Jake Schmitz

Sr. Director of Application Development

20+ Years Building High-Performance Engineering Teams | 15+ Years Leading at Vail Systems

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About

I've spent two decades building software and the teams that create it.

As Sr. Director of Application Development at Vail Systems, I lead engineering teams that deliver web applications powering telecommunications solutions our customers rely on every day. Over 15 years with Vail, I've grown from software developer to senior leadership. What I'm most proud of? The talented engineers I've hired, mentored, and watched grow into leaders themselves.

Beyond engineering leadership, I work closely with product strategy for FreeClimb, leveraging insights from Kellogg's Chief Product Officer Program to bridge the gap between technical execution and product vision.

My Leadership Philosophy

Great teams are built on continuous learning, hard work, and having fun along the way. I create environments where engineers are encouraged to explore new technologies, share knowledge, and push boundaries—while enjoying the journey. We're currently evolving from traditional web applications into AI-powered solutions, and that journey requires curiosity, experimentation, and a willingness to learn together.

My Background

I've been with Vail Systems for over 15 years, growing from a software developer into senior leadership. This journey—from writing code to leading engineering organizations—has given me deep insight into what it takes to build scalable web applications and the teams that create them. I've experienced firsthand the challenges of rapid growth, technical transformation, and evolving customer needs in the telecommunications industry.

Before joining Vail, I spent five years as a consultant delivering enterprise content management solutions for Fortune 500 companies including PepsiCo, Northwestern Mutual, and Safeco. Working across the entire software development lifecycle and engaging directly with customers throughout taught me how to navigate complex requirements, lead diverse teams, and deliver solutions that create real business value.

What I Bring

  • 20+ years of software development and engineering leadership
  • Deep expertise in web application architecture and telecommunications
  • Track record of building, scaling, and mentoring high-performance engineering teams
  • Leading technical transformation from web apps to AI-powered solutions
  • Kellogg Chief Product Officer Program graduate—expanding leadership into product strategy
  • Passion for continuous learning and innovation

I'm always interested in connecting with fellow engineering leaders, discussing the evolving landscape of software development and AI, and sharing what we're building at Vail Systems.

Experience

2024 - Present · 2 years

Sr. Director of Application Development

Vail Systems

Greater Chicago Area

Leading engineering teams that deliver web applications powering telecommunications solutions. Building high-performance teams, mentoring engineers, and driving technical transformation from web apps to AI-powered solutions.

Jul 2012 - 2024 · 12 years

Director of Application Development

Vail Systems

Greater Chicago Area

Aug 2011 - Jul 2012 · 1 year

Software Engineering Manager

Enova International · Full-time

Chicago, Illinois, United States · On-site

Led a greenfield project to deliver a new platform within a condensed timeframe using pair programming, continuous delivery, and a microservice architecture.

Feb 2008 - 2011 · 3 years

Web Development Manager

Vail Systems

Greater Chicago Area

As the team and product portfolio grew, took on management of developers across multiple teams and projects simultaneously—all while remaining hands-on in the codebase. Continuously refined engineering processes to improve collaboration, consistency, and delivery across teams.

Feb 2007 - Feb 2008 · 1 year

Software Engineer

Vail Systems

Greater Chicago Area

Built a greenfield web application from the ground up—one that remains in production and actively used today. Bootstrapped everything from scratch: team processes, development workflows, deployment practices, and engineering culture. Drove deep architectural conversations to make the right foundational decisions early, resulting in a system with the durability and flexibility to stand the test of time.

Aug 2002 - Aug 2007 · 5 years 1 month

Professional Services Consultant

Technology Services Group - Chicago · Full-time

Greater Chicago Area · On-site

Worked with clients through the RFP, requirements, design, development, and deployment phases to deliver Enterprise Content Management solutions. Solutions were primarily created and delivered using Documentum and Java Web Application technologies. Clients included PepsiCo, Safeco, Northwestern Mutual, and Abraxis Pharmaceutical.

C# Requirements Analysis Java Documentum
1996 - 1998 · 2 years

Software Quality Assurance Intern

Kingland Systems · Internship

Clear Lake, Iowa, United States · On-site

Created Test Plans and Test Scripts for multiple web-based financial products. Implemented end-to-end automated tests using WinRunner.

Automated Software Testing Test Planning

Education & Certifications

Iowa State University

Bachelor of Science (BS), Computer Science

1998 - 2002

Kellogg Chief Product Officer Program

Northwestern University

2024

Let's Connect

I'm always interested in connecting with fellow engineering leaders and discussing the evolving landscape of software development and AI.

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