Winning Ways is hiring : Grant Writer (Contract-to-Hire) in Branford

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)

Qualifications

Contract & Work Setup

How to Apply (rolling)

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

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.