Shopmonkey - Senior Director, Platform Engineering & Reliability
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Requirements
• 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. • 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 • 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.
Benefits
• 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: • benefits below are mainly for U.S. based, full-time employees). • 💪🏼 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 • ✈️ Time Off • 11 paid holidays • Flexible time off - take the time off you need! • 🥰 Giving Back • 🥰 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. • 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. • 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 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.
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