Director, Major Gifts

Position Title: Director, Major Gifts

Location: Toronto - Hybrid

Reports to: Chief Development Officer

Salary: $105,000-$115,000/ year

Closing Date: August 14, 2025

POSITION DESCRIPTION:

Reporting directly to the Chief Development Officer, the Director, Major Gifts is responsible for leading and executing innovative major gift fundraising strategies that generate transformational philanthropic support for Stella's Place, thereby advancing its mission and building meaningful, lasting relationships with passionate donors and community champions.

This dynamic, senior-level role encompasses strategic donor engagement, creative relationship building, and inspiring team leadership, with a strong emphasis on securing game-changing gifts and partnerships, while managing development staff and thriving in a vibrant, fast-paced organizational environment.

The successful candidate will cultivate and manage a portfolio of major gift donors and prospects, including visionary individuals and impactful foundations, who share our commitment to supporting young adults in living their lives the way they choose.

The ideal candidate is a relationship-building superstar with 5+ years of progressive MG fundraising experience, a proven track record of closing 5 and 6-figure gifts, mature and nuanced team leadership abilities, a talent for navigating complex environments with diverse stakeholders, experience building strong foundation partnerships, an entrepreneurial approach, skills in uncovering compelling prospect opportunities, and exceptional tact and expertise in donor relations and stewardship that turns supporters into lifelong advocates.

RESPONSIBILITIES:

Major Gift Fundraising and Leadership -- 75%

Cultivation, Solicitation and Stewardship:

● Develop and implement comprehensive strategies that identify, engage, cultivate, solicit and steward a pipeline of individual, corporate and foundation prospective donors from all stages of the development cycle as they become MG donors for targets of $1.5M to $2M.

● Oversee an active prospect portfolio of approximately 100-150 major gift prospects, maintaining their records in Raiser’s Edge NXT

● Design and implement identification and qualification strategies for high-capacity prospects and create donor cultivation, moves management, and solicitation opportunities to further major gift development

● Execute across a broad range of solicitations, including securities, life insurance, detailed grants and multi-year gift agreements for transformational gifts

● Prepare compelling and strategic major gift materials, including briefing notes, tailored proposals and presentations, correspondence and gift agreements

Volunteer Management and Partnership:

● Support and manage senior fundraising volunteers by ensuring they are properly oriented to Stella's Place

● Brief and prepare volunteers in advance of any contacts being made with prospects, coaching and partnering with senior volunteers on cultivation, solicitation and stewardship strategies

● Develop and implement customized donor journeys to support donor management and stewardship strategies and activities

Foundation and Corporate Relations:

● Research, qualify and manage relationships with individuals, major foundations and corporate partners for gifts of $50,000+

● Write and prepare major proposals and multi-year partnership agreements

● Meet regularly with foundation program officers, corporate executives, and major individual donors to support the programs and strategic initiatives of Stella's Place

Community Engagement and Strategic Networking:

● Actively lead and attend high-level community events and major donor engagement opportunities

● Cultivate impactful event plans and follow-up engagement opportunities

● Research event attendees in advance and develop sophisticated strategies and executions to build cultivation pipelines.

● Brief senior leadership and volunteers with comprehensive briefing notes and follow-up plans

● Collaborate with the Chief Development Officer to create strategy and lead the execution of major gift cultivation and stewardship plans

● Partner with and mentor other fundraising channels to execute comprehensive revenue generation strategies focused on Stella's Place priorities

Planning, Administration and Team Leadership: (25%) Strategic Planning:

● Collaborate with the Chief Development Officer to set annual and long-term major gift revenue plans and goals

● Self-monitor to meet or exceed fundraising activity metrics (annual and long-term)

● Provide supervision and mentorship to the team of Development Officers, including Annual Campaigns, and directly oversee Mid-Level Giving

Database Management and Reporting:

● Maintain accurate records in Raiser's Edge NXT, including meeting notes, gift agreements, moves/action items and call reports

● Write and submit customized impact reports for major donors

● Participate and often lead donor and other organizational events

Team Collaboration:

