Senior Specialist, Grants and Donor Stewardsh

Windmill Microlending•Toronto, ON

3d•CA$70,000 - CA$80,000•Hybrid

About The Position

Windmill Microlending is a registered Canadian charity that empowers skilled immigrants and refugees by offering affordable loans, coaching and mentorship to restart their careers in Canada. Since 2005, we have provided over 15,000 loans, helping newcomers triple their incomes. We are proud to be Great Place to Work certified, boasting an 85%+ average employee engagement score driven by a culture of inclusivity, exceptional teamwork and strong leadership. The role: Windmill Microlending is seeking a highly skilled, and results-driven Senior Specialist, Grants and Donor Stewardship to join our national Development team. Reporting to the National Director, Philanthropy and Campaigns, this role operates at the critical intersection of high-stakes fundraising, complex corporate/institutional compliance, and impact storytelling. The successful candidate will serve as the lead writer for major proposals, complex institutional grant reporting, and advanced donor journeys. Acting as a critical partner to senior development staff, you will manage complex project work, execute deep prospect research, and design sophisticated stewardship frameworks that protect and grow Windmill’s philanthropic revenue.

Requirements

Proven track record of drafting successful proposals for multi-year investments of $10,000 to $500,000
Proven track record of creating and managing stewardship reports for multi-year investments.
Superb written communication skills in English, with an ability to distill complex socioeconomic data into moving, logical cases for support.
Methodical project-management skills with strict adherence to deadlines.
Familiarity with and commitment to the donor cycle and the processes associated with guiding prospective supporters to give and renew their giving.
Goal-oriented self-starter, driven and motivated to meet and exceed targets.
Ability to craft compelling cases for support that resonate with diverse stakeholders.
Ability to analyze donor trends, measure fundraising effectiveness, and adapt strategies accordingly.
Excellent written and verbal communication in English.
Flexible and team-oriented, taking pride in setting others up for success and meeting new challenges and change with positivity.
Collaborative, values-driven and results-oriented.
Bachelor’s Degree or equivalent education/experience
Minimum of 4–5 years of progressive experience in a fund development role, with a strong emphasis on grant/proposal writing, prospect research, and major gift stewardship.
Experience in stakeholder engagement within the nonprofit, corporate, or public sectors
Intermediate to advanced Google Workspace skills (Gmail, Drive, Gemini, Docs, Sheets, Calendar)

Nice To Haves

Understanding of innovative non-profit funding models, corporate social responsibility (CSR) priorities, or social finance is highly desirable.
Bilingualism in French is an asset.
Experience with donor-advised funds, planned giving, and capital campaigns
Knowledge of Salesforce software preferred

Responsibilities

Draft, edit, and project-manage complex, high-quality proposals, business cases, and customized funding applications for foundations, corporations, and government funders.
Lead the creation of intricate, customized impact and financial reports for major donors ($10K+), private funders, and institutional partners, translating data into compelling narratives.
Collaborate closely with program, finance, and client success teams to gather, verify, and accurately report on outcomes, complex budgets, and impact data.
Build and maintain a sophisticated, centralized repository of standardized language, case studies, metrics, and outcomes to optimize proposal and reporting efficiency.
Rigorously track complex reporting obligations and milestones to ensure 100% timely submission of all deliverables.
Design, implement, and optimize a comprehensive donor recognition and stewardship strategy aimed at increasing retention and donor lifetime value across major gift and corporate portfolios.
Develop and evaluate structured, high-touch stewardship journeys for corporate partners, foundations, and leadership donors.
Partner with the marketing and communications team to capture client success stories and elevate high-impact donors across digital channels and stewardship materials.
Support senior development staff by using research tools to identify, vet, and profile potential new individual, foundation, and corporate prospects.
Align research and proposal development with Windmill's diverse priorities, identifying prospects with an interest or linkage to operating needs, capital campaigns, or the Community Bond program.
Maintain meticulous records within Salesforce, tracking donor engagement metrics, reporting requirements, and moves management timelines.
Audit and recommend system enhancements to improve donor experience data, segmentation strategies, and overall fundraising effectiveness.