Outreach & Enrollment Specialist (Remote - United States)
About The Position
Upside is hiring an Outreach & Enrollment Specialist to serve as the first point of contact for members referred through our health plan partners. This is a high-volume outreach role focused on calling referred members, explaining Upside’s services, completing efficient intakes, and driving timely enrollments. The role is performance-driven and incentive-oriented, with clear daily goals and a direct connection between effort and results. You’ll manage a steady pipeline of warm referrals, handle inbound and outbound calls, and follow up consistently to keep members moving through enrollment and scheduling. This role reports to our VP, Care Enablement.
Requirements
- 1–3 years of experience in outreach, enrollment, intake, admissions, member services, customer support, call center, or inbound/outbound sales environments
- Comfort working in a high-volume, phone-heavy role with daily metrics or quotas, and the organization to track performance goals and follow-ups consistently
- Strong verbal communication and active listening skills, with the ability to explain services simply and clearly
- Ability to build rapport quickly, handle objections, and move conversations toward clear next steps
- Strong organization, follow-through, and attention to detail across documentation and scheduling
- Comfort working across multiple systems (Salesforce or similar CRM experience is a plus)
- Ability to work independently in a fully remote environment
Nice To Haves
- Spanish fluency is a plus
Responsibilities
- Conduct high-volume inbound and outbound outreach to referred and existing members to drive enrollments
- Explain Upside’s services, set expectations, and guide members through enrollment and next steps
- Complete streamlined intakes that capture key demographic, eligibility, and high-level clinical details
- Schedule members based on availability, location, and internal matching criteria
- Follow established scripts and workflows while tailoring conversations to build trust and reduce friction
- Document all interactions accurately and on time in Salesforce and related phone systems
- Track follow-ups and outreach activity to prevent drop-off and keep referrals moving
- Meet daily, weekly, and monthly performance goals tied to enrollments, calls completed, and appointments scheduled
- Partner with internal teams to troubleshoot outreach challenges, scheduling constraints, or member barriers
- Maintain HIPAA and confidentiality standards when handling member information
- Participate in training, coaching, and quality initiatives to continuously improve performance
Benefits
- Medical, dental, and vision coverage
- Paid time off and company holidays
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What This Job Offers
Job Type
Full-time
Career Level
Entry Level
Education Level
No Education Listed
