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, Training & Quality Manager to build and scale the training, coaching, and quality assurance function across member-facing operations. In this role, you’ll ensure Care Guides and other frontline team members are equipped with the tools, workflows, knowledge, and support needed to deliver a consistent, compassionate, and high-quality member experience.

This is a hands-on, operationally focused role for someone who enjoys building structure in a fast-paced environment. You’ll lead onboarding for new hire classes, create scalable training materials, develop quality scorecards, conduct call audits and case reviews, identify performance trends, and partner with leaders to improve team consistency. This role sits at the intersection of training, QA, operations, and member experience, helping Upside scale responsibly while maintaining a high standard of support for members navigating housing instability. This role reports to the SVP, Operations.

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 onboarding and training for new hire classes across Care Guide and member-facing operations

• Build and maintain scalable training materials, including onboarding curricula, SOPs, playbooks, call scripts, role plays, and knowledge base content

• Facilitate live trainings, workshops, refresher sessions, and ongoing education to reinforce workflows, quality standards, and best practices

• Develop and manage Upside’s quality assurance process, including call audits, critical listenings, documentation reviews, case reviews, and spot checks

• Evaluate member interactions for empathy, professionalism, accuracy, documentation quality, workflow adherence, and overall member experience

• Create and refine quality scorecards, audit frameworks, coaching templates, and operational standards to ensure consistency across teams

• Partner with Care Guide Managers and operational leaders to identify knowledge gaps, quality trends, workflow issues, and targeted coaching needs

• Deliver actionable coaching and feedback to frontline team members and managers to improve performance, consistency, and member engagement

• Track and report on key training and quality metrics, including onboarding completion, ramp progress, audit scores, coaching trends, and member experience indicators

• Support rollout and education for new clients, programs, workflows, tools, and operational updates

• Collaborate cross-functionally with Operations, Clinical, Product, Client Success, and leadership to improve workflows and support change management

• Continuously improve training programs, QA frameworks, and operational resources as Upside scales
  
  

What We’re Looking For:

• 3+ years of experience in training, quality assurance, learning and development, healthcare operations, care coordination, customer support, member services, or a similar operational environment

• Experience building or leading onboarding, new hire training, continuous education, or team enablement programs

• Experience conducting call audits, documentation reviews, coaching sessions, case reviews, or quality assurance initiatives

• Strong facilitation and coaching skills, with the ability to lead trainings, role plays, workshops, and feedback conversations with confidence

• Ability to identify performance trends, diagnose root causes, and turn findings into practical training, coaching, or workflow improvements

• Strong operational judgment, with the ability to create structure, standardize processes, and reinforce consistency across a growing team

• Excellent written communication skills, including experience creating SOPs, workflows, playbooks, training guides, scripts, or knowledge base content

• Strong attention to detail, especially when reviewing documentation, audit findings, member interactions, and process adherence

• Comfort working in a fast-paced, high-growth environment where priorities, workflows, and tools may continue to evolve

• Experience with Salesforce, telephony systems, LMS platforms, QA tools, dashboards, or operational reporting tools preferred

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

• Ability to work independently and effectively in a fully 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.