Full-Time
AI Engineer
Posted on 9/12/2025
Underdog Fantasy
501-1,000 employees
Custom-team fantasy sports with rewards
Compensation Overview
$160k - $240k/yr
Remote in USA
Remote
 AI & Machine Learning (2) |
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- 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
- 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
- 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.
Underdog Fantasy operates a fantasy sports gaming platform that lets users build their own teams and compete against others. Users draft players, assemble lineups, and enter contests; scoring is based on real-player performance and rewards are earned for success. Unlike traditional fantasy platforms, it emphasizes user-created teams and customized strategies, giving players a personalized, flexible competition and incentives to win. The goal is to provide a straightforward, engaging way to play fantasy sports with tangible rewards.
Company Size
501-1,000
Company Stage
Series C
Total Funding
$115M
Headquarters
New York City, New York
Founded
2020
Simplify's Take
What believers are saying
- Acquires Aristotle Exchange DCM and DCO for compliant national prediction platform.
- Secures St. Louis Blues multi-year deal enhancing Missouri fan activations.
- $100M Series C in March 2025 boosts valuation to $1.2 billion.
What critics are saying
- CFTC rejects Aristotle acquisition within 3-6 months, halting prediction launch.
- FanDuel dominates Missouri post-2025, nullifying Blues and Royals partnerships.
- Layoffs gut fraud team, sparking user exodus and lawsuits in 6-12 months.
What makes Underdog Fantasy unique
- Underdog pivots to CFTC-regulated prediction markets via Aristotle Exchange acquisition.
- Offers in-house sports event contracts independent of Crypto.com partnership.
- Combines DFS drafting with prediction markets for personalized fan engagement.
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Benefits
Unlimited Paid Time Off
401(k) Company Match
Home Office Stipend
Health Insurance
Dental Insurance
Vision Insurance
Parental Leave
Growth & Insights and Company News
6 month growth
↑ 6%1 year growth
↑ 7%2 year growth
↑ 10%Underdog to expand prediction markets with new in-house offering. 10th March 2026 10:34 am Underdog is set to expand its prediction markets offering under its own exchange after acquiring Commodity Futures Trading Commission (CFTC) registered Aristotle Exchange. The fantasy sports operator has purchased Aristotle Exchange DCM and Aristotle Exchange DCO, which are a CFTC registered Designated Contract Market (DCM) and a Derivatives Clearing Organization (DCO), respectively. The acquisition enables Underdog to offer its own prediction market exchange, having launched sports prediction markets in its app last September through a partnership with Crypto.com. "We look forward to working with the CFTC to offer an exchange that brings even more options to enjoy sports to our customers," said Jeremy Levine, CEO and co-founder of Underdog. "We're in the early innings of what prediction markets can be, especially for sports fans. "We'll use this opportunity to bring the same relentless focus on innovation and experience that we've always brought to our customers. The reality is, prediction markets are primarily about sports and no company knows how to engage with sports fans and create products for sports fans better than Underdog." Underdog has pivoted to prediction markets after withdrawing its licence application ahead of Missouri's market opening in December, which was followed by its exit from North Carolina's sports betting market. Underdog is acquiring the two business from Aristotle Inc., which specialises in data mining voter data and also operates the PredictIt prediction markets platform on behalf of Victoria University of Wellington. The details of the transaction have not been disclosed.
