Strategy & Operations Lead: Pillar Delivery & Alignment

Checkout Ltd; Greater London; Hybrid; GBP 120,000 - 180,000; Full time

Job summary

Checkout.com is seeking an experienced Strategy & Operations Lead in its CEO Office. You will own delivery across a pillar, partnering with Product and Engineering to ensure aligned execution and successful launches.

You’ll lead cross-functional initiatives, challenge roadmaps, and build a high-performing S&O team, driving practical standards across Checkout to improve delivery and impact.

Qualifications

• Strong problem solving and analytical skills.
• Ability to frame ambiguous business questions, test hypotheses and quantify trade-offs.
• Experience leading cross-functional work and delivery.
• Ability to build practical operating mechanisms using data, automation or AI.
• Influence without relying on authority; communicate clearly to stakeholders.
• Formal line-management experience is helpful, leadership matters more.

Responsibilities

• Own execution across the pillar, keeping priorities, delivery tempo, progress, dependencies and risks visible.
• Build deep expertise in the pillar’s products and value streams.
• Challenge priorities with the product leader and adjust roadmaps and commitments.
• Lead the pillar’s most important cross-functional initiatives from alignment to launch.
• Build and lead the S&O team within the pillar, including hiring, development and performance management.

Skills

Problem solving

Analytical skills

Strategy execution

Cross-functional leadership

Data-driven decisions

Automation / AI

Influence without authority

Leadership

Job description

Checkout.com is seeking an experienced Strategy & Operations Lead in its CEO Office. You will own delivery across a pillar, partnering with Product and Engineering to ensure aligned execution and successful launches.

You’ll lead cross-functional initiatives, challenge roadmaps, and build a high-performing S&O team, driving practical standards across Checkout to improve delivery and impact.