Senior Product Manager
Pear VC
Senior Product ManagerWe're looking for a Senior Product Manager with 5+ years of product management experience and meaningful experience in healthcare or health tech to help us turn complex healthcare operations into simple, scalable products.This is a highly hands-on, customer-facing product role. You'll work directly with health center executives, frontline teams, engineers, operations, and the founders to deeply understand problems, identify what we should build, and drive products from discovery through launch and iteration.You'll be in the room with our customers. You'll lead working sessions, understand how their workflows operate today, identify where things break down, and work alongside them to design better ways of working. You'll turn those conversations into product ideas and clear product direction, bring concepts back to customers for feedback, and partner closely with engineering to bring the best solutions to life.Our customers operate in complex environments where workflows often span patients, staff, payers, EHRs, external systems, phone calls, spreadsheets, and manual follow-up. Your job is to make that complexity feel simple.You won't manage a backlog from a distance. You'll talk to users, map workflows, make product decisions, write clear requirements, test ideas, and stay close to customers after launch to make sure what we build actually works.You'll have significant ownership over our product as we scale from high-value workflows into a broader platform for healthcare administrative automation.What You'll DoOwn products and workflows end-to-end, from customer discovery and problem definition through development, launch, measurement, and iteration.Lead product conversations directly with customers, including healthcare executives, operational leaders, and frontline staff.Co-design solutions with customers. Understand how work happens today, identify where it can improve, and translate real operational problems into better workflows and product experiences.Facilitate ambiguous customer conversations and create clarity. Ask the right questions, surface the real problem, align on the desired future state, and determine what the product team should do next.Turn customer conversations into scalable product direction, separating individual feature requests from broader problems and identifying patterns across customers.Prototype and test ideas quickly. Put concepts in front of users, gather feedback, and iterate before and after launch.Translate complex healthcare operations into intuitive products that reduce administrative burden and make it easier for teams to get work done.Partner closely with engineering to translate customer and business needs into clear product requirements and make thoughtful tradeoffs around scope, usability, speed, and reliability.Map current-state and future-state workflows, including the people, systems, decisions, handoffs, and exceptions involved.Define and track success metrics and use product data, operational outcomes, and customer feedback to understand what's working and where we should improve.Prioritize thoughtfully, balancing customer needs, product strategy, engineering capacity, scalability, and business impact.Stay close to implementation and adoption. The job doesn't stop when something ships; you'll work with customers and internal teams to understand how products perform in the real world and continuously improve them.Help shape the broader product strategy and roadmap as BridgeHealthAI grows.Qualifications & RequirementsRequired5+ years of product management experience, with meaningful experience building products in healthcare or health tech.Experience owning meaningful products or workflows from discovery through launch and iteration, rather than primarily managing requirements or a backlog.Strong understanding of healthcare operations and the complexity of building products involving patients, providers, payers, clinical teams, and administrative staff.Exceptional customer-facing skills. You're comfortable leading working sessions with healthcare executives and frontline teams, asking the right questions, challenging assumptions respectfully, and turning messy conversations into clear product ideas and decisions.Demonstrated ability to conduct strong customer and user discovery, identify the underlying problem behind a request, and translate insights into scalable solutions.Strong product and user experience judgment. You care about making complex workflows feel simple and intuitive and can recognize when a product experience is confusing, overly complicated, or solving the wrong problem.Strong business judgment. You understand how product decisions connect to customer value, adoption, scalability, and company priorities—not just feature delivery.Experience working closely with engineers and translating ambiguous customer and business problems into clear product direction and requirements.Comfortable working with modern AI tools. You regularly use tools such as ChatGPT, Claude, Cursor, or similar tools to work faster across research, synthesis, prototyping, and product development. You don't need to be an engineer, but you should be curious about what's possible with AI and comfortable experimenting with new tools.Strong analytical skills and comfort using both quantitative and qualitative information to evaluate product performance and make decisions.Excellent written and verbal communication. You can communicate clearly with engineers, healthcare executives, frontline staff, customers, and founders.Ability to operate effectively in ambiguity. You can create structure where none exists, make decisions with incomplete information, and move quickly without waiting for a perfect playbook.Strong ownership mindset. You care about whether something actually works for the customer—not simply whether the feature shipped.Strongly PreferredExperience at an early-stage health tech startup, ideally Seed through Series B.Experience building technology for providers, health systems, FQHCs, Medicaid populations, payers, or value-based care organizations.Experience with healthcare administrative workflows such as eligibility, enrollment, revenue cycle, patient access, care coordination, referrals, scheduling, prior authorization, or patient engagement.Familiarity with EHRs, payer systems, and healthcare data workflows.Understanding of HIPAA, PHI, healthcare compliance, and the reliability expectations associated with healthcare software.Experience building products that combine technology with real-world operational workflows, rather than purely self-service software.Experience designing products for users who are busy, operationally constrained, and not necessarily highly technical.Comfortable using modern tools to quickly prototype or communicate product ideas.Chicago-based or willing to work hybrid. We value regular in-person collaboration, particularly for product and strategy work.What We ValueCustomer Obsession: You want to understand how the work actually happens. You get close to users, ask questions, observe workflows, and care about solving the real problem—not simply delivering the requested feature.Product Judgment: You can simplify complexity and make thoughtful tradeoffs between customer needs, usability, scalability, speed, and business impact.Business Judgment: You understand that not every customer request should become a feature and can connect product decisions to the broader company strategy.AI-Native Mindset: You're comfortable using emerging AI tools to research, synthesize, prototype, and work more effectively. You treat AI as a tool to move faster—not a substitute for judgment.Bias Toward Action: You don't need months of research before testing an idea. You find the fastest responsible way to learn, get feedback, and iterate.Clarity: You can walk into an ambiguous customer conversation and leave with a clear understanding of the problem, the desired future state, and what should happen next.Ownership: You see things through. Shipping is a milestone, not the finish line.Systems Thinking: You understand that healthcare workflows rarely exist in isolation and think through downstream effects, handoffs, edge cases, and operational realities.Learning Agility: You can quickly learn a new healthcare workflow, customer environment, technology, or AI tool and apply that knowledge effectively.High Standards: Healthcare users need products they can trust. You care deeply about quality, usability, reliability, and the details that determine whether a workflow succeeds.Why Join Us?Build with Purpose: Your work will directly support organizations serving underserved communities, helping keep patients covered while reducing the administrative burden on care teams.Build Directly With Customers: You'll have unusually close access to healthcare leaders and frontline teams and work alongside them to turn real problems into products.Own Meaningful Product Problems: You'll tackle complex, high-value healthcare workflows where great product thinking can eliminate hours of manual work.Shape the Product
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