Outreach & Enrollment Specialist (Remote - United States)

About Upside:

Upside is a housing-focused care partner helping people experiencing housing instability take the next step toward stability. We partner with health plans and care organizations to identify members at risk, build a clear housing plan, and drive the work forward through placement and stabilization.

Upside owns the entire housing process from start to finish. Our team engages members, coordinates with local providers and community resources, manages logistics and documentation, and stays involved until the issue is resolved. Our approach is human-first and outcome-driven, measured by real results like stable housing, completed moves, safer living environments, and successful transitions.

About the Opportunity:

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.

Work Location and Schedule:

• Full-time, fully remote (must be based in the United States)

• Coverage aligned to Eastern and Pacific time zones

• Schedule is starting Monday–Friday, but may be adjusted based on business needs and member caseload coverage (including occasional evenings and, over time, weekends)

What You’ll Do:

• 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

What We’re Looking For:

• 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

• Spanish fluency is a plus

Compensation and Benefits:

• Hourly pay: $18–$22 per hour

• Commission-style incentive structure based on performance

• Medical, dental, and vision coverage

• Paid time off and company holidays

Upside is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex, marital status, ancestry, disability, genetic information, veteran status, gender identity or expression, sexual orientation, pregnancy, or other applicable legally protected characteristic. Upside is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans. If you have a disability or special need that requires accommodation, please let us know.