Executive Director (Volunteer), Toronto, ON.

Who We Are:

Founded in 2000, Daytrippers (www.daytrippers.ca) is a non-profit children's charity that funds educational school trips for in-need children across Canada. Daytrippers is a grassroots, Toronto-based charity run by its volunteers, supported by a small number of paid third-party partners. In 2026, its 25th year, Daytrippers raised $1.3 million (including its flagship Battle of the Brains gala), approved $890,000 in funding for 960 school trips reaching more than 63,000 students, and grew its network of destination partners to 28 organizations. Applications come from every province, led by Ontario and British Columbia, and the organization is now expanding its reach into Quebec, with a goal of $1 million in trip funding in the year ahead.

Executive Director:

This volunteer position is the senior-most operational and strategic leader of the organization. As the ED you will lead eight executive committees, with 11 chairs and co-chairs reporting to you directly, with indirect oversight of ~15 dedicated volunteers. You will work with the nine-member Board of Daytrippers (senior leaders in finance, law, private equity and philanthropy) and will also be a voting member of the Board. You will also be the primary point of contact and decision-maker for the charity's paid partners: Redstone Agency (administrative and executive support), the event planner for Battle of the Brains, and the technology partner that maintains the website, portal and reporting tools.

The ED role is designed to fit alongside a busy professional life, while offering a meaningful leadership opportunity. We ask for a three-year commitment to support continuity and impact. During the school year, the role typically takes about 8–12 hours a week. That rises to around 15 hours a week in the busy, exciting stretch leading up to Battle of the Brains (March–May). Activity is lighter between June and August (~2–3 hours a week), though vendor management, governance items, volunteer onboarding and planning for the year ahead continue through the summer. Committee and board meetings take place outside of business hours to accommodate volunteers with full-time jobs, and a meaningful share of the work happens over email in evenings and on weekends.

What You Will Do:

Leadership & Governance

• Oversee the day-to-day operations of the organization and act as the primary decision-maker between board meetings
• Drive annual strategic planning to set targets and work plans for each committee
• Partner with our administrative agency to map out the year ahead, setting the board and executive committee meeting schedule around key milestones and decisions.
• Ensure rigorous governance and controls are in place and adhered to for all funding decisions
• Act as an authorized signatory on behalf of the charity for banking matters, vendor agreements and institutional correspondence (e.g., letters to the bank and technology providers)
• Work with the recruitment and engagement teams to lead annual succession planning, including recruiting, onboarding and transitioning executive committee chairs and co-chairs (e.g., Trips, Marketing), and helping new volunteers settle into the team.
• Act as the custodian of up to $1 million+ in financial assets; review financial statements and accounts and liaise with the Treasurer and Finance Committee
• Support the annual audit, including reviewing and signing off on year-end audit materials alongside the Treasurer and Board
• Review and approve vendor invoices, volunteer reimbursements and payment requests, and route them to the finance team for processing

Paid Partners & Operations

• Direct and leverage Redstone Agency, which provides paid administrative and executive support: set priorities, manage day-to-day requests, follow up on outstanding items and hold the agency accountable to agreed deliverables (e.g., school outreach, board scheduling, event communications)
• Oversee our technology partner, Art & Science, for the website, trip-funding portal and reporting. Work with the chairs to set development priorities and approve deployments and spending.
• Ensure Redstone is managing the charity's digital accounts (domain, hosting and website platform) and ensure renewals and updates are handled
• Provide high-level oversight of Battle of the Brains, with the Battle of the Brains Chair serving as the main point of contact for our third-party event planner and Eden Events.

Fundraising & Events

• Provide oversight of Battle of the Brains, the charity's flagship annual fundraiser, which is run by the Battle of the Brains Chair and our event producer, Eden Events.
• Support committee-led fundraisers (e.g., Spin for Daytrippers) by attending, promoting them and connecting prospective donors and sponsors to the relevant chair
• Act as key representative of Daytrippers at public events (i.e., Battle of the Brains, donor appreciation and volunteer appreciation events) and at partner-hosted events

Marketing & Community

• Support the Marketing Chair, who leads the committee, by attending meetings when needed, making introductions to key contacts and offering ideas where helpful.
• Champion Daytrippers in the community, enhancing and sustaining the brand to support fundraising, recruitment and educator relations
• Foster a sense of community and high-energy culture by building relationships with volunteers and spearheading engagement activities (i.e., volunteer WhatsApp group, volunteer appreciation events)

Growth

• Guide Daytrippers' growth, including our current expansion into Quebec. Work with the team on school outreach, bilingual materials and city specific launch events
• Drive the shift from teacher reimbursements to a virtual card payment program (Ramp) and related portal improvements so teachers are reimbursed faster

Who You Are:

As an Executive Director, you will have the following:

• Exceptional leadership skills, ability to align, motivate and mobilize volunteers to achieve a vision. Preferred candidates will have previous experience leading volunteer teams
• Ability to manage down (lead the team) and up (leverage the Board)
• Strong organizational and planning skills, including the ability to keep multiple vendors and committees on track through follow-up
• Ability to work independently and resourcefully
• Basic financial acumen, some experience with interpreting financial statements and approving spend
• Comfort managing external vendors and contracts, and a working comfort with technology (websites, online portals, reporting tools)
• Strategic thinking capabilities to build on Daytrippers' strong operational position to scale impact across geographies, (low income) communities and schools
• Willingness to leverage your personal and professional network to host, invite and cultivate donors
• French language skills are an asset given the Quebec expansion
• Desire to build your personal network and brand in a high-profile role working with community leaders

How to Apply:

Please state your interest and email your resume to [email protected], noting 'Executive Director Volunteer Opportunity' in your email subject line.