Product Manager, Payments & Operations

About Chalkboard:

Chalkboard is building the future of sports gaming. Our mission is to blur the line between watching and playing by turning real-money sports gaming into a social, immersive experience built for fans who play to win. We're reimagining how sports fans engage with the games they love.

At our core, we’re a team of sports-obsessed builders who value clarity, fairness, and the thrill of helping fans turn insight into action.

About Chalkboard:

Chalkboard is building the future of sports gaming. Our mission is to blur the line between watching and playing by turning real-money sports gaming into a social, immersive experience built for fans who play to win. We're reimagining how sports fans engage with the games they love. At our core, we’re a team of sports-obsessed builders who value clarity, fairness, and the thrill of helping fans turn insight into action.

The Role:

We’re looking for a Product Manager, Payments & Operations to join Chalkboard and own the systems that power how money moves through our platform and how our business operates behind the scenes.

In this role, you’ll work closely with Engineering, Design, Finance, Compliance, RevOps, Trading, Customer Support, and Data Science, playing a meaningful part in delivering both seamless customer-facing payment experiences and high-leverage internal tooling.

Your Game Plan:

Own and evolve both the payments experience and internal operations tooling to reduce friction, improve conversion, manage risk, and enable smarter, faster decision-making across the business.

• Own the end-to-end roadmap for deposits, withdrawals, account management, and internal operations tooling

• Continuously optimize the deposit funnel through experimentation to improve conversion and increase average deposit amounts

• Reduce payment errors and operational inefficiencies by identifying root causes and shipping scalable solutions

• Partner cross-functionally with Engineering, Finance, Compliance, RevOps, Trading, and Support to deliver reliable, compliant, and scalable systems

• Translate complex payment, risk, and operational constraints into clear product decisions and priorities

• Manage vendor and processor relationships, holding partners accountable to performance standards

• Build systems that proactively reduce fraud, chargebacks, and unprofitable exposure

• Develop smarter user controls, segmentation, and personalization to balance risk and revenue

• Use data rigorously to define success metrics, prioritize opportunities, and measure impact

• Work closely with internal stakeholders to deeply understand workflows, pain points, and decision-making needs

• Incorporate user research, support insights, and operational data into product direction

• Communicate roadmaps, progress, and tradeoffs clearly to stakeholders and leadership

What You Bring to the Team:

• Experience owning end-to-end product roadmaps in fintech, payments, marketplaces, or similar complex systems

• Strong analytical mindset with experience using data to drive product decisions and experimentation

• Ability to operate in regulated environments and navigate compliance, risk, and financial constraints

• Experience working cross-functionally with technical and non-technical stakeholders

• Proven ability to ship high-quality products in fast-paced, ambiguous environments

Pro Points:

• Experience with payments systems, fraud prevention, or money movement infrastructure

• Experience building internal tools or operational platforms

• Familiarity with A/B testing frameworks and conversion optimization

• Background in sports gaming, marketplaces, or consumer fintech

Why Chalkboard:

We care about results, but also how we get there. New problems, bigger plays, and opportunities to step up when it matters most happen often here. We want our team performing at their best, so here’s how we support our players:

• Comprehensive medical, dental, and vision coverage starting day 1, with the majority of premiums covered by Chalkboard

• 401(k) with company match

• Lunch on us everyday with a corporate DoorDash account

• Refuel in the office with protein shakes, energy drinks, and a snack buffet

• Flexible time off policy, plus 10 company holidays, WFH during the holidays

Compensation:

The base salary range for this role is $200-225k, with additional compensation in the form of equity, bonuses, and benefits.

Chalkboard is an equal opportunity employer:

We celebrate diversity and are committed to creating an inclusive environment for all employees. Chalkboard does not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity or expression, national origin, age, disability, veteran status, or any other legally protected status.

Work Authorization: We welcome applicants who are currently authorized to work in the United States. At this time, we’re unable to provide visa sponsorship for this role.

Why Chalkboard:

We care about results, but also how we get there. As Chalkboard grows, so do you. New problems, bigger plays, and opportunities to step up when it matters most happen often here. We want our team performing at their best, so here’s how we support our players:

• Comprehensive medical, dental, and vision coverage starting day 1, with the majority of premiums covered by Chalkboard

• 401(k) with company match

• Lunch on us everyday with a corporate DoorDash account

• Refuel in the office with protein shakes, energy drinks, and a snack buffet

• Flexible time off policy, plus 10 company holidays, WFH during the holidays