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Rated among Built In's 2026 Best Midsize Places to Work in Chicago and in the US.

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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 torecruiting@vailsys.comand let us know how you can contribute to Vail.

Open Positions

All Positions

Technical Project Manager II

Project Management | Greater Chicago Area | Full-Time

Software Engineer, Test & Infrastructure II (Bilingual Spanish)

QA Team | Greater Chicago Area | Full-Time

Software Engineer, Test & Infrastructure III

QA Team | Greater Chicago Area | Full-Time

Technical Project Manager II

Project Management
Greater Chicago Area
Full-Time
Apply Now

Who You Are

Interested in managing the entire lifecycle of projects and building innovative enterprise communication solutions on voice, web, and messaging channels?

As a Technical Project Manager II, you will be expected to coordinate between business, product, and engineering teams to ensure project deliverables are identified, stakeholder needs are addressed, and deadlines are met. You would assist in gathering requirements, identifying crucial resources, assisting with task completion, and providing regular project status updates.

The ideal candidate will have a strong background in project management frameworks and agile methodologies to coordinate research, strategically develop project plans, translate unique customer requirements into tasks, facilitate software development, and partner with operations to quickly deliver solutions to the marketplace. This role is team-oriented, as you will collaborate with highly technical and cross-functional teams in a dynamic, client-centered environment.


What You’ll Do
  • Partner closely with Business, Product, Engineering, Operations, Support, and other key leaders to establish project scope, timeline, technical direction, and success metrics for projects. Projects will include building new product features, creating new applications, expanding platform capabilities, and tooling enhancements that will improve customers’ experience or engineering velocity.
  • Deliver Engineering objectives by executing the projects and providing visibility to resource allocation and prioritization. Develop frameworks for execution and adapt to the team’s needs & context.
  • Develop a full understanding of our technical stack, the interdependencies, and contribute to designs to ensure they are scalable, reliable, and efficient.
  • Track, prioritize, and execute projects, enhancements, or bugs from the team backlog.
  • Manage timely and succinct communications to leadership and across teams to ensure accountability and timeline management.
  • Document project artifacts, including work steps, deployments, release notes, and monthly reporting.
  • Gain sign-off from user-acceptance testing and coordinate releases.
  • After project completion, facilitate retrospective meetings.

    • Qualifications: We encourage you to apply if you think your experience may be a match, even if you do not meet all of the qualifications.
  • A Bachelor’s degree in Computer Science, Software Engineering, or a related field.
  • 3-4+ years of experience in a technical project management role.
  • Proficiency with Jira or similar ticketing system.
  • Knowledge of Scrum practices (sprint planning, review, standups, project grooming).
  • Experience in directly interacting with internal and external customers.
  • Experience working with diverse groups in a highly technical environment.
  • Knowledge of project management lifecycle.
  • Excellent verbal and written communication skills, including technical writing.
  • A Master’s degree in Computer Science, Software Engineering, or related field, preferred.
  • Previous experience as a software engineer or software testing engineer, preferred.
  • Knowledge of telecommunications/telephony, VoIP, call routing, IVR functionality, and call flows, preferred.
  • Knowledge of Docker & Kubernetes or similar cloud technologies, preferred.
  • Project Management Professional (PMP) certification, preferred. 

    • 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.