Company Description

We’re Checkout.com – you might not know our name, but companies like eBay, ASOS, Klarna, Uber Eats, and Sony do. That moment when you check out online? We make it happen.

Checkout.com is where the world checks out. Our global network powers billions of transactions every year, making money move without making a fuss. We spent years perfecting a service most people will never notice. Because when digital payments just work, businesses grow, customers stay, and no one stops to think about why.

With 19 offices spanning six continents, we feel at home everywhere – but London is our HQ. Wherever our people work their magic, they’re fast-moving, performance-obsessed, and driven by being better every day. Ideal. Because a role here isn’t just another job; it’s a career-defining opportunity to build the future of fintech.

Job Description

Checkout is hiring an exceptional Regional People Leader to spearhead our ambitious expansion across North America. Based in New York and reporting to the Regional Americas Director, this highly strategic, results-oriented role blends senior business partnership with hands-on leadership. You will serve as a key senior People Partner in the region and act as a trusted advisor to senior leaders, shaping our organizational strategy and leading the execution of People Programs, Processes, and Projects across the US and Canada. If you are a seasoned HR leader eager to influence leadership, champion culture, and ensure operational excellence while scaling People initiatives in a high-growth fintech environment, we encourage you to apply.

What You'll Be Doing

Strategic Business Partnership

• Executive Coaching: Serve as a trusted advisor to the North American Revenue Leader and senior stakeholders to enhance leadership effectiveness and team performance.

• Organizational Strategy: Design and deploy talent strategies that align with regional business goals, leveraging data-driven insights to manage engagement, retention, and succession.

• Talent Stewardship: Partner with Talent Acquisition to hire and develop senior talent, championing internal mobility and a high-performance culture.
  

Workplace Experience & Real Estate

• Regional Strategy & Mentorship: Serve as the North American functional leader for workplace experience team members, providing strategic direction and mentorship to ensure a cohesive regional vision that respects local nuances.

• Operational Excellence: Audit and refine workplace processes and workflows to remove roadblocks, drive regional efficiency, and enable local teams to operate at their best.

• Financial & Cultural Stewardship: Oversee North American workplace budgets and vendor spend while empowering teams to execute engagement and recognition strategies that sustain a high-performance culture.

• Strategic Real Estate & Expansion: Act as the primary stakeholder for the real estate lifecycle within assigned business units; liaise directly with the Head of Real Estate (HQ) to coordinate office moves and build-outs tailored to the modern workforce.
  

HR Operations & Program Delivery

• Global-to-Local Integration: Tailor and execute global People programs (Performance, Comp, Learning) to fit the North American cultural and legal context.

• Manager Development: Coach managers through complex organizational changes, team effectiveness challenges, and performance management cycles.

• Cross-Functional Collaboration: Partner with Departmental HR leads and COEs to ensure seamless regional execution of corporate policies.
  

Employee Relations & Compliance

• ER Excellence: Resolve complex employee relations issues and investigations in partnership with Legal and Global ER leads.

• Regional Compliance: Ensure 100% compliance with federal, state, and provincial laws across the US and Canada, including policy development and SOP refinement.
  

Expansion & Analytics

• Growth Innovation: Evaluate and implement new People programs as the region expands, ensuring market competitiveness and scalability.

• Data Insights: Synthesize engagement data and exit feedback into actionable recommendations for the executive leadership team.

• Financial Stewardship: Oversee budget planning and management for regional People initiatives, ensuring alignment with business priorities, accurate tracking of headcount costs, and effective use of resources.
  

Requirements & Qualifications

• Bachelor's degree in Human Resources, Psychology, Business or any other related field preferred and/or CIPD, SHRM qualification or relevant years of experience;

• 10+ years of demonstrable experience as People Advisor, HR Business Partner or HR Generalist in a fast-paced, global start-up environment ideally in the payments or tech sector.

• Progressive HR experience, with at least 5 years in a senior HR Business Partner role supporting executive leaders and driving strategic initiatives.

• Demonstrated success as a trusted advisor and coach to senior executives, with the ability to influence leadership and drive transformation.

• Deep knowledge of US and Canadian employment practices, labor law, and compliance requirements,

• Strong business and financial acumen with experience aligning people strategies with organizational priorities in high-growth or fast-paced, matrixed environments.

• Expertise with HR systems (e.g., Workday, Paychex), ER case management, and performance management frameworks.

• High analytical capability with a proven ability to use HR metrics, survey data, and reporting tools to inform strategic decisions and demonstrate impact.

• Experience with office management/workplace operations oversight and managing site-specific projects (e.g., real estate projects, vendor management) strongly preferred.
  

Nice-to-Haves

• Professional certification (e.g., SHRM-SCP, SPHR) is strongly preferred.

• Professional experience in fast-paced, start-ups, tech or financial services companies.

• Experience supporting GTM/Commercial leaders.

• Fluency in Spanish or Portuguese is a strong plus.

• Master’s degree in a relevant field.

Bring all of you to work

We create the conditions for high performers to thrive – through real ownership, fewer blockers, and work that makes a difference from day one.

Here, you’ll move fast, take on meaningful challenges, and be recognized for the impact you deliver. It’s a place where ambition gets met with opportunity – and where your growth is in your hands.

We work as one team, and we back each other to succeed. So whatever your background or identity, if you’re ready to grow and make a difference, you’ll be right at home here.

It’s important we set you up for success and make our process as accessible as possible. So let us know in your application, or tell your recruiter directly, if you need anything to make your experience or working environment more comfortable.

Life at Checkout.com

We understand that work is just one part of your life. Our hybrid working model offers flexibility, with three days per week in the office to support collaboration and connection.

Curious about what it’s like to be part of our team? Visit our Careers Page to learn more about our culture, open roles, and what drives us.

For a closer look at daily life at Checkout.com, follow us on LinkedIn and Instagram