Product Design Lead

SETTING THE STAGE

Sports betting content is exploding, but the experience around it is fragmented. Talented sports handicappers (“cappers”) are building large audiences, while bettors are searching for people they trust and an edge. Today, that happens across social media, messaging apps, sportsbooks, and other tools. The company brings it together in one place; helping cappers build their businesses and bettors discover, follow, and act on the people they trust..

OUR VISION AND OUR MISSION

The company is building the destination where cappers and fans Win More Together.

• For fans: the company is creating unified and highly valuable experience for fans that love tailing cappers. Get the best advice, in the smoothest fashion, and enjoy rewards that keep you engaged.

• For cappers: the company is a business-building engine that helps you turn your passion into a profitable business. Cappers are the stars of the game, and enjoy a best-in-class operating system, automated marketing, and purpose-built discovery that grows their business on auto-pilot.

• For the company: It’s the ecosystem and unified "Win More Together" experience that cappers and fans have been waiting for. It's the value-add layer that brings richness to the experience of betting, tailing, and discovering new cappers.

ABOUT THE ROLE

We’re looking for a Lead Product Designer to shape the company’s mobile product across both sides of our marketplace: helping creators build and manage subscription businesses, and helping fans discover creators, subscribe, and engage with their content.

This is a senior individual contributor role with ownership of design direction and meaningful influence over product decisions. You’ll stay hands-on in design and prototyping while guiding product quality across the team. You’ll combine strong product thinking, interaction design, and visual craft to create intuitive, engaging experiences. Working closely with Product, Engineering, Creator Success, and company leadership, you’ll lead design from problem definition through launch and iteration.

LOCATION AND ENGAGEMENT

Chicago-based candidates are preferred. We’re seeking a long-term, full-time team member but are open to a fractional or contract-to-hire engagement to start.

WHAT YOU'LL DO

• Lead end-to-end product design, including discovery, information architecture, user flows, prototypes, visual design, and implementation review.

• Build a deep understanding of the company’s business and users, proactively identify problems and opportunities, and bring ideas and perspectives that help shape product priorities.

• Design complete user journeys, considering the decisions, information, and interactions that help people accomplish their goals.

• Develop consistent navigation, interaction patterns, and visual design across the company’s mobile experiences.

• Design and iterate on core fan journeys, including discovery, subscription, onboarding, content access, engagement, and renewal.

• Create tools that help creators launch offerings, communicate with subscribers, understand performance, and grow their businesses.

• Use focused user research, usability testing, and competitive analysis to inform product direction, evaluate concepts, and guide iteration.

• Work fluidly with engineers across early UX exploration, rapid prototyping, active development, and refinement of shipped experiences, adapting your involvement to what each project needs.

• Use AI and rapid prototyping tools to explore ideas and validate concepts, and collaborate effectively with engineers using AI to prototype and build.

• Contribute to shared design patterns and provide constructive feedback that supports quality across the team.

WHAT WE'RE LOOKING FOR

• Senior- or lead-level experience designing and shipping digital products as a hands-on individual contributor, with a portfolio showing your contribution from problem definition through launch and iteration.

• Strong interaction design and information architecture skills, with demonstrated experience independently defining and solving complex consumer experience problems from early exploration through shipped solutions.

• Strong visual design skills across responsive web and mobile, including thoughtful use of hierarchy, typography, and interaction details to create engaging products.

• Experience with consumer subscriptions, marketplaces, creator tools, commerce, or similarly complex products serving more than one type of user.

• Sound product judgment: you can connect user needs to business goals, prioritize high-impact opportunities, and explain design decisions and tradeoffs clearly.

• A portfolio that demonstrates how you think across user journeys, with evidence of your reasoning, exploration, and approach to validation.

• A proactive approach to understanding the business, identifying opportunities, and constructively challenging assumptions.

• Comfort working directly with users, navigating incomplete information, and adapting your design approach as priorities and development evolve.

• A practical approach to balancing craft, learning, and speed, with the judgment to contribute effectively at different stages of development.

• Experience collaborating closely with engineers and an understanding of how design decisions translate into production software.

• Fluency with Figma and prototyping, plus curiosity about emerging tools that can improve design and product development.

• A willingness to stay hands-on while guiding the quality and direction of work beyond your own projects.

• Experience in sports betting, prediction markets, marketplaces, or creator platforms is a plus. You should be motivated to develop a deep understanding of the company’s business and how creators and fans use the product.

We are an equal opportunity employer and do not discriminate on the basis of any status protected under federal, state, or local law.