Regional People Leader - North America

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 Atlanta and reporting to the Regional Americas Director, this highly strategic, results-oriented role blends senior business partnership with hands‑on site leadership. You will serve as the most senior People Partner in the region and act as a trusted advisor to executives, shaping our organizational strategy and leading the execution of People Programs, Processes, and Projects across the US and Canada with an increased focus in supporting the growth and expansion of Checkout’s footprint in Atlanta. 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 Partnership & Leadership Enablement: Executive Coach – act as a trusted thought partner and coach to senior leaders in North America, particularly to the CEO of Checkout Atlanta, fostering leadership effectiveness, self‑awareness, and high‑performing team principles. Business Expert – leverage a strong understanding of business priorities to shape and deploy holistic talent and organizational strategies that align with Checkout’s growth goals. Talent Steward – partner with leaders and Talent Acquisition to attract, hire, develop, and retain senior-level talent. Champion succession planning and internal mobility across the region. Transformer – drive adoption of global People initiatives across assigned scope and geographies, ensuring appropriate tailoring to local needs and cultural context. Data‑Led – utilize People metrics, engagement data, and business insights to inform strategic decisions around engagement, mobility, performance, and retention. Workplace and Site Leadership HR Site Lead – Atlanta: Operate as the most senior People Partner in the Atlanta hub, leading the local People strategy and execution, and managing all key People processes for the site. Office Management Oversight – oversee the operational and administrative functions of the Atlanta office to ensure a safe, efficient, and professional work environment. Workplace Experience – partner with internal teams (e.g., IT, Security, Finance) and external vendors to design and deliver an outstanding employee experience for the Atlanta office. Local Engagement & Culture – plan, manage, and support local engagement events, culture forums, and moments of recognition to sustain a strong team environment. Real Estate Projects – serve as the local lead for real‑estate and office build‑out projects, partnering closely with HQ’s dedicated Center of Excellence (COE) and internal stakeholders. Core HR Leadership & Regional Partnering Regional Partnering – partner with people leaders across North America to ensure HR actions are aligned with business priorities and workforce needs. Global People Team Community – partner with Departmental People Partners and Central COEs to help represent the Region and ensure local processes are executed smoothly in accordance with local practices, policies and laws. End‑to‑End Program Delivery – deliver expert, end‑to‑end support for cyclical People programs, including performance management, compensation planning, employee development, and change programs. Manager Coaching – coach and develop managers through complex employee issues, performance discussions, team effectiveness challenges, and the performance improvement process (PIP). Employee Relations & Compliance ER Resolution – resolve complex and sensitive employee relations issues, handling grievances, disputes, and complaints in a timely and effective manner. Partner with Legal and global ER leads for high‑complexity cases. Investigations & Terminations – conduct investigations, ensuring fair processes, quality documentation and recommending appropriate disciplinary measures. Oversee involuntary termination meetings and required documentation. Policy & Operations – interpret People policies, handle flexible work requests and contribute to the development and refinement of HR policies and SOPs and ensure regulatory requirements are met at Checkout Atlanta and beyond. Compliance Oversight – ensure robust compliance with local, state, and federal laws across US and Canadian operations, providing manager training on key compliance areas. Expansion, Reporting & Budget Expansion & Innovation – help evaluate and implement new People programs as Checkout expands across the Americas. Stay informed on local market practices to ensure competitiveness and inclusion. 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. Data & Insights – analyze and synthesize key data, including quarterly engagement results and exit interview feedback. Proactively provide digestible insights and make data‑driven recommendations to leaders for improving employee experience and culture. Regulatory reporting – partner with the Checkout Atlanta Leadership Team to comply with regulatory reporting to the Department of Banking and Finance of Georgia, audits and other requests tied to the US License for that entity. 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 Tech industry. 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 U.S. (especially Georgia state) and Canadian employment practices, labour law and compliance requirements. Strong business and financial acumen with experience aligning people strategies with organisational priorities in high‑growth or fast‑paced, matrixed environments (Fintech or Tech preferred). Experience with office management/workplace operations oversight and managing site‑specific projects (e.g., office build‑outs, vendor management). 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. Nice‑to‑Haves Professional certification (e.g., SHRM‑SCP, SPHR, CEBS) is strongly preferred. Experience supporting business units in a regulatory environment. 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 recognised 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. #J-18808-Ljbffr 0011 Checkout LLC