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.
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.
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.
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
We’re on the lookout for a Senior Software Engineer in Test to join our team at Headout. In this role, you’ll dive deep into Headout’s ecosystem, ensure every feature rolls out flawlessly, and help scale our quality practices across the engineering organization. You'll be hands-on with automation, system analysis, CI/CD, and production reliability—while also mentoring other engineers and shaping QA processes that raise the bar for quality and speed.
This is a high-impact role where your expertise will directly influence product stability, engineering velocity, and customer experience.
Own and scale automation frameworks, CI/CD pipelines, and testing infrastructure.
Collaborate with multiple teams to ensure high-quality, reliable releases at speed.
Lead system-level testing initiatives and strengthen Headout’s automation-first culture.
Mentor junior SETs and contribute to building strong, scalable QA practices.
Gain exposure to diverse technical domains while contributing to a global consumer product.
3–6 years of experience in automation for web, mobile, and backend systems.
Strong expertise with automation frameworks (Selenium, Playwright, Appium, RestAssured, etc.).
Proven ability in building and scaling CI/CD pipelines and automation infrastructure.
Familiarity with Docker, Kubernetes, and Unix-based systems.
Solid grounding in computer science fundamentals, OOP concepts, and test design.
Experience working with distributed systems, microservices, and API testing.
Ability to break down ambiguous problems, build structured solutions, and think systemically.
Strong Java skills with the ability to build reusable automation libraries.
Experience contributing to open-source tools, frameworks, or libraries.
Exposure to AI-assisted automation or tooling.
Experience designing system-level test strategies for high-scale platforms.
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 [email protected].
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.
Our workplace mission is simple: enable people to do their life's best work. We do this by ensuring you have challenging work you love alongside an environment that supports you in it. We think workplace happiness is a simply a by-product of this. Join an exceptionally talented team on their quest to connect the world’s best in-person experiences with people all across the globe.
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