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About the Role

Big Brothers Big Sisters of Toronto is seeking an exceptional and visionary leader to serve as its next Vice President, Community Investment. This role offers an opportunity for a dynamic relationship-builder and strategic fundraiser to shape the future of a respected youth-serving organization. Reporting to the President & CEO, the Vice President will lead the community investment strategy, driving revenue growth and cultivating partnerships to advance the mission of providing life-changing mentorship to young people.

Responsibilities

Developing and executing a comprehensive fundraising strategy that strengthens annual, major, foundation, corporate, planned, and transformational giving.
Identifying, cultivating, soliciting, and stewarding major philanthropic investors capable of making significant gifts.
Expanding the organization's network by introducing new donors, corporate partners, community leaders, and philanthropic champions.
Building trusted relationships with CEOs, senior executives, foundations, government representatives, and influential community stakeholders.
Leading donor stewardship strategies that deepen engagement and increase long-term investment.
Working closely with the President & CEO, Board of Directors, and volunteer leaders to leverage networks and maximize philanthropic opportunities.
Providing leadership for fundraising events while ensuring the organization continues to diversify revenue beyond special events.
Overseeing the preparation, review, and strategic positioning of major grant proposals, ensuring compelling, evidence-based submissions that align with organizational priorities.
Using data, financial analysis, and performance metrics to evaluate fundraising performance, identify opportunities, and guide strategic decision-making.
Managing and mentoring a high-performing Community Investment team, fostering accountability, collaboration, innovation, and professional growth.
Contributing as an executive leader to organizational planning, budgeting, business operations, and long-term sustainability.

Requirements

A proven record of securing transformational philanthropic investments and cultivating major donors.
Exceptional networking, relationship-building, and business development skills.
Strong executive presence with the confidence to engage senior corporate leaders, philanthropists, foundations, and government partners.
Experience developing and implementing strategic fundraising plans that produce measurable results.
Knowledge of grant development, proposal writing, and funding strategy, including the ability to critically review and strengthen complex funding submissions.
Strong financial acumen and the ability to understand budgets, revenue forecasting, investment strategy, and organizational sustainability.
Outstanding analytical and strategic thinking skills with the ability to translate data into action.
Experience leading, coaching, and developing high-performing teams.
Excellent communication, presentation, negotiation, and storytelling abilities.
The ability to balance strategic leadership with hands-on execution.
A collaborative leadership style grounded in integrity, accountability, and emotional intelligence.
7-10 years of experience in fund development with a strong track record of significant demonstrated success in attracting major gifts at six-figure levels.
Direct experience in the identification and cultivation of new relationships and stewarding of existing donors.
A strategic thinker coupled with front-line fundraising experience generating multiple streams of revenue and strong management and communications experience particularly with monthly giving and annual giving.
Demonstrated experience, and success, in Government, corporation and Foundations grant writing.
Experience leading small to mid-size team and growing departments.
University or college equivalent in fundraising education or a minimum three-year fundraising experience.
Ability to work outside customary business hours during periods leading up to and during major events – includes some weekends and evenings.
Successful vulnerable sector police clearance.

Skills

Relationship-building
Strategic fundraising
Networking
Business development
Grant development
Proposal writing
Financial acumen
Analytical thinking
Strategic thinking
Team leadership
Coaching
Communication
Presentation
Negotiation
Storytelling
Raiser's Edge
Microsoft Office (Word, Excel, PowerPoint and Outlook)

Location

Toronto

Work Type

Full-Time
Permanent

Experience Level

7-10 years of experience in fund development
Experience leading small to mid-size team

Education Level

University or college equivalent in fundraising education

About the Company

Big Brothers Big Sisters of Toronto is one of Canada's oldest and most respected youth-serving organizations.
We believe that an equitable, diverse, and inclusive workplace is essential for innovation and success.
Every investment creates opportunities for young people to build confidence, resilience, and brighter futures through the power of mentorship.

Equal Opportunity

We welcome applications from all qualified individuals, including Indigenous people, persons with disabilities, members of visible minorities, and members of the 2SLGBTQIA+ community, and encourage them to apply.