🚀 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 Senior Manager – Inventory Operations, you will lead and scale one of Headout’s most critical operational functions, ensuring seamless connectivity between Headout experiences and our global supply partners. You will oversee Program Managers, Team Leads, and a 15 member operations team responsible for maintaining reliable integrations, automation workflows, and partner connectivity across the marketplace.

This role sits at the intersection of operations, product, analytics, and automation. Your mandate is to strengthen the reliability of our supply infrastructure, significantly improve automation success rates across APIs and cron jobs, and build a high performing team capable of supporting Headout’s rapidly scaling marketplace. Working closely with Engineering, Product, Market Managers, and Supply teams, you will ensure our systems, processes, and team structures are built for scale.

🤩 What makes this role special?

• Own the operational backbone of Headout’s supply infrastructure.
  You will be responsible for the connectivity layer that powers our marketplace, ensuring experiences remain reliably connected between Headout and supply partners. Your work will directly influence customer experience, partner satisfaction, and Headout’s ability to scale supply globally.


• Build and lead a high performing operations team.
  You will lead Program Managers, Team Leads, and Associates, building a culture of ownership, accountability, and continuous improvement. By setting clear KPIs, establishing structured performance frameworks, and mentoring talent, you will shape a team that consistently delivers high throughput and operational excellence.


• Drive automation, reliability, and operational efficiency.
  You will partner closely with Engineering, Product, and Data teams to improve integrations, close automation gaps, and prioritize tooling improvements that materially reduce operational effort. You will lead investigations into integration failures, outages, and automation breakdowns, driving strong root cause analysis and preventive system improvements that improve API and cron success rates while minimizing manual interventions.


• Bring structure, visibility, and operational discipline.
  You will define and track core operational metrics across automation reliability, SLA performance, throughput, and effort reduction. By building clear reporting frameworks, capacity models, and forecasting systems, you will provide leadership with visibility into the health of Inventory Operations while continuously improving operational efficiency.


• Design the systems that power Headout’s next phase of growth.
  As Headout scales globally, you will prepare the Inventory Operations function for 10x scale by redesigning processes, strengthening automation, evolving team structures, and evaluating vendor strategies where required. Over time, success in this role will mean stronger automation reliability, faster issue resolution, clear operational metrics, and a highly efficient Inventory Ops team operating as a low noise, high performance engine for the business.

💝 What skills & experience do you need?

• You have 4 to 6 years of experience in Operations, Business Operations, Program Management, or similar roles, with a strong track record of improving processes, reducing operational effort, and scaling operational functions in fast growing environments.


• You have experience managing multi layer teams, including Team Leads and Associates, and are comfortable building structured performance frameworks, mentoring talent, and driving accountability across teams.


• You are highly analytical and data driven, with strong proficiency in SQL and Excel or Google Sheets, and the ability to use data to uncover operational insights, measure performance, and guide decision making.


• You have experience working with automation workflows, dashboards, and operational tooling, and are comfortable partnering with Product and Engineering teams to define requirements, prioritize improvements, and drive execution.


• You are an excellent communicator and structured problem solver, capable of navigating ambiguous challenges, translating complex operational problems into scalable solutions, and collaborating effectively across Operations, Product, Engineering, and Supply teams.

➕ Bonus Points

• You have experience leading connectivity, integrations, or technical operations teams.


• You have worked in marketplaces, travel tech, SaaS operations, or high growth startup environments.


• You are familiar with automation frameworks, cron jobs, and reliability systems, and have helped build operational processes designed for scale.

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.