VP/Director of TechOps (DevOps + SecOps) at Shopmonkey in California

Summary: Shopmonkey is the leading auto-repair shop software company, and they are seeking a VP/Director of Technical Operations to ensure the reliability, scalability, security, and operational excellence of their platform. This senior leadership role involves managing teams and practices to maintain high performance and trust in their product while collaborating closely with other departments. Responsibilities: - Define and enforce SLOs, SLAs, and error budgets across Shopmonkey's production systems - Lead incident management end-to-end: on-call frameworks, blameless postmortems, and systemic remediation - Drive observability maturity — OpenTelemetry, Prometheus, and the dashboards and alerts that give every team a clear signal - Ensure 99.9%+ availability for a platform processing critical business operations for thousands of shops - Own Shopmonkey's GCP-based cloud infrastructure: provisioning, scaling, cost optimization, and architectural evolution - Lead the internal platform team that builds developer tooling, CI/CD pipelines, and deployment infrastructure that accelerates every engineering squad - Champion infrastructure-as-code practices, making our environments reproducible, auditable, and fast to provision - Partner with senior engineers on scalability decisions as we grow our customer base and data volumes - Own the engineering infrastructure and software budget as well as vendor relationships - Own the technical security posture of the platform: vulnerability management, secrets management, network security, and hardening - Lead compliance programs and certifications relevant to Shopmonkey's enterprise customers and growth trajectory (SOC 2 Type II, and beyond) - Build a culture of security that is embedded into the development lifecycle — not bolted on at the end - Treat compliance not as a checkbox but as a multi-pillar investment that compounds trust with customers over time - Evangelize and operationalize DevOps principles across engineering: CI/CD, feature flags, progressive deployment, automated testing infrastructure - Drive down time-to-deploy, mean time to recovery (MTTR), and toil across the org - Partner with engineering leadership to ensure platform investments directly accelerate squad velocity - Build, retain, and grow a high-performing team spanning DevOps, SRE, Platform Engineering, and Infrastructure - Define org structure, hiring plans, and career ladders for TechOps disciplines - Develop managers and senior ICs; establish a culture of ownership, psychological safety, and continuous learning - Lead with a servant-leadership mindset — remove blockers, amplify great work, and hold the bar high Required Qualifications: - 10+ years in infrastructure, platform engineering, SRE, or DevOps — with at least 4–5 years in a senior leadership role (Director or VP level) - Proven experience owning production reliability at a SaaS company with significant scale and uptime requirements - Demonstrated track record in building and evolving DevOps/platform engineering organizations from the ground up or through significant transformation - Experience leading cloud-native infrastructure on GCP, AWS, or Azure — with deep familiarity with Kubernetes, container orchestration, and managed cloud services - Prior ownership of security and compliance programs (SOC 2, ISO 27001, or similar); able to fluently translate security requirements into engineering work - Experience in companies ranging from growth-stage to mid-scale SaaS ($50M–$500M ARR range), where you've had to build structure while maintaining velocity - Strong working knowledge of modern observability stacks (OpenTelemetry, Prometheus, Grafana, Datadog, or equivalent) - Fluency in infrastructure-as-code tooling (Terraform, Pulumi, or equivalent) - Solid understanding of CI/CD architectures, deployment strategies (canary, blue/green, progressive rollout), and release engineering - Comfortable reviewing architectural decisions at the system design level and contributing to technical roadmaps alongside principal engineers - Familiarity with data infrastructure considerations (managed databases at scale, streaming platforms like NATS/Kafka, ClickHouse-style OLAP) - Exceptional communicator who can contextualize technical risk and infrastructure investment in business terms for a C-suite audience - Track record of building inclusive, remote-first teams with strong async communication habits and high accountability - Able to operate in ambiguity — defining the problem, structuring the org, and making progress before the perfect playbook exists - Sound business judgment: able to sequence investments, make trade-offs between speed and stability, and push back when priorities don't make sense Required Skills: Platform Reliability, Infrastructure Engineering, Security Compliance, DevOps Principles, Cloud Infrastructure Important Skills: GCP, Kubernetes, CI/CD, Observability Tools Nice-to-Have Skills: Team Building Benefits: Medical, dental, vision, and life insurance benefits available the 1st of the month following hire date, Short term and long term disability, Employee assistance program, Reimbursement for a personal health and wellness membership, Generous parental leave, 401(k) available upon hire, 11 paid holidays, Flexible time off - take the time off you need!, Matching donations for approved charitable organizations, Group volunteer efforts