How Dare2Tri Transformed Bold Vision Into Strategic Action

“PlanPerfect gave us exactly what we needed—a structured framework to break down big ideas into manageable objectives. It’s been transformative for our team’s accountability and engagement.”
– Keri Serota, Executive Director, Dare2Tri

Executive Summary 

Dare2Tri, a nonprofit dedicated to empowering athletes with disabilities, leveraged PlanPerfect’s software platform to bring structure, clarity, and real-time engagement to their strategic planning.

Using PlanPerfect’s premium plan–which combines software with consulting hours–Dare2Tri was able to engage their leadership and board teams, coordinate with their philanthropy consultant, and prepare confidently for an ambitious expansion plan and fundraising campaign.

Client Background 

Dare2Tri, based in Chicago, has spent over 15 years creating athletic opportunities for people with disabilities. Their current strategic focus is on community growth, impact expansion, and organizational sustainability. "This is our third strategic plan in our 15 years," said executive director and cofounder Keri Serota. "But this one is more campaign-like—it’s programmatic expansion, building on all that we have accomplished in the past. It’s very exciting!”

The Challenge 

In past planning cycles, Dare2Tri used a traditional model with an outside consultant. While yielding useful plans, this approach wasn’t a fit for this round. As Serota explained: "The consultant would go and basically come back with a plan. While this was right for us at one part of our history, this time we felt we could do it more internally. We wanted to own more of the work ourselves, but also realized that we wanted to be able to draw on expert assistance when we needed it. We also needed a structured way to manage and track the plan. So, the software provides the building and tracking, and Sophia, as our consultant, was there for us to bounce ideas off of and help guide us best-practice planning steps."

Their pre-planning challenges included:

• Difficulty translating broad expansion goals into detailed, measurable steps.

• Lack of centralized systems for tracking progress and responsibilities.

• Dispersed planning documents with no clear version control.

• Lack of strategic planning expertise to complement the executive director and leadership team’s experience.

• Absence of a user-friendly platform to support tracking and measurement.

The Solution 

PlanPerfect’s software offered the exact structure Dare2Tri needed. What began with large, high-level goals was quickly broken into trackable goals and objectives as well as measurable outcomes through the platform.

"Even taking our big-picture programmatic goals and breaking them into more manageable objectives and measurables and putting in timelines really helped professionalize the process," Serota shared.

Key PlanPerfect features that Dare2Tri used include:

• Goals, Objectives & Metrics Builder – Translated high-level ambitions into structured, time-bound objectives.

• Progress Tracker – Offered quick visibility into task status: completed, in progress, or not yet started.

• Board-Ready Exports – Enabled rapid creation of board materials. "Our comms lead was able to pull from PlanPerfect and build a board PowerPoint in no time."

• Budget Planning – Linked strategic priorities with feasible financial goals. "The budget part felt overwhelming. PlanPerfect’s experienced team gave us a structure for that."

Results 

PlanPerfect’s software directly enabled Dare2Tri to:

• Create Team Ownership: Rather than handing staff a finished plan, the team built it together. "Everyone’s voice wasn’t just heard—it helped shape the plan."

• Improve Donor & Board Confidence: As Serota noted, "One major donor told me, ‘I want to know what you didn’t pursue—that tells me you’ve really thought it through.’ And we had that clarity because of this process."

• Increase Internal Accountability: "Our team is going to be in charge of tracking their programs and projects inside PlanPerfect. That’s a different level of engagement."

• Streamline Operations: "Having it all in one place made our meetings sharper. We knew what was done, what was next, and what was falling behind."

"PlanPerfect gave us structure. I’m not super tech-savvy, but I could figure it out, and the tool made it simple. We wouldn’t want to do this any other way." – Keri Serota, Executive Director, Dare2Tri

Looking Ahead 

Dare2Tri is moving from planning to implementation. As Serota put it, "Now it’s about following the recipe—checking things off, tracking progress, and keeping it up to date."

PlanPerfect will serve as the living dashboard for this next phase, as team members begin logging into the software regularly to update goals and track progress. Most notably, Dare2Tri’s upcoming fundraising campaign will be rooted in the plan housed within the system, helping them connect strategy to narrative to execution.

About PlanPerfect

PlanPerfect is a strategic planning platform built by and for mission-driven leaders. Combining human-centered design with AI-assisted tools, PlanPerfect supports nonprofits in developing, implementing, and tracking strategy—so they can spend less time managing plans and more time creating impact.