Director of Engineering (AI)

Location: North Andover, Massachusetts, United States; hybrid schedule with up to two work-from-home days per week after training for eligible associates

Company

Develops software platforms and connected-vehicle technology for automotive dealerships, rental services, and telematics customers.

What you will do

• Lead one of three engineering organizations: Dealer Services, Rental Services, or Telematics.
• Build, develop, and retain engineering teams across multiple scrum teams and technical leadership groups.
• Own the software development lifecycle, Agile delivery, release management, engineering metrics, quality standards, and CI/CD practices.
• Define technology roadmaps and architectural direction with Product, Architecture, Security, and executive leadership.
• Drive modernization, scalability, resiliency, security, observability, cloud optimization, and operational excellence.
• Own production health, incident response, escalation management, support readiness, and responsible AI adoption.

Requirements

• 12+ years of software engineering experience, including 5+ years leading software development organizations.
• Prior Director-level or equivalent second-line leadership experience.
• Experience leading engineering teams supporting mission-critical, customer-facing applications.
• Strong background in software architecture, quality engineering, DevOps, CI/CD, cloud-native technologies, application security, and performance engineering.
• Experience hiring, developing, and managing engineering talent, as well as adopting AI technologies within engineering organizations.
• Bachelor's degree in Computer Science, Engineering, or equivalent experience.

Nice to have

• Dealer or Rental Services experience with .NET, C#, ASP.NET Core, React, REST, event-driven microservices, SQL Server, Redis, and AWS.
• Telematics experience with Python, Google App Engine, Vue/Quasar, Node, MQTT, AWS Kinesis, device integration, and streaming data platforms.
• Experience with Flutter, Power BI, large-scale data processing, connected vehicles, fleet systems, or IoT.

Culture & Benefits

• Medical, dental, vision, life insurance, and health savings account.
• 401(k) with up to 6% matching.
• Professional development, training, and promotion from within.
• Paid vacation, sick days, and eight paid holidays.
• Referral bonuses and a non-smoking work environment.