Head of Talent Acquisition

Head of Talent Acquisition

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.

CharterUP is entering its next major phase of growth and is seeking a Head of Talent Acquisition to build and lead a high-performing recruiting organization capable of scaling alongside the business. This leader will operate as both a strategic advisor and an execution-oriented builder, partnering directly with executive leadership to drive hiring strategy, organizational growth, recruiting operations, and recruiting team leadership.

The scope extends far beyond traditional recruiting leadership. This role owns the development of the TA function itself: building the team, establishing operating rigor, improving recruiter performance, strengthening hiring manager partnership, and creating scalable systems capable of supporting aggressive company growth. The right person is highly operational, performance-oriented, and comfortable operating in fast-paced, high-accountability environments. They know how to build recruiting infrastructure while simultaneously leading critical searches, influencing executives, solving organizational challenges, and driving measurable hiring outcomes.

This role reports directly to executive leadership and partners closely with leaders across Revenue, Product, Engineering, Operations, Finance, Marketing, and People.

What You'll Do

Talent Acquisition Strategy & Execution

• Own and drive company-wide hiring strategy across all business functions including GTM, Product, Engineering, Operations, G&A, Marketing, and executive hiring
• Partner with executive leadership on workforce planning, org design, headcount prioritization, and hiring roadmaps
• Lead full-cycle recruiting for critical and executive-level roles when needed
• Build scalable recruiting processes that improve speed, quality, and candidate experience
• Develop and maintain high hiring bars across the organization
• Drive operational excellence across pipeline management, interview process design, interviewer enablement, and offer strategy

Executive Partnership & Talent Advisory

• Act as a strategic advisor to executive leadership on talent market dynamics, compensation calibration, organizational structure, and hiring decisions
• Influence and guide hiring managers through role scoping, competency development, interview strategy, and candidate evaluation
• Help leaders identify talent gaps and proactively build hiring strategies aligned to company growth goals
• Operate as a trusted thought partner during periods of organizational change and rapid scaling

Recruiting Operations & Infrastructure

• Own recruiting systems, workflows, reporting, and operational scalability
• Manage ATS strategy and optimization (Greenhouse experience strongly preferred)
• Develop recruiting KPIs, funnel analytics, conversion metrics, and hiring reporting for leadership
• Evaluate and implement recruiting tools, AI solutions, vendor partnerships, and process automation opportunities
• Build repeatable recruiting infrastructure that can scale with company growth

Team Leadership

• Build, scale, and lead a high-performing Talent Acquisition organization capable of supporting CharterUP's next stage of growth
• Coach recruiters on sourcing strategy, stakeholder management, candidate calibration, and closing
• Help establish clear recruiting priorities during periods of rapid organizational change
• Foster a culture of accountability, urgency, ownership, and partnership within the TA function
• Build scalable recruiting infrastructure, workflows, and operational processes that can support continued rapid growth

What You'll Bring

• 10+ years of recruiting and talent acquisition experience, including leadership experience in start-up and high-growth environments
• Experience leading recruiting across multiple functions including GTM, technical, operations, and executive hiring
• Proven ability to operate both strategically and hands-on in lean, fast-paced organizations
• Strong executive presence with the ability to influence senior stakeholders and drive alignment
• Deep understanding of recruiting operations, funnel metrics, compensation calibration, and talent market dynamics
• Experience building recruiting processes and infrastructure that scale
• Strong sourcing and recruiting instincts with the ability to assess talent beyond resumes
• High ownership mentality with comfort operating in ambiguity and rapidly changing environments
• Excellent judgment, prioritization, communication, and stakeholder management skills
• Experience with Greenhouse and modern recruiting tools strongly preferred

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.

• Flexible Work Model: CharterUP operates as a remote-first company, with select roles requiring regular, in-office presence based on team and business needs. Role-specific expectations will be shared during the hiring process. 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.