VP/Director of TechOps (DevOps + SecOps)

Shopmonkey•Washington, DC

3d•$200,000 - $260,000•Hybrid

About The Position

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.

Requirements

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.

Responsibilities

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.

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