Care Team Manager

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 Care Guide Team Manager to lead and develop a team of Care Guides supporting members navigating housing instability, complex social needs, and moments of crisis. In this role, you’ll be responsible for driving team performance, coaching Care Guides, reinforcing quality standards, and ensuring members receive timely, compassionate, and consistent support throughout their housing support journey.

This is a fast-paced, metrics-driven leadership role for someone who can balance empathy with accountability. You’ll manage day-to-day team operations, lead huddles and 1:1s, review member documentation and care plans, monitor performance dashboards, and identify workflow gaps that impact member experience or operational outcomes. You’ll also serve as a key bridge between frontline execution and leadership strategy, helping Upside scale repeatable, high-quality programs across teams and clients.

This role reports to the VP, Clinical Operations. Internally, this position is referred to as a Care Guide Manager.

Work Location and Schedule:

Full-time, fully remote

Coverage aligned to Eastern and Pacific time zones

Schedule is expected to be Monday–Friday, with flexibility needed based on business needs, team coverage, client implementations, and member support needs

What You’ll Do

Lead, coach, and develop a team of Care Guides supporting members through housing-related needs and complex social barriers

Run regular team huddles, 1:1s, call reviews, and coaching touchpoints to drive alignment, urgency, accountability, and continuous improvement

Monitor team performance using dashboards, activity metrics, documentation quality, member engagement, and program outcomes

Conduct live case audits and documentation reviews to ensure Care Guides are completing accurate assessments, clear notes, timely follow-ups, and actionable member plans

Review and approve individualized member plans to ensure next steps are practical, member-centered, and aligned with Upside’s program standards

Serve as the first point of escalation for Care Guides, helping troubleshoot member barriers, workflow issues, documentation gaps, and operational blockers

Support onboarding, training, staffing, and coverage planning to ensure the team is prepared to meet member and program needs

Own day-to-day program execution after handoff from Sales or Implementation, ensuring programs are launched, communicated, and managed effectively

Partner cross-functionally with Operations, Sales, Client Success, Implementation, and leadership to support program rollouts, client needs, and internal alignment

Provide regular updates to leadership on team performance, program health, operational risks, and areas for improvement

Roll out and reinforce consistent scripts, workflows, best practices, and quality standards across the Care Guide team

Support the development and upkeep of training materials, SOPs, knowledge base content, and operational documentation

Identify opportunities to improve workflows, templates, reporting, and processes as Upside continues to scale

Serve as a subject matter expert on Upside’s care guide model, including supporting client-facing conversations and implementation needs as needed

What We’re Looking For:

3+ years of experience in healthcare operations, care management, member services, social services, housing support, or a similarly fast-paced member-facing environment

1+ year of experience leading, managing, mentoring, or coaching teams in an operational environment

Experience managing team performance metrics, dashboards, KPIs, QA processes, or activity-based goals

Strong coaching skills, including the ability to give direct feedback, improve performance, and build trust with frontline team members

Comfort leading in a fast-paced, evolving environment where workflows, priorities, and programs may continue to change as the business scales

Strong operational judgment, with the ability to identify gaps, create structure, and help a team execute consistently

Excellent communication skills with the ability to align internal teams, support external conversations, and clearly translate priorities into action

High empathy and strong boundaries, with the ability to support complex member situations while maintaining accountability and forward momentum

Strong organization and attention to detail, especially when reviewing documentation, care plans, follow-ups, and member status updates

Experience with Salesforce, CRM tools, care management platforms, or workflow management systems preferred

Knowledge of Medicaid, housing instability, care coordination, social determinants of health, or community-based support programs strongly preferred

Ability to work independently and effectively in a remote environment

Spanish fluency is a plus

Compensation and Benefits:

Competitive base salary (target range $70,000–$80,000 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.