service Job board SEO course AI Apply Copilot OpenClaw job finder Jobs by Country Remote jobs anywhere in the world (Worldwide remote jobs) Remote jobs United States Remote jobs Australia Remote jobs Brazil Remote jobs Canada Remote jobs France Remote jobs Ireland Remote jobs Germany Remote jobs Netherlands Remote jobs Spain Remote jobs UK Popular Jobs Remote data analyst jobs Remote customer support jobs Remote executive assistant jobs Remote marketing jobs Remote product designer jobs Remote product manager jobs Remote project manager jobs Remote recruiter jobs Remote sales jobs Remote software engineer jobs Jobs by Type Remote full-time jobs Remote part-time jobs Remote contract jobs Remote internship jobs Remote entry-level jobs Remote jobs with no experience required Remote junior jobs (1-3 years of experience) Digital nomad jobs Remote jobs with no degree required Freelance remote jobs Temporary remote jobs Remote jobs hiring now Stay at home mom jobs

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Hard Skills & Tools

Business DevelopmentSales QualificationProposal DevelopmentData ManagementBenefits Administration Outsourcing

Soft Skills

Excellent Communication SkillsOrganizational SkillsRelationship Building