Head of People at Charterup

About CharterUP. CharterUP is transforming the $450+ billion group transportation and mobility market with an AI native platform that powers modern charter, shuttle, and emerging autonomous vehicle operations. Trusted by many Fortune 500 companies, CharterUP connects enterprises, institutions, and event organizers to thousands of bus operators nationwide, while increasingly serving as the operating system for large scale shuttle and transit programs across airports, campuses, industrial sites, and major events. Through real time availability, transparent pricing, intelligent routing, and AI driven dispatch and optimization, CharterUP replaces a fragmented and opaque industry with automation, accountability, and scale. Why Join Us • Innovative Impact: Be part of the team that's revolutionizing group travel, setting new standards in an industry overdue for change. • Growth Opportunities: As a hyper growth company and one of the fastest-growing companies recognized by Inc., there’s no better time to join our dynamic, growth-stage organization. • Driven Team: Collaborate with some of the most driven minds in tech, all while working in a remote-first environment with a tech hub in Austin, TX. • Funding and Stability: Our $60 million Series A funding was just the start—we’re poised for even greater expansion, and you can be part of this exciting journey. CharterUp has achieved this growth profitability and efficiently, ensuring long-term stability. Title: Head of People Location: Austin, Texas As we scale, we need a People leader who can help the company move from reactive HR support to a disciplined, high-accountability People function that protects the business, enables leaders, and builds the infrastructure required for growth. This person will create the structure, processes, and standards that help the company run well as it scales. They will work at both the strategic and day-to-day levels, setting direction, solving problems directly, and building an operation that is consistent, reliable, and built to last. This is not a traditional culture-programs-first HR role, and it is not a handoff role. We are looking for a senior Head of People who is equally comfortable operating as a strategic executive, a compliance-minded risk leader, and an HR operations builder. This person will bring order, rigor, and sound judgment to complex employee matters while building the systems, processes, and management practices that reduce risk and improve performance over time. The Head of People will build and strengthen CharterUP’s approach to employee relations, HR operations, performance management, leadership enablement, and people analytics, while partnering closely with the executive team to align people strategy with company growth. This person should know how to work backward from business goals, operating needs, and customer expectations to build people practices that support how the company runs. What You’ll Do • Build the People function CharterUP needs for its next stage of growth. • Create the structure, processes, and standards that help the company run well as it scales. • Build and improve the systems and programs that support employee relations, HR operations, performance management, leadership enablement, and people analytics. • Help ensure compensation and benefits programs are practical, competitive, and able to scale with the business. • Build practical, repeatable processes that help leaders set expectations, give feedback, address issues early, and lead their teams more effectively. • Partner with the executive team on organizational design, workforce planning, and key people decisions as the company grows. • Lead complex employee matters with sound judgment and strong follow-through. • Build in close partnership with Legal to ensure people practices are compliant, practical, and well managed. • Partner with Finance on headcount planning, compensation, people-related reporting, and other key workforce decisions. • Improve visibility and analytical rigor into headcount, attrition, hiring, performance, and other key people trends. • Build a People operation that is clear, reliable, and able to support a growing business with consistency and accountability. • Lead and strengthen the People team over time, raising the bar on execution, judgment, and service to the business. What You’ll Bring • 10+ years of HR leadership experience. • Strong depth in employee relations, compliance, HR operations, and performance management. • Experienced with HRIS systems and related technology • Experience building or improving a People function in a growing company. • A builder’s mindset and the ability to operate at both a strategic and hands-on level. • Strong judgment in employee relations, compliance, and people risk. • Experience handling sensitive and high-stakes employee matters. • Strong manager coaching skills, especially around feedback, accountability, documentation, and performance issues. • The ability to work backward from company goals, operating needs, and customer expectations rather than relying on generic HR playbooks. • Experience building people processes in close partnership with Legal. • Comfort with people systems, reporting, and using data to support better business decisions. • Experience partnering with executive leaders on organizational needs, workforce planning, and change. • Multi-state experience required; international experience is a plus. Recruiting Process • Step 1 - Video call: Talent Acquisition interview • Step 2 - Video call: Team Interviews • Step 3 - Video call: Executive Interviews • Step 4 - Offer & Background Check • Welcome aboard! Global Benefits & Perks at CharterUP We believe great people can live anywhere—and they deserve great benefits, too. While offerings may vary slightly by location, we prioritize hiring near our hubs in Austin, Atlanta, Miami, and Denver as we grow our global team. • Remote-First Flexibility: Work from anywhere we hire, with built-in flexibility. U.S.-based employees may reside in any of our 19 approved states. • Comprehensive Health & Wellness: Medical, dental, and vision insurance, mental health support, virtual care, gym discounts, and family-building benefits. In the U.S., we cover 100% of premiums for employees. International benefits align with local standards. • Time Off to Recharge: Paid time off so you can truly unplug. U.S.: 15 PTO days (increasing to 20 after 2 years) + 8 paid holidays. International policies vary by country. • Financial Peace of Mind: Company-paid life, short-term, and long-term disability insurance where available. • Performance-Driven Culture: Join a fast-moving, ambitious, and collaborative team that wins together. • Referral Rewards: Earn bonuses for bringing top talent to the team. • Planning for the Future: Long-term financial planning support. U.S.: 401(k) plan. International: region-specific savings programs where applicable. • Top-Tier Tech: Choose a Mac or PC, plus monitor, keyboard, and mouse to hit the ground running. CharterUP is an Equal Opportunity Employer. We are committed to creating an inclusive, accessible, and respectful workplace. We consider all qualified applicants without regard to race, color, religion, sex, sexual orientation, gender identity or expression, age, national origin, ancestry, disability, medical condition, marital status, veteran status, or any other protected characteristic in accordance with applicable federal, state, and local laws in the United States and Canada. If you require accommodation during the recruitment process, please let us know. CharterUP is committed to providing reasonable accommodations during the hiring process. If you need assistance or an accommodation, please contact your recruiter. Hiring Locations: CharterUP U.S.-based candidates and employees must reside in one of the following states: Arizona, California, Colorado, Florida, Georgia, Hawaii, Mississippi, Missouri, North Carolina, New Hampshire, Nevada, New York, Oklahoma, South Dakota, Tennessee, Texas, Utah, Washington, and Wyoming. We hire in the U.S. and Canada and are actively expanding our global footprint.