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.

About the role

We are looking for an AI Product & Transformation Lead to build the next generation of AI-enabled ways of working across Legal and Enterprise Risk. Please, note experience within Legal or Risk would be useful, but it is not essential. We are particularly interested in people who combine strong AI product, technical, operational or design instincts with enough domain empathy to build trusted solutions.

This is a hands-on AI role for someone who enjoys turning emerging technology into products and capabilities that people genuinely use. You will lead discovery with lawyers, risk professionals, legal operations and business stakeholders, identify high-value opportunities, and turn them into practical AI solutions.

You will not be working only at the level of strategy. You will build and ship AI products, agents, automations, workflows and playbooks; test what works with end users; learn quickly; and create the conditions for other people across Legal and Enterprise Risk to build as well.

You will be embedded in the Legal and Enterprise Risk organisation and partner closely with Compliance, Technology, Data, Information Security and other enabling functions to scale AI capabilities safely across the business.

What you will do

Build and scale AI products:

• Lead structured discovery with Legal and Enterprise Risk teams to identify high-value AI opportunities, recurring friction, manual work and decision bottlenecks.

• Turn real user problems into clear use cases, lightweight prototypes and scalable solutions.

• Build, configure or product-manage AI-enabled tools, agents, workflow automations, self-service experiences and knowledge systems.

• Take solutions from idea to pilot to adoption, including testing, iteration, documentation and handover.

• Balance speed and experimentation with appropriate controls for confidentiality, privilege, data protection, security and legal risk.
  

Help others build products:

• Make practical AI-building skills accessible to lawyers, risk professionals and Legal Operations colleagues through hands-on sessions, guides and coaching.

• Establish an AI builder community or similar forum for sharing use cases, prompts, prototypes, lessons and reusable components across Legal and Enterprise Risk.

Apply AI to improve how work gets done:

• Map and redesign workflows across Legal and Enterprise Risk, using AI to improve speed, quality, consistency and capacity.

• Create repeatable processes, templates, playbooks and operating rhythms that reduce unnecessary manual effort.

• Design better ways to capture, organise, retrieve and reuse organisational knowledge through AI-enabled search, summarisation and assistance.

• Identify opportunities to improve intake, triage, matter management, contract workflows, reporting and business self-service.

• Establish simple measures of impact, such as time saved, cycle-time reduction, quality improvements, user satisfaction and adoption.

Build alignment and momentum

• Own a prioritised AI product and use-case pipeline based on user need, value, feasibility, adoption potential and risk.

• Bring stakeholders together around clear problems and decisions rather than abstract technology discussions.

• Communicate progress, learnings and trade-offs in a way that works for both technical and non-technical audiences.

• Build strong relationships with Technology, Data, Information Security, Procurement and other partners needed to deliver safely at scale.

• Help Legal and Enterprise Risk leadership make informed choices about AI tools, investment, capability, governance and ways of working.

What we are looking for:

• Experience building AI products, automation, digital capabilities or technology-enabled ways of working in a complex organisation.

• A track record of taking ambiguous problems from discovery through to a practical outcome that people actually use.

• Deep practical experience with generative AI, AI agents, workflow automation, knowledge management, no-code or low-code tools, or similar technologies.

• Strong user-centred instincts: you listen carefully, understand how work is really done and design for adoption rather than theoretical capability.

• Strong judgement about confidentiality, privilege, data protection, security, accuracy and responsible use of AI.

• A coaching mindset and the ability to help others become more confident and capable builders.

• Curiosity, pragmatism and a bias towards learning by doing.

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