Senior Chief of Staff – Strategic Execution

Senior Chief of Staff – Strategic Execution

• Sri Lanka

Position Overview

We are seeking a highly experienced and commercially minded Senior Chief of Staff – Strategic Execution to work closely with the Founder as a trusted strategic partner and senior execution leader.This is a high-impact leadership position within the Founder’s Office, responsible for translating the Founder’s vision and priorities into structured execution across multiple ventures. The role will work across strategy, business development, investments, partnerships, special projects, and executive-level initiatives.The ideal candidate will bring strong business judgment, strategic thinking, exceptional execution capability, and the confidence to operate independently at senior leadership level. This individual must be comfortable challenging assumptions, identifying risks, coordinating senior stakeholders, and ensuring that critical priorities move from decision to execution.

Key Responsibilities

1. Founder Partnership & Executive Decision Support

• Serve as a trusted strategic thought partner and execution counterpart to the Founder.
• Evaluate business opportunities, strategic proposals, risks, investments, and major decisions.
• Conduct analysis and develop clear recommendations to support Founder-level decision-making.
• Prepare executive briefings, decision papers, presentations, and strategic frameworks.
• Identify and prioritize high-value matters requiring the Founder’s attention.
• Provide objective perspectives and respectfully challenge assumptions or decisions when appropriate.
• Maintain a high level of confidentiality and discretion when handling sensitive business and personal matters.

2. Strategic Execution & Business Performance

• Translate the Founder’s vision and strategic priorities into clear objectives, ownership, timelines, milestones, and measurable deliverables.
• Lead and coordinate high-priority, cross-functional initiatives across multiple businesses and ventures.
• Monitor execution against agreed priorities and identify bottlenecks, dependencies, and execution risks.
• Drive accountability across senior stakeholders and ensure commitments are followed through to completion.
• Establish effective tracking, reporting, and follow-up mechanisms for strategic initiatives.
• Identify organizational gaps, competing priorities, and opportunities to improve execution.
• Ensure strategic decisions are converted into measurable business outcomes.

3. Strategic Transactions, Investments & Special Projects

• Support the Founder on acquisitions, investments, partnerships, capital initiatives, and other strategic transactions.
• Coordinate internal teams, external advisors, legal representatives, financial professionals, and other stakeholders throughout transaction processes.
• Support due diligence by coordinating information, analysis, documentation, risks, and action items.
• Track negotiations, commitments, documents, approvals, milestones, and closing requirements.
• Evaluate transaction-related risks, dependencies, and execution issues and escalate critical matters appropriately.
• Ensure strategic projects and transactions remain aligned with the Founder’s objectives and broader business strategy.
• Take ownership of selected high-priority special projects from initial concept through completion.

4. Executive Leadership & Governance

• Coordinate strategic priorities across executives, department heads, business leaders, and external advisors.
• Prepare leadership meetings, strategic agendas, decision materials, and action-tracking systems.
• Ensure key decisions, commitments, and follow-up actions are clearly documented and executed.
• Identify conflicts in priorities, organizational risks, and gaps in accountability.
• Facilitate alignment between senior leaders and business units on Founder-driven priorities.
• Represent the Founder in selected internal and external discussions and meetings.
• Maintain strong relationships with senior stakeholders while protecting the Founder’s priorities and interests.

5. Strategic Analysis & Business Intelligence

• Research and analyze markets, industries, competitors, business opportunities, and strategic trends.
• Develop insights that support investment, growth, partnership, and business decisions.
• Evaluate business cases, proposals, operating models, and strategic initiatives.
• Convert complex information into concise, actionable recommendations for the Founder and senior leadership.
• Continuously identify opportunities to improve business performance, scalability, and strategic positioning.

Required Qualifications & Experience

• Minimum 8 years of relevant professional experience, with 10+ years preferred, in one or more of the following areas:
  • Corporate Strategy
  • Management Consulting
  • Corporate Development
  • Investment / Private Equity / Venture Capital
  • Executive Operations
  • Strategic Planning
  • Senior Project / Program Leadership
  • Business Transformation
• Proven experience working directly with a Founder, Chairman, CEO, or senior executive in a strategic or execution-focused capacity.
• Demonstrated ability to operate at senior management or director level and independently manage complex, high-impact initiatives.
• Strong exposure to U.S. businesses, international businesses, transactions, investments, partnerships, or multi-venture environments.
• Demonstrated experience supporting or coordinating strategic transactions, investments, acquisitions, partnerships, or major special projects.
• Strong commercial and financial understanding with the ability to evaluate business opportunities and risks.
• Exceptional written and verbal English communication skills.
• Strong executive presence, stakeholder management, organization, discretion, and follow-through.
• Ability to operate confidently with senior executives, advisors, investors, and external stakeholders.
• Demonstrated ability to exercise independent business judgment and make sound recommendations.
• Comfortable respectfully challenging senior leadership when necessary and providing an objective point of view.
• Highly organized with the ability to manage multiple high-priority initiatives simultaneously.
• Proven ability to work independently in a remote, fast-paced, high-accountability environment.
• Strong proficiency in Microsoft Office / Google Workspace and executive-level presentation and reporting.
• Mandatory availability during the stated Pacific Time working hours.