Jr Field Service Representative - Chicago, IL

About With Me, Inc.

With Me, Inc. delivers convenient technology-powered amenities to clients and their guests. On the forefront of innovation, we're a remote first company that emphasizes a healthy work/life balance. We are profitable, operate in all 50 states, and have been ranked as one of the 5000 fastest-growing private companies in the United States for three consecutive years. Watch our employee video to learn more about working at With Me and discover why we were named a top employer by the National Apartment Association!

Print With Me makes printing convenient for everyone, everywhere. We're an automated printing solution found nationwide in coffee shops, co-working spaces, and multifamily apartment building locations.

Sip With Me is specialty coffee made simple. Our mission is to provide an innovative and cost-effective automated coffee solution for multifamily, coworking, and other business verticals.

With Me, Inc. is actively scaling with many of the National Multifamily Housing Council Top 50 managers and owners in the country, including Lincoln Property Company, Greystar, Fairfield, Avenue5, and many others.

Are you a hands‑on problem‑solver with a passion for delivering exceptional service? With Me is hiring a Jr Field Service Representative in Chicago, IL to support our printing and coffee solutions! You’ll make deliveries, service calls, and ensure our clients have a seamless experience. This position requires a valid driver’s license and the ability to operate a motor vehicle.

As a Jr Field Service Representative, you’ll report to the Field Service Supervisor and serve as the face of With Me, Inc. to our customers—making sure their equipment is installed, serviced, and maintained to the highest standards.

• Provide courteous, outstanding customer service during site visits.
• Install, program, calibrate, and maintain bean‑to‑cup coffee equipment with guidance from senior team members and manufacturers.
• Work directly with coffee equipment manufacturers via phone or video to repair machines in the warehouse and at client sites.
• Visit client locations in your designated region to deliver products, perform preventative maintenance, and change water filters.
• Support wireless printer stations as needed and implement solutions for new customers.
• Maintain accurate inventory of parts and tools.
• Collaborate closely with Operations and Client Experience teams.

• Located in Chicago, IL, with at least 1 year of experience in a customer‑facing or field service role.
• Strong communication skills and a customer‑obsessed mindset.
• Mechanical aptitude; basic plumbing knowledge or willingness to learn.
• Interest in coffee and/or printing technology is a plus.
• Valid driver’s license and ability to travel regionally.
• Ability to lift 65–90 lbs. (with assistance) and perform regular physical tasks such as standing, sitting, squatting, crouching, and reaching.
• Self‑motivated, detail‑oriented, and committed to high‑quality service delivery.
• Willingness to learn new systems, equipment, and processes.

• 100% remote work environment.
• Employee equity and a chance to shape the future of an innovative company.
• Comprehensive health, dental, vision, life, and disability coverage.
• Retirement plan with company match, plus FSA and HSA accounts.
• Competitive paid time off and an annual training/education allowance.

Ready to make an impact? Join our team today!

Full compensation packages are based on position location as well as candidate experience and qualifications.

This position will also qualify for annual bonus opportunity.

Hourly Rate Range: $25.50 – $30 USD

• The majority of our roles offer a 100% remote work environment although some may require residence in a specific geographic location/region
• You’ll get some skin in the game with employee equity
• We stand behind our core values:
  Performance, Customer Obsession, Candor & Transparency and Respect
• There’s transparent communication from the top down
• You’ll have a collaborative, smart, and forward‑thinking team to share ideas with
• You’ll have direct, meaningful impact as we scale
• There are fun…