Lead, Machine Learning Engineer

🚀 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 a Machine Learning Engineer at Headout, you will play a pivotal role in developing AI-powered solutions that enhance our platform and create exceptional experiences for travelers worldwide. At Headout, we firmly believe that intelligent algorithms can transform how people discover and engage with travel experiences. Collaborating closely with multifaceted teams across the organization, you'll design, develop, and deploy sophisticated ML models across various applications including recommendations, search optimization, pricing, and operational efficiency.

🌟 What makes the role stand out?

• Global Impact: Your algorithms will serve millions of travelers across 190+ countries, optimizing experiences throughout the customer journey - from discovery and decision-making to post-purchase engagement.

• Diverse AI Applications: Work on a variety of machine learning projects spanning different domains. One day you might be improving our recommendation engine, the next you could be optimizing search rankings or developing forecasting models for operational planning.

• End-to-End Ownership: Take ML solutions from ideation to production. You'll help identify opportunities where ML can add value, design solutions, implement models, and measure real-world impact.

• Data-Rich Environment: Leverage rich, multi-dimensional data from user behavior, transaction patterns, content characteristics, and operational metrics to build comprehensive models that drive meaningful outcomes.

• Tangible Results: See the concrete impact of your work through key business metrics. Your models will contribute to increased conversion rates, enhanced user engagement, optimized operations, and improved customer satisfaction.

• Technical Innovation: As machine learning and AI technologies evolve, you'll be at the forefront of evaluating and implementing new approaches that keep Headout competitive in a dynamic industry.

🎯 What skills you need to have

• You have a minimum of 4 years of experience in machine learning engineering across different applications such as recommendations, classification, prediction, or natural language processing

• A strong foundation in ML fundamentals and techniques is essential. Proficiency in Python is a must, with experience in frameworks like TensorFlow, PyTorch, scikit-learn, or similar ML libraries (Hugging Face, XGBoost etc)

• You have practical experience taking ML models from development to production, including data preprocessing, feature engineering, model training, evaluation, and deployment

• Experience with A/B testing and experimentation frameworks to measure and validate the impact of ML solutions

• You possess strong problem-solving skills and the ability to translate business requirements into effective technical implementations

• Your communication skills enable you to work effectively with cross-functional teams and explain complex technical concepts to non-technical stakeholders

• Familiarity with large-scale data processing technologies (Spark, Kafka, Flink etc.) and cloud-based ML services (Vertex AI, Sagemaker etc) is a plus

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 [email protected].

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.