Engineering Manager

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 an Engineering Manager at Headout, you will lead one of our product engineering pod, shaping both the technical and people aspects of the team. You will play a crucial role in designing scalable systems, ensuring alignment with business outcomes, fostering a high-performance engineering culture, and driving impactful product experiences. Your leadership will empower engineers to innovate, execute efficiently, and build a world-class product loved by travelers worldwide.

What makes this role special?

• Technical Leadership: Guide and mentor a team of talented engineers, making key decisions in design, architecture, and implementation to build scalable and efficient systems.
• Ownership of Outcomes: Take full responsibility for the success of critical projects, ensuring measurable business impact rather than just focusing on project delivery. Collaborate closely with product managers as co-owners of problem statements, driving alignment between engineering efforts and business goals to deliver meaningful results.
• Impact at Scale: Work on high-impact initiatives that shape the future of travel experiences, influencing millions of users across countries.
• Ownership and Autonomy: Drive end-to-end execution of critical projects, collaborating with cross-functional teams while maintaining autonomy in decision-making.
• Talent & Culture Building: Recruit, develop, and retain top engineering talent while fostering a culture of excellence, collaboration, and continuous learning.
• Innovation-Driven Environment: Work with cutting-edge technologies and a modern tech stack to solve complex challenges in travel tech.
• Global Exposure: Be part of a distributed team working across multiple locations, bringing a global perspective to your work.

What skills & experience do you need?

• 7+ years of experience in software development with at least 2 years of experience in leading engineering teams.
• Strong technical expertise in system design, architecture, and backend/frontend development. Hands-on experience with cloud technologies (AWS, GCP, or Azure) and containerization (Docker, Kubernetes).
• Proficiency in building scalable distributed systems, microservices, and high-performance applications.
• Ability to bridge technical expertise with business and product goals, ensuring that engineering efforts drive meaningful business impact.
• Exceptional problem-solving skills with a focus on performance, reliability, and scalability.
• Experience in stakeholder management, project execution, and collaborating with product teams to deliver impactful solutions.
• Strong communication skills with the ability to convey technical concepts clearly and concisely.
• Passion for mentoring and growing engineers, fostering an inclusive and high-performing engineering culture.