Founding Product Lead

Location: Remote About Upside: Upside is redefining how housing stability drives health outcomes. Through one integrated platform, Upside partners with health plans, government payers, and employer groups to identify members at risk, develop individualized housing plans, secure placements quickly, and track outcomes over time. By addressing housing as a core social determinant of health, Upside helps reduce avoidable utilization, improve member stability, and deliver measurable ROI. At Upside, we operate in a rapidly evolving environment where client requirements, policy changes, operational needs, and technology capabilities constantly shift. We are looking for a builder who can translate these external demands into scalable internal solutions. About the Role This is a highly cross functional leadership role focused on transforming external client needs into scalable products, workflows, and operational systems that improve frontline efficiency and business performance. The Director of Product Development, Business Systems Operations will sit at the intersection of Operations, Sales, Product, Technology, Data, and Client Success to identify opportunities, define requirements, and build systems that enable scale. This individual will act as the connective layer between what clients ask for, what operations needs, and what technology should build. Success in this role means increasing Care Guide efficiency and capacity, enabling teams to support 300+ member cases without increasing workload, improving reporting and operational automation, and ensuring product investments create measurable business impact. The ideal candidate can think strategically while also moving quickly to build MVPs, launch workflows, create operational and sales artifacts, and drive execution. Your Responsibilities Product Development & Business Systems Strategy Own the roadmap and evolution of internal operational systems and tooling across Care Guide, Clinical Operations, Data Operations, and Client Success teams Translate external client requirements from health plans, employer groups, and government payers into actionable internal product requirements Partner with Sales and leadership to identify emerging market needs and convert them into scalable product opportunities Partner closely with Sales, Operations, Product, Technology, and Executive Leadership to determine high impact priorities Define near term MVP solutions while establishing long term scalable product strategies Continuously identify workflow inefficiencies and opportunities to reduce administrative burden Frontline Workforce Optimization Design and improve workflows that increase Care Guide efficiency and enable significantly larger caseload capacity without increasing workload Partner directly with frontline teams to understand friction points and operational bottlenecks Leverage automation, AI, and workflow redesign to eliminate manual effort Design workflows and documentation experiences that improve data quality and ensure critical information is captured in a structured, scalable manner Develop systems that allow frontline teams to focus on member engagement rather than administrative work Client Translation & Sales Enablement Distill client requirements, payer expectations, policy updates, and market demands into internal workflows and product enhancements Create artifacts and supporting collateral that enable Sales and Client Success teams to effectively communicate product capabilities Partner with Sales leadership to prioritize market requests and create implementation roadmaps Support product positioning, workflow demonstrations, and client solution design Ensure operational and technical capabilities align with what is being sold Technology Roadmap & Product Prioritization Make prioritization decisions across competing business requests, balancing client demands, operational needs, and long term strategic goals Partner with Engineering and Technology teams to prioritize initiatives that drive measurable improvements Create business requirements, user stories, workflow documentation, and implementation plans Make prioritization recommendations balancing short term business demands with long term scalability Act as primary liaison between business stakeholders and technology teams Data, Reporting & Operational Intelligence Help establish, build, and scale the team that will ultimately own client reporting and business analytics functions Develop the organizational structure, roles, workflows, and processes necessary to support long term reporting and analytics operations Create reporting frameworks that consistently showcase ROI, outcomes, and client value Build repeatable reporting packages including QBRs, monthly reporting, and operational scorecards Establish governance standards around reporting accuracy, data quality, and audit readiness Partner with Data and Technology teams to create scalable reporting infrastructure and automation capabilities Transition mature processes and reporting ownership to the appropriate long term team structure as the function evolves Cross Functional Leadership & Execution Own rollout strategy, training inputs, adoption metrics, feedback loops, and iterative improvements to ensure released solutions drive measurable impact Establish mechanisms to continuously collect frontline feedback and incorporate findings into future product enhancements Work closely with Operations leadership to rapidly test and implement new ideas Lead projects requiring coordination across multiple functions Build structure and ownership where processes do not currently exist Drive implementation and adoption of new workflows Ensure operational feedback continuously informs future product direction What Success Looks Like Increased Frontline Capacity Frontline teams can support significantly larger member populations through better tooling, automation, and workflow design while maintaining quality and member experience Product Driven Operational Scale Internal systems become a competitive advantage that improves efficiency, reduces manual work, and supports rapid growth Strong Client Translation Client requirements consistently translate into scalable products and workflows without creating operational complexity Faster Reporting & Demonstrated ROI Client reporting packages and outcome narratives can be generated quickly, accurately, and consistently Technology Investment Alignment Technology resources and roadmap priorities focus on initiatives creating the greatest operational and business impact. Qualifications 7+ years of experience in Product Management, Business Systems, Operations, Strategy, or related leadership roles Demonstrated experience building products, workflows, or business systems from concept through implementation in rapidly evolving environments Experience within healthcare, digital health, value based care, SDOH, payer environments, or healthcare technology strongly preferred Strong experience translating business needs into product requirements Demonstrated experience building MVPs and scaling products from concept through implementation Experience partnering across Sales, Operations, Product, and Engineering teams Strong understanding of workflow optimization and operational systems design Experience with AI enabled workflows, reporting automation, and internal tooling strongly preferred Exceptional communication and prioritization skills Ability to thrive in ambiguity and rapidly changing environments.