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

We're looking for a VP/Director of Technical Operations to own the reliability, scalability, security, and operational excellence of Shopmonkey's platform. This is a senior leadership role sitting at the intersection of engineering and infrastructure — responsible for the teams and practices that keep our product running at the highest levels of performance and trust. This is not a title for someone who manages from a distance. You will be deeply embedded in the technical and organizational fabric of the company. You'll bring strong opinions about how infrastructure should be built, how incidents should be managed, how security posture should evolve, and how DevOps culture creates faster, safer product delivery. You'll own multi-year roadmaps, manage and grow a team of strong individual contributors, and partner closely with Product, Engineering, and Security to translate business priorities into operational reality. Please note for San Francisco-based area candidates, this would be a hybrid role with 2-3 days/week in office for collaboration and connection. What You'll Own Platform Reliability & SRE • 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. Infrastructure & Platform Engineering • 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. Security & Compliance • 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. DevOps Culture & Developer Experience • 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. People & Organizational Leadership • 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. What You'll Bring Experience • 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. Technical Depth • 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). Leadership & Communication • 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. In the United States the range is typically $200,000 to $260,000 with bonus + equity + benefits. The range provided is Shopmonkey’s reasonable estimate of the base compensation for this role. The actual amount will be based on job-related and non-discriminatory factors such as location, experience, training, skills, and abilities. Consult with your Recruiter during the initial call to determine a more targeted range based on these job-related factors. In addition to this base compensation company stock options and benefits as outlined below are included. Why Shopmonkey? Shopmonkey has become an amazing environment where employees feel that they are valued as people, and not just worker bees. To ensure that our team thrives, we invest in the following perks (benefits below are mainly for U.S. based, full-time employees). Other benefits vary upon location outside of the United States, and employment status: 💪🏼 Health & Wellness • 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 ✈️ Time Off • 11 paid holidays • Flexible time off - take the time off you need! 🥰 Giving Back • Matching donations for approved charitable organizations • Group volunteer efforts Check out our founder’s story, life page, or hear from real employees about what it’s like to work at Shopmonkey. Join our team of hungry, humble, smart people who love what they do, and change the auto industry by helping every shop thrive. About the Industry The U.S. is the second largest passenger vehicle market with more than 260 million registered passenger vehicles, and the global car repair market is estimated to be worth more than $500B. Shopmonkey aims to change the status quo and enable auto shops to become more efficient and give their customers a more delightful experience. About Shopmonkey Shopmonkey is the leading auto-repair shop software company; it is a cloud-based solution that helps auto-repair shops consolidate tools, save time, and streamline their entire operation onto a simple, easy-to-use platform. Headquartered in Silicon Valley and trusted by more than 3,500+ auto shops across the U.S. and Canada, Shopmonkey aims to change the status quo of the car repair market, estimated to be worth more than $500B. In 2021 Shopmonkey raised a $75 million Series C, supported by top-tier Silicon Valley venture capital firms Bessemer Venture Partners, Index Ventures, Headline, I2BF, and ICONIQ Growth. In 2022, Shopmonkey was named #4 on Forbes' annual ranking of America's Best Startup Employers list (and #1 in Business Products & Software Services). Shopmonkey was once again named as one of America's Best Startup Employers by Forbes in 2023, 2024, and 2026! Shopmonkey is committed to building a diverse and inclusive team. We are looking for team members from all backgrounds that are committed to the Shopmonkey mission. Shopmonkey provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws. This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation and training. Shopmonkey is committed to the full inclusion of all qualified individuals. In keeping with our our commitment, Shopmonkey will take the steps to assure that people with disabilities are provided reasonable accommodations. Accordingly, if reasonable accommodation is required to fully participate in the job application or interview process, to perform the essential functions of the position, and/or to receive all other benefits and privileges of employment, please contact our Talent Team at [Upgrade to PRO to see contact]. Please note: Shopmonkey will never request sensitive information such as your social security number, bank account information, or other non-publicly available information during the application and interview process. If an applicant is extended an offer of employment, such sensitive information will be requested at that time. Shopmonkey will never ask you to receive and ship packages or goods as part of the interview. Other practices to be on alert for: • Contact initiated via unsolicited text message or cold call. Shopmonkey does not follow up with candidates through instant messaging applications. • Our Talent Acquisition team only corresponds from email addresses with the domain ‘@Shopmonkey.io’. If a generic email ID ending with Gmail/Yahoo or other domain is used while receiving a job offer or interview call, there is a likelihood of a scammer. • While some of our jobs can be found on third party job sites, all of our current job opportunities and descriptions are posted on Shopmonkey’s Careers page, or our official LinkedIn Company Page The U.S. Federal Trade Commission has published helpful articles to help individuals learn more about protecting themselves from recruiting scams and financial fraud. If you believe you were a victim of such a scam, you may contact your local law enforcement agencies. Shopmonkey is not responsible for any claims, liability, losses, damages, or expenses resulting from scammers or impersonators.