Why Headout

Were 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 were just getting started. Weve raised $60M from top-tier investors and are building a durable company for the long term because thats what our mission needs and deserves. Were 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. Weve hit profitability built momentum and proven the model but theres so much more to build. If youre 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 isnt easy but thats the fun part.
We care deeply about ownership craft and impact and were here to do the best work of our careers. We wont pretend like its for everyone but if youre a builder who loves solving tough problems youll feel right at home. Read more about our unique values here: The role

As a Senior Manager Inventory Operations you will lead and scale one of Headouts 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 Headouts 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 Headouts 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 Headouts 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 Headouts 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 dont 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. Headoutprovidesequal employmentopportunities (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 .

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 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.