🚀 Why Headout?

We’re a rocketship: 9-figure revenue, record growth, and profitable

With $130M in revenue, guests in 100+ cities, and 18 months of profitability, Headout is the fastest-growing marketplace in the travel industry, and we’re just getting started. We've raised $60M+ from top-tier investors and are building a durable company for the long term — because that's what our mission needs and deserves. We’re growing, profitable and nowhere near done.

What we do is important

In an increasingly digital world, there is a desperate need to augment our human experience by getting us to interact with the real world around us and the people in it. At Headout, our mission is to be the easiest, fastest, and most delightful way to head out to a real-life experience — from immersive tours to museums to live events and everything in between.

Why now?

The foundation is strong. The opportunity ahead is even bigger. We’ve hit profitability, built momentum, and proven the model — but there’s so much more to build. If you’re looking to join a company where the trajectory is steep and your impact is real, this is the moment.

Our culture

Reinventing the travel industry isn't easy, but that's the fun part.
We care deeply about ownership, craft, and impact, and we’re here to do the best work of our careers. We won’t pretend like it’s for everyone but if you’re a builder who loves solving tough problems, you’ll feel right at home. Read more about our unique values here: https://bit.ly/HeadoutPlaybook

👩‍💻The Role

Our Senior Site Reliability Engineer would own end-to-end platform responsibilities, including managing and optimizing Kubernetes-based cloud infrastructure, building reusable CI/CD workflows (e.g., GitHub Actions), and enabling canary releases. They will design observability systems with dashboards, fine-tuned alerts, and incident management processes; enhance application performance through backend, API, and database optimizations; and architect scalable, cross-team platform tools. The role involves improving developer velocity via tooling and workflows, implementing security guardrails and standardization, and driving org-wide best practices through mentorship, collaboration, and RCA facilitation.

🤩What makes this role special?

• Full Platform exposure - work on problem statements encompassing Devops, Application Performance, Observability and many more. 
• Architecture Decisions - Directly influence how we evolve our stack with benchmarks and relevant metrics.
• High Impact - Build tools that reduces deployment TAT, boosts p99s etc - metrics the whole company celebrates.
• Flexible - Flexibility to work on different stacks, tools & platforms.

💝What skills & experience do you need?

• 3-5 years of experience in operating customer facing services at scale.
• Proficiency in operating, debugging & optimising Kubernetes Clusters & its workloads
• Experience in any service mesh & tracing tools like Istio, Jaeger etc.
• Comfortable working with any Cloud Provider - AWS,GCP, Azure etc. Preferably AWS.
• Hands on with monitoring & alerting stacks - Prometheus + Grafana + Thanos, NewRelic/Datadog.
• Designed robust CI/CD workflows in any platform - Github, GitLab, Jenkins etc.
• Proficiency in IaC with Terraform or Pulumi.
• Fluency in Python, Go or Java/Kotlin languages & shell scripting.
• Experience working with databases like mysql, mongodb etc.
• Ability to profile applications, DB queries and tracing.
• Understanding of Security best practices and compliance requirements.
• High Agency to proactively identify and fix issues.

➕Bonus

• Interested in travel, local experiences, and hospitality personally.
• Interested in being in a rapidly growing startup.
• Anything out-of-the-box that can surprise us.

EEO statement

At Headout, we don’t just accept differences — we celebrate it, we support it, and we thrive on it for the benefit of our employees, our partners, and the community at large. Headout provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age or disability. During the interview process, if you need assistance or an accommodation due to a disability, you may contact the recruiter assigned to your application or email us at life@headout.com.

Privacy policy

Please note that once you apply for this job profile your personal data will be retained for a period of one (1) year. Headout shall process this data for recruitment purposes only. Once the relevant job profile is filled or once the time period of one (1) year from the date of the job application has passed, whichever is later, Headout shall either delete your data or inform you that it shall keep it in its database for future roles. In compliance with the relevant privacy laws, you have the right to request access to your personal data, to request that your personal data be rectified or erased, and to request that the processing of your personal data be restricted. If you have any concerns or questions about the way Headout handle your data, you can contact our Data Protection Officer for more information.