Entry Level Leadership (Remote)
Boston, Massachusetts, United States (Remote)
Job Description
Entry-Level Leadership Representative — Remote
100% Remote | Commission-Based | Training Provided | Entry-Level
Are you looking for a career opportunity where you can help people, develop leadership skills, and build your professional future—all from home?
We are seeking motivated individuals to join our team as Entry-Level Leadership Representatives, working with union members, families, and community-focused programs to help eligible individuals understand and access valuable benefits and services.
What You’ll Do
Connect with union members and their families to provide information about available benefits and community service programs
Conduct virtual presentations and one-on-one consultations
Build strong relationships with the individuals and communities we serve
Assist families in understanding their available options and resources
Participate in ongoing leadership and professional development
Learn and implement proven communication and client-service strategies
Work toward personal and team goals while maintaining a high standard of service
What We Provide
100% remote work
Entry-level opportunity — no previous experience required
Comprehensive training and ongoing mentorship
Flexible scheduling
Leadership development and advancement opportunities
Support throughout the licensing process
A mission-driven environment focused on helping working families and communities
Compensation
This is a commission-based opportunity, with compensation tied to performance. Individuals who are motivated, coachable, and consistent have the opportunity to grow their income as they develop their skills and leadership responsibilities.
What We’re Looking For
Strong communication and interpersonal skills
Professional, positive, and dependable attitude
Self-motivated and comfortable working independently
Willingness to learn and receive coaching
Ability to build rapport with people from diverse backgrounds
Desire to grow into a leadership role
Must be willing to obtain the required license; we provide assistance and guidance throughout the licensing process
No prior industry experience is required. Training is provided.
If you’re looking for more than just another job and want an opportunity to develop professionally while making a meaningful impact on families and communities, we’d love to hear from you.
Responsibilities
Responsibilities
Conduct virtual meetings with union members and community members to explain available benefits, services, and programs
Build and maintain professional relationships with members, families, and community organizations
Educate individuals on available programs and help them identify resources that may meet their needs
Follow up with members and prospective clients to answer questions and provide continued support
Complete virtual consultations, presentations, and enrollment processes
Maintain accurate records and follow established procedures and compliance guidelines
Participate in weekly training, coaching, and professional development sessions
Develop strong communication, presentation, and leadership skills through hands-on experience
Set and work toward individual and team performance goals
Collaborate with leadership and team members in a fully remote environment
As experience is gained, take on additional leadership responsibilities, including mentoring and supporting new team members
Requirements
Requirements
Must be 18 years of age or older
Must have a valid Social Security Number and be legally authorized to work in the United States
Must be willing and able to obtain the required state license; assistance and guidance are provided throughout the licensing process
Strong verbal and written communication skills
Professional, reliable, and comfortable interacting with members and families virtually
Self-motivated and able to work independently in a 100% remote environment
Comfortable learning new systems, technology, and communication tools
Coachable with a willingness to participate in training and ongoing development
Goal-oriented and motivated by performance-based compensation
Must have a reliable internet connection and a computer or compatible device for remote work
Previous sales, insurance, or leadership experience is not required — training is provided
Benefits & Perks
Benefits & Perks
100% Remote: Work from the comfort of your home with no daily commute
Flexible Schedule: Build a schedule that works around your personal and professional commitments
Licensing Support: We help guide you through the required licensing process
Entry-Level Opportunity: No previous industry experience is required
Leadership Development: Develop communication, presentation, mentoring, and leadership skills
Career Advancement: Opportunity to grow into additional leadership and management responsibilities
Performance-Based Income: Commission-based compensation with opportunities to increase your earnings as you develop
Mentorship & Team Support: Work alongside experienced leaders who provide guidance and accountability
Meaningful Work: Help union members, families, and communities access programs and services designed to support them
Health and Dental: After 90 days, health insurance reimbursement and dental programs through Humana.
Screening Questions
Question 1 *
Are you based in the United States?
Question 2 *
Are you able to pass a Background Check?
Required Documents
Job Info
Full-time
Mid
Leadership
Boston, Massachusetts, United States
Sep 14, 2026
$50K - $120K/yr
Dec 31, 2026
Required
Optional