Director of Software Engineering

Caliola Engineering, LLC•Colorado Springs, CO

8d•$155,000 - $215,000•Hybrid

About The Position

Caliola is a woman-owned small business that is improving and protecting our Nation's way of life through secure collaboration and resilient communications. Our engineers, subject matter experts, and veterans are developing and delivering trusted solutions for mission-critical communications. We seek teammates who share our core values: I3 for C3 - Insight, Innovation, and Integrity for Command, Control, and Communications. These values guide how we work every day. At Caliola, you will find technically challenging, mission-focused work within a flexible and collaborative culture that is uncommon in the defense industry. We offer flexible PTO, subsidized health insurance, 401(k) matching, professional development, and a competitive compensation structure designed to support long-term growth. Our performance has driven rapid growth and national recognition, being named twice to the Deloitte Technology Fast 500™ and inclusion on the 2025 Inc. 5000 list of America's fastest-growing private companies. We have also been recognized as a Colorado Company to Watch, a ColoradoBiz Top Company in Aerospace & Defense, and the #2 Gazette's Best Workplace (medium size) in 2025. Headquartered in Colorado Springs, CO, we operate in a leading aerospace and defense hub with proximity to major military installations. Set against the Rocky Mountains, the region offers year-round outdoor recreation and a high quality of life for professionals and families considering relocation. Caliola is seeking a Director of Software Engineering to lead Caliola's software organization as we scale our mission-critical communications products, programs, and technical solutions. Reporting to the VP of Engineering, this leader will provide Leadership, Management, and Accountability for software engineers building software solutions, including web applications, backend signal processing for communications and alternate positioning/navigation/timing solutions, and applications that run over mesh networks. Caliola's software teams operate in complex and restricted environments, including secured development spaces, classified programs, controlled workflows, and systems that must meet customer, accreditation, and mission requirements. As Caliola scales, this role will mature the software organization from project-by-project execution into a disciplined, repeatable software delivery engine by developing technical leads, strengthening engineering standards, improving delivery predictability, supporting productization of DoD-funded solutions, and guiding adoption of AI-enabled software engineering practices.

Requirements

Bachelor's degree in Computer Science, Electrical Engineering, or a related technical discipline.
10+ years of progressive software engineering experience, including experience leading software teams, technical leads, or complex software delivery efforts.
Demonstrated ability to provide Leadership, Management, and Accountability for software engineers and technical leads across in-person, remote, and restricted development environments.
Strong working knowledge of modern software engineering practices, including agile development, software architecture, code quality, automated testing, CI/CD, secure development, documentation, and release discipline.
Ability to manage staffing, priorities, dependencies, technical risk, quality, technical debt, and delivery commitments across multiple programs or development efforts.
Ability to partner effectively with program management, business development, product/design, engineering leaders, and customers as needed to support proposals, technical planning, and execution.
Ability to work under pressure, manage challenging situations with professionalism, and communicate clearly with technical and non-technical stakeholders.
Ability to obtain and maintain a U.S. Government Secret security clearance.

Nice To Haves

Master's degree or higher in Computer Science, Electrical Engineering, Computer Engineering, or a related technical discipline.
Active U.S. Government Secret or Top Secret clearance.
Experience leading software organizations that deliver both customer-funded programs and internally funded or productized software capabilities.
Experience developing or delivering software in DoD, Federal Government, defense contractor, restricted, regulated, classified, or mission-critical environments, including familiarity with statements of work, proposal support, and formal program execution.
Familiarity leading teams across technologies such as C++, Python, TypeScript/JavaScript, Vue.js or similar front-end frameworks, Node.js or comparable backend technologies, GitLab, CI/CD pipelines, containers, Linux, and secure or restricted development environments.
Experience scaling software engineering practices in a growing small business, defense contractor, or mission-focused technology organization.
Experience guiding adoption of AI-enabled software engineering practices, development tools, or knowledge-management workflows.
Ability to travel periodically for critical meetings at customer sites and other business locations.

Responsibilities

Provide Leadership, Management, and Accountability for Caliola's software organization, including establishing software leads, mentoring technical talent, and strengthening team capability across in-person, remote, and restricted development environments.
Define, maintain, and continuously improve software engineering standards for architecture, code quality, testing, CI/CD, documentation, secure development, and AI-enabled software engineering practices.
Maintain awareness of Caliola's software technology stack and guide standards, tooling, and staffing decisions across languages, frameworks, development environments, and deployment targets.
Improve delivery predictability by monitoring staffing, dependencies, technical risks, quality, technical debt, execution blockers, and team capacity across current contracts, future awards, and internally funded development efforts.
Establish and continuously improve agile software development practices, including sprint planning, backlog management, prioritization, estimation, retrospectives, accountability, issue escalation, and follow-through.
Partner with program management, business development, product/design, engineering leaders, and customers as needed to support proposals, translate requirements into executable software plans, and validate technical approaches, staffing assumptions, and delivery commitments.
Support productization of DoD-funded and internally developed solutions by promoting reusable components, common patterns, maintainable architectures, disciplined software sustainment practices, and appropriate adoption of approved AI-enabled tools and workflows.
Drive healthy team dynamics by setting clear expectations, coaching through conflict, escalating issues early, and creating an environment where software teams can execute with focus and accountability.