🚀 Why Headout?
We’re a rocketship: 9-figure revenue, record growth, and profitable
With $200M+ in revenue, guests in 700+ 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.
👨💻 The Role
As a Staff Engineer at Headout, you will drive architectural excellence and technical strategy across multiple product engineering pods. You'll solve some of our most complex, high-impact engineering challenges: designing very low-latency systems that power dynamic pricing strategies, processing large-scale inventory data across tens of thousands of products, and managing vendor ecosystem coordination spanning almost half a million vendors growing everyday. Beyond building systems, you'll be a force multiplier for technical excellence, partnering with Engineering Managers to eliminate technical debt, improve deployment stability, and build resilient system boundaries that allow our teams and business to scale sustainably. Your work will shape how we architect systems for the next phase of growth.
🤩 What Makes This Role Special?
- Large-Scale System Design: Design very low-latency systems solving critical business challenges: dynamic pricing strategies, large-scale inventory data processing across tens of thousands of products, and vendor ecosystem management spanning almost half a million vendors. See your architecture impact millions of travelers in real-time.
- Strategic Technical Debt Reduction: Lead systematic reduction of technical debt across pods, reshaping system architecture to improve deployment stability, reduce operational complexity, and enable teams to scale with confidence. This is career-defining work that prevents future chaos.
- Architectural Ownership Across Boundaries: Own architectural decisions that span multiple pods and teams. Guide the design of resilient, high-availability systems without needing direct authority—influence through technical excellence and clear thinking.
- Technical Excellence Meets Business Impact: Partner closely with Engineering Managers to balance technical excellence with delivery velocity. Influence critical decisions on architecture trade-offs, ensuring we build for both today's needs and tomorrow's scale.
- Design Leadership & Mentorship: Elevate engineering standards across your pod ecosystem through design reviews, code reviews, and mentorship. Shape how systems are built and help other engineers grow as technical thinkers.
- Profitable, Sustainable Growth: Work on systems directly powering millions of travelers worldwide in a profitable, bootstrapped company. Your architectural decisions have immediate business impact—no endless VC burn, real product-market fit.
- Modern Distributed Systems Stack: Build with cutting-edge technologies solving real distributed systems challenges: Kafka for event-driven architectures, Kotlin and Spring Boot for backend excellence, PostgreSQL and MongoDB for complex data models, and AWS for cloud-native infrastructure.
💝 What Skills & Experience Do You Need?
- 7+ years of software development experience with at least 5+ years in backend systems and distributed architectures. Prior experience mentoring engineers and driving technical initiatives across organizational boundaries without direct authority.
- Deep expertise in backend technologies: Spring Boot, Kotlin, and Java. Strong foundation in distributed systems concepts (eventual consistency, scalability, fault tolerance, high availability, CAP theorem trade-offs) with proven ability to design systems at scale.
- Hands-on experience with modern distributed tech stack: Kafka or similar event-driven architectures, relational databases (PostgreSQL, MariaDB), NoSQL systems (MongoDB), Redis for caching, and AWS cloud infrastructure. Able to make informed architectural trade-offs across the full stack.
- Exceptional problem-solving skills with focus on performance, reliability, and scalability. Strong commitment to code quality, testing practices, and engineering standards. Drive adoption of best practices and raise the bar for how systems are built.
- Ability to communicate complex technical concepts clearly to both engineers and non-technical stakeholders. Can articulate trade-offs, justify decisions, and make technical strategy accessible.
- Collaborative mindset with high agency and ownership mentality. Comfortable working across team boundaries, influencing without direct authority, and taking initiative on technical challenges.
- Growth mindset, grit, and resilience in fast-paced environments. Excited about continuous learning and staying current with emerging technologies. Able to navigate ambiguity, handle complex stakeholder situations, and maintain focus on long-term technical vision.
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.
