Director of Software Engineering

The Director of Software Engineering owns engineering delivery, technical direction, and team leadership for Safe-Guard's externally facing enrollment, incentives, reporting, contracting, rate configuration user management, and role-based access control platforms. You will lead a team of approximately 20 engineers—including full-time employees and contractors—building and operating the systems that dealers and OEM partners rely on daily. Reporting to the Head of Software Engineering, you will partner with Product Management, Operations, and business stakeholders to align your team's roadmap with company priorities, while championing Safe-Guard's AI-native development vision, including the use of Claude, Cursor, and similar tools, across your engineering team.

Lead, mentor, and develop a team of approximately 20 engineers (full-time employees and contractors) across enrollment, incentives, reporting, contracting portals, and rate configuration platforms.

Own hiring, onboarding, and retention of engineering talent; build career progression that rewards technical excellence and leadership growth.

Establish and sustain a culture of ownership, accountability, and continuous learning where engineers do their best work.

Conduct regular 1:1s, performance reviews, and career development conversations; develop future technical leads and senior engineers.

Partner with HR and Talent Acquisition to support recruiting efforts and strengthen the team's reputation within the engineering community.

Own the engineering roadmap and delivery outcomes for Safe-Guard's enrollment, incentives, reporting, contracting, and rate configuration platforms.

Define and drive technical architecture strategy across the platform portfolio (Angular, NestJS, AWS, Okta/OIDC), balancing modernization and scalability in a fast-moving, client-facing environment.

Define and own the user management and role based access control strategy across dealer-facing platforms, ensuring dealers and OEM partners can self-service user provisioning and access control within compliant guardrails.

Partner with Product Management, Operations, and business stakeholders to translate requirements into executable technical roadmaps.

Drive continuous improvement in system reliability, performance, and security; establish engineering standards for code quality, testing, observability, and incident response.

Make sound architectural and build/buy decisions, clearly communicating trade-offs to the Head of Software Engineering and other stakeholders.

Champion Safe-Guard's AI-first vision by embedding AI-assisted development practices, including Claude and Cursor, as standard practice across your team.

Collaborate with the Head of Software Engineering and technology leadership to design and deliver AI-native capabilities across enrollment, incentives, reporting, contracting, and rating workflows.

Build a team culture where engineers default to AI-first thinking: leveraging AI to accelerate development velocity, improve code quality, and expand platform capabilities.

Stay current on AI tooling and agentic AI approaches; bring informed recommendations to technology leadership on capabilities applicable to your platforms.

Help ensure AI capabilities deployed to production meet Safe-Guard's quality, compliance, security, and reliability standards.

Serve as the primary technical point of contact for your platforms in both internal and client-facing conversations, translating complex technical topics for non-technical stakeholders.

Partner with Operations, Compliance, and Legal teams to ensure your platforms meet the regulatory requirements of automotive and insurance administration.

Collaborate directly with the dealer network, OEM partners, and Key Partner teams to incorporate external feedback into the platform roadmap.

Align with peer engineering and technology leaders to deliver cohesive, integrated platform experiences.

Own end-to-end delivery accountability for your team, ensuring predictable, high-quality releases in a fast-paced environment.

Implement and refine delivery practices, release cadences, and engineering health metrics that give leadership clear visibility into team and platform health.

Drive operational excellence: runbooks, post-incident reviews, and a culture of proactive reliability over reactive firefighting.

Identify and remove organizational and technical blockers that impede team velocity.

10+ years of progressive software engineering experience, including 4+ years leading engineering teams.

Experience managing a team of roughly 20 engineers, including a mix of full-time employees and contractors.

Demonstrated success building AI-native engineering practices and embedding AI-assisted development (Claude, Cursor, or similar tools) into daily workflows.

Track record delivering client-facing, externally facing platforms in a fast-paced B2B SaaS environment.

Automotive industry experience—dealer networks, OEM brands, or automotive F&I platforms—strongly preferred.

Experience in insurance or insurance-adjacent domains (rating, quoting, contracting, or similar regulated workflows) is a plus.

Full-stack proficiency across Angular (frontend) and NestJS (backend), with a strong understanding of enterprise architecture and microservices patterns.

Hands-on experience with AWS cloud infrastructure, including container orchestration (e.g., ECS Fargate).

Deep understanding of Okta and OIDC/PKCE authentication flows.

Experience designing and operating user management and role-based access control (RBAC) systems across dealer platforms, including provisioning, permission modeling, and delegated administration for dealer network users.

Strong command of the full software development lifecycle: CI/CD pipelines, automated testing, code quality standards, and production observability.

Understanding of the regulatory and compliance landscape relevant to automotive protection products and insurance product administration is a plus.

Proven ability to operate as a client- and business-facing technical expert, translating complex technical concepts into clear guidance for non-technical stakeholders.

Comfortable operating in a fast-paced environment with shifting priorities and competing demands.

Strong track record building trust with both internal teams and external partners, including dealers and OEM brands.

High emotional intelligence; skilled at navigating organizational complexity and leading through change.

Bachelor's degree in computer science, engineering, or a related field required; equivalent experience will be considered.

In your first 90 days, you will have built strong relationships with your engineering team, Product partners, and key business stakeholders; completed a candid assessment of your platforms' health, team capabilities, and delivery practices; and established your presence as a trusted, decisive leader within the Technology organization. Within 6 months, your team will be operating with measurably improved delivery predictability, AI-assisted development will be embedded in daily engineering workflows, and you will have a clear roadmap for advancing your platforms' capabilities, and a unified user management model will be in place across all dealer platforms. At one year, your team will reflect your leadership: higher engineering velocity, strong dealer and client satisfaction with your platforms, AI-powered capabilities in production, and an engineering culture where the best people want to stay and grow.