Director, Software Development

About Bridgeway

Bridgeway is a rapidly growing Pittsburgh based company that is already among the country’s largest specialty transportation providers. Join an exciting and dynamic work environment where Team Members work together to deliver world class support to our customers, drivers, agents and carriers. With over a half a million loads annually, and a legacy of service to customers in critical industries, Bridgeway has a history of solving the country’s toughest transportation problems.

Join our Team and become the Future of Freight!

About the Position

The Director of Software Development provides enterprise leadership for Bridgeway’s software engineering function, setting the vision, strategy, and operating model for the platforms and applications that support the Bridgeway family of companies and their customers. As a member of the technology leadership team, this role converts business strategy into a multi-year technology roadmap, governs a portfolio of high-impact initiatives, and ensures investments deliver measurable improvements in growth, customer experience, operational efficiency, security, and scalability. The Director leads leaders, builds organizational capability, and maintains executive accountability for talent, architecture, delivery, quality, financial stewardship, and production performance.

Responsibilities

Lead, mentor and manage a team of software developers

Communicate effectively with stakeholders, including senior management, clients and internal departments

Foster a positive and collaborative team environment

Identify and address skills gaps within the team

Participate in the planning, execution and delivery of software projects

Coordinate with various departments to ensure alignment and effective communication

Manage project risks and implement mitigation strategies

Provide technical guidance and support to the development team

Continuously improving software development processes and practices

Implement and maintain development tools and methodologies

Ensure quality assurance and testing processes are followed

Monitor and improve the efficiency and effectiveness of the development process

Provide regular updates on project status, risks and issues

Manage team workload and ensure balanced distribution of tasks

Hire, onboard and train new team members as needed

Manage code production deployments and post go-live technical support

Qualifications and Education Requirements

Bachelor’s degree in Computer Science, Software Engineering, Information Technology, or a related field required; master’s degree or equivalent advanced business or technology education preferred.

Typically 12 or more years of progressive software engineering experience, including substantial experience leading managers, senior technical leaders, and multidisciplinary teams.

Demonstrated success defining enterprise technology strategy and delivering a complex portfolio of business-critical products, platforms, and modernization initiatives.

Proven experience scaling engineering organizations, developing leadership talent, building succession pipelines, and leading through significant organizational change.

Strong command of modern application architecture, cloud platforms, systems integration, APIs, DevOps, secure software development, observability, and quality engineering.

Experience governing enterprise architecture, technical debt, platform reliability, cybersecurity risk, and software lifecycle standards.

Demonstrated financial acumen, including ownership of operating and capital budgets, workforce plans, vendor portfolios, forecasts, and investment cases.

Ability to connect technology strategy and delivery decisions to revenue growth, customer value, operational performance, risk reduction, and return on investment.

Exceptional executive communication, judgment, influence, and change-leadership skills, with the ability to build alignment across technical and nontechnical stakeholders.

Experience in transportation, logistics, supply chain, or another high-volume, transaction-intensive industry preferred.