Director of Software Engineering

About the position

As a Director of Software Engineering, you will lead engineering teams focused on delivering high-quality, scalable SaaS solutions while working cross-functionally with Product, DevOps, and QA. While you won’t directly manage DevOps or QA, you’ll have influence over cloud infrastructure decisions, CI/CD improvements, and overall engineering quality. You will play a key role in modernizing legacy technology, pushing innovation in AI, NLP, and mobile solutions, and ensuring engineering efforts align with customer needs and business goals. We need someone who is not just a strategist but a hands-on leader—willing to write and review code, work through complex system design challenges, and help engineers level up their technical skills.

Responsibilities

• Innovate & Modernize Our Tech Stack
• Lead efforts to modernize our legacy Visual Basic-based platform, breaking down monolithic systems into scalable microservices.
• Drive innovation in AI-driven dispatch, NLP-powered search, and open API development.
• Provide technical vision for Shipper and Carrier mobile applications, ensuring seamless user experiences.
• Advocate for cloud-native architectures and best practices in cloud infrastructure and DevOps collaboration.
• Technical Leadership & Hands-On Development
• Be a hands-on leader, mentoring engineers, reviewing code, and setting high engineering standards.
• Guide teams on architecture, system design, and implementation strategies.
• Influence technical decisions around story sizing, backlog prioritization, and Agile best practices.
• Collaborate with DevOps to enhance CI/CD pipelines and improve engineering velocity.
• Engineering Execution & Agile Delivery
• Improve the software development lifecycle (SDLC), ensuring efficient Jira workflows, sprint planning, and roadmap execution.
• Champion Agile methodologies, making sure teams balance speed with quality.
• Drive technical execution on high-impact projects, ensuring engineering aligns with business goals and customer needs.
• Customer-Facing & Cross-Functional Collaboration
• Work closely with Product, Sales, and Customer Success to build customer-centric solutions.
• Join key client conversations to understand real-world challenges and develop solutions that drive business value.
• Bridge the gap between engineering and product, ensuring technical decisions align with market demands and user needs.

Requirements

• Minimum of 8 years of engineering experience.
• Minimum of 3 years leading teams in a hands-on technical role.
• Deep expertise in SaaS software development, ideally in commercial B2B applications.
• Strong coding skills in modern programming languages (e.g., Java, Kotlin, Swift, Python, JavaScript, or C#). Yes, a technical assessment will be part of the initial interview process.
• Experience building and scaling API-driven, cloud-native applications (AWS, Azure, or GCP).
• Familiarity with legacy modernization, including breaking monolithic applications into microservices.
• Proven ability to mentor engineers, lead technical discussions, and drive innovation.
• Understanding of Agile SDLC, Jira workflows, backlog management, and iterative development.
• Ability to collaborate cross-functionally with DevOps, QA, and Product teams to drive efficiency and innovation.
• A problem-solving mindset, with a passion for tackling complex challenges and delivering impactful solutions.

Benefits

• Comprehensive benefits plan for full-time employees and their dependents.
• 401k with a 4% match.
• Unlimited PTO package.
• Hybrid work environment with 3 days in the office and 2 days remote.
• Paid training and development opportunities.
• Employee recognition programs.
• Opportunities for career growth.