Tools and tactics for fundraising success in uncertain times

In an uncertain fundraising climate, it comes down to one thing: adaptability. Nonprofits that stay agile, diversify their funding sources, and proactively engage their donors are the ones best positioned to weather uncertainty and grow through it. At FreeWill, we believe that the right mix of technology and strategy can help organizations do just that.

To explore how nonprofits can stay competitive in this new environment, we sat down with two of our in-house experts: Nicole Walton, our Senior Director of Planned and Major Giving Strategy, and Sasha Castroverde, our Senior Product Marketing Manager during our latest strategy showcase. Between them, they bring decades of fundraising experience from organizations like Make-A-Wish ® America, Harvard University, and more!

Nicole and Sasha share how technology, like FreeWill’s Grant Assistant and a renewed focus on donor relationships can help nonprofits work more efficiently, secure hard-to-get funding, and build a more sustainable future.

Q: Sasha, given recent shifts in funding, especially with federal funding freezes, what tips do you have for organizations trying to remain competitive for grants?

“The most important thing I can say is: don’t stop. Keep fundraising. During the 2008–2009 recession, the organizations that paused their fundraising efforts struggled to catch up later. The same rule applies today. Despite the uncertainty, there’s still a lot to be optimistic about, especially when it comes to foundations.

Also, with increased competition, attention to detail is more important than ever. Make sure your proposals are polished and aligned with every single requirement of the grant. You don’t want to spend hours crafting something only to be disqualified over formatting or a minor detail.

Organizations also need to be clear about their impact. What makes your work uniquely powerful? Why are you the best fit to drive change?

And finally, get organized. You might not have the perfect RFP in front of you right now, but when it does appear, you need to be ready. That means having past proposals on hand, a strong internal process for collaboration, and the ability to move quickly.”

Q: How can organizations work more efficiently when it comes to grant writing?

“Time is one of our most precious resources, and that’s where tools like Grant Assistant come in. It's helping grant writers save massive amounts of time while improving the quality of their proposals.

What’s special about Grant Assistant is that it’s trained on over 7,000 winning proposals, so it acts like an expert grant writer added to your team. And unlike general AI tools like ChatGPT, it only uses the information you provide like your past proposals, your tone, your data, so what it generates is super relevant to your organization.

It also continuously checks what you’re writing against the RFP and funder requirements, making sure everything aligns. One customer told me it helps close the "memory gap,” pulling out programs or accomplishments they may have forgotten to mention. It brings clarity and structure to what can otherwise feel overwhelming.

It even includes features like a solicitation summarizer, which boils down a 100-page RFP into a few sentences, and a compliance checker that ensures you’re hitting every “must” and “should” in the grant.”

Q: You mentioned efficiency—how much time are people really saving?

“A lot! We’ve heard from customers that big grants that used to take weeks now take days. Smaller grants that took days now take hours. And in some cases, organizations were able to apply for grants they wouldn’t have had time to pursue otherwise, and they won them. That’s real money going back into their programs.”

Q: One concern people often have with AI is privacy. How does Grant Assistant protect sensitive information?

“Great question. Grant Assistant operates in a completely private, black box environment. Everything you upload stays within your organization’s account. It’s not used to train any models, and even our team can’t access it. That’s important not just for privacy, but also for accuracy. Since the tool only pulls from what you give it, you don’t get the “hallucinations” or irrelevant content you might see with other tools.”

Q: Can Grant Assistant also help organizations discover new grant opportunities?

“Yes! It’s still in beta, but we’ve launched a grant discovery tool called Discover. Traditional search tools are keyword-based, so if the right word isn’t in the listing, you might miss a great fit. Discover uses AI to understand your programs and match you with grants based on that understanding. It's still growing, but early users are already finding it incredibly helpful.”

Q: Nicole, you work with thousands of nonprofits. How are successful organizations adapting to economic uncertainty right now?

“Like Sasha said, the biggest thing is: don’t stop asking. Not everyone is affected equally during tough times, and many donors still want to give, they just need to be approached thoughtfully.

Cultivation, stewardship, and retention are absolutely key. It’s far more cost-effective to retain a donor than to find a new one, so now’s the time to focus on relationships. During COVID, I was leading the planned giving team at Make-A-Wish and worked closely with major gifts as well. The strategies we used then like emphasizing retention, thoughtful communication, and deep stewardship are still what works today.

Also, think about specific funding opportunities. Not all donors want to give to general operations. Can you invite someone to sponsor your gala? Or match donations? Or adopt a program? The more tangible and specific the ask, the easier it is for people to say yes.”

Q: What about donors who might be more impacted financially? How can organizations engage them?

“It’s important to give them new ways to give. Tools like stock giving, crypto, qualified charitable distributions (QCDs), and donor-advised funds (DAFs) let people make a meaningful impact, even if cash feels tight. These methods can diversify your fundraising and reduce vulnerability during uncertain times.”

Q: Legacy giving is often understood by fundraisers, but not always by boards or leadership. Any advice on helping them see its value?

“It’s definitely a challenge because planned giving doesn’t show immediate results. But I always say, ‘Do the work now to be the smartest person in the room five years from now.’ Planned gifts are often 200 times larger than annual gifts. They’re transformational.

For boards and executive directors, emphasize that their job is to ensure the long-term sustainability of the organization. Planned giving is the path to that. And with the right tools, it's easier than ever to market these opportunities with confidence.”

Fundraising may be more challenging than ever—but with the right tools, the right mindset, and the right support, nonprofits can not only survive but thrive. 

At FreeWill, we make it easier for organizations to pursue impactful, often underutilized giving opportunities like appreciated assets or legacy gifts, while also streamlining institutional fundraising through solutions like Grant Assistant.