Development Associate
Reports to: Founder & CEO
Position Status: Independent Contractor
Compensation: $1,500/month
Time Commitment: At least 20 hours per week, with flexibility to adjust hours around major events, deadlines, and organizational needs. A base weekly schedule will be established, with additional flex time used for donor meetings, fundraising events, or urgent grant deadlines.
Contract Start Date: September 1, 2025
Contract Duration: September 2025 - August 2026
JOB SUMMARY
The Development Associate (Contractor) will drive key fundraising, grant, and donor engagement activities to sustain and grow You Matter 2’s mission. This role is ideal for a self-motivated, results-driven professional who can work independently while collaborating effectively with leadership.
The contractor will manage the fundraising pipeline, execute grant submissions, coordinate donor engagement activities, support fundraising events, and execute and modify the organization’s fundraising calendar. The position requires proactive relationship-building, excellent writing skills, strong organizational abilities, and comfort working in a fast-paced, mission-driven environment.
Primary Responsibilities
Fundraising & Development
Qualifications and Education Requirements
Application Requirements:
Organizational Background
Founded in 2014, You Matter 2 provides South Suburban youth and families with opportunities to develop leaders and engage communities through exposure to new experiences, building connections, and highlighting cultural heritage. Each year, You Matter 2 provides over 1,000 youth with holistic, out-of-school support, including afterschool and summer learning programs, and experiential learning through partnerships. The organization is in a transition period, growing to become the go-to youth and community serving organization across the Chicago Southland. Our staff is a diverse collection of passionate individuals, committed to social justice, trauma-informed care, inclusion, equity, and anti-racist ideologies, and helping youth realize their full potential.
Position Status: Independent Contractor
Compensation: $1,500/month
Time Commitment: At least 20 hours per week, with flexibility to adjust hours around major events, deadlines, and organizational needs. A base weekly schedule will be established, with additional flex time used for donor meetings, fundraising events, or urgent grant deadlines.
Contract Start Date: September 1, 2025
Contract Duration: September 2025 - August 2026
JOB SUMMARY
The Development Associate (Contractor) will drive key fundraising, grant, and donor engagement activities to sustain and grow You Matter 2’s mission. This role is ideal for a self-motivated, results-driven professional who can work independently while collaborating effectively with leadership.
The contractor will manage the fundraising pipeline, execute grant submissions, coordinate donor engagement activities, support fundraising events, and execute and modify the organization’s fundraising calendar. The position requires proactive relationship-building, excellent writing skills, strong organizational abilities, and comfort working in a fast-paced, mission-driven environment.
Primary Responsibilities
Fundraising & Development
- Partner with the Founder & CEO to implement a diversified fundraising strategy, including grants, contracts, corporate sponsorships, individual donors, and special events.
- Execute and modify the annual fundraising calendar to align with evolving priorities and opportunities.
- Manage the full grant cycle — research, write, submit, and track grants; ensure timely reporting.
- Support donor cultivation and stewardship through proactive outreach and engagement.
- Lead the coordination of fundraising campaigns (e.g., Gala, Giving Tuesday) and identify one-off revenue opportunities.
- Maintain accurate, up-to-date donor and funder data in the CRM.
- Support planning and execution of signature fundraising events, including vendor and sponsor outreach.
- Manage in-kind giving campaigns with retail, corporate, and community partners.
- Assist in creating marketing materials and social media content to promote events and campaigns.
- Draft and send donor acknowledgments for both in-kind and monetary donations.
- Ensure consistent communication with supporters through email, social media, and other channels.
- Collaborate with the marketing team to align fundraising messaging with the organization’s brand.
- Assist with volunteer event coordination as needed.
- Complete other agreed-upon tasks related to fundraising, communications, and community engagement.
Qualifications and Education Requirements
- Bachelor’s degree preferred; equivalent experience considered.
- At least 2 years of nonprofit development experience, with demonstrated success in fundraising and donor relations.
- Proven grant-writing skills with a successful track record.
- Strong written, verbal, and interpersonal communication skills.
- Highly organized with the ability to manage multiple priorities and meet deadlines.
- Self-starter who thrives in a contractor role with minimal supervision.
- Proficiency in Google Workspace; experience with Salesforce Nonprofit Cloud a plus.
- Social media marketing experience is desirable.
- Knowledge of and connections within the Chicago Southland philanthropic community is a plus.
- Availability to work occasional evenings/weekends for events.
Application Requirements:
- Cover Letter
- Resume
- Names/contact information of three professional references
Organizational Background
Founded in 2014, You Matter 2 provides South Suburban youth and families with opportunities to develop leaders and engage communities through exposure to new experiences, building connections, and highlighting cultural heritage. Each year, You Matter 2 provides over 1,000 youth with holistic, out-of-school support, including afterschool and summer learning programs, and experiential learning through partnerships. The organization is in a transition period, growing to become the go-to youth and community serving organization across the Chicago Southland. Our staff is a diverse collection of passionate individuals, committed to social justice, trauma-informed care, inclusion, equity, and anti-racist ideologies, and helping youth realize their full potential.