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 Founding Product Lead to own product strategy and execution across internal operational tools and emerging customer experiences. This is a hands-on, high-impact role for someone who can translate frontline, customer, and business needs into scalable products, workflows, and technology solutions. The Founding Product Lead will work closely with the COO, CTO, Operations, Customer Success, and GTM teams to define priorities and move products from early concept through launch and adoption.
A key focus will be improving the systems and workflows that support Care Guide efficiency, member navigation, data quality, and customer reporting. This person will explore how AI, automation, voice technology, enhanced Salesforce functionality, and potentially proprietary tools can reduce administrative burden and support greater operational scale. The role will also help shape Upside’s employer-facing product as the company expands beyond government-sponsored programs. This role reports to the COO.
Work Location and Schedule:
Full-time, remote within the United States
South Florida preferred due to proximity to company leadership
Must be available to travel as needed for leadership meetings, customer discussions, and product discovery
What You’ll Do:
Own product strategy, roadmap, and prioritization across internal tools and emerging customer-facing products
Partner closely with the CTO and Engineering team to translate business and operational needs into clear product requirements
Spend time with Care Guides and Operations leaders to understand workflow friction, administrative burden, and opportunities to improve capacity
Design and launch tools that reduce manual data entry and allow frontline teams to focus more time on member engagement
Evaluate opportunities to enhance Salesforce through plugins, automation, voice tools, and AI while helping determine when proprietary systems may be needed
Help develop an AI-enabled resource platform that supports navigation across housing, food, transportation, financial assistance, domestic violence resources, and other member needs
Improve how service activity, member outcomes, and customer reporting are captured, structured, and shared
Lead product discovery and development for Upside’s employer-facing offering
Translate customer, payer, and market needs into scalable products without creating unnecessary platform complexity
Create product requirements, user stories, workflow documentation, and implementation plans
Make prioritization decisions across competing customer, operational, and technology requests
Own product rollout, adoption, training inputs, feedback loops, and ongoing iteration
Establish product processes and operating rhythms that support growth without adding unnecessary bureaucracy
Help define the structure and future needs of Upside’s product organization
What We’re Looking For:
7+ years of experience in product management, product strategy, business systems, or related roles
Experience owning products from early discovery through launch, adoption, and iteration
Strong 0–1 product experience and comfort building where processes and systems do not yet exist
Demonstrated success translating operational and customer needs into products engineers can build
Experience partnering closely with Engineering, Operations, Sales, and Customer Success teams
Strong understanding of workflow design, internal tooling, automation, and operational systems
Experience using AI, voice technology, or automation to improve frontline workflows is strongly preferred
Strong product judgment and the ability to make clear prioritization decisions in a fast-moving environment
Excellent written communication and ability to create clear requirements, roadmaps, and decision frameworks
Strong design and user-experience instincts, particularly for operational tools
Ability to operate independently, move quickly, and thrive in ambiguity
Experience in healthcare, digital health, payer environments, SDOH, care navigation, or an operations-heavy business is a plus
Experience building or improving Salesforce-based workflows is a plus
Compensation and Benefits:
Competitive base salary
Performance-based bonus opportunity
Meaningful equity
Medical, dental, and vision coverage
Paid time off and company holidays
Remote work within the United States
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.