Software Development Manager

Overview

Outdoor Cap has been a leader in the headwear industry for more than 45 years, serving retail, team sports, and promotional markets with innovative products and exceptional service. With a heritage of steady growth and strong customer relationships, we are now investing in modernizing our systems and processes to position the company for the future. Our technology team plays a key role in this transformation by balancing legacy stability with forward-looking innovation.

We are seeking an experienced forward-thinking Manager of Software Development to lead our development team as we modernize legacy systems, implement new technologies, and build the foundation for scalable, future-ready solutions. This role is critical in balancing transformation with operational stability while delivering value today and positioning the organization for tomorrow.

The ideal candidate brings strong technical leadership, deep experience in scaling engineering organizations, and a proven ability to drive modernization efforts in complex environments.

• Define and execute the engineering roadmap that modernizes legacy systems while enabling growth and innovation.
• Partner closely with business, operations, and product leaders to ensure technology investments align with strategic goals.
• Champion a pragmatic approach that balances short-term needs with long-term modernization.

• Lead, mentor, and grow a team of engineering managers and software developers.
• Establish clear goals, accountability, and career development pathways.
• Foster a culture of collaboration, ownership, and continuous learning across the engineering organization.
• Commitment to building inclusive, diverse, and resilient teams.

• Oversee the migration and integration of legacy platforms with modern technologies while ensuring minimal disruption to operations.
• Drive high standards for software quality, reliability, and performance.
• Implement metrics and development productivity frameworks to measure and improve team performance.
• Champion Agile/Scrum practices to drive effective project management and delivery, adapting frameworks as needed to support modernization initiatives.

• Introduce and scale modern development practices such as CI/CD, cloud adoption, Dev Ops, automated testing, and security by design.
• Guide decisions on re-platforming, system integration, and technical debt reduction.
• Stay informed on emerging tools and approaches that can accelerate digital transformation in manufacturing and related industries.

• Experience in manufacturing, supply chain, or other complex operational environments is preferred.
• Familiarity with ERP, CRM, MES, or shopfloor systems and their integration with modern web applications (microservices, cloud platforms, scalability patterns, etc.) is preferred.
• Track record of scaling engineering practices in companies balancing legacy systems with modernization is preferred.

• 7+ years of software engineering experience with at least 3+ years in leadership roles.
• Demonstrated success leading to modernization of legacy systems while maintaining critical business operations.
• Strong technical background with expertise in enterprise-scale platforms, integration patterns, and cloud architectures such as AWS, Azure, or equivalent.
• Proven ability to drive large-scale change initiatives across multiple stakeholders.
• Excellent communication and collaboration skills with experience building alignment across business and technology teams.

• Must be able to sit at a computer as well as stand and/or walk as needed throughout the day. May occasionally reach, bend and move inside the facility and office areas.
• Required to have close visual acuity to perform computer tasks, and expansive analysis and reading.
• Ability to lift up to 25 pounds infrequently.

Nothing in this job description restricts management’s right to assign or reassign duties and responsibilities to this job at any time.