The Pennywise Foundation

The Pennywise Foundation

Nonprofit

The Pennywise Foundation

The Pennywise Foundation is a Vermont-based grantmaking foundation supporting innovative, grassroots solutions to global problems. From voting rights initiatives to community-led development, Pennywise backs small organisations that leverage limited resources into outsized impact, and helps donors give with confidence through rigorous vetting.

Client
The Pennywise Foundation

Sector
Nonprofit

Duration
4 weeks


Project Overview

We delivered a complete Squarespace rebuild of pennywise.org, including homepage design, wider site build, two revision rounds and full handover, alongside an operational toolset: Squarespace Payments for donations, a QuickBooks Online integration for clean bookkeeping, Weglot for multilingual visitors and Email Campaigns for donor communications. The first homepage concept was in front of the client within the first week, and the whole project ran from kick-off to handover in around four weeks.

The Pennywise Foundation
The Pennywise Foundation

Our approach

We designed the site to put grantees and outcomes front and centre, communicating the foundation's impact clearly to donors while keeping the platform simple enough for a small team to run entirely in-house. Just as important was what sits underneath: by integrating payments, accounting and email into one stack, we removed the administrative friction that quietly eats nonprofit hours. Pennywise now has a website that works as hard as its grantees do, in more than one language, with a back office to match.

 
The Pennywise Foundation
Sam Crawford

by Crawford is led by Sam Crawford, a multi-award-winning Squarespace website designer with 700+ sites launched for clients in over 30 countries. He builds fast, mobile-friendly Squarespace 7.1 websites designed for SEO, clear structure, and conversion.

As a Squarespace Expert, Enterprise Partner, Circle Member, and community speaker, Sam is known for pushing the platform’s limits. With 200+ reviews, clients highlight by Crawford’s clarity, precision, and real-world results like higher rankings and stronger lead generation.

https://bycrawford.com
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