Chalkboard

Full-stack Engineer

• Build and scale product features and backend services that power core user experiences
• Contribute to system architecture with a focus on scalability, reliability, and performance
• Write high-quality, maintainable code and uphold strong engineering standards
• Partner with Product and Design to deliver impactful features from concept to production
• Participate in sprint planning, estimation, and delivery
• Identify gaps in systems, processes, and code quality—and proactively address them
• Improve system performance, observability, and reliability
• Collaborate closely with engineers across pods to ship cohesive solutions
• Take ownership of projects and drive them through completion
• Contribute to a culture of accountability, craftsmanship, and continuous improvement

Senior Software Engineer

• Lead, coach, and scale a high-performing engineering team while driving predictable, high-quality execution across mobile and backend systems
• Drive weekly team alignment through sprint planning, prioritization, retros, and reviews
• Partner with Product to define roadmaps, scopes, trade-offs, and delivery expectations
• Ensure the team ships high-quality features on predictable timelines
• Improve team productivity through better process, tooling, and communication
• Elevate standards across architecture, testing, reliability, and code quality
• Conduct meaningful 1:1s, performance reviews, and career development conversations.
• Run design reviews and RFC discussions, providing strong technical guidance
• Hire, onboard, and retain exceptional engineering talent
• Make clear decisions and manage trade-offs across technical and business constraints
• Own service reliability, system performance, and engineering accountability
• Collaborate cross-functionally with Product, Design, QA, Data, and DevOps
• Maintain strong relationships with stakeholders and set transparent expectations
• Foster a culture of trust, ownership, feedback, and continuous improvement
• Partner tightly with Product while serving as the technical owner of your domain

VP of Product Engineering

Growth Marketing

• Own and scale Chalkboard’s full-funnel growth engine by building acquisition, lifecycle, and product-led growth systems that drive engagement, optimize spend, and deliver measurable business impact
• Build and scale full-funnel growth across acquisition, activation, retention, and monetization
• Define KPIs, forecasting models, and growth investment strategies (CAC, LTV, payback)
• Establish experimentation frameworks to continuously optimize performance
• Lead lifecycle strategy to improve onboarding, engagement, and long-term retention
• Own the growth roadmap and align cross-functional initiatives with company goals
• Scale acquisition across paid media, social, affiliates, influencers, and emerging channels
• Break down funnels, identify opportunities, and execute high-impact experiments
• Partner with Product to drive product-led growth and engagement loops
• Collaborate with Data Science, Marketing, and Finance to align insights and investments

Head of Growth

Product Manager

• 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

Product Manager, Payments – Operations

Product Designer

• Own the end-to-end design process across key product surfaces, from early discovery and wire-framing to polished UI and shipped features.
• Turn complex gaming flows into simple, intuitive experiences.
• Partner cross-functionally to rapidly test, iterate, and refine features that drive engagement, retention, and revenue.
• Lead product discovery alongside Product and Engineering to deeply understand user behavior, motivations, and friction points.
• Present work clearly and confidently, grounding decisions in user needs, business impact, and data.
• Simplify complex sports gaming mechanics into intuitive, frictionless user journeys.

Senior Product Designer

Product Analyst

• Own product event instrumentation strategy, including taxonomy design, tracking plans, and governance
• Design and roll out scalable measurement frameworks that work across pods
• Establish best practices that ensure data quality, consistency, and trust
• Partner with Product and Engineering to define what success looks like before features ship
• Proactively analyze product and user behavior data to uncover insights that influence roadmap decisions
• Support and guide experimentation across pods — from setup to monitoring to analysis
• Serve as the internal subject-matter expert for tools like Amplitude
• Raise the bar for analytical rigor without slowing teams down
• Scaling instrumentation in a fast-moving product environment
• Driving alignment across Product, Engineering, and Data without direct authority
• Making progress when systems, documentation, and context are still evolving
• Helping teams make strong decisions without perfect information
• Create clarity for PMs on what to measure and why
• Higher standards for experimentation
• Stronger analytics literacy
• More disciplined measurement before launch
• Better decisions under uncertainty

DevOps Engineer

• Own platform reliability end-to-end, proactively identifying and mitigating risks before they impact users
• Build and evolve observability (metrics, logs, tracing) to enable fast detection, diagnosis, and resolution of issues
• Scale infrastructure ahead of demand by identifying bottlenecks and implementing durable architecture improvements
• Reduce developer friction by improving CI/CD pipelines, deployment workflows, and internal tooling
• Lead incident response and root cause analysis, driving systemic fixes—not just short-term patches
• Establish and enforce best practices for infrastructure, deployments, and system reliability
• Build reusable, self-service infrastructure that enables teams to ship quickly and safely
• Continuously improve systems through automation and Infrastructure-as-Code

Principal SRE

Performance Marketing

• Bring ownership of our highest impact paid social channels in house
• Increase spend and efficiency across these channels
• Bring sharper analysis, projections, and funnel visibility to our performance marketing efforts
• Balance left-brain analytical rigor with right-brain creative instincts
• Translate performance insights into clear, actionable recommendations
• Raise the bar on experimentation, measurement, and accountability
• Ramp spend intelligently around key sports calendars (NBA, NFL, etc.)
• Align paid social efforts with broader marketing channels (organic, CRM, email, SMS, in-app messaging)

Paid Social Manager

• Act as the technical leader for your pod, partnering with Product to shape roadmap and delivery
• Own system architecture, ensuring scalability, reliability, and performance across services
• Establish and uphold best practices in system design, data integrity, and engineering quality
• Lead sprint planning, technical decision-making, and release coordination
• Drive clarity through strong documentation and improved engineering processes
• Identify gaps in systems, processes, and architecture—and take action to address them
• Improve team velocity, predictability, and execution through better planning and communication
• Coach and support engineers while remaining hands-on in building and problem-solving
• Build strong partnerships across Product, Engineering, and other cross-functional teams
• Increase collaboration and trust across distributed teams
• Raise the bar for ownership, accountability, and technical excellence across pods

Senior Software Engineer

VP of Product Engineering

Head of Growth

Product Manager, Payments – Operations

Senior Software Engineer

Senior Product Designer

Product Analyst

Principal SRE

Paid Social Manager

Lead Software Engineer