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Checkout.com is a global fintech platform powering over 10 billion transactions yearly for more than one billion shoppers. This is a strategic operations role reporting to the Head of Operational Excellence, focused on bridging strategy and execution within Merchant Operations.
You will own the strategic evolution of Merchant Operations, translating complex operational challenges into decision-ready narratives and identifying where AI and intelligent automation can drive step-change improvements. Key responsibilities include:
- Build business cases for structural and technology changes: cost-to-serve analysis, capacity modelling, AI investment sizing, and trade-off frameworks across Merchant Care and Configuration.
- Develop the strategic narrative for how Merchant Operations evolves from reactive support to a proactive, insight-led merchant success function.
- Own the AI opportunity roadmap for Merchant Ops: identify where LLMs, autonomous agents, and intelligent automation can reduce manual handling, improve first-contact resolution, or unlock new service capabilities.
- Evaluate and shape AI vendor strategy—assessing build vs. buy decisions, trialling new tooling, and building business cases for adoption.
- Work with Data and Product teams to translate operational requirements into AI product direction, including optimization of AI bot (Fin) and knowledge management tooling.
- Define how AI performance is measured operationally: design metrics, tracking, and feedback loops validating whether AI tooling delivers against service quality and efficiency outcomes.
- Partner with Data Analytics to commission and interpret analysis that shapes strategic insights.
- Collaborate with Process Architects to identify automation and AI integration points within process-level redesigns.
- Synthesise inputs across operational data, product roadmap changes, merchant feedback, and AI capability developments into coherent strategic views.
- Provide scenario-based recommendations for headcount planning, geographic expansion, service tiering, and technology investment with AI impact modelled explicitly.
- Own the operating cadence for Merchant Ops: leadership meetings, planning cycles, OKR setting, retrospectives, and cross-functional syncs.
- Act as a triage and prioritisation layer for inbound requests to leadership.
Checkout.com operates a hybrid model with three days per week in the office. The company has 20 offices across six continents with London as headquarters.
REQUIREMENTS:
- 3+ years in strategy, operations, consulting, business operations, or Chief of Staff role—ideally in fintech, payments, or B2B SaaS.
- Exposure to merchant support, customer operations, or B2B service delivery environments (strong advantage).
- Demonstrable experience designing or contributing to operating model decisions: org design, service tiering, channel strategy, or workflow redesign.
- Genuine curiosity about AI and its applications in support and operations; familiarity with LLMs, agents, and conversational AI.
- Experience evaluating or deploying AI/automation tooling in an operational context: shaped a build-vs-buy decision, run a vendor pilot, or defined success metrics for an AI or automation initiative.
- Exceptional communication skills: write board-quality documents, present confidently to senior audiences, distil complexity into clarity.
- Strong commercial instinct: think about merchant operations through cost-to-serve, contact avoidance, and merchant lifetime value lenses.
- Analytical fluency: understand how AI systems make decisions, interrogate outputs critically, spot when models produce nonsense. SQL or model training not required.
- High agency, low ego, comfort with ambiguity: create structure where there is none.
