A Company Is Only
As Good As Its People

All Current Positions

Rated as one of Chicago’s Best Midsize Places to Work in 2023 by Built In.

Working at Vail

Vail’s technology makes millions of voice interactions better every day. Are you ready to join the conversation?

Telecommunications has drastically evolved since our founding in 1991, but so has our technology. We’re growing and looking for passionate employees to join our team.

Don’t see a position that matches your skill set? Vail is continuously recruiting and open positions can change frequently, so check back periodically or get in touch with an email to recruiting@vailsys.com and let us know how you can contribute to Vail.

Open Positions

  • All Positions
  • Accounting/Finance
  • Application Development
  • Data & Analytics
  • Engineering
  • Human Resources
  • Operations
  • Prosodica
  • Service Delivery
  • Versay

All Positions

General Opportunity

All Teams | Greater Chicago Area | Full-Time

Perks & Benefits

  • Health

    When you work hard, it’s important to stay healthy. Our competitive benefits package includes medical, dental, and vision insurance options to keep you healthy and happy.

  • Financial/Savings

    We pride ourselves with rewarding great work with great compensation. Plan ahead with our 401(k) Retirement Plan with company match. Take advantage of our pre-tax transit program to save money from parking to train tickets.

  • Work/Life Balance

    With flexible work hours, open workspaces, casual office attire, and employee outings, it’s easy to work hard, play hard, and enjoy a balanced lifestyle.

  • Vacation

    We believe that time away from the office is important, and key to employees’ satisfaction and productivity at work. With a generous accrual of vacation in addition to holidays, our team members can take off the time they need to come back revitalized.

  • Wellness

    We encourage an active lifestyle by providing memberships to gyms near each of our office locations. We also host periodic wellness events and keep our office kitchens stocked with yummy, healthy snacks!

  • Have Some Fun!

    We encourage employees to engage with each other outside of their teams. We sponsor runners in the JP Morgan Chase Corporate Challenge, the annual Vail Ringers softball team, and have a group training for the Chicago Triathalon, as well as host book clubs, hackathons and game nights.