🚀 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

As the 'Lead Software Engineer, Backend' at Headout, you'll be diving deep into the heart of our technical ecosystem. Your realm will encompass the design and construction of the core modules on both the application and infrastructure layers. With a team of young, dynamic, and driven professionals by your side, you'll tackle intricate architectural and design challenges. From clustering to replication, from databases to building systems, and infrastructure automation, you'll be hands-on. Your contributions won't just be internal; you'll have the chance to contribute to open-source libraries and components. Ultimately, you'll be the guardian of concurrent, efficient, and scalable services that form the backbone of the Headout ecosystem.

🤩 What Makes This Role Stand Out

• Ownership: Take the reins and mold a high-performing team. Your leadership will be key in recruiting, nurturing, and ensuring the success of a top-tier team that will be the backbone of our initiatives.
• Innovation: Don't just follow the norm. Here, you'll be encouraged to think outside the box, spearheading projects from concept to completion and infusing them with fresh, effective solutions that can redefine our approach.
• Explore the Tech Landscape: Embrace the opportunity to work in a rich technological environment. From varied services to distinct platforms and databases, you'll touch multiple facets of tech, ensuring a dynamic work experience. We believe in using the right tool for the job. Experience the versatility of multiple tech stacks, allowing you to pick and choose the best technologies that align with project needs.
• Growth and Influence: It's not just about scaling; it's about influence. Play a pivotal role in the company's ambitious 5x growth trajectory, directly impacting our direction and shaping architectural solutions that set the foundation for our future.

🎯 Essential skills & experience

• Strong CS fundamentals, good working knowledge of classic algorithms and data structures.
• 5+ years experience developing server-side technologies using any language or framework.
• Excellent communication, collaboration and people management skills.
• Experience working with Spring, Relational Databases, Concurrent Programming, NoSQL flavors, AWS.
• Experience designing scalable, fault-tolerant systems and databases.
• Experience with setting up systems and infrastructure.
• Solid understanding of how the web works and its underlying communication protocols.
• Knack for writing the most performance optimized code along with it being modular and scalable.

💫 Bonus

• An interest in travel, local experiences & hospitality.
• An experience in starting or scaling a successful 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.