Salary Range: 105000 to 120000 (Currency: USD) (Pay period: per-year-salary)

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.

Who We Are

At Vail, we believe in the unique power of voice interactions to create more expressive, more intimate, and more efficient interpersonal interactions. Using Vail technology, we make millions of voice interactions better every day. We process around 10% of all toll-free call traffic in the U.S.; 1 in 10 times, when someone calls a customer support hotline, Vail is routing or interacting with that call.

We are rapidly growing across multiple dimensions, including our customer base, the scope of products we offer, and the size of our team. Now is the right time for a strong candidate to join and grow with us. We have a supportive culture where employees are encouraged to achieve both personal and team goals because we believe growth leads to both business impact and personal fulfillment.

We offer competitive compensation and affordable benefits with flexibility and choice to meet individual and family (including Domestic Partnerships) needs, including:

Multiple medical, dental, and vision plan options
Company-paid life insurance, short and long-term disability
401(k) savings plan with company match (50% on first 6% of employee contribution)
35 days total annual PTO
Annual Bonus Program
Paid maternity and paternity leave
Relocation allowance
Employee referral bonus
Gym membership
Technical and Professional Development stipend

We are striving to implement and sustain an inclusive and equitable work environment for all employees by sourcing underrepresented groups and continually empowering those individuals within our organization to further enrich Vail’s communication solutions. We recognize that equitable and unique individuals benefit our teams’ problem-solving, innovation, and development efforts.

Our offices are located in Deerfield and Chicago, IL. Interviews and onboarding are conducted in our offices when possible. We observe a hybrid work format that provides employees with the flexibility to collaborate with team members based on business needs.

About the company

Vail Systems provides scalable, fault-tolerant telephony software services for large enterprises across financial services, retail and hospitality, software, and wireless industries. Its offerings include advanced network routing and call control, caller authentication and risk scoring, conversational IVR/IVA solutions, and customer experience analytics. Customers can engage Vail Professional Services or build on the FreeClimb voice and messaging API to integrate telephony features into their apps. The goal is to help enterprises deliver safer, more reliable, and scalable customer care by combining strong security, platform reliability, and a broad suite of telephony tools in one ecosystem.

Company Size

51-200

Company Stage

N/A

Total Funding

N/A

Headquarters

Deerfield, Illinois

Founded

1991

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Simplify's Take

What believers are saying

Vail keeps hiring in 2026, including DevSecOps, SRE, and information security roles.
FreeClimb's 2026 messaging targets AI automation, risk scoring, and call routing buyers.
Updated 2026 site claims billions of events and 35-plus years of engineering expertise.

What critics are saying

Cloud and CPaaS rivals can bundle voice APIs, squeezing FreeClimb pricing by 2026.
A telecom outage or fraud-model failure would hit enterprise trust and stall renewals.
Prosodica, Versay, and FreeClimb integration complexity risks slowing product execution and sales cycles.

What makes Vail Systems unique

Carrier-grade voice infrastructure processes 36 million minutes daily, with under-10-millisecond risk scoring.
FreeClimb routes over 10% of U.S. call center traffic using Vail's telecom stack.
Patented data framework analyzes billions of historical call events for authentication and routing.

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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.

Company News

Tribune-Star

Oct 20th, 2023

Columbus Speedway Go-Karts to host final points race

Vails was named Rookie of the Year.

SVDaily

Feb 22nd, 2021

Vail Systems, Inc. recognized as Level 1 Service Provider on Feb 22nd 21'.

Credit Suisse has partnered with UnitedLe CHICAGO--(BUSINESS WIRE)-- #HIPAA--Vail Systems announced today that FreeClimb is certified as a Level 1 Service Provider under the Payment Card Industry Data Security Standard (PCI DSS), and is compliant with the Health Insurance Portability and Accountability Act (HIPAA).

Vail Systems

Technical Project Manager 2

About the job