Grant Writer (Contract-to-Hire)

Title: Part-Time Grant Writer (Contract, Remote) — 20 hrs/week for 12 weeks, path to hire

Compensation: $30–$35/hour (W-9 contractor) + $250 milestone bonus upon completing all 90-day deliverables (see below)

Reports to: Executive Director | Start: late October/early November (flexible)

About Winning Ways, Inc.

Winning Ways (Branford, CT) empowers people impacted by incarceration and recovery through trauma-informed, family-centered programs in financial literacy, employment readiness, digital skills, and expressive arts. We help individuals rebuild stability and thrive.

Role Summary

You’ll own prospecting, proposal drafting, and light systems-building to expand our grants pipeline. You’ll turn program info into clear, funder-ready narratives and set us up with simple tracking so we can sustain growth after the contract.

What you’ll do (20 hrs/week)

• Research values-aligned public/private funders; build a prioritized prospect list.
• Maintain a grant calendar (deadlines, LOIs, submissions, reports).
• Draft LOIs/proposals, budgets, and boilerplates (org overview, program blurbs, budget narrative).
• Stand up a lightweight tracking system (Google Sheets or Airtable) + simple weekly report.
• Collaborate with ED/program leads to gather data, stories, outcomes, and budget inputs.
• Provide weekly updates: what was submitted, what’s in draft, what’s next.

90-Day Deliverables (contract success = eligible for extension/FT)

• Prospect list: 30+ qualified opportunities with due dates, $ range, fit notes.
• Calendar live + shared; all deadlines through the next 6 months entered.
• Boilerplates: org overview (350–500 words), 2 program descriptions (Spit & Paint™, Money Talk™) + standard budget narrative.
• Submissions: 6–9 total (mix of LOIs/proposals), with at least $150k–$300k in total asks.
• Tracking & reporting: one dashboard (Sheet/Airtable) + weekly one-pager update template.

Qualifications

• 2–4+ years professional grant writing with closed awards (please include examples).
• Excellent writing/editing; can translate program info into outcomes-focused cases for support.
• Organized, deadline-driven; comfortable managing multiple submissions.
• Systems thinker: can set up a simple, durable grants tracker for a small team.
• Familiarity with CT funders and/or justice-impacted communities is a plus, not required.
• Tools you’ve used (any): Google Workspace, Airtable/Sheets, Instrumentl/GrantStation, Foundation Directory, Asana/Trello.

Contract & Work Setup

• Type: 1099 contractor; you provide your own equipment and set your work hours.
• Collab: Weekly 30-min check-in; async via email/Drive.
• Location: Remote.

How to Apply (rolling)

Email kevin@winningwaysct.org with subject “Grant Writer — [Your Name]” and include:

1. Resume
2. Short cover note (≤250 words) with a 12-week plan for the deliverables above
3. Two writing samples (≤3 pages each; excerpts fine; redact as needed)
4. One reference (name, role, email) we may contact

EEO

Winning Ways is an equal opportunity employer. We value lived experience and welcome applicants from communities we serve, including those with justice involvement.

Confidentiality & IP

All work created under this contract is owned by Winning Ways; an NDA and IP assignment will be required upon engagement.

• Fully remote with flexible schedule (set your own hours around deadlines).
• Weekly 30-minute check-in/mentorship with the Executive Director.
• Access to our grant research tools and shared knowledge base (templates, past proposals, budgets).
• Mission-driven work with a trauma-informed, justice-focused nonprofit.

If converted to full-time:

• Eligible for a competitive salary, paid time off, paid holidays, and a benefits package (details provided at offer stage).
• Professional development opportunities aligned to fundraising and nonprofit leadership.