When residents at Presidential Towers in Chicago go to pay their rent through the online portal this month, they’ll see a new option before they submit the payment – a drop-down menu with optional donation amounts for a local charity.
Chicago-based Waterton, a multifamily investor and operator, launched this new program in late July after the concept was submitted through the company’s new Innovation Portal, where its 2,000 employees can suggest ideas to benefit the company and its communities.

“This practice has been a success in the retail sector, with shoppers encouraged to make a charitable donation at checkout, so we thought, ‘Why not take this same model and apply it to our own industry?’” says Holly Jacobson, general manager of Presidential Towers.
Presidential Towers is Waterton’s first property to initiate the program, which is currently benefitting Cara, a Chicago-based non-profit providing job training and placement services to individuals affected by homelessness and poverty. When residents log into their online portal, the Cara logo and a description of its mission, history, and impact are listed alongside a drop-down menu with optional donations starting at just $1.
As Presidential Towers is the largest rental community in Chicago with 2,346 units, a $1 donation from each resident every month could make a sizable contribution to the organization. Waterton CEO and co-founder David Schwartz says that if every resident donated $1 a month for a year, it could help roughly 100 students complete Cara’s foundational training. Waterton will also match the first $5,000 in resident contributions.

Waterton has been actively supporting Cara for six years, through hosting professional development activities, like mock interviews. The company hopes this charitable donation platform will open doors for residents to become actively involved with the organization as well. Waterton has also hosted Cara representatives at one of its recent outdoor resident events so they could introduce themselves and ask questions about the organization. Jacobson says she plans to host a work-appropriate clothing drive, as well as a holiday bazaar in December, to benefit Cara recipients.
“We are working to make this a well-rounded partnership that provides support for Cara on all levels, not just monetarily. Given that Cara’s offices are in our backyard, we hope residents will find it easy and meaningful to get involved in whatever way works best for them,” says Jacobson.
Piloting the donation platform at Presidential Towers was also an easy pick for Waterton as it already has a long standing commitment to charitable giving. In past years, staff and residents have participated in toy and book drives benefitting organizations like Toys for Tots and Open Books, and the community is the longtime site sponsor of the American Lung Association in Greater Chicago’s annual “Fight for Air” stair climb, which has raised nearly $3 million since the first Presidential Towers climb in 2009.
“Building connections between residents and local charities helps cultivate a sense of pride within the community. Providing opportunities for our residents to engage with these causes not only benefits the overall community, but also helps residents feel more at home at our properties,” says Schwartz, who says Waterton hopes to emulate this type of engagement at more properties.