Product Manager - Checkout Experience

Cherry; Northern (KY); Hybrid; USD 120,000 - 180,000; Full time

Benefits offered by this job

Fully remote company

Quarterly in-person retreats

Medical, vision, and dental benefits

Job summary

Cherry is seeking a rockstar Product Manager to join the Checkout Experience pillar, focused on growing revenue for providers and maximizing the transaction volume processed through Cherry. You will lead end-to-end product development and own the roadmap, partnering with engineering, design, data, and GTM teams to deliver best-in-class checkout experiences.

The role requires strong product instincts, startup experience, and the ability to prototype with AI tools.

Qualifications

• Previous product management experience with demonstrated impact.

Responsibilities

• Launch new products and features. Design elegant solutions to complex problems and drive measurable impact. Balance short-term needs with long-term goals. Ship fast and iterate quickly.
• Execute cross-functionally. Partner closely with engineering, design, go-to-market, and data teams to deliver best-in-class experiences.
• Own product surfaces end-to-end. You’ll be responsible for the success of your domain, from strategy through day-to-day execution.
• Define the product roadmap. Identify pain points by speaking with real users to deeply understand their needs. Prioritize the most important problems to solve based on competitor research, data analysis, and company priorities.
• Build personally. Use AI coding tools to creatively prototype and test ideas with real users in hours, not weeks.
• Go deep on data. Run your own analyses, design your own experiments, and validate your hypotheses with facts.

Skills

Product management

Startup experience

AI prototyping

Prioritization

Customer empathy

Feedback mindset

Communication

Tools

Cursor

Claude Code

Job description

About Cherry

Cherry is a Series C unicorn backed by top-tier investors such as Kleiner Perkins and CapitalG. We’re making healthcare more affordable by offering payment solutions (buy-now-pay-later, payment processing, etc.) for medical practices.

About the Role

We are looking for a rockstar Product Manager to join our Checkout Experience pillar, which is focused on growing revenue for our providers and maximizing the transaction volume processed through Cherry. Everything our teams work on drives top line growth for one of the fastest growing Fintechs in the world.

Responsibilities

• Launch new products and features. Design elegant solutions to complex problems and drive measurable impact. Balance short-term needs with long-term goals. Ship fast and iterate quickly.
• Execute cross-functionally. Partner closely with engineering, design, go-to-market, and data teams to deliver best-in-class experiences.
• Own product surfaces end-to-end. You’ll be responsible for the success of your domain, from strategy through day-to-day execution.
• Define the product roadmap. Identify pain points by speaking with real users to deeply understand their needs. Prioritize the most important problems to solve based on competitor research, data analysis, and company priorities.
• Build personally. Use AI coding tools to creatively prototype and test ideas with real users in hours, not weeks.
• Go deep on data. Run your own analyses, design your own experiments, and validate your hypotheses with facts.

Example Initiatives

• Some providers are unhappy with their fees while others are willing to pay more for higher approvals. Build and launch a system that allows providers to customize their Pricing to fit their preferences.
• Providers have difficulty using Cherry because total cost often changes during the course of treatment. Launch a feature to allow purchase amount to be modified post-checkout.
• Applicants are dropping off after being approved. Redesign the approval experience to improve conversion.

Qualifications

• Previous product management experience with demonstrated impact
• Experience in a fast-paced startup environment
• Ability to build working prototypes using AI coding tools (Cursor, Claude Code, etc.), debates architecture and system trade-offs with engineering as a peer, and reads technical documentation/API specs well enough to scope feasibility independently.
• Able to prioritize when there are many things that need your attention
• Can roll up your sleeves and live the life of your users to develop a deep empathy for their problems
• Open to feedback and hungry for opportunities to learn and grow
• Effective verbal and written communication skills for internal and external audiences

Compensation Package

• Attractive base pay with additional bonus incentives
• Generous equity grant
• Medical, vision, and dental benefits
• Fully remote company
• Quarterly in-person retreats

Cherry provides equal employment opportunity (EEO) to all persons regardless of age, color, national origin, citizenship status, physical or mental disability, race, religion, creed, gender, sex, sexual orientation, gender identity and/or expression, genetic information, marital status, status with regard to public assistance, veteran status, or any other characteristic protected by federal, state or local law.