Founding Product Lead

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.