Director of Engineering

The Reynolds and Reynolds Company; Massachusetts; Hybrid; USD 180,000 - 260,000; Full time

Benefits offered by this job

Medical insurance

Dental insurance

Vision insurance

Life insurance

401(k) with up to 6% matching

Professional development

Hybrid work schedule

Job summary

The Reynolds and Reynolds Company seeks experienced Directors of Engineering to lead one of three engineering organizations within our technology portfolio. These roles span talent strategy, software delivery, architecture, security, and production operations for customer-facing platforms, supporting high-volume, reliable services.

Leaders will oversee multidisciplinary teams across Scrum teams, partnering with Product, Architecture, Security, and executive leadership to align roadmaps with

Qualifications

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

Responsibilities

• Build, develop, and retain high-performing engineering teams across multiple scrum teams and technical leaders.
• Own talent strategy, hiring, onboarding, performance management, succession planning, and leadership development.
• Provide coaching, feedback, and career growth opportunities for direct and indirect reports.
• Own the SDLC, including Agile planning, sprint execution, release management, and change control.
• Establish and improve engineering metrics, quality standards, CI/CD practices, and technical debt management.
• Deliver predictable, high-quality software releases on schedule and within budget.
• Partner with Product leadership to align roadmap commitments and execution plans.
• Define technology roadmaps and architectural direction in partnership with Architecture, Security, and Product teams.
• Drive modernization, scalability, resiliency, security, observability, and operational excellence.
• Manage technology investments, vendor relationships, and cloud optimization initiatives.
• Accelerate engineering productivity through AI-assisted development practices.
• Evaluate and implement AI-enabled product capabilities where they create customer and business value.
• Promote responsible AI adoption, governance, and measurement across the engineering organization.
• Own production health, incident response, escalation management, and support readiness.
• Improve reliability through monitoring, observability, automation, and root-cause analysis practices.

Education

Bachelor's degree in Computer Science, Engineering, or equivalent experience

Tools

CI/CD

Cloud-native

Job description

TSD is seeking experienced Directors of Engineering to lead one of three growing engineering organizations within our technology portfolio: Dealer Services, Rental Services, or Telematics. These second-line leadership roles are responsible for people leadership, software delivery, engineering processes, technology strategy, and production operations for business-critical, customer-facing platforms. Each leader will oversee a multidisciplinary organization of software developers, automation engineers, and QA professionals while partnering closely with Product, Architecture, Security, and executive leadership.

Lead engineering for the platforms automotive dealerships rely on every day, supporting high-volume transactions, integrations, and customer-facing services where uptime, accuracy, and data integrity are critical.

Rental Services

Lead engineering for our reservation, fleet, billing, counter, and partner-integration platforms that power always-on services for a global customer base.

Lead engineering for our connected vehicle platform, including device integration, streaming data ingestion, real-time processing, and the applications that transform vehicle data into business value.

Key Responsibilities

• Build, develop, and retain high-performing engineering teams across multiple scrum teams and technical leaders.
• Own talent strategy, hiring, onboarding, performance management, succession planning, and leadership development.
• Provide coaching, feedback, and career growth opportunities for direct and indirect reports.

Engineering Process & Delivery

• Own the SDLC, including Agile planning, sprint execution, release management, and change control.
• Establish and improve engineering metrics, quality standards, CI/CD practices, and technical debt management.
• Deliver predictable, high-quality software releases on schedule and within budget.
• Partner with Product leadership to align roadmap commitments and execution plans.

Technology & Architecture Leadership

• Define technology roadmaps and architectural direction in partnership with Architecture, Security, and Product teams.
• Drive modernization, scalability, resiliency, security, observability, and operational excellence.
• Manage technology investments, vendor relationships, and cloud optimization initiatives.
• Accelerate engineering productivity through AI-assisted development practices.
• Evaluate and implement AI-enabled product capabilities where they create customer and business value.
• Promote responsible AI adoption, governance, and measurement across the engineering organization.

Production Operations

• Own production health, incident response, escalation management, and support readiness.
• Improve reliability through monitoring, observability, automation, and root-cause analysis practices.

Required Qualifications

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

Preferred Technical Experience

Candidates should bring strong hands-on experience relevant to one of the following technology portfolios:

• NET / C#, ASP.NET Core, React, REST and event-driven microservices
• SQL Server, Redis, AWS cloud services, CI/CD, and modern observability practices
• Flutter, Power BI, and data platform experience preferred
• Python, Google App Engine, Vue/Quasar, Node.js, and streaming data platforms
• MQTT, AWS Kinesis, device integration, cloud-native architectures, and large-scale data processing
• Connected vehicle, telematics, fleet, or IoT experience preferred

Why Join TSD?

You'll have the opportunity to lead talented engineering teams, shape the technology strategy for mission-critical products, and drive innovation across software delivery, cloud platforms, data services, and AI-powered solutions that support customers around the world.

We offer a comprehensive benefits package including:

• Medical, dental, vision, life insurance, and a health savings account
• 401(k) with up to 6% matching
• Professional development and training
• Promotion from within
• Reynolds offers a hybrid work schedule, based on position eligibility. Following completion of your training period, eligible associates may work-from-h EOF