Executive Assistant/Personal Assistant (to the CEO)

Hi, we’re Underdog!

We’re the fastest-growing sports gaming company ever.

We build innovative games and products for American sports fans.

Founded in 2020, our team built four of today’s most widely played fantasy games and recently launched our Underdog Sportsbook. We are the only sportsbook to ever launch on our own home grown technology, which allows us to build different and innovative experiences. We believe there’s so much more to be built for sports fans, and we’ll continue to win by building the best products and experiences for our customers.

The opportunity in front of us to become the biggest company in our space is massive; after all, we’re currently sitting in the fastest-growing consumer industry in the U.S. In just over two years, we reached a nearly $500 million valuation through some of the best investors in the game, including Mark Cuban, Kevin Durant, BlackRock, and SV Angel. We are many times larger now and our growth is not slowing down.

At Underdog, we believe that sports are for everyone and are building a tomorrow for every fan. Want to help create that future? Join us.

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,