Director of Engineering Software Development North Andover, MA

The Reynolds and Reynolds Company; Andover, Northern (MA, KY); Hybrid; USD 180,000 - 240,000; Full time

Benefits offered by this job

Health insurance

401(k) with up to 6% matching

Professional development and training

Promotion from within

Hybrid work schedule

Paid vacation and sick days

Eight paid holidays

Referral bonuses

Job summary

The Reynolds and Reynolds Company is seeking three Directors of Engineering to lead Dealer Services, Rental Services, and Telematics engineering teams. You will manage delivery, architecture, and production operations for customer-facing platforms and partner with Product, Security, and exec leadership.

You will build and develop high-performing teams, drive talent strategy, and oversee Agile processes, CI/CD, and modernization initiatives to ensure reliable, scalable systems globally.

Qualifications

• 12+ years of software engineering experience with 5+ years in leadership.
• Proven track record managing mission-critical, customer-facing applications.
• Strong background in software architecture, DevOps, cloud-native tech.
• Experience hiring, developing, and managing engineering talent.
• Knowledge of security, performance, and modern delivery practices.
• Experience adopting AI technologies in engineering groups.

Responsibilities

• Build, develop, and retain high-performing engineering teams across multiple scrum teams.
• Own talent strategy, hiring, onboarding, performance management, and succession planning.
• Provide coaching and career growth opportunities to reports.
• Own the SDLC, Agile planning, sprint execution, release management, and change control.
• Establish metrics, quality standards, CI/CD, and debt management.
• Deliver high-quality releases on schedule and budget.
• Partner with Product to align roadmap commitments.

Skills

People leadership

Engineering management

Software delivery

Agile / Scrum

Cloud-native

DevOps / CI/CD

Architecture knowledge

AI adoption

Communication

Vendor management

Education

Bachelor's degree in CS/Engineering or equivalent

Tools

.NET / C#

ASP.NET Core

React

SQL Server

AWS

CI/CD

Flutter

Power BI

Python

MQTT

Google App Engine

Job description

Job Description:

Director of Engineering (3 Openings)

Dealer Services | Rental Services | Telematics

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.

Available Opportunities

Dealer Services

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.

Telematics

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.

AI & Innovation

• -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:

Dealer Services & Rental Services

• -.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

Telematics

• -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.

#LI-Hybrid

Benefits:

We strive to offer an environment that provides our associates with the right balance between work and family. 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-home up to two days per week.
• - Paid vacation and sick days
• - Eight paid holidays
• - Referral bonuses

Reynolds and Reynolds promotes a healthy lifestyle by providing a non-smoking environment. Reynolds and Reynolds is an equal opportunity employer.