Are You a Type A Dynamo with a Heart for Adventure, Health, and High Vibes? Do you love a good spreadsheet but also light up when things get a little fun and fast-paced? Do you get a thrill from being the organized rock behind a thriving team? If you're the kind of person who color-codes your calendar but still knows how to cut loose, we want you at the heart of our growing operation. Bobby's Bike Hike — America's top-rated outdoor adventure and food tour company — is hiring a full-time Office Manager / Administrator to join our leadership team in Chicago. We're growing fast, with roots in Chicago and new energy fueling our Miami market. This role is for someone who loves process and purpose, thrives on details, and wants their work to mean something. This is a high-impact role. You'll be the behind-the-scenes MVP who keeps everything humming — from payroll to team comms, guest emails to big-picture strategy. No travel required — but you'll help power up two iconic cities from our home base in Chicago. A Little About Us We create unforgettable bike, walking, and food tours in Chicago and Miami. We move people — literally and emotionally — through experiences rooted in Travel, Community, Health, and 5-Star Service. We're proud to be Chicago's go-to outdoor activity with over 10,000 glowing reviews, and in Miami, we've already earned the top spot for food tours. We're high-energy, values-driven, and a little obsessive about quality. We work hard and laugh harder. And as we expand, we're looking for someone who's ready to grow with us. If You're Saying "Yes, That's Me," You Probably… Crave structure and clarity — and know how to build it Keep your inbox at zero (or close!) Like being the go-to person who solves problems and keeps things moving Get energized by a fast-paced, team-oriented environment Take ownership, communicate clearly, and stay two steps ahead Love spreadsheets and embrace AI Care about doing great work with great people

Your Role Will Include:

Leading with warmth and professionalism across phones and email Mastering our reservation software (Fareharbor) — and teaching others like a pro Managing guest requests, refunds, and rebookings with empathy and efficiency Owning the numbers: balancing cash reports, business metrics, and Google Sheets (pivot tables welcome!) Prepping and processing payroll with precision Overseeing all HR functions: onboarding, offboarding, and compliance (ILSC, PTO, etc.) Reporting metrics and trends to leadership Monitoring and managing food costs across both cities to ensure efficiency, accuracy, and sustainability — a critical function in delivering our 5-star food tours Keeping the office dialed in — stocked, organized, and buzzing with good energy Supporting guest experiences and daily shop flow Leading as Manager on Duty and part of our core leadership team Supporting our restaurant partners and tracking partner relationships Helping with social media, email newsletters, and internal communications Pitching in during Summer Camp season with family inquiries and support Developing forms, spreadsheets and advancing AI initiatives company-wide to help make everyone's role easier. Helping run weekly team meetings and shaping company strategy Collaborating across both Chicago and Miami teams

Your Superpowers Should Include:

2-3 years of admin experience in a fast-paced, guest-facing environment Experience with tools like Google Workspace, Trello, Slack Spreadheet Pro AI embracement Clear, proactive communication across roles and levels Strong time management and a take-charge attitude A brain for systems, a heart for service, and a healthy sense of humor Comfort working with numbers and cost controls — especially food-related Tech confidence — you'll learn our systems quickly and teach others, too Reliability, accountability, and commitment to your team Bonus points for familiarity with Fareharbor (but we'll train the right person) Perks +

Benefits:

Competitive salary Full-time, year-round stability Potential for profit sharing as we grow A chance to shape a company that's all about purpose and people A fun, mission-driven team that values movement, connection, and impact Ready to Lead with Heart (and a To-Do List)? Send us your resume and a cover letter telling us why you're the perfect fit. We want to know what excites you and why you're fired up to help drive the future of Bobby's. Let's roll. Chicago, Miami, and beyond.

Job Type:

Full-time Pay:

$24.00 - $27.00 per hour

Benefits:

401(k) Health insurance Paid time off Ability to

Commute:

Chicago, IL 60611 (Required) Ability to

Relocate:

Chicago, IL 60611: Relocate before starting work (Required)

Work Location:

In person