Founding Product Lead

UpsideHom, Inc.•Fort Lauderdale, FL

15h•Remote

About The Position

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.

Requirements

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
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

Nice To Haves

Experience using AI, voice technology, or automation to improve frontline workflows is strongly preferred
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

Responsibilities

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