Forward Deployed AI Accelerator, Operations

Company Description

We’re Checkout.com. You might not know our name, but companies like eBay, Spotify, Klarna, Uber, and Sony do, because we’re behind many of the digital experiences you use every day.

We are where the world checks out, enabling over 10 billion transactions yearly for more than one billion global shoppers.

Whether you want to book a holiday, order food, renew a subscription, or check out online, there’s a good chance our tech powers the payments behind the scenes. Our platform helps the most ambitious businesses deliver effortless digital experiences, at scale.

If you want to do career-defining work, you’ve come to the right place. We move fast, think globally, and believe great teams are built by hiring exceptional people with conviction, curiosity, and the desire to make an impact.

With 20 offices across six continents and London as our HQ, we’re shaping the future of fintech – and we’re just getting started.

Checkout.com’s Operations organisation is undergoing a fundamental transformation in how it works. We're building a team of Forward Deployed AI Accelerators embedded directly within Operations to make AI the default mode for all work - not an occasional tool, but the foundation of how every frontline operations analyst at Checkout.com works.

Today, our frontline teams are already using AI to reduce multi-hour processes. The FDA team exists to take what's working and systematically scale it across the entire operations organisation.

What you'll do

As a Forward Deployed AI Accelerator, you'll be embedded with a function of

approximately 20-30 analysts organised by team or workflow. You'll build alongside them, and you will help them fundamentally change how they operate. Your measure of success is the number of workflows you've permanently transformed and the extent to which those in your group start any task with an AI tool.

Responsibilities

• Identify and document the highest-leverage workflow transformations within your group's day-to-day work by deeply understanding their processes and outputs

• Build custom tools, agents, automations, and skills tailored to each operations analyst's specific responsibilities

• Coach and partner with each operations analyst through a progressive journey: from awareness, to first win, to regular AI integration, to full workflow transformation, to self-sufficiency

• Teach analysts to build and iterate on their own tools over time, creating independence

• Recognise patterns across your cohort and systematically scale what works - a tool built for one operations analyst should become reusable for their peers

• Document every tool, playbook, and transformation pattern you build so the entire FDA team can use each other's work

• Share wins visibly within your cohort and with leadership to build momentum, inspire, and celebrate success

• Track individual and cohort progress rigorously against a defined maturity model, moving every operations analyst toward self-sustaining, AI-first work

• Prepare operations analysts for an agentic future - not just prompt writing, but designing, building, and overseeing autonomous, multi-agent workflows

Who you are

• We're looking for people who have already lived the transformation they'll be driving for others. You've used AI to fundamentally change how you work - not as a novelty, but as your default operating mode.

• You are a deep AI practitioner. You build agents, automations, and tools fluently. You don't just know what AI can do in theory - you've built things that changed how real work gets done. You can build in real time alongside the people you support.

• You are an exceptional coach and communicator. You can meet people wherever they are. You create desire for progress, and you adapt your approach to each person.

• You understand how operations work. You either have direct experience in operations or can quickly learn the workflows, deliverables, tools, and pressures of your assigned group. You know that understanding someone's work is a prerequisite to transforming it.

• You are a pattern recogniser. When you build something that works for one person, you immediately see how it applies to others. You think in systems, not one-off solutions.

• You are high-caliber, persistent, and versatile. Your skills and experience are valuable across the company. You're the kind of person who could succeed in many roles at Checkout.

• You bias toward action and speed. You'd rather show someone a working proof-of-concept on their own deliverable today than present a polished deck about what's theoretically possible next quarter.

• You are comfortable with ambiguity and evolution. This is a new team building a new operating model. The playbook will be rewritten as we learn. You thrive in that environment.

Minimum requirements

• 3+ years of professional experience in a role requiring analytical thinking, problem-solving, and cross-functional collaboration

• Demonstrated, hands-on experience building AI-powered tools, agents, automations, or workflows that transformed real work processes (not just using AI as a chatbot - building with it)

• Track record of coaching, teaching, or enabling others - formally or informally - with evidence that people you've helped actually changed how they work

• Strong written and verbal communication skills, with the ability to explain technical concepts to non-technical audiences and adapt your style to different learners

• Comfort working across multiple workstreams and relationships simultaneously (you'll be supporting up to 30 analysts at varying stages of their AI journey)

Preferred qualifications

• Experience in risk, fraud, compliance, or a closely adjacent function

• Proficiency with AI development tools and platforms (e.g., Claude, Claude Code, Codex, custom agent frameworks, API integrations, workflow automation tools)

• Experience with change management, organisational transformation, or large-scale enablement programs

• Familiarity with the following technology stacks (e.g., Zendesk, Salesforce, analytics platforms, content management tool)

• Experience building and scaling internal tools, templates, or playbooks that were adopted beyond your immediate team

• Background in consulting, solutions engineering, technical account management, or other client-facing technical roles

Additional Information

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

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