Underdog undergoes mass layoffs, as company pivots to prediction markets. Last Updated on March 3, 2026 Underdog has laid off at least 125 people as the company changes its business model to focus on prediction markets. Underdog CEO & Founder Jeremy Levine confirmed the layoffs, which include the majority of the company's fraud team. Levine explained the job cuts, stating, "We transitioned our business this year. We went from a focus on a state-by-state framework to a national prediction markets platform with seamless offerings across the country." Underdog partnered with Crypto.com in October last year, and its focus on prediction markets led it to end its sports betting operation in North Carolina and withdraw its license application to launch in Missouri's newly regulated market. The shift away from regulated sports betting means the needs of the company have changed. Levine added, "It's simply a different operation, and the changes we made are a part of that transition." Among those laid off are the majority of the company's fraud team, customer support, graphics, marketing, and its DFS department. Employees angered by abrupt news. Front Office Sports reported that employees were abruptly told they were no longer required on Friday. One of those who lost their job said that they had "put my heart and soul into my job only to get f***ed over in the most unserious way." Staff members said that a meeting was suddenly added to their calendar, and a message was sent apologizing for the short notice but urging those who had received the invite to attend. The call informing them of their layoff was short, and by the time the meeting ended, access to company property, including email and internal communications, was cut off. CEO delivers 'gut punch' Levine personally delivered the bad news, with one employee saying he popped up on the screen, looking "distraught," before apologizing and saying that whoever received the message had been laid off. The employee said it was a "gut punch." Levine said other companies will be lucky to have the newly unemployed staff, commenting, "We take pride in hiring people who are passionate, good human beings and who really care about their work, so if you're hiring and come across an ex-Underdog person you'd be lucky to have them and call me for a reference." Some of those laid off posted come-and-get-me pleas on LinkedIn. Marco Sandoval, the company's social media strategist, wrote, "I believe God doesn't waste seasons. And this one feels like alignment. If you're hiring in social media, digital marketing, or content - or know someone who is - let's connect." Sandoval also posted a YouTube video saying he was laid off without warning. Underdog core values include 'give a sh*t' While laying off staff, the company is also hiring in other areas. Last week, Underdog posted job adverts for an EPD Operations Manager, Senior Product Designer, and Senior Analytics Engineer. The job ad stated, "At Underdog, we're constantly building, shipping fast, and pivoting as we learn. One of our core values is give a sh*t - because our people care about the product, the work, our customers, and doing things better than last week." It remains to be seen whether the gamble on prediction markets will pay off. The company was ranked third among US startups last year after a funding round valued it at $1.2 billion. Adam Roarty Adam Roarty is a journalist covering sports betting, regulation, and industry innovation for CasinoBeats. His coverage includes tax increases in the UK, covering breaking stories in the ever-evolving landscape of US betting...
Fliff unveils Superstars DFS as California sweeps play goes dark. As the California ban takes effect, Fliff revamps its strategy by launching "Superstars DFS" as a possible revenue source California's ban on sweepstakes casinos may have started on January 1, but for some operators, it's the start of something new. Enter Fliff, a popular sweepstakes sportsbook, which faced multiple class-action lawsuits related to "illegal gambling". Although it has complied with the regulatory changes under AB 831, it immediately pivoted into a new model, launching its peer-to-peer "DFS Superstars". It's a P2P daily fantasy contest where users compete against each other in fantasy sports contests to claim cash prizes. At launch, Fliff's DFS Superstars is live in 11 states, including California, New Mexico, and Kansas, deemed "a creative workaround" for AB 831. Sweepstakes casinos' dual-currency model out, Fliff's DFS Superstars in. Fliff's launching of a new business model comes with specific objectives, including: * A pivot to address regulatory changes. Fliff's new model was launched on the first day of California's ban on sweepstakes casinos. DFS Superstars represents a strategic play, especially in states where sweepstakes models are no longer allowed. * Taps into the growing DFS market. By pushing this model, Fliff now competes with established DFS operators like PrizePicks and Underdog. * Diversifies its product portfolio. With bans and tightening regulations on sweepstakes casino games, DFS Superstars will expand the portfolio, supporting the company's long-term growth. Where is Fliff's DFS Superstars available? DFS Superstars is now live and available in roughly 11 states, including California, South Carolina, and Minnesota. For Fliff, the new business model is a creative workaround to address the existing bans in most states. Fliff isn't the first gaming operator to transition into a P2P model. PrizePicks transformed its DFS service into a P2P contest model called "Arena", where users compete against each other. Sleeper and Underdog also shifted their focus to P2P formats. These shifts reflect operators' increasing regulatory compliance and a move to differentiate their services from house-banked wagering.
