Manager, Cloud & Container Operations at KAYAK – Concord Office | Jobyssey

KAYAK, part of Booking Holdings (NASDAQ: BKNG), is a leading travel search engine. With billions of queries across our platforms, we help people find their perfect flight, stay, rental car and vacation package. We're also transforming business travel with a new corporate travel solution, KAYAK for Business.

As an employee of KAYAK, you will be part of a travel company that operates a portfolio of global metasearch brands including momondo, Cheapflights and HotelsCombined, among others. From start-up to industry leader, innovation is in our DNA and every employee has an opportunity to make their mark. Our focus is on building the best travel search engine to make it easier for everyone to experience the world.

KAYAK is seeking a Manager, Kubernetes Operations to lead the team responsible for the reliability, scalability, and security of our container orchestration platform. In this role, you will combine deep technical expertise with a genuine passion for people leadership — guiding a team of platform engineers while shaping the strategy that keeps our containerized production environment running at global scale. You will be a key partner to engineering, security, and infrastructure teams, helping KAYAK move faster and more safely by building a platform your colleagues can depend on.

In this role you will:

Own the technical roadmap and operational strategy for the Kubernetes platform, ensuring cluster reliability, scalability, and security across production and non-production environments.
Lead a team of container platform engineers, taking full responsibility for hiring, performance management, and career development to build a high-performing, inclusive team.
Deliver a continuously improving container platform by driving cluster lifecycle management — including version upgrades, node provisioning, capacity planning, and workload migration from legacy orchestration platforms.
Coach engineers on Kubernetes best practices, container security, RBAC design, and operational excellence, fostering a culture of ownership and continuous learning.
Collaborate closely with software engineering, security, and infrastructure teams to ensure containerized workloads are reliable, observable, and deployable with confidence.
Drive the adoption of infrastructure-as-code and GitOps practices for cluster configuration and application deployment, reducing manual toil and improving consistency across environments.
Design and enforce standards for Kubernetes observability — including metrics collection, alerting, and dashboarding — so the team can detect and resolve incidents quickly and conduct effective post-incident reviews.
Hold the team to a high standard of operational excellence, including on-call practices, incident response, and blameless post-mortems.
Collaborate with adjacent operations and engineering leaders to align the Kubernetes platform roadmap with broader infrastructure and product engineering goals.
Advance the team's security posture by partnering with security teams on cluster hardening, network policy enforcement, and compliance requirements.

Please apply if you have:

8+ years of experience in SRE, DevOps, or platform/infrastructure engineering, with at least 3 years in an engineering leadership or management role.
A proven track record of operating large-scale, 24/7 production Kubernetes environments, including cluster lifecycle management (upgrades, node provisioning, capacity planning) and workload migration from legacy container orchestration platforms.
Deep, hands-on expertise with Kubernetes — including RBAC design, network policy, cluster hardening, and multi-environment operations spanning on-premises and cloud infrastructure.
A strong technical foundation in both on premise and cloud infrastructure (GCP and/or AWS) and infrastructure-as-code tools such as Terraform and Ansible.
Experience as a people manager with a demonstrated ability to hire, develop, and retain engineering talent, and a commitment to building inclusive, high-performing teams.
Solid experience with modern observability tooling — such as Prometheus, Grafana, or equivalent — including alerting, dashboarding, and incident-driven tuning.
Proficiency in at least one scripting or automation language (Python, Go, or Bash) to support infrastructure-as-code workflows and reduce operational toil.
Excellent communication skills, with the ability to articulate a clear technical vision and work effectively with cross-functional engineering, security, and product teams.
A degree in Computer Science or a related technical field, or equivalent practical experience.

Benefits and Perks

Work from (almost) anywhere for up to 20 days per year
Focus on mental health and well-being:
- Company-paid therapy sessions through SpringHealth
- Company-paid subscription to HeadSpace
- Company-wide week off a year - the whole team fully recharges (and returns without a pile-up of work!)
- No meeting Fridays
Paid parental leave
Generous paid vacation + time off for your birthday
Paid volunteer time
Focus on your career growth:
- Development Dollars
- Leadership development
- Access to thousands of on-demand e-learnings
- Travel Discounts
- Employee Resource Groups
Competitive retirement and health plans
Free lunch 2 days per week
Fun quarterly events such as boat trips, arcades, ski trips, Thursday happy hours, and more

EQUITY ELIGIBLE

There are a variety of factors that go into determining a salary range, including but not limited to external market benchmark data, geographic location, and years of experience sought/required. The range for this Massachusetts based role is $175,000-$200,000, not inclusive of annual bonus and recurring RSU grants.

We offer a competitive base salary and benefits including: health benefits; flexible spending account; retirement benefits; life insurance; paid time off (including PTO, paid sick leave, medical leave, bereavement leave, floating holidays and paid holidays); and parental leave benefits.

INCLUSION

At KAYAK, we want everyone to have the space to grow, share ideas and do great work. That's why we're focused on hiring the best talent from all walks of life and experiences, supporting them well and making sure no one feels like they have to fit a mold to belong here.

Need any adjustments for the interview, application or on the job? No problem - just give us a heads-up. We've got you.

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