Vice President of Community Investment

 

Vice President, Community Investment

Position Title: Vice President of Community Investment

Employment Type: Full-Time (35 hours per week), Permanent 

Executive Candidate Profile

The Opportunity

Big Brothers Big Sisters of Toronto is seeking an exceptional and visionary leader to serve as its next Vice President, Community Investment. This is an opportunity for a dynamic relationship-builder and strategic fundraiser to help shape the future of one of Canada's oldest and most respected youth-serving organizations.

Reporting directly to the President & CEO and serving as a member of the Executive Leadership Team, the Vice President will lead the organization's community investment strategy, driving sustainable revenue growth while cultivating meaningful partnerships that advance the mission of ensuring more young people have access to life-changing mentorship.

This role requires far more than an accomplished fundraiser. We are seeking a leader who is equally comfortable in a boardroom, a corporate office, a philanthropic foundation, or a community gathering: someone who naturally builds trust, inspires confidence, and creates lasting relationships that translate into long-term investment and impact.

Who You Are

• You are an energetic, charismatic, and highly engaging executive with a passion for people and purpose. Your ability to connect authentically with individuals from diverse backgrounds allows you to build relationships that create meaningful opportunities for investment and collaboration.
• You possess an entrepreneurial mindset and thrive in environments where innovation, strategic thinking, and execution intersect. You understand that philanthropy is ultimately about relationships, trust, and demonstrating measurable impact.
• You are equally motivated by financial sustainability and social impact, recognizing that strong organizations require both mission-driven leadership and sound business practices.
• You have a deep appreciation for equity, inclusion, and the lived experiences of marginalized communities, and you are inspired by the opportunity to create pathways that improve outcomes for young people.

What You Will Lead

The Vice President will provide strategic leadership across all areas of community investment, including:

• 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.

What You Bring

The successful candidate will demonstrate:

• 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.

Personal Characteristics

The ideal candidate is:

• Dynamic, energetic, and inspiring.
• Naturally curious and entrepreneurial.
• A skilled connector who opens doors and creates opportunities.
• Confident without ego and influential without being overbearing.
• Highly organized and results-oriented.
• High level of professionalism
• Comfortable navigating ambiguity and leading change.
• Passionate about youth, mentorship, and creating equitable opportunities.
• A relationship-first leader who believes trust is the foundation of philanthropy.
• Resilient, optimistic, and motivated by achieving ambitious goals.

Why This Role Matters

• At Big Brothers Big Sisters of Toronto, every investment creates opportunities for young people to build confidence, resilience, and brighter futures through the power of mentorship.
• The Vice President, Community Investment will play a pivotal role in ensuring the organization has the financial strength, partnerships, and community support required to expand its impact for generations to come.
• This is an opportunity to build something meaningful to mobilize philanthropy, strengthen communities, and help transform the lives of thousands of young people across Toronto.

 

Job Qualifications & Skills:

• 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
• Knowledge and practical usage of Raiser’s Edge is a strong asset
• Superior written and oral communication skills
• Ability to work outside customary business hours during periods leading up to and during major events – includes some weekends and evenings
• Strong knowledge and practical usage of Microsoft Office (Work, Excel, PowerPoint and Outlook
• Successful vulnerable sector police clearance

 

BBBST does not use AI to screen, assess, or select applicants. The posting will be live until the position is filled, or until a candidate has been identified. We thank all applicants for your interest. Only those selected for an interview will be contacted.

 

At Big Brothers Big Sisters of Toronto, we believe that an equitable, diverse, and inclusive workplace is essential for innovation and success. 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.