Program Manager, Culture & Talent at Headoutcareers

🚀 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: [Upgrade to PRO to see link] 👩‍💻The role As Headout scales, many of the most important People initiatives cut across teams — hiring, performance, career development, culture, systems and leadership programs. We’re looking for a Program Manager in the People & Culture team who can take these initiatives from idea → structure → execution → adoption. In this role, you will run the operating rhythm of Culture & Talent initiatives while owning the analytics that steer them. You will work hands-on in Excel/Sheets with raw data to build dashboards, surface insights, and inform decisions. You will plan and execute policy rollouts and change initiatives across functions, scoping, sequencing, aligning stakeholders, tracking momentum, and reporting outcomes. You will also research internally and externally to prepare crisp, decision-ready proposals for leadership. 🤩What makes this role special? • True end-to-end ownership: Scope the work, do the analysis, run the rollout, and report impact — no silos. • Hands-on analytics: Work directly in Excel/Sheets with raw HR data; your dashboards will be used by leadership. • Define the operating playbook: Limited legacy systems mean you set the cadences, artifacts, and reporting that make programs ship. • High visibility and pace: Present proposals and see changes land across multiple functions in weeks. • Breadth of scope: Switch contexts between people analytics, program management, and change management. • Career runway: Designed for 3 to 5 year talent to grow into broader People Analytics or Program leadership. 💼 What You'll Do • Track and manage multiple C&T programs and initiatives at the same time, keeping stakeholders aligned and timelines on track. • Act as the link between C&T and other teams (Finance, Marketing, Business, etc.) during policy rollouts and change-related work. • Own projects end to end, from initial scoping and data gathering through to delivery and post-launch tracking. • Do deep-dive data analysis using Excel to support reviews, benchmarking, and proposals for leadership. • Lead internal and external research to surface market insights that support decision-making. • Build and maintain program trackers, reports, and documentation to keep everyone in the loop. • Spot gaps in existing processes and suggest improvements, especially in areas where structure is still being built. 💝What skills & experience do you need? • 4-6 years of experience in program management, consulting, business operations, or HR program management • Strong ability to structure ambiguous problems and drive execution • Excellent stakeholder management and communication skills • High ownership and ability to run initiatives independently • Comfortable working across strategy and operational execution • Strong organizational and project management skills • Analytical mindset — able to use data to evaluate programs • Experience with policy rollouts and change management across multiple functions. • Excellent written communication: concise docs, status updates, and leadership briefs. • Comfort operating with limited systems and lightweight processes. ✨ Nice to Haves • Experience at startups or growth-stage companies (e.g., consumer internet, fintech, e-commerce). • Exposure to building or improving C&T operating cadences such as OKRs, trackers, and weekly reviews. • Basic data visualization best practices for HR reporting. 🚀 What success looks like in this role • Key People initiatives are well-structured, well-run and delivered on time • Programs are adopted across teams, not just launched • Processes become clearer and more scalable as the company grows • Leaders and managers find it easier to navigate People programs • Programs drive visible needle movement on the success metrics defined for them (e.g., adoption, participation, cycle completion, manager effectiveness, hiring velocity, employee engagement) 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 [Upgrade to PRO to see contact]. 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.