Underdog partners with St. Louis Blues. Underdog strikes multi-year marketing deal with St. Louis Blues. The St. Louis Blues have partnered with Underdog in a multi-year marketing deal, aimed at elevating the fan experience both at the Enterprise Center and on TV broadcasts. This strategic move marks Underdog's second major partnership in the Missouri sports market, following their recent deal with the Kansas City Royals. As the Missouri sports betting market prepares to launch on December 1, 2025, Underdog is poised to make a significant impact, leveraging its commitment to fan engagement to carve out a niche in the competitive landscape. Partnership focuses on fan experience. According to Steve Chapman, Chief Revenue and Marketing Officer of the St. Louis Blues, the team chose to partner with Underdog due to their emphasis on being present for fans. "Throughout our preparations for the upcoming launch of sports betting in Missouri, Underdog quickly rose to the forefront of our conversations because of the value they placed on being present for Blues fans at Enterprise Center," Chapman noted. This partnership builds upon the existing relationship between the two entities, which previously collaborated on daily fantasy offers for fans attending games at the Enterprise Center. Underdog will now have access to St. Louis Blues IP, video assets for use in home and away broadcasts, and in-person activations, further solidifying their presence in the Missouri market. Key partnership highlights. The partnership between Underdog and the St. Louis Blues boasts several key highlights, including: * Enhanced fan experience through in-arena and broadcast activations * Introduction of Underdog to the Missouri sports betting market ahead of its launch * No restriction on the Blues' ability to partner with future sportsbook operators Josh Anderson, Underdog's Director of Strategy, emphasized the importance of this partnership, stating, "We've learned how rabid Blues fans are when it comes to leveling up their sports experience, making this partnership an obvious choice as we continue to introduce ourselves to the St. Louis market." This sentiment is echoed by Dr. Rachel Kim, a sports marketing expert, who notes, "Partnerships like this one demonstrate the growing importance of fan engagement in the sports betting landscape. By prioritizing the fan experience, Underdog is positioning itself for success in the Missouri market." Market access and licensing. Underdog's partnership with the Kansas City Royals, announced in late September, grants the company market access in Missouri. As part of the state's sports betting licensing process, tethered applicants like Underdog must partner with either a Missouri-based casino or a professional sports team. With this partnership, Underdog joins a growing list of operators vying for market share in Missouri, including FanDuel, bet365, and Caesars. According to a study by the Sports Betting Research Institute, "the Missouri market is expected to generate significant revenue, with an estimated $1.1 billion in handle in the first year alone." As the market prepares to launch, operators are eager to establish a strong presence, and partnerships like the one between Underdog and the St. Louis Blues will play a crucial role in shaping the competitive landscape. Blues remain open to future partnerships. The partnership between Underdog and the St. Louis Blues does not preclude the team from partnering with other sportsbook operators in the future. In fact, the Blues remain open to discussions with potential partners, as do other Missouri-based teams. Currently, only three of the state's six professional teams have secured market access partners: * Kansas City Royals: Underdog * St. Louis Cardinals: bet365 * St. Louis City FC: FanDuel As the Missouri sports betting market continues to take shape, it is likely that Zecode will see additional partnerships emerge, further solidifying the state's position as a hub for sports betting activity. Dr. John Taylor, a gaming industry expert, notes, "The Missouri market has the potential to be one of the most competitive in the country, with a strong mix of established operators and new entrants vying for market share." With its partnership with the St. Louis Blues, Underdog has taken a significant step towards establishing itself as a major player in this emerging market. As the launch date approaches, all eyes will be on Missouri, watching to see how the market unfolds and which operators will ultimately emerge victorious.
Underdog partners with Crypto.com to offer sports prediction markets in gaming first.