Naples software firm uses AI to help nonprofits fundraise, strategize

Bottom line

Key takeaway: Naples software firm PlanPerfect aims to grow its presence in the nonprofit marketplace with a powerful artificial intelligence model. 

Core challenge: Educating clients on the software’s capabilities and ways it can be used. 

What’s next: Company has some 20 clients now, with its eye on reaching 100 by the end of 2025. 

Most nonprofits understand the value and benefits of a strategic plan. Having a document that details the organization’s mission, vision and goals, along with measurable steps for accomplishing objectives, can lead to better fundraising success and ensure everyone involved with the organization is on the same page. 

“You wouldn’t go on a road trip without a map, and you wouldn’t run a business without a plan,” says Naples-based Sophia Shaw, who has 35 years of experience as a nonprofit CEO, trustee, board president, donor, volunteer and consultant. “And it’s the same thing with a nonprofit.”

But for small and mid-size nonprofits, creating a strategic plan can be challenging, time consuming and expensive, especially for those with small staffs and limited resources. That’s where PlanPerfect comes in. 

The firm’s AI-assisted strategic planning software helps simplify the process for small and mid-sized nonprofits. The company was founded in 2024 by Shaw and Miami-based Adam Wolford. They met while Shaw was an adjunct professor of social impact and program director of the Kellogg Board Fellows program at the Kellogg School of Management at Northwestern University and Wolford was a student in the Board Fellows program.

Wolford worked with Shaw on consulting projects for organizations like the Catalina Island Conservancy, and the two spotted an unmet need in the nonprofit sector they could combine their skills and expertise to address. Shaw, 56, has spent her entire career in nonprofits. Wolford, 32, has expertise in technology and business strategy. And their age gap gives them insight into different generational ways of thinking that helps nonprofit executives and board members of all ages understand the software’s ease of use and benefits.

The two see themselves as copilots as a nonprofit creates and executes a strategic plan, which is formulated through an online feedback and review process. “We never thought of this as plugging in your information and all of a sudden you get a strategic plan,” says Wolford. “It was more so, how could we take the knowledge that existed between our two brains and put it into a way that would be scalable for small to mid-size organizations, and then empower them to leverage AI?

“I think the tools that exist today are very powerful, but they’re not contextualized in the nonprofit space and require a lot of technical know-how to get there,” he continues. “So we’ve really thought about what would it look like to take the power of that technology but bring it into the nonprofit sector in a way that felt like it was built for nonprofits.”

Laser-focused

Finding a software developer to help create the product was a big initial challenge. But once they found Minneapolis-based Cloudburst about a year ago, things began to fall into place. By September 2024, PlanPerfect had its first pilot users, and in January 2025 the service began opening up to paid users.

PlanPerfect now has almost 20 nonprofit clients, which include Florida-based organizations like Collier Resource Center, Immokalee Fair Housing Alliance and The Reef Institute as well as nonprofits nationwide like Dare2tri and the Sovereign Native Village of Igiugig in Alaska. Access to the software costs $4,800 per year, or nonprofits can opt for the PlanPerfect Premium plan for $9,600 a year. The plan includes monthly coaching sessions and other guidance.

Immokalee Fair Housing Alliance has made significant progress since its founding seven years ago to create affordable housing for farmworker families and low-income residents of Immokalee, in eastern Collier County. But to build on that success, it needs a strong path forward, especially when it comes to fundraising. “As larger foundations are starting to look at what we’re doing, they want to know, do you have a strategic plan?” says Lisa Casey, vice chairman of the alliance’s board of directors.

The alliance is currently in the process of surveying its strategic planning committee through the PlanPerfect software, with the goal of creating a three- to five-year strategic plan. “We will have a really nice document so that foundations or people looking to invest in Immokalee Fair Housing Alliance will feel comfortable that we’re a legitimate organization who is forward-thinking and is driving toward a plan,” says Casey. “Some of these foundations make very large donations, so people want to make sure they’re giving to an organization that is actually going to come through.”

The Reef Institute is in the middle of a major growth phase, meanwhile, and creating a strategic plan by using PlanPerfect will help the West Palm Beach coral conservation organization remain laser focused on its objectives. “We are at a place where we could pretty easily end up with mission creep,” says Leneita Fix, executive director of The Reef Institute. She adds that “it’s really easy to kind of go sideways into things that are great things but not your mission,” because there is so much that can be done in environmental conservation.

That gives getting a solid strategic plan an even greater sense of urgency. One more factor adding to the urgency? Strategic plans have become even more important for nonprofits today with changes and uncertainty around federal funding in the Trump administration. 

“If you don’t have a plan, if you don’t have a map, then you can’t pivot because you don’t know where you’re going,” says Shaw. “So we’ve seen a lot of interest in what we’re doing now, because it’s more adaptable. If you just have this document that’s in a binder that’s literally on a shelf, then you can’t adapt it because it’s not agile.”

Easy-going

PlanPerfect’s goal is to have 100 customers by the end of 2025. “We want to become the gold standard for strategic planning software, whether that’s direct to the nonprofit or through a consultant,” says Shaw. “Arguably, we’re already there in terms of the product. It’s now getting the number of customers to really build a sustainable business model.”

Shaw and Wolford are connecting with nonprofits through a variety of methods, including social media and offering software demos. And PlanPerfect itself is agile, with the ability to make tweaks and add new features requested by users.

“Everybody knows that they need a strategic plan,” says Shaw. “This is allowing them to feel that it can be easy, it can be fun, it can be rewarding and it can be affordable.”