● Manage direct reports in strategy, goal setting and execution

● Participate actively as a member of an integrated development team; engage positively with other stakeholder groups and cultivate strong professional relationships with members of other departments

● Stay informed on Stella's Place projects and strategic initiatives to effectively discuss them with donors and prospects

● Assist in other duties as assigned in advancing the goals of the development team and Stella's Place

QUALIFICATIONS:

Required Experience:

● Minimum of 5 years of progressive experience in Major Gift fundraising with a demonstrated track record of closing 5 and 6-figure gifts required

● Experience with campaign fundraising in the healthcare or social service sector is helpful

● Proven track record of cultivating and securing major gifts of $50,000+

● Mature experience in team-building and managing direct-report relationships

● Strong understanding of Raiser's Edge NXT or equivalent donor/CRM database; proficiency with Raiser's Edge is preferred, experience with DonorPerfect is an asset

Essential Skills:

● Extremely effective interpersonal skills with a professional presence and manner, and capable of exercising independent judgment, initiative, and flexibility

● Demonstrated ability to think strategically, work proactively, and manage competing priorities in a complex and evolving environment

● Excellent organization, planning and time management skills combined with a strong attention to detail

● Superb critical and analytical thinking, decision-making and problem-solving skills with an ability to tell a story through metrics

● Excellent oral and written skills with a demonstrated ability to write effectively and persuasively, and present to diverse groups

● Experience with public speaking/presentations is an asset

● Strong computer skills, including experience with Google Docs and online applications

● The ability to conduct high-level discovery calls and sophisticated donor meetings

● The ability to structure complex financial gifts for sophisticated funders

● Strategic thinker and exceptional listener, genuinely interested in others

● Qualities of integrity, credibility, and dedication to the mission of Stella's Place

● Effectively uses empathy in interactions with others

● Knowledge of relationship building, major gift fundraising and stewardship is essential

PREFERENCE will be given to candidates with:

Education and Certifications:

● A university degree or college diploma in fundraising, or a related field, OR 5+ years' experience in a major gift role

● Gift Planning courses and/or a CFRE designation are an asset

Additional Preferred Qualifications:

● Experience developing and implementing major gift and campaign strategies

● Interest in or lived experience in supporting young adults and/or mental health

● Experience working with diverse populations/equity-deserving groups

● Existing experience managing and mentoring development staff

● Knowledge of the Google operating system and the Google suite of tools

● Knowledge of Microsoft Office -- Word, Excel, and PowerPoint

WORKPLACE, HOURS & REPORTING:

Stella's Place is an innovative, award-winning, designed facility located in the vibrant neighbourhood of Queen West and Bathurst. Regular communication, coaching, mentoring, personal and professional development, and evaluation will take place with the Chief Development Officer and you will be offering the same to direct report(s).

This is a full-time, hybrid, senior leadership position working 35+ hours per week, Monday to Friday, including 3 in-office days per week.

As a key leader of the development team, occasional weekend and evening work will be required based on

events, donor needs, and strategic initiatives.

SALARY & BENEFITS:

$105,000-$115,000/ year - commensurate with experience

Stella's Place offers a competitive annual salary commensurate with experience and professional development for your career growth. We offer a comprehensive rewards package including medical, dental and vision health benefits, which start immediately.

Stella's Place offers 3 weeks of vacation and 15 health days in year one, increasing to 4 weeks of vacation in year two.

DIVERSITY, EQUITY, AND ACCOMMODATION:

Stella's Place is committed to having a workforce that reflects the diversity of the City of Toronto, in general, and of our participants, in particular. We encourage applications from racialized persons, Indigenous persons, persons of diverse sexual orientation, gender identity and gender expression and all those who can provide and contribute to the diversification of perspectives at Stella's Place.

Stella's Place is committed to hiring practices that are inclusive and barrier-free. Stella's Place commits to support persons with disabilities to apply and will provide reasonable and appropriate accommodation during all stages of the hiring process in accordance with the Ontario Human Rights Code to ensure the equal and fair assessment of all job applicants. Applicants are asked to make any accommodation request in advance.

Please submit a cover letter and CV to apply.