Strategic Execution Leader, CEO Office

Checkout Ltd; Greater London; Hybrid; GBP 120,000 - 190,000; Full time

Benefits offered by this job

Payments/Fintech exposure

AI automations

Advanced SQL

International experience

Entrepreneurial experience

Job summary

Checkout.com is seeking a high-judgment, high-ownership operator to join the CEO Office and turn priorities into outcomes. You will balance strategic thinking, research, and hands-on delivery, collaborating across teams to drive maximum impact and support leadership with structure and execution.

You will design solutions, drive complex initiatives, and become a trusted partner to leadership, expanding scope across Checkout.

Qualifications

• Strong problem-solving and analytical skills across complex problems.
• Excellent communication with senior executives and cross-functional teams.
• Comfort with unknowns and ability to learn quickly with first-principles thinking.
• Humility and low ego as a mission ambassador.
• AI-native approach to research, analysis, build and automate.
• Builder mindset: own the outcome, build lasting solutions.
• Track record of impact and rapid growth in responsibility or achievements.
• Experience in consulting, high-growth tech, investing, or strategic finance environments.

Responsibilities

• Lead day-to-day cross-functional initiatives with the CEO Office and enable collaboration across departments.
• Scale departments by establishing clear structures, objectives and KPIs; implement robust processes.
• Identify complex problems, design durable solutions, and drive measurable business outcomes.
• Navigate ambiguity, accelerate execution and align across the company.
• Own ambiguous, high-priority problems spanning multiple teams or lacking a natural owner.
• Define problems before developing and implementing effective solutions.
• Projects may include: organisational design, international expansion, new business lines, strategy, go-to-market planning, regulatory, data and financial infrastructure, board reporting.

Skills

Problem-solving

Analytical thinking

Communication

Ambiguity tolerance

Humility

AI-native working

Builder mindset

Impact track record

Tools

SQL

AI automation tools

Low-code/no-code

Job description

Checkout.com is seeking a high-judgment, high-ownership operator to join the CEO Office and turn priorities into outcomes. You will balance strategic thinking, research, and hands-on delivery, collaborating across teams to drive maximum impact and support leadership with structure and execution.

You will design solutions, drive complex initiatives, and become a trusted partner to leadership, expanding scope across Checkout.