Chief of Staff to the Principal

I am looking for a Chief of Staff to work alongside me across a growing portfolio of private-sector ventures and international development initiatives spanning financial services, infrastructure, technology, cybersecurity and education.

The work sits at the intersection of investment, institution building and execution. The portfolio is Caribbean-anchored but international in scope, with counterparties across government, development institutions, professional services and the private sector.

This is a fractional engagement, but the mandate is not junior.

I make the decisions on direction. What I need is someone who makes sure those decisions become actions, and that nothing disappears between decision and execution. You would be helping establish the operating discipline and external institutional presence of a portfolio expected to grow materially over time.

In a given week, you might secure a discussion with an international organization, move an outstanding matter through a government office, follow up with counsel, coordinate with a development or financial institution, prepare a briefing for me, and make sure a commercial workstream in another country has not quietly stalled.

What you would own

Several workstreams run simultaneously, each with different counterparties, deadlines and dependencies. Your job is to maintain the execution picture across them.

You will know what is outstanding, who owns the next action, what is approaching a deadline, what has gone quiet, where a relationship needs advancing, and where intervention is required.

In practice, you will:

• Maintain the portfolio-level action, dependency and decision register.
• Drive follow-up with external counterparties without waiting to be prompted.
• Acting as an agent of the Principal, open, advance and maintain institutional relationships with ministries, agencies, development banks, professional firms and commercial partners.
• Identify the right institutional entry points where no direct relationship exists.
• Coordinate and secure calls with senior external stakeholders.
• Prepare concise briefings before important meetings.
• Capture decisions and commitments afterward and drive them to completion.
• Track statutory, regulatory, funding and institutional deadlines.
• Identify stalled workstreams early and recommend the next action.
• Escalate matters requiring my intervention while resolving routine execution issues independently.

You will often be the first voice counterparties encounter from the Principal's office. You should be comfortable engaging senior officials and international institutions in a way that conveys substance, confidence and institutional seriousness from the outset.

This role requires more than persistence. It requires the judgment to know how to approach a senior institution, how to find the right entry point, when to escalate, how to read an institutional response, and how to ensure an inquiry from the Principal's office is treated as substantive rather than routine.

This is not primarily an administrative role.

Who this suits

What matters most is the environment you have operated in, not the title you carried.

A Special Assistant inside a UN country office, a Program Officer on a major donor program, or an Executive Associate in a ministry's executive office may be far better suited to this than someone holding a Chief of Staff title at a small private company. Institutional fluency is the qualification. Seniority of title is not.

You have probably spent part of your career close to senior decision makers in an international organization, development finance institution, government, donor-funded program, diplomatic mission, NGO, professional-services firm, or complex private-sector organization.

You may have held roles such as Program Officer, Senior Program Officer, Program Manager, Partnerships Manager, External Relations Officer, Institutional Partnerships Lead, Government Relations Manager, Country Office Manager, Executive Associate, Special Assistant, Protocol Officer, Liaison Officer, Deputy Chief of Party, Portfolio Manager, Chief of Staff, or similar.

You understand institutional environments. You know how to identify the right person, create a credible entry point, make the call, follow up professionally and persistently, and determine what an answer actually means. You are comfortable with hierarchy without being intimidated by it.

You have likely managed multiple programs, principals, countries, clients or institutional relationships simultaneously.

Most importantly, you act without waiting for every instruction. If something important has been silent for ten days, your instinct is to determine why, follow up, find another route if necessary, and tell me what you learned. Not to ask whether you should chase it.

Judgment matters as much as organization. What you notice on a call I am not on, including hesitation, institutional dynamics, urgency, political sensitivity or an unexpected opening, may be as important as the meeting you arranged.

Excellent written and spoken English is essential.

Prior experience with organizations such as the United Nations, World Bank or IFC, regional development banks, bilateral development agencies, government ministries, diplomatic missions, Big Four public-sector advisory teams, or major donor-funded programs is particularly relevant.

Terms

Independent contractor engagement.

Approximately 15 hours per week.

US$1,500 monthly retainer, with discretionary performance bonuses tied to significant outcomes.

Other clients are welcome.

The initial engagement is 90 days, followed by a mutual review.

The role requires the ability to conduct calls and handle time-sensitive matters during 9am to 1pm Atlantic Time (UTC-4), Monday through Friday. Continuous availability throughout that window is not required.

You would be joining during formation: ventures moving from concept into execution, institutions being established, partnerships being developed and platforms being built. As the portfolio grows, the role is intended to grow with it in responsibility, scope and compensation.

Shortlisted candidates will complete an approximately two-hour paid practical exercise designed to reflect the actual work of the role.

Location: Remote and global. Particular interest in candidates based in major international development and institutional hubs in Africa and Latin America, including Nairobi, Accra, Abuja, Lagos, Johannesburg, Pretoria and Bogotá.

What we are screening for

Strong candidates will demonstrate:

• Institutional credibility and judgment
• Confidence with senior external stakeholders
• Proactive execution
• The ability to build institutional entry points quickly
• Excellent written and verbal polish
• The ability to manage multiple workstreams without losing context
• The ability to distinguish what requires the Principal's attention from what should be handled independently

Candidates who default to asking permission before routine follow-up, escalation or coordination are unlikely to be a fit.