---
title: 'Technical Project Manager II at Vail Systems Inc.'
canonical: 'https://feeny.ai/job/technical-project-manager-ii-vail-systems-inc-chicago-kk88k1n9qtef'
type: 'job'
last_seen: '2026-09-17'
---

# Technical Project Manager II at Vail Systems Inc.

- **Company:** Vail Systems Inc.
- **Location:** Chicago, IL
- **Compensation:** $105k–$120k
- **Employment:** full-time
- **Work type:** hybrid
- **Posted:** 2026-09-16
- **Last confirmed live:** 2026-09-17
- **Apply:** https://jobs.lever.co/vailsys/3d3e28d6-0913-454f-aaf0-171ec9ee7beb

## Job description

## 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 Vail Systems Inc.

## Company Overview
- **One-liner**: Vail Systems develops innovative cloud-based voice communication technology that enhances millions of voice interactions every day.
- **Entity Type**: Private (bootstrapped; no external funding disclosed)
- **Headquarters**: Chicago, Illinois, USA (with offices in Chicago Loop and Deerfield) [vailsys.com](https://www.vailsys.com/about/company/)
- **Founded**: 1991 [vailsys.com](https://www.vailsys.com/about/company/)
- **Founders**: Jim Whiteley [vailsys.com](https://www.vailsys.com/about/company/)

## Core Business
- Primary industry: Telecommunications / Voice Communication Technology
- Target customers: B2B; enterprise clients requiring high-volume, reliable voice interaction solutions (e.g., call centers, customer experience platforms)
- Mission: “Create business value for our clients and growth opportunities for our employees by developing solutions that inspire people to interact freely and authentically.” [vailsys.com](https://www.vailsys.com/about/culture/)

## Products & Services
- **Voice Interaction Platform**: Cloud-based software that enhances voice communication by moving logic from premise to the network, then to the internet and cloud. Handles routing, analytics, and quality optimization for millions of calls daily. [vailsys.com](https://www.vailsys.com/about/company/)

## Market Standing
- **Valuation/Market Cap**: Not publicly available (private, bootstrapped company)
- **Key Metric**: 274 total employees (as of 2025) [builtin.com](https://builtin.com/company/vail-systems-inc)
- **Notable Investors/Partners**: Not disclosed; company has been self-funded since founding in 1991.
- **Growth Signals**: Rated among Built In's 2025 Best Midsize Places to Work in Chicago and in the US; actively hiring for multiple engineering and project management roles; expanding bilingual (Spanish) capabilities. [builtin.com](https://builtin.com/company/vail-systems-inc) [vailsys.com](https://www.vailsys.com/about/careers/)

## Competitive Advantages
- **Deep domain experience**: Over 30 years of continuous innovation in voice communication, transitioning from on-premise to cloud.
- **Proprietary technology**: Custom-built platform that optimizes voice interactions at scale, difficult to replicate.
- **Long-term client relationships**: Emphasis on cultivating lasting partnerships rather than transactional deals. [vailsys.com](https://www.vailsys.com/about/culture/)
- **Culture of continuous learning**: Hackathons, workshops, book clubs, and tuition reimbursement support ongoing employee growth. [vailsys.com](https://www.vailsys.com/about/culture/)

## Strategic Focus
- **Cloud-first evolution**: Continuing to move voice logic to the cloud to support scalability and reliability.
- **Bilingual expansion**: Hiring Spanish-speaking engineers to serve broader markets.
- **Talent development**: Investing in employee growth through training, cross-team collaboration, and internal mobility.

## Why Work Here
- **Culture**: Collaborative, innovative environment with a strong emphasis on work/life balance, diversity, and continuous learning. [vailsys.com](https://www.vailsys.com/about/culture/)
- **Work Policy**: Hybrid – flexible combination of remote and on-site work (Chicago Loop and Deerfield offices). [builtin.com](https://builtin.com/company/vail-systems-inc)
- **Perks & Benefits**: Competitive compensation with performance bonuses, 401(k) match, generous vacation, gym memberships, wellness events, casual dress, and social activities (softball team, triathlon team, game nights, hackathons). [vailsys.com](https://www.vailsys.com/about/careers/)
- **Engineering Culture**: Hands-on, collaborative teams; opportunities to work on impactful voice infrastructure; emphasis on test and infrastructure engineering. [jobs.lever.co/vailsys](https://jobs.lever.co/vailsys)

## Sources
1. [vailsys.com - Company Overview](https://www.vailsys.com/about/company/)
2. [vailsys.com - Careers](https://www.vailsys.com/about/careers/)
3. [vailsys.com - Culture](https://www.vailsys.com/about/culture/)
4. [builtin.com - Vail Systems Inc. Profile](https://builtin.com/company/vail-systems-inc)
5. [jobs.lever.co/vailsys - Open Positions](https://jobs.lever.co/vailsys)

## Other roles at Vail Systems Inc.

- [Network Operation Center (NOC) Technician – Day Shift](https://feeny.ai/job/network-operation-center-noc-technician-day-shift-vail-systems-inc-chicago-as148vja4tyx) — Chicago, IL
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