The posting, in Insomnia Cookies's own words
archived Nov 6, 2026Insomnia Cookies was founded in a college dorm room by then-student, Seth Berkowitz. Fast forward 20 years and so... many....cookies... later, our innovative bakery + delivery concept has become a cult brand known for its rabid following of cookie lovers who crave Insomnia’s warm, delicious delivery all day and late into the night. With an expanding footprint of over 350 stores globally, an experiential, “sweet-easy” flagship concept, and large scale operations and delivery capabilities ... Insomnia Cookies is revolutionizing the cookie game by truly "Imagining What’s Possible"! As a Bike Delivery Driver at our Chicago store located at 1350 N Wells ST, Chicago IL 60610, you are our “Boots on the ground!”, and the main face that our Insomniacs see outside of the bakery! You give the word “Delivery” a whole new meaning by delivering the Cookie Magic to our fans wherever they are.
SOME OUR SWEET DELIVERY DRIVER PERKS:
· Pay rate: Up to $18.00/hr · Pay on Demand (why wait until the end of the week…get paid your earned wages at the end of the day!) · Small but busy delivery zones · Paid vacation and sick time off · Flexible part-time work schedules · Pet insurance for your furry loved ones · Job stability with a rapidly growing and reputable company · Achievable growth/promotion opportunities · FREE cookies with every shift! WHAT WILL I DO AS A DELIVERY DRIVER? · Check orders for quality and accuracy before they leave the store. · Deliver our cookies, milk and ice cream to our loyal fan base, in a timely and safe fashion. · Provide quality customer service through positive and professional interaction with customers whether in-person or by phone. · Use Insomnia’s delivery app to approved company standards and provide accurate status updates to customers.
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DESIRED SKILLS/EXPERIENCE:
· Excellent time management and organizational skills · Knowledge of the 2-mile radius surrounding the store is a plus! · Must have your own bike in working order · Must have a smartphone with data plan · Must be legally eligible to work in the United States · Must be 18 years or older to be employed At Insomnia Cookies, warm cookies are just the beginning. As a Cookie Crew Bike Delivery Driver , you'll be the face of Insomnia Cookies—bringing warm cookies, brownies, and other sweet treats directly to our guests by bicycle. Whether it's a late-night study break, birthday celebration, office snack, or just someone's cookie craving, you'll help create memorable moments with every delivery. When you're not making deliveries, you'll be part of the bakery team—helping prepare orders, assisting guests, and keeping the bakery running smoothly. Every shift is fast-paced, active, and never quite the same. If you enjoy staying active, know your city well, and love working with great people, this could be the perfect role for you.
WHAT YOU’LL DO:
Every shift is a mix of driving, hospitality, and teamwork. You'll: Deliver orders safely, accurately, and efficiently by bicycle. Ensure every order arrives warm, complete, and on time. Navigate city streets safely while following all traffic laws and company safety guidelines. Communicate with guests professionally during every delivery. Assist with preparing, packaging, and organizing delivery orders before heading out. Welcome guests and provide exceptional service inside the bakery between deliveries. Help bake, decorate, package, and stock products as needed. Keep the bakery clean, organized, and food-safe. Support your teammates during busy shifts to keep orders moving quickly and accurately. Help create the kind of guest experience that keeps people coming back.
QUALIFICATIONS
Must be 18 years of age or older Ability to safety operate a bicycle in an urban environment Own a Smartphone capable of running company delivery applications. Availability to work evenings, nights, weekends, and holidays. Physical Requirements
This position regularly requires the ability to:
Ride a bicycle for extended periods throughout a shift. Frequently mount and dismount a bicycle. Carry and transport delivery bags weighing up to 30 pounds. Stand, walk, bend, reach, squat, and twist throughout the workday. Work in varying outdoor weather conditions. Enter and exit apartment buildings, offices, and residences, including climbing stairs when elevators are unavailable. Work safely around bakery equipment, ovens, refrigeration units, and cleaning products. Communicate effectively with guests and team members. Work Environment You'll divide your time between our bakery and city streets. Inside the bakery, you'll work in a fast-paced environment with ovens, refrigeration equipment, cleaning chemicals, and moderate noise levels. Outside, you'll ride in changing weather conditions, varying traffic patterns, and urban environments while following all safety policies and local traffic laws. Schedule Expectations Our busiest times are evenings, late nights, weekends, and holidays. Bike Delivery Drivers should have availability during these peak business hours. Scheduling needs vary by location.