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Director of Software Engineering

CareGard Warranty Services, Inc., Granite Heights, WI, United States


Join Our Team Join our team and be part of something truly transformational! We are different. Under the name of CareGard Warranty Services, Automotive Financial Group (AFG) was founded in 1994. Within the past 30 years, AFG has become a leader in vehicle service contracts and protection products. Through partnerships with car dealerships, finance companies, and automotive manufacturers (OEM), CareGard has redefined the standards of service in the automotive industry. Driven by a profound mission to enhance the automotive landscape, CareGard has tirelessly worked towards nurturing talent and fostering a culture rooted in values of trust and reliability. Today, it stands as a titan among extended warranty providers, celebrated for its exceptional Google ratings and unwavering commitment to excellence.

Excellence is in Our DNA At CareGard, we are always looking for the best talent on the planet. Our people have an ownership mentality in everything we do. We exude initiative, accountability, and an unyielding pursuit of excellence. Our culture is built on integrity, innovation, and passion. Together, these values create an atmosphere that allows us to surpass customer expectations and cultivate deep‑seeded relationships built on trust.

Once in a Lifetime Opportunity AFG is growing rapidly, and we are looking for a Director of Software Engineering who can lead our software development strategy and drive the delivery of high‑quality, scalable applications and services. This is a role for a leader who sees beyond daily execution, understands how technology intersects with business objectives, and builds systems and teams that truly make an impact.

Summary AFG is looking for a skilled and motivated engineer who is ready to take the next step in their career and help shape the future of our software development efforts. This role is ideal for a strong junior, mid‑level, or senior engineer who enjoys mentoring others, influencing technical direction, and wants the opportunity to grow into a broader leadership role over time.

In this position, you will contribute directly to building high‑quality, scalable applications and services while also supporting team collaboration, improving engineering practices, and helping guide technical decision‑making. You’ll work closely with cross‑functional partners to support project planning, execution, and delivery within a SOC2 security‑focused environment.

As you grow in the role, you will gradually take on more responsibility in areas such as roadmap planning, technical oversight, and supporting the development of other engineers.

Responsibilities

Partner closely with other organizations in the company on priorities and tradeoffs

Lead architecture and design decisions; stay hands‑on in critical or complex areas

Own delivery of product and platform commitments across teams

Manage and develop technical leads and managers who also maintain IC responsibilities

Set and enforce standards for code quality, testing, security, and reliability

Oversee CI/CD, releases, QA practices, and operational readiness

Act as the escalation point for technical and delivery issues

Drive incident response, postmortems, and continuous improvement

Stay abreast of industry trends and best practices – research, test, and execute new techniques which could improve software deployment strategies

Establish and enforce engineering standards for code quality, monitoring and alerting, testing, security, and reliability

Skills & Qualifications

Experience leading engineers in a hands‑on leadership role

Strong software engineering background with ability to guide architecture and design decisions

Ability to balance hands‑on technical work with people leadership and delivery ownership

Experience overseeing DevOps, CI/CD pipelines, and release management

Working knowledge of QA practices, test automation, and quality standards

Strong understanding of system reliability, scalability, and operational best practices

Experience owning production systems and leading incident response and postmortems

Ability to translate business and product goals into executable engineering plans

Strong communication skills and ability to work cross‑functionally

Experience hiring, coaching, and developing high‑performing engineers

Must be capable of developing a good rapport with other people in AFG, inspiring trust and confidence from managers, peers, and subordinates

Must be a self‑motivated, results‑oriented individual capable of multi‑tasking, meeting deadlines, managing uncertainty, and working in a highly collaborative environment

Experience with containerization and orchestration using products like AWS ECS

Experience working with observability stacks, such as Grafana or ELK

1+ years of DevOps‑specific roles focusing on cloud infrastructure, CI/CD, and automation

7+ years of experience in software engineering

Hands‑on experience with AWS, Azure, or GCP

Salary Range: $165,000 – $185,000

The following questions are entirely optional. To comply with government Equal Employment Opportunity and/or affirmative action regulations, we are requesting (but NOT requiring) that you enter this personal data. This information will not be used in connection with any employment decisions, and will be used solely as permitted by state and federal law. Your voluntary cooperation would be appreciated. Learn more.

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