Title:

Executive Assistant

Reporting to:

Chief Executive Officer

Location:

This role is based in Toronto and follows a hybrid work arrangement, with three days per week in the Toronto office and the remaining workdays remote.

About Raising The Village Raising The Village's mission is to build and strengthen pathways out of ultra-poverty through an approach guided by data, designed with communities, and scaled by partnerships. We work with last-mile communities to implement solutions that raise incomes, sustain impact, and chart sustainable pathways to possibility within 24 months. To date, we have supported more than two million people in Uganda, Rwanda, and the Democratic Republic of Congo, with support from our partners and our team in North America. Find out more about our programs and impact at www.raisingthevillage.org.

Position Overview The Executive Assistant (EA) plays a key role in enabling the effectiveness of Raising The Village's Founder and CEO, providing trusted executive, administrative, and operational support in a dynamic, mission-driven workplace. Working closely with the CEO, the EA balances hands-on administration—including calendar and inbox management, travel arrangements, expense reporting, meeting logistics, and technology coordination—with broader executive coordination, bringing structure to complexity and helping manage competing priorities.

The EA synthesizes information, identifies priorities, connects related issues across meetings and workstreams, and maintains visibility into commitments to ensure timely follow-through on decisions and agreed actions. As a trusted partner, the EA exercises sound judgment, discretion, and independence, anticipating needs and challenges, adapting to shifting priorities,



and determining when matters can be resolved independently or require escalation.

Success requires resourcefulness and initiative to research information, identify practical solutions, resolve issues with limited direction, and maintain momentum—even when processes, information, or next steps are not fully defined—enabling the CEO to focus on the relationships, decisions, and organizational priorities that matter most.

Key Responsibilities Executive Support & Prioritization

Actively manage the CEO’s calendar and inbox, balancing strategic priorities, leadership needs, stakeholder requests, travel, and focus time across multiple time zones.

Anticipate conflicts, surface urgent matters, and exercise judgment about what requires the CEO’s attention, delegation, or independent resolution.

Draft executive correspondence, briefing notes, agendas, talking points, and internal updates in the CEO’s voice and style.

Prepare the CEO for meetings and decisions by synthesizing relevant context, checking facts, identifying gaps or inconsistencies, and highlighting matters requiring a decision, analysis, delegation, or follow-up.

Maintain organized, accessible executive records, correspondence, contacts, and working documents, protecting highly confidential information.

Leadership, Board & Stakeholder Coordination





Coordinate meetings and engagements with the Executive Leadership Team and Board, including scheduling, materials coordination, logistics, and action tracking.

Capture decisions, commitments, and action items, proactively tracking them to completion with the CEO and relevant stakeholders.

Coordinate with Board members, senior leaders, funders, government and implementing partners, advisors, and other executive offices.

Maintain stakeholder contact information and track key engagements and commitments, connecting related issues across meetings and workstreams.

Represent the CEO’s office with professionalism, responsiveness, diplomacy, and cultural awareness aligned with RTV’s values.

Travel, Executive Office Operations & Special Projects

Arrange complex domestic and international travel, including itineraries, accommodations, transportation, visas or travel documentation, and contingency planning.

Coordinate meeting and event logistics and prepare complete travel briefs with schedules, contacts, background materials, and objectives, responding resourcefully to last-minute changes.

Manage executive administration, including expense reporting, and oversee office administrative operations, which may include lease management.

Coordinate IT support, equipment, and virtual meeting setup, and maintain practical systems for tracking priorities, decisions, commitments, and deadlines.

Support special projects by researching information, coordinating inputs, preparing concise summaries, and driving defined workstreams to completion.

Required Qualifications

5+ years of progressive executive support experience, ideally supporting a CEO, C-

📌 Executive Assistant (Winnipeg)
🏢 Raising The Village
📍 Winnipeg