[Hiring] Head of People @CharterUP

Role Description

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.

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.

Because this role will work in close partnership with Legal and the People function will report into that structure, it must be built on a strong foundation of compliance, employee relations, and disciplined execution. 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.

Qualifications

• 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 Interview
• Step 3 - Video call: Executive Interview
• Step 4 - Offer & Background Check

Benefits

• 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.