Member Service Representative (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 a Member Service Representative to support high-need members navigating housing instability. In this role, you’ll serve as a member’s primary point of contact and a steady guide through next steps. This role is equal parts member support and operational execution. You will manage a caseload of members, run structured check-ins, identify barriers, and connect patients to the right resources.

This is a fast-paced, metrics-driven role for someone who brings high empathy and high urgency. You know how to build trust, prioritize member needs, and operate efficiently so you can provide consistent support across your full caseload. You’ll use Salesforce daily to track outreach, prioritize follow-ups, and ensure a strong member experience that drives satisfaction and retention. This role reports to the SVP, Clinical Operations. Internally, this position is referred to as a Care Guide.

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

• Own a caseload of members and serve as their primary point of contact throughout their housing support journey

• Conduct structured weekly (or as-needed) check-ins to assess progress, remove blockers, and maintain engagement

• Create clear, practical next steps with members and keep momentum through consistent follow-up and accountability

• Coordinate housing-related actions, including gathering information, supporting applications, and working with partners to move placements forward

• Refer members to other community resources when needed (food resources, local CBOs, and other supports)

• Use Salesforce daily to track outreach, update member status, document interactions, and manage tasks and follow-ups

• Prioritize your day using workflow queues, urgency, and member risk to ensure timely outreach and resolution

• Identify barriers early (documentation issues, communication gaps, readiness, access challenges) and escalate appropriately to unblock progress

• Partner closely with internal teams and external partners to coordinate handoffs, align on next steps, and ensure members receive consistent information

• Maintain high-quality documentation and outcomes tracking to support reporting and continuous improvement

• Contribute feedback on workflows, templates, and resources to improve speed, clarity, and member experience over time

What We’re Looking For:

• 1–3+ years of experience in member services, care navigation, eligibility/referrals, community-based services, healthcare call center, or a similarly fast-paced member-facing role

• Experience supporting housing navigation or related programs, and/or relevant certifications or licenses (HUD certification, CHW certification,  MSW, LCSW) preferred but not required

• Experience supporting Medicaid members and/or unhoused or housing-insecure populations

• Comfort working in a structured, metrics-driven environment with clear activity expectations and follow-up SLAs

• Strong phone presence with the ability to build rapport quickly, communicate clearly, and keep conversations focused on next steps

• High ownership and organization, including experience managing a book of work or caseload and staying on top of follow-ups

• Strong attention to detail and ability to document accurately in tools like Salesforce (or similar CRM/workflow systems)

• Ability to navigate complex member situations with empathy while maintaining boundaries and moving work forward

• Familiarity with housing instability and social determinants of health is a plus

• Spanish fluency is a plus

Compensation and Benefits:

• Competitive base salary (target range $50,000–$60,000 depending on experience)

• 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.