Trapeze Group

Manager, Modernization and AI Engineering

Trapeze Group$100K — $130K *
Transportation
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • Bachelor’s degree in computer science, Engineering, or related field; equivalent experience accepted.
  • 4+ years in software engineering or development.
  • 5+ years in leadership roles managing engineering teams.
  • Understanding of the North American Transit Industry and Agencies is preferred.
  • Azure and/or AWS expertise strongly preferred.

Responsibilities

  • Lead teams through modernization initiatives, including architectural improvements and API modernization.
  • Create an environment for engineers to excel via clear priorities and quality focus.
  • Partner with cross-functional teams to translate business needs into scalable solutions.
  • Drive continuous improvement in delivery processes and DevOps practices.
  • Collaborate to integrate AI/ML capabilities into existing platforms.

Benefits

  • Fostering a culture of innovation and mentorship for long-term team growth.
  • Emphasis on modernizing key technical platforms that enhance daily operations.
  • Opportunity to shape the future of AI integration in practical applications.
  • Access to a wide range of collaborative partnerships within the company.
  • Support for professional development and maintaining high-quality engineering practices.
Full Job Description

Job Summary:

Job Summary:
The Manager, Modernization and AI Engineering is a highly visible leadership role responsible for guiding multiple engineering teams through large-scale technical modernization and thoughtful adoption of AI-driven capabilities. This role blends people leadership, technical strategy, and delivery execution, with a focus on improving the quality, scalability, and longevity of mission-critical systems.

You will partner closely with Product, Architecture, QA, Professional Services, and other engineering leaders to modernize our OnRoute and Orion platforms, strengthen engineering practices, mature DevOps and quality processes, and help shape how AI is responsibly integrated into existing workflows. This position reports to the Director, Software Development.

Job Description:

Job Posting Title:

Manager, Modernization and AI Engineering

Job Profile:

Manager, Software Development

Job Summary:

The Manager, Modernization and AI Engineering is a highly visible leadership role responsible for guiding multiple engineering teams through large-scale technical modernization and thoughtful adoption of AI-driven capabilities. This role blends people leadership, technical strategy, and delivery execution, with a focus on improving the quality, scalability, and longevity of mission-critical systems.

You will partner closely with Product, Architecture, QA, Professional Services, and other engineering leaders to modernize our OnRoute and Orion platforms, strengthen engineering practices, mature DevOps and quality processes, and help shape how AI is responsibly integrated into existing workflows. This position reports to the Director, Software Development.

Why This Role Matters:

  • You will help modernize CAD/AVL platforms that are central to daily transit operations, balancing innovation with reliability, scalability, and real-world operational constraints.
  • You will influence both how we build software and what our products become next, shaping technical direction across architecture, delivery, and quality.
  • You will play a key role in integrating AI/ML capabilities in practical, value-driven ways.
  • You will grow and mentor software developers, strengthening the organization for the long term while delivery results today.

What You’ll Be Doing (High-Level):

  • Lead teams through modernization initiatives, including architectural improvements, API modernization, and cloud-readiness efforts.
  • Create an environment where engineers can do their best work through clear priorities, strong engineering practices, and a sustained focus on quality.
  • Partner with Product Management, Architecture, Professional Services, Sales, and Marketing to translate business needs and customer opportunities into scalable technical solutions.
  • Drive continuous improvement across delivery process, DevOps, testing strategies, and reliability engineering.
  • Collaborate across the teams to identify, design, and integrate AI/ML capabilities into existing platforms where they deliver meaningful value.

Supervisory Duties/Responsibilities:

  • Lead in talent acquisition systems and processes, including recruitment activities and decisions on selections.
  • Identify and nurture talent within the team for future leadership roles.
  • Collaborate with the team to drive, develop, and execute innovation in our current products and solutions.
  • Establish and communicate clear performance expectations.
  • Identify performance gaps and monitor performance to ensure development plans are met.
  • Provide direct support, guidance, and transparent communication across distributed teams, including offshore contributors.
  • Ensure fair and equal treatment of employees, avoiding favoritism, addressing difficult issues (with assistance from Human Resources), and practices empathy and compassion.
  • Promote Company policies, procedures, mission, and values by training and providing direction to direct reports in their use and application.
  • Other duties as assigned.

Duties/Responsibilities:

  • Own execution of modernization initiative for OnRoute and Orion platforms.
  • Assist with other teams revolving: Retrospectives, Sprint Planning, Backlog Grooming, Roadmap Planning, Reporting. Story Definitions, and prioritization of tasks.
  • Take an agile approach to workload planning by utilizing JIRA administratively.
  • Coordinate cross-functionally with other Team Managers to develop comprehensive solutions for our customers.
  • Assist with ad hoc requests and take on required initiatives related to improving efficiency and quality of work across the “design and build” cycle.
  • Other duties as assigned.

Required Skills/Abilities:

  • Excellent communicator and active listener capable of influencing team outcomes.
  • Well versed in the latest tools and technologies to support development initiatives.
  • Azure and/or AWS expertise strongly preferred.
  • Hands-on understanding of CI/CD pipelines (Azure DevOps, GitHub Actions, Jenkins, etc.)
  • Knowledge of automated testing, regression, and pipeline-based quality gates.
  • Ability to guide teams in reliability engineering practices.
  • Proficient in Microsoft Office Suite and related software(s).

Education and Experience:

  • Bachelor’s degree in computer science, Engineering, or related field; equivalent experience accepted.
  • 4+ years in software engineering or development.
  • 5+ years in leadership roles managing engineering teams.
  • Understanding of the North American Transit Industry and Agencies is preferred.

Physical Requirements:

  • Prolonged periods sitting at a desk and working on a computer/laptop.
  • Ability to travel (including domestic and international), sometimes for extended periods, which may involve sitting during transit and walking at various locations. Expected travel for this role is up to 10%.
  • Must be able to life up to 10 pounds at a time.
  • Must be able to handle high utilization of hand and wrist dexterity.

Disclaimers:

  • All job requirements are subject to possible revision to reflect changes in the position requirements or to reasonably accommodate individuals with disabilities. Some requirements may exclude individuals who pose a threat or risk to the health and safety of themselves or other employees.
  • This job description in no way states or implies that these are the only duties to which will be required in this position. Employees will be required to follow other job-related duties as requested by their supervisor/manager (within guidelines and compliance with Federal and State Laws). Continued employment remains on an “at-will” basis.

Worker Type:

Regular

Number of Openings Available:

1

We thank all applicants for their interest; however, only those who qualify for an interview will be contacted. *Professional recruiting agents or consultants need not call.

About Trapeze Group

Trapeze Software Inc. is an operating company of [Volaris Group] which is an operating group of Constellation Software that is engaged in the development, installation and customization of intelligent transportation systems. Its product offerings include scheduling, route optimization, staffing asset management, and communication systems. The division is headquartered in Mississauga, Ontario, and has offices across Canada and the United States, with operating subsidiaries across North America, Northern Europe, Australia and the United Kingdom.
Learn more about Trapeze Group

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