Fractional Hybrid Executive Director

Hybrid Fractional Executive Director (Independent Contractor)

Position Summary

The Executive Director (ED) is the senior strategic leader of the Greater Stouffville Chamber. This fractional role focuses on governance, advocacy, strategic partnerships, sponsorship revenue, and high-impact community leadership. Operational execution of membership services, events (except premier events), communications, and administration is led by the Director of Operations and contracted support. The ED reports directly to the Board of Directors and plays a critical role in advancing the Chamber’s purpose, vision, and mission and strengthening the voice of the business community.

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Start Date: March 1st, 2026

Compensation: Monthly retainer $4,200.00 (+ HST). Additional hours available with pre-approval at

$75/hour for busy periods within the year as mutually agreed between the President, Treasurer, and

Executive Director. An annual performance bonus may be available at the sole discretion of the Board which would be tied to exceptional revenue generation and/or profitability beyond the approved budget.

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Key Responsibilities

Governance & Board Relations

• Oversee Board meeting preparation, agenda planning, pre-reads, and follow-ups in conjunction with the Board President.
• Provide strategic updates, financial oversight, and policy input.
• Partner with the Board President to execute strong governance practices.
• Support the AGM and board and annual reporting of all other staff/contractors.

Sponsorship Revenue and Strategic Partnerships (Core Priority)

This is a central, mission-critical function.

• Lead all sponsorship strategy, including development, pitch design, and negotiations.
• Cultivate and maintain long-term relationships with top sponsors, stakeholder members, contra stakeholder members and corporate partners (including affinity partners).
• Drive year-round sponsor stewardship to increase renewal and upgrade rates.
• Identify new revenue streams aligned with the Chamber’s operational plan and its purpose and vision.
• Serve as the primary relationship manager for premier event sponsors.

Advocacy & Government Relations

• Monitor and analyze municipal, regional, and provincial issues affecting business.
• Represent the Chamber at meetings, committees, and public engagements.
• Maintain active relationships with elected officials, Town staff, and economic development partners.
• Lead the creation of policy submissions, position letters, and business-facing advocacy initiatives.
• Coordinate Chamber involvement in the Ontario Chamber of Commerce / Canadian Chamber of Commerce programs and campaigns.
• Stay informed and knowledgeable about the business environment and economic development initiatives within the Town
• Lead the Chamber’s Policy Advisory Councils (approximately 10 councils meeting twice annually for 2-hour meetings)
• Analyze and disseminate results of quarterly business barometer surveys in collaboration with the Director of Operations.
• Proactive and reactive advocacy at the direction of the Board and aligned with the board approved Advocacy Guiding Principles.

Member & Community Leadership

• Membership growth is a joint responsibility of the Executive Director and Director of Operations, with the Board setting annual strategic membership targets. The Director of Operations leads operational execution, while the Executive Director strengthens strategic relationships and visibility to support growth.
• Act as senior representative of the Chamber at key community, and business events, and political events where mandated by the Board (e.g. municipal election debates).
• Support member acquisition and retention, high-value member engagement and enterprise-level member relationships.
• Represent the Chamber and the interests of our business community at all levels of government in conversations that influence business conditions and community prosperity, to ensure that our members have a strong, respected voice in shaping policy and participating in critical debates.
• Be the go-to for staff where necessary and ensure all staff/contractors are performing in accordance with their roles

Event Leadership (Premier Events Only)

The ED provides strategic leadership, sponsorship support, and program excellence oversight for:

1. Economic Outlook Breakfast
2. Annual Spring Dinner & Mayor’s State of the Town Address
3. Business Hall of Fame Induction Dinner
4. Annual Golf Tournament
5. Tradeshows and Symposiums ED involvement includes:

• Securing and stewarding premier event sponsors, speakers, entertainment as required, etc.
• Collaborating with the Director of Operations on program design, speakers, content, and run-of-show.
• Participating in select planning meetings and partner engagements.
• Attending each premier event as the Chamber’s senior representative.
• Delivering remarks, facilitating VIP interactions, and supporting high-level logistics as needed.

All other events (Networking Nights, SIGs/Women in Business, seasonal mixers, workshops, etc.) are fully led and executed by the Director of Operations. It is, however, expected that the ED attend some networking nights throughout the year to ensure member relations are upheld. There may also be other events which are not regular throughout the year (i.e. Wellness Symposium, SMB trade show, etc.) which will benefit the ED in achieving overall goals by attending and assisting in the same or similar capacity as a premier event.

Strategic Oversight (Not Day-to-Day Operations)

• Provide high-level supervision of financial health and budgeting (bookkeeping outsourced).
• Ensure alignment between operational work and the Chamber’s operating plan and more broadly the Chamber’s purpose and vision.
• Support the Director of Operations in removing roadblocks and refining processes.
• Conduct regular check-ins with the Director of Operations to guide priorities, not execution.
• Lead the development of the annual operating plan and budget with input from the Director of Operations and Bookkeeper.

Exclusions: What This Role Does Not Include

To protect the ED’s strategic bandwidth, the following are not part of the role. These belong to the Director of Operations and contracted specialists.

• Daily administration or event logistics (except selective involvement in the three premier events).
• Routine member servicing, ChamberMaster updates, or renewals.
• Social media execution, content creation, or design tasks.
• Bookkeeping, invoicing, payroll, or statutory filings.
• Website administration or IT troubleshooting.
• Vendor/supplier coordination for non-premier events.
• General administrative duties.

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Qualifications and Expectations

• Senior leadership experience in business, advocacy, economic development, government relations, or a related field.
• Strong track record in sponsorship development, business development, partnership negotiation, or commercial revenue growth.
• Exceptional emotional intelligence (EQ), including diplomacy, active listening, political sensitivity, and the ability to build trust and maintain positive relationships across diverse stakeholders.
• Experience engaging with municipal, regional, and provincial government officials, with strong political acuity and the ability to maintain neutrality and credibility.
• Exceptional communication, relationship-building, and public-facing presence.
• Experience working with Boards, governance processes, and volunteer committees.
• Comfort operating in a fast-paced community environment with varied stakeholders.
• Familiarity with Chamber networks and business associations is an asset.
• Ideal candidate is expected to contribute 10-15 hours per week to this role.
• Ideal candidate will have flexibility to accommodate fluctuating time commitment needs.
• Regular onsite presence in the community required for advocacy, board meetings, and key events. ✓Must operate as an incorporated entity.

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How to Apply

Send your cover letter, professional CV, and references to Indu Bains, Vice-President of the Board indu@bainsco.ca