Director of Software Engineering at Caliola – Colorado Springs | Jobyssey

Director of Software Engineering

City/State: Colorado Springs, CO USA

Type and Schedule: Full-Time, Salary/Exempt, on-site with limited remote work flexibility.

Annualized Salary Range: $155,000 - $215,000 commensurate with experience.

About Us: 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.

As a part of our selection process, we ask all applicants to complete a short, 10–12-minute survey from Culture Index. This is a survey, not a test; no passing or failing. The purpose of this survey is to identify your unique strengths as they relate to our open positions. Please copy and paste the following link into a separate browser window to complete: https://go.cultureindex.com/s/5i6Gpe3wge

Position Description: 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.

Essential 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.

What We Require:

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.

What We Value:

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.

Minimum Physical Requirements:

Must possess exceptional written and verbal English communication skills, with the ability to convey complex technical concepts to both technical and non-technical audiences.
Must be able to navigate a standard office environment including prolonged periods at a desk and frequent use of computers, screens, and digital communication tools.
Ability to maintain high levels of cognitive focus, analytical thinking, and attention to detail for extended periods when reviewing architectural designs, code repositories, and technical proposals.
Must be able to frequently move about the office environment to facilitate team collaboration and engage with stakeholders. Requires the occasional ability to lift, move, and set up office and personal technical equipment (e.g., laptops, monitors, and peripherals) up to 20 lbs.

Please contact Human Resources with questions about ADA accommodations.

Expression of Interest: By applying to this job, you are expressing interest in this position and could be considered for other career opportunities at Caliola Engineering. Should a match be identified between your skillset and Caliola's requirements for this or a future opening, you may be contacted.

The posted salary range represents our good faith estimate for this role based on current organizational needs and the qualifications reasonably expected for the position. Final compensation will be determined based on factors such as experience, skills, education, clearance status, and business needs.

This position will remain open until filled, and applications will be reviewed on a continuous basis.

At Caliola, we believe that true innovation can only occur when teammates bring their authentic selves to collaborate in a supportive, encouraging environment. We are an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability or veteran status, age, or any other federally protected class.

Caliola participates in E-Verify, an internet-based system used to confirm the employment eligibility of all new hires. Upon hire, all employees are required to complete Form I-9 to verify their identity and employment eligibility to work in the United States.

All candidates will be required to pass a basic background screening.

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