Head of Software Engineering

The Head of Software Engineering owns software engineering strategy and execution across Safe-Guard's core platform portfolio. You will lead a multi-team engineering organization that builds and operates the systems underpinning dealer enrollment, incentive programs, rating, quoting, and remitting workflows, claims adjudication, cancellations, payment processing, and direct-to-consumer product experiences. You will partner with Sales, Key Partner Management, Operations, and executive leadership to align engineering capacity and roadmaps with company strategy, and you will help champion Safe-Guard's vision of AI-native software development, operationalizing the use of Claude, Cursor, and similar LLMs and software tools across engineering teams.

Note: This role does not have responsibility for ERP / Financial Systems or Business Analytics / BI reporting platforms., * Lead, mentor, and develop a high-performing software engineering organization across multiple product domains, client-facing dealer and OEM platforms, internal operations systems, and direct-to-consumer applications.

• Own recruiting, hiring, and retention of top engineering talent; build career progression that reward technical excellence and leadership growth at every level.
• Establish and sustain a culture of ownership, accountability, and continuous learning for engineers do their best work.
• Conduct regular 1:1s, performance reviews, and career development conversations; actively develop direct reports into future leaders.
• Partner with HR and Talent Acquisition to strengthen Safe-Guard's employer brand within the software engineering community.
• Own the engineering roadmap and outcomes for Safe-Guard's client-facing platforms (dealer enrollment, rating, quoting, contract remittance, incentive management, direct-to-consumer) and internal platforms (claims adjudication, cancellations, and payments).
• Define and help drive the technical architecture strategy, balancing modernization, and scalability, across a portfolio of applications serving automotive and insurance workflows.
• Partner with Sales, Product Management, and Operations to translate business objectives into executable technical roadmaps, ensuring alignment between engineering capacity and company priorities.
• 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/partner decisions, clearly communicating trade-offs to senior leadership and stakeholders.
• Help champion Safe-Guard's AI vision by embedding AI-assisted development practices as standard practice across all engineering teams.
• In collaboration with technology leadership, help design and delivery of AI-native platform capabilities, including intelligent automation in claims adjudication, contract processing, rating workflows, and dealer-facing experiences.
• Build a team culture where engineers default to AI-first thinking: leveraging AI to accelerate development velocity, improve code quality, reduce operational work, and expand product capabilities.
• Stay current on AI tooling and agentic AI approaches; bring informed recommendations to the technology and product leadership on emerging capabilities applicable to Safe-Guard's platforms.
• Establish evaluation frameworks and responsible-use guidelines ensuring AI capabilities deployed in production meet Safe-Guard's quality, compliance, security, and reliability standards.
• Serve as the primary engineering voice in executive and cross-functional forums; communicate technical strategy, progress, risks, and trade-offs clearly to both technical and business stakeholders.
• Partner with Operations, Compliance, and Legal teams to ensure platforms meet the regulatory requirements of automotive and insurance administration.
• Collaborate closely with our dealer network, OEM partners, and Key partner executive teams to incorporate external feedback into the platform roadmap.
• Drive alignment across peer technology leaders-Product, Architecture, Data, Security, and IT to deliver cohesive, integrated platform experiences.
• Own end-to-end software delivery accountability ensuring teams execute with predictability, quality, and a consistent sense of urgency.
• Implement and refine delivery practices, release cadences, and engineering health metrics that give leadership clear visibility into team performance 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.

The above statements are intended only to describe the general nature of the job and should not be construed as an all-inclusive list of position responsibilities.

• 15+ years of progressive software engineering experience, including 7+ years leading engineering organizations of 70 or more engineers across multiple teams and domains including offshore contracting resources.
• Demonstrated success building and scaling AI-native engineering cultures to fundamentally transform how engineering teams design and build software.
• Hands-on experience building AI-powered production platforms; familiarity with LLMs, agentic AI architectures, and practical integration patterns for regulated business workflows.
• Direct experience with AI-assisted development tooling including Anthropic's Claude, Cursor, and similar LLMs and products at team or organizational scale.
• Proven track record in the automotive industry with direct experience working with dealer networks, OEM brands, or automotive F&I platforms strongly preferred.
• Meaningful experience in insurance or insurance-adjacent domains (policy administration, claims processing, coverage rating and quoting, or similar regulated workflows).
• Track record delivering complex, client-facing SaaS or platform products in a B2B environment where uptime, performance, and compliance are non-negotiable.
• Strong command of modern software architecture patterns: microservices, event-driven systems, API-first design, cloud-native infrastructure, and DevSecOps practices.
• Deep familiarity with the software development lifecycle: code quality standards, CI/CD pipelines, automated testing, release management, and production observability.
• Understanding of the regulatory and compliance landscape relevant to automotive protection products, vehicle service contracts, and insurance product administration.
• Experience with payment processing platforms, financial transaction workflows, or claims administration systems is a strong advantage.
• Exceptional ability to translate complex technical concepts into clear, actionable narratives for executive, business, and cross-functional audiences.
• Proven ability to build trust with internal and external customers operating as a credible technology partner, not just an internal function.
• High emotional intelligence; skilled at navigating organizational complexity, building
• consensus across competing priorities, and leading through change.
• Bachelor's degree in computer science, engineering, or a related field required; advanced degree a plus. Equivalent experience will be considered.

Company Benefits:

• Medical, Dental, and Vision Insurance
• Flexible Spending Account
• Health Savings Account
• 401(k) Plan with Company Match
• Company-paid Short-Term and Long-Term Disability
• Company-paid Life Insurance
• Paid Holidays and Vacation
• Employee Referral Program
• Employee Assistance Program
• Wellness Programs
• Paid Community Service Opportunities
• Tuition Reimbursement
• Ongoing Training & Personal Development
• And More!

About Safe-Guard Products International

Safe-Guard serves Original Equipment Manufacturers (OEMs), top retailers, and independent agents in the automotive finance and insurance industry with the leading Protection Products Platform. Our platform delivers innovative protection products and solutions that protect consumers from the perils of ownership, while providing Finance &Insurance professionals the tools to ignite scalable and sustainable business growth. Safe-Guard's success is driven by over 850 employees, who serve more than 12,000 dealers and support contract holders across the U.S. and Canada. For 30 years and counting, our team continues to transform the motor vehicle space, earning a stellar reputation from our partners and peers by providing: 1) the highest quality protection products in the industry, 2) a broad platform of branded product, technology, marketing, and training solutions, and 3) an unwavering commitment to uncomplicated care and customer service.