Underdog Fantasy is hiring: Executive Assistant/Personal Assistant (to the CEO)

We’re looking for an experienced and driven Executive / Personal Assistant hybrid to provide comprehensive support to our founder/CEO as he leads Underdog’s mission to become the largest company in our space. This role will empower our CEO to focus on what he does best. As the Executive Personal Assistant, you’ll be the CEO’s right hand, facilitating his effectiveness and efficiency across all aspects of his work and personal life. This position is ideal for a proactive, highly organized individual who excels at problem-solving, gets stuff done, and knows how to anticipate and prioritize the needs of a fast-paced, high-level leader. If you’re energized by providing total support to our ambitious leader and helping drive our vision forward, we want you on our team. About the role and why it’s unique: Coordinate and manage a complex calendar, scheduling appointments, meetings, and personal commitments. Organize travel arrangements, including flights, accommodations, remote work setup, and local transportation. Monitor and manage the CEO’s inbox, responding where appropriate, flagging high-priority items, and ensuring timely follow-up. Act as a liaison between the CEO and internal departments/external stakeholders, facilitating timely and effective communication. Provide personal support with at home tasks, managing household logistics, organizing events and managing personal commitments. Handle various personal errands, such as coordinating groceries, shopping, returns, dry cleaning, gifts or managing special purchases, so the CEO can focus on professional responsibilities. Track and manage personal bills, subscriptions, and payments. Support the CEO in prioritizing health and wellness by integrating regular exercise, meal planning, evaluating health-conscious regimens, and fostering a sustainable routine that helps the CEO maintain high energy and focus. Coordinate with trainers, nutritionists, and wellness coaches to keep the CEO’s health goals on track. Proactively manage wellness initiatives such as fitness programs, clean eating, sleep optimization tools, and bodywork, ensuring the CEO maintains peak physical and mental well-being to keep up with demanding work hours. Handle sensitive and confidential information with discretion and integrity. Help organize and prioritize schedule using task management tools and calendar. Who you are: 4+ years of experience as an EA/PA, preferably for a fast-paced individual. Excellent communication skills, with the ability to communicate effectively to all levels of the organization. Highly organized with exceptional time management skills. Ability to manage competing priorities. Incredibly trustworthy with the ability to handle sensitive and confidential information. Tech-savvy; you quickly learn new software and leverage technology to streamline tasks and solve problems efficiently. Experience with Google’s product suite: sheets, slides, etc. Even better if you have… Experience with productivity and communication tools; like Notion, etc. 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 #J-18808-Ljbffr