Full-Time

DevSecOps Engineer 2

Vail Systems

Vail Systems

51-200 employees

Scalable telephony software with APIs

Compensation Overview

$108k - $125k/yr

+ Annual Bonus Program + Relocation allowance + 401(k) match + Employee referral bonus + Development stipend

Chicago, IL, USA + 1 more

More locations: Highland Park, IL, USA

Hybrid

Hybrid role; must be within commuting distance to Deerfield or Chicago offices; interviews/onboarding conducted in offices when possible.

Category
DevOps & Infrastructure (2)
,
Required Skills
TCP/IP
Bash
Kubernetes
Python
Computer Networking
Docker
SOC 2
Go
Jenkins
Requirements
  • 2+ years of hands-on, production-level experience with Kubernetes and containerization, including running and troubleshooting workloads in production environments is required.
  • Experience with on-premises Kubernetes is a bonus.
  • Familiarity with CI/CD pipelines and tooling (Jenkins, GitLab CI, ArgoCD).
  • Basic scripting and automation skills (Python, Bash); experience with Go (Golang) is a bonus.
  • Experience with vulnerability scanning and container security workflows (Sysdig, Trivy, or similar).
  • Familiarity with CNAPP and SIEM platforms (Sysdig, Rapid7, or similar), or a strong interest in developing expertise with them.
  • Understanding of networking concepts (TCP/IP, DNS, load balancing, firewalls, and Kubernetes network policies).
  • Familiarity with compliance frameworks (PCI DSS, HIPAA, SOC 2, NIST, ISO 27001) and how to support evidence/reporting needs.
  • Understanding of security fundamentals such as Secure Software Development Life Cycle and secure coding principles.
  • Strong collaboration and communication skills, with the ability to translate security requirements into practical guidance for developers.
Responsibilities
  • Improve the security of containerized workloads in Kubernetes by leveraging CNAPP tooling for vulnerability scanning, runtime security, and compliance reporting.
  • Partner with developer, DevOps, and security teams to integrate CNAPP and SIEM tools into CI/CD pipelines and infrastructure-as-code workflows.
  • Test and refine Kubernetes security policies to strengthen enforcement and adoption.
  • Support investigation and remediation of container-related security issues.
  • Create documentation and best practices for secure container usage and deployment.
  • Provide reporting and evidence to support compliance with frameworks such as PCI DSS, HIPAA, SOC 2, NIST, and ISO 27001.
  • Stay current with new tools and approaches to improve Kubernetes and container security.
  • Support DevOps needs by participating in deployments and troubleshooting developer workloads.
  • Participate in an on-call rotation shared across 13 engineers. Each engineer typically covers one weekday every two weeks. If your shift falls on a Friday, the on-call period extends through the weekend until Monday at 10 AM. The on-call rotation begins after 3 months of employment.
Desired Qualifications
  • None

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

Simplify Jobs

Simplify's Take

What believers are saying

  • STIR/SHAKEN compliance deadline September 18, 2025 creates demand for authentication services among non-compliant providers.
  • FCC removal of 1,200+ non-compliant providers August 25, 2025 consolidates market toward compliant operators like Vail.
  • Enterprise reliance on legacy VoiceXML hosting creates sticky customer relationships resistant to cloud migration.

What critics are saying

  • Twilio's FreeClimb acquisition commoditizes Vail's API platform, eroding pricing power and differentiation.
  • Amazon Connect captures 35% market share with AI-native IVR, undercutting Vail's legacy VoiceXML hosting.
  • Microsoft Azure Communication Services migrates Vail's 30% OCS hosting clients via forced platform upgrades.

What makes Vail Systems unique

  • Carrier-grade collocation facilities across Chicago, Southfield, and Aurora ensure fault-tolerant delivery for Fortune 500 clients.
  • Comprehensive platform handles billions of interactions yearly with 24/7 monitoring across voice, messaging, and conferencing.
  • FreeClimb API enables enterprise customers to build custom voice applications without vendor lock-in constraints.

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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

TribTown
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).