Head of Cloud Engineering

Job Type:

Permanent

Build a brilliant future with Hiscox
 

Head of Cloud Engineering

Hiscox US is searching for an individual to join the US Technology Leadership Team as Head of Cloud Engineering.

This role reports to the US CTO and is responsible for leading the strategy, architecture, and execution of our technology platform. This role is pivotal in ensuring that our infrastructure and developer experience support our business’s growth, resilience, and security. You will drive initiatives around Infrastructure as Code (IaC), resiliency, zero-downtime deployments, immutable infrastructure, automation, security, and observability to create a world-class platform for commercial insurance.

This is an opportunity for an experienced leader who is passionate about scalability, automation, developer productivity, and security. You will work across engineering, security, and product teams to create a high-velocity, high-trust environment where engineers can ship code confidently and securely.

Key Responsibilities

Platform Strategy & Architecture:

• Define and drive the vision for a highly scalable, resilient, and secure technology platform.

• Architect and implement Infrastructure as Code (IaC) best practices to ensure repeatability, security, and consistency.

• Design for resiliency through fault tolerance, automated failover, and disaster recovery strategies.

• Ensure support for zero-downtime deployments, reducing risk while allowing for continuous feature delivery.

Automation & Developer Experience:

• Lead efforts to automate everything—from infrastructure provisioning to application deployment, eliminating manual processes.

• Build and optimize Continuous Integration / Continuous Deployment (CI/CD) pipelines to support fast, reliable software delivery.

• Advocate for immutable infrastructure, ensuring environments are predictable, reproducible, and free of configuration drift.

• Collaborate with engineering teams to improve the developer experience, reducing friction in testing, deployment, and operations.

Security & Compliance:

• Enforce Defense in Depth principles with layered security controls.

• Ensure all infrastructure follows least privilege access, secure network design, and zero-trust architecture.

• Oversee security automation for infrastructure provisioning, auditing, monitoring, and compliance.

• Implement and maintain end-to-end encryption for data in transit and at rest. Monitor and respond to security incidents, driving root-cause analysis and long-term improvements.

Observability & Reliability:

• Define and implement logging, monitoring, and telemetry strategies to gain deep insight into system performance and failures.

• Ensure all critical infrastructure components are observable, self-healing, and proactively managed.

• Establish an incident response and game-day testing culture to regularly validate resilience strategies.

• Drive data-driven decision-making using logs, traces, and system metrics.

Leadership & Collaboration:

• Build and mentor a high-performing Platform Engineering team using a combination of full-time employees and contractors, both on-and-near shore.

• Foster a culture of continuous improvement, learning, and knowledge sharing. Collaborate closely with software engineers, security, and SREs to ensure platform initiatives align with business and product goals.

• Promote a shared responsibility model where platform and security practices are embedded in all teams.

Desired Qualifications:

• 10+ years of experience in cloud-native infrastructure, platform engineering, DevOps, or site reliability engineering.

• 5+ years in technical leadership roles with experience managing and mentoring teams.

• Proven experience with Infrastructure as Code (IaC) using Terraform, CloudFormation, or Pulumi.

• Expertise in cloud platforms (AWS, Azure, GCP) and designing highly available, fault-tolerant architectures.

• Deep understanding of CI/CD automation, containerization, and service meshes.

• Strong background in security best practices, zero-trust principles, and compliance frameworks.

• Hands-on experience with observability tools (e.g., Datadog, Dynatrace, Prometheus).

• Track record of driving developer experience improvements and advocating for engineering enablement.

• Excellent communication and leadership skills, with the ability to drive cross-functional collaboration.

What We Offer:

• 401(k) with competitive company matching 

• Comprehensive health insurance, vision, dental and FSA plans (medical, limited purpose, and dependent care)  

• Company paid group term life, short- term disability and long-term disability coverage 

• 24 Paid time off days plus 2 Hiscox days,10 paid holidays plus 1 paid floating holiday, and ability to purchase up to 5 PTO days 

• Paid parental leave 

• 4-week paid sabbatical after every 5 years of service 

• Financial Adoption Assistance and Medical Travel Reimbursement Programs 

• Annual reimbursement up to $600 for health club membership or fees associated with any fitness program 

• Company paid subscription to Headspace to support employees’ mental health and wellbeing 

• 2023 Gold level recipient of Cigna’s Healthy Workforce Designation for having a best-in-class health and wellness program 

• Dynamic, creative, and values-driven culture 

• Modern and open office spaces, complimentary drinks 

• Spirit of volunteerism, social responsibility, and community involvement, including matching charitable donations for qualifying non-profits via our sister non-profit company, the Hiscox USA Foundation 

**Please note that this position is hybrid and requires two (2) days in our office weekly**

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