Job Description

We’re Underdog.

The fastest-growing sports gaming company, ever. We’re here to make sports more fun. We pair intuitive user experiences with innovative game designs to build the best experience for sports fans in America.

Since 2020, we’ve launched four of today’s most widely played fantasy games, and built the Underdog Sportsbook entirely in-house with our own tech. We move fast, act with urgency, and create experiences you won’t find anywhere else.

With a $1.2 billion valuation and backing from investors like BlackRock, Spark Capital, SV Angel, Mark Cuban, Kevin Durant, Adam Schefter, and more, we’re just getting started.

At Underdog, we play and win as a team. We take chances and are unafraid to attack hard problems. We face challenges with ambition and optimism. We play for the love of the game.

We’re Underdog. And winning as an Underdog is just more fun.

Join us.

The AI Engineer role at Underdog is a unique position that combines deep technical execution with broad organizational impact. You accelerate high-value AI initiatives by rapidly prototyping, validating, and deploying production-ready solutions that deliver measurable ROI. Beyond building, you centrally own the integration and scaling of in-house and third-party AI, ensuring secure and unified architectures that enable scalable adoption. Acting as both a technical partner and an evangelist, you drive faster time-to-value, close bandwidth gaps, and embed an AI-first culture across the company by upskilling teams and shaping strategy in GenAI, agentic frameworks, and LLM-driven tooling.

About the role

• Rapidly prototype, validate, and deploy production-ready AI solutions that drive measurable ROI.
• Partner cross-functionally to shape GenAI, agentic frameworks, and LLM-driven tooling strategy and execution.
• Own integration and scaling of in-house and third-party AI with unified, secure architectures.
• Serve as technical partner and evangelist to accelerate time-to-value, close bandwidth gaps, and upskill teams.
• Ensure AI-first adoption and enable scalable workflows across the company.

Who you are

• Experience architecting, prototyping, and shipping end-to-end AI-powered solutions including agents, automations, copilots, and AI workflows for business and product use cases
• Experience evaluating, selecting, and integrating best-of-breed AI products—balance in-house development with secure, compliant adoption of third-party solutions
• Being hands on, leading technical initiatives, evangelizing best practices in prompt engineering, edge deployment, MLOps, and continuous improvement of our AI platform.
• Experience researching, prototyping, and implementing the latest advances in generative AI, including prompt orchestration, vector DBs, RAG, and agentic workflows.
• Experience with MCP servers and client interactions, message schemas, and ensuring context can be shared between AI models and external systems.
• Experience with model lifecycle management, prompt engineering, serving, and optimizing deep learning or generative AI systems.
• Experience working with cross functional collaboration with Security and IT to identify high-leverage AI data integrations, interfaces, and features, advocate for their enablement, and work to securely deploy them for safe adoption

Even better if you have

• Hands-on experience with OpenAI, Anthropic, Mistral APIs; RAG pipelines using LangChain, LlamaIndex, DSPy
• Experience integrating modern LLMs, agentic frameworks, and generative AI models into Underdog’s tech stack—drive platform enhancements, orchestration, and security
• Experience designing, shipping, and scaling prototypes or production-ready AI applications (internal workflow agents, copilots, automation, customer-facing AI features)
• Knowledge of data security, privacy, compliance issues and responsible AI deployment; familiarity with regulated industries a plus
• Experience leading AI initiatives, automation adoption, or agentic workflow pilots at scale in a rapidly changing environment
• Contributed to the open-source AI community.

Our target starting base salary range for this position is between $150,000 and $190,000, plus target equity. The starting base salary will depend on a number of factors including the candidate’s skills and experience, among other things.

What we can offer you:

• Unlimited PTO (we're extremely flexible with the exception of the first few weeks before & into the NFL season)
• 16 weeks of fully paid parental leave
• A $500 home office allowance
• A connected virtual first culture with a highly engaged distributed workforce
• 5% 401k match, FSA, company paid health, dental, vision plan options for employees and dependents

#LI-REMOTE

This position may require sports betting licensure based on certain state regulations.

Underdog is an equal opportunity employer and doesn't discriminate on the basis of creed, race, sexual orientation, gender, age, disability status, or any other defining characteristic.

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