Job Type

Full-time

Description

Position Overview

We are looking for an experienced and forward-thinking Director of IT Infrastructure & Security to lead the design, reliability, security, and cost efficiency of the company's infrastructure platform across cloud, network, and core systems. This role ensures high availability, scalability, reliability, and operational excellence while enabling rapid product development and secure data operations leveraging AI as a platform.

This leader owns the managed environments, cloud-native environments, databases, and DevOps, as well as the company's security posture and penetration testing program - and will evaluate where AI-assisted tooling can meaningfully improve delivery and operations.

You will report to the CTO. This role blends deep technical leadership with organizational influence and hands-on execution. You will be accountable for driving the strategy to build a safe, secure, and scalable infrastructure platform from concept to production, partnering closely with Engineering, and ensuring our solutions meet enterprise-grade standards of reliability, performance, and security.

If you're a self-driven individual with a strong understanding of infrastructure, IaC, DR/BCP, security operations, penetration testing and vulnerability management, SOC 2 compliance, and CI/CD automation and you want to make an impact on technology that reaches dealerships and consumers globally, we want to hear from you.

Key Responsibilities

Infrastructure & Cloud Strategy

• Own cloud strategy and architecture across our platforms, prioritizing high availability, disaster recovery, and business continuity
• Standardize infrastructure patterns across environments and modernize away from legacy dependencies
• Own day-to-day cloud and platform operations, including compute, storage, networking, and uptime monitoring
• Implement and enforce Infrastructure as Code to make builds repeatable, auditable, and less manual
• Security & Compliance
• Own the company's security posture: proactive monitoring, an Incident Response Plan (including a ransomware runbook), and escalation to an MDR/MSSP partner where deeper coverage is needed
• Own the penetration testing program end to end - vendor engagements, findings triage, and remediation SLAs
• Drive SOC 2 Type II readiness and infrastructure-level security controls (network segmentation, IAM, encryption, secrets management)
• Report security posture and open risk to leadership on a defined cadence

DevOps, AI & Cost Efficiency

• Partner with Engineering to improve CI/CD pipelines, reduce deployment friction, and embed security scanning without slowing delivery
• Evaluate and integrate AI-assisted tooling into the delivery lifecycle - code generation, test generation, anomaly detection, and security triage - where it measurably improves quality or signal
• Monitor and optimize cloud spend, implementing cost controls (rightsizing, reserved instances, autoscaling) and providing regular cost visibility to leadership

Team Leadership & Vendor Management

• Directly manage and develop the DBA, DevOps, and Desktop Support team members, driving accountability and continuous improvement
• Own end-user IT support (helpdesk, device lifecycle, endpoint security) delivered through the Desktop Support team member, and stand up security operations primarily through an MDR/MSSP partnership
• Evaluate and manage vendors across cloud, security, and monitoring using a Cost / Scale / Quality / Risk framework, ensuring SLAs are met

Requirements

• 12+ years in infrastructure, cloud, or DevOps engineering, including 3-5+ years in a leadership role
• Deep experience with cloud platforms (AWS, Heroku, Linode, or equivalent), Infrastructure as Code (Terraform, Ansible), and modern networking/security architecture
• Experience creating and owning an Incident Response Plan and running a penetration testing program, with working knowledge of frameworks like NIST CSF, CIS Controls, OWASP Top 10, and CVSS scoring
• Experience with observability/monitoring platforms (SigNoz or equivalent) and proactive alerting
• Experience managing production-scale, high-growth SaaS environments
• Strong understanding of DR/BCP and compliance frameworks (SOC 2, ISO)
• Exposure to data platforms (Databricks, analytics pipelines, AWS QuickSight) is a plus

Education & Certifications

• Bachelor's or Master's in Computer Science, Engineering, or related field - or equivalent experience
• Relevant certifications (preferred, not required): Certified Solutions Architect / DevOps Engineer (AWS, Heroku, Linode), ITIL (service management)