Lead Software Engineer, 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 not just creating another betting app. 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 Tech Lead, Operations to join Chalkboard and help us scale the internal systems that power our day-to-day business. This role sits at a principal-level impact and is critical to reducing operational friction across Customer Support, RevOps, Marketing, and Product.

In this role, you'll work cross-functionally, not just with Engineering, playing a meaningful part in how internal teams deliver promos, support users, and operate efficiently in real time. If you love building from scratch, automating messy workflows, and bringing order to chaos in fast-moving environments, this role is for you.

Your Game Plan:

You'll own the technical foundation that supports Chalkboard's internal operations, with a focus on automation, tooling, and documentation.

Level Up Our Game:

Deeply understand Chalkboard's operational workflows across Customer Support, RevOps, Marketing, and Product

Identify high-leverage opportunities to eliminate manual work through automation

Centralize fragmented operational workflows into the admin panel and internal tooling

Build and evolve tooling for promo delivery, push notifications, and internal integrations

Partner closely with RevOps to support daily promo execution and operational needs

Play Like a Captain:

Lead without direct authority by earning trust across CS and RevOps teams

Create documentation processes from scratch and drive adoption across the org

Establish clarity in areas that are currently messy, undocumented, or ambiguous

Serve as a technical thought partner for non-engineering stakeholders

Find a Way to Win:

Make progress even when context is incomplete or requirements are evolving

Navigate cross-functional priorities while balancing speed and quality

Improve operational reliability without slowing down the business

We Are Better Together:

Act as a connective tissue between Engineering and operational teams

Help teammates leverage internal systems more effectively

Raise the bar for how Chalkboard builds and maintains internal tools

What You Bring to the Team:

Strong backend engineering experience, with comfort owning systems end-to-end

Microservices architecture experience

Full stack experience with Node.js, React.js, React Native, PostgreSQL, MongoDB, and GCP

Proven ability to automate operational workflows and internal processes

Experience partnering closely with non-engineering teams (CS, RevOps, Marketing)

Track record of building internal tools, admin panels, or operational platforms

Ability to create and maintain clear documentation in low-documentation environments

Comfort operating at a principal-level scope with high autonomy and accountability

Pro Points:

Python experience, particularly in risk or operations-focused microservices

Experience integrating third-party tools (e.g., Intercom-like systems) into internal platforms

Background supporting high-velocity operational teams

Why Chalkboard:

We care about results, but also how we get there. Our core tenants aren't slogans here, they're how we operate. 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:

Employee Sponsored medical, dental, & vision coverage starting within 30 days. We cover 80% for employees and 70% for dependents.

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

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.