Senior Specialist, Benefits

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

As we continue our rapid growth, we're seeking a proactive Benefits SME to take ownership of designing, implementing, and enhancing our benefits programs across the Americas Region (strong focus in the US, Canada and Brazil but may expand over time). You'll drive the end-to-end benefits strategy and operations, collaborating closely with Checkout leadership, People Onboarding, and external vendors, as well as employees, to build best-in-class benefits offerings while ensuring seamless delivery.

If you excel at balancing strategic thinking with hands-on execution, leveraging data-driven insights, and tackling challenges in a dynamic environment, we'd love to discuss how you can contribute to our journey!

What You'll Be Doing

• Lead Benefits Administration: You'll own and execute the day-to-day operations of our regional benefits programs across the Americas. This includes managing enrollments, ensuring seamless payroll integrations, handling compliance, and resolving employee inquiries with a strong focus on exceptional service.

• Manage Vendors and Systems: Serve as the primary point of contact for external benefits providers and partners. You'll negotiate contracts with our procurement team, oversee invoices, and manage our benefits systems, including AON and other platforms, to ensure they're efficient and accurate.

• Drive Strategic Planning and Benchmarking: Go beyond day-to-day tasks by actively shaping our benefits stirategy. You'll research market trends, use data to analyze plan utilization, and recommend improvements to ensure our offerings are competitive and employee-centric. You'll also be responsible for developing and presenting a long-term benefits roadmap to leadership.

• Manage Renewals and Implementations: Take full ownership of benefits renewals and new program implementations throughout the year. This involves everything from surveying employees to creating and delivering engaging communications and presentations that help our people understand the full value of their benefits.

• Solve Problems and Handle Escalations: Act as the go-to expert for all benefits-related issues. You'll troubleshoot system errors, resolve complex employee escalations, and streamline processes to ensure a seamless benefits experience for everyone.

• Collaborate Cross-Functionally: Partner closely with internal teams like Payroll, People Onboarding, Finance, and Procurement to ensure the smooth and compliant execution of all benefits programs. You'll serve as the subject matter expert and a key advisor to your colleagues.

• Take Full Ownership: This is a role for a true self-starter. You'll be expected to work with a high degree of autonomy, independently managing the full scope of benefits for the Americas while ensuring both operational excellence and long-term strategic enhancements.

Required Qualifications

• 5+ years of Benefits Expertise: Extensive experience managing end-to-end benefits programs, with a deep understanding of benefits strategy, design, and administration for the US and Canada. Experience with benefits in Brazil and Mexico is a plus.

• In-depth understanding of key health, welfare, and retirement benefits administration functions, including vendor coordination, handling employee changes, processing qualifying life events and appeals, and managing annual enrollment.

• Strong understanding of benefits compliance and regulations, including US federal and state laws. Strong knowledge of US FMLA and leave administration in a multi-state environment, as well as Workers' Compensation, IRS, and ERISA regulations.

• Vendor and Systems Management: Proven ability to manage vendors, negotiate contracts, and oversee benefits systems and platforms. You should be comfortable navigating complex administrative processes.

• Strategic & Analytical Skills: Experience using data to analyze trends, benchmark against the market, and recommend strategic improvements to benefits offerings.

• Project Leadership: A hands-on, proactive approach to managing projects and solving problems autonomously. You should be comfortable leading benefit renewals and new implementations from start to finish with minimal guidance.

• Excellent communication, both written and verbal, and presentation skills, with the ability to clearly articulate complex benefits information to employees and leadership while consistently demonstrating empathy, patience, and compassion.

• Excellent interpersonal skills, with the ability to connect with employees and management.

• Advanced Microsoft Excel skills, including proficiency with PivotTables, VLOOKUP functions.

• Ability to thrive in a fast-paced work environment.

• Experience using Workday, including launching Open Enrollment, updating benefit plans, and running reports.

Preferred Qualifications

• Experience in a fast-paced, high-growth technology or FinTech environment.

• Professional certifications (e.g., CEBS, PHR/SPHR).

• Fluency in Spanish.

• Fluency in Portuguese.

Additional Information

Apply without meeting all requirements stated

If you don't meet all the requirements but think you might still be right for the role, please apply anyway. We're always keen to speak to people who connect with our mission and values.

We believe in equal opportunities

We work as one team. Wherever you come from. However you identify. And whichever payment method you use.

Our clients come from all over the world - and so do we. Hiring hard-working people and giving them a community to thrive in is critical to our success.

When you join our team, we'll empower you to unlock your potential so you can do your best work. We'd love to hear how you think you could make a difference here with us.

We want to 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. We'll be happy to support you.

Take a peek inside life at Checkout.com via:

• Our Culture video https://youtu.be/BEwnpHuadSw

• Our careers page https://www.checkout.com/careers

• Our LinkedIn Life pages bit.ly/3OaoN1U

Our Instagram https://www.instagram.com/checkout_com/

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