Associate Program Manager, Founders' Office

🚀 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

Working closely with our founding CXO team, you’ll be part of the Founders’ Office to drive high-impact initiatives across growth, marketing, and operations. This role is designed for someone early in their career who thrives in ambiguity, takes ownership instinctively, and enjoys building from scratch.

You’ll own projects end-to-end, from defining loosely scoped problems to coordinating cross-functional execution, and gradually grow with increasing exposure to strategy and decision-making. A key part of the role is using AI and automation to move faster, smarter, and more efficiently.

🌟 What makes the role stand out?

• A front row seat to working with leadership. Act as a force multiplier for the CXO team, helping cover critical problem statements that don’t yet have clear owners.

• 0→1 ownership, 1→∞ impact. You’ll work on initiatives that are still being shaped by defining scope, process, and success metrics before scaling what works.

• Cross-functional by design. Partner closely with teams across marketing, supply, and operations to drive outcomes, not just plans.

• AI-first execution. Use AI to build workflows, tools, automations, dashboards, or experiments that exponentially improve how work gets done.

• A fast track to strategy. Over time, you’ll move beyond execution to spotting patterns, surfacing insights, and contributing to how growth problems are solved at scale.

🎯 What skills you need to have

• Experience & agency. 1–3 years of experience with demonstrated high agency — you take initiative, figure things out, and don’t wait for perfect clarity.

• Program/project management exposure. Comfortable coordinating across multiple stakeholders, tracking progress, and driving follow-through.

• Strong communication. Clear, structured written and verbal communication; able to juggle multiple problem statements simultaneously.

• Technical curiosity with proof. Hands-on experience experimenting with AI (personal automation projects, tools built independently, workflows on platforms like Replit, or similar).

• Comfort with data & structure. Solid with spreadsheets, basic analysis, and structured problem-solving in ambiguous environments.

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.