Some organizations exist to hit revenue targets. Others exist to change what's possible for a kid who needs a shot.
Step Up For Students is the second kind. Since 2001, they've funded scholarships for lower- to middle-income families, students with unique abilities, students who've experienced bullying or violence, and students who struggle with reading. Today, they serve more than 500,000 students across six scholarship programs in Florida alone, a scale that would have been hard to imagine when the organization launched.
When the mission is that concrete, it raises the stakes on everything, including how you manage the work behind it.
The Problem With Growing Fast
Rapid growth is a good problem to have. It's still a problem.
As Step Up For Students scaled, their IT department managed an increasingly complex project portfolio across Microsoft Project and Excel. Getting information into a format that leadership could actually use required hours of manual effort. Resource management was a constant challenge. While they had a strategy platform in place, it wasn't user-friendly and didn't give anyone a clear picture of whether the work being done was advancing the mission.
That last part mattered most. The team didn't just want better project tracking. They wanted to map every project to the organization's objectives and measure progress against them. To know, at any given moment, that the work they were investing in was the work that would deliver the most value to the students they serve.
As Craig Gonsalves, then Vice President of the Enterprise PMO, described it: "It is very difficult to find information, and we are unable to easily and effectively visualize our OKR hierarchy, which limits our perspective greatly. Furthermore, it and many other strategic platforms do not connect OKRs to projects or other smaller pieces of work."
That gap between strategy and execution is one of the most common challenges we see in education and mission-driven organizations. The tools exist to manage tasks. Connecting those tasks to the goals that actually matter is a different problem entirely.
Finding the Right Fit
Step Up For Students knew what they needed: a platform that could handle project, portfolio, and resource management while giving them a flexible way to manage Objectives and Key Results, without requiring a dedicated development team to configure and maintain it.
As a nonprofit, budget was also a key consideration. When we introduced Broadcom's Clarity platform, it checked nearly every box. We worked with Step Up For Students to structure an approach that fit the organization's current state, starting with a focused implementation and a clear path to scale as adoption grew and value was realized. The goal was to lower the barrier to entry without limiting what was possible down the road.
Gonsalves noted: "During the [Clarity] demos, it became clear that the flexibility of Clarity would allow us to customize and extend its capability to effectively connect 'Objectives to Outcomes' and allow us to gain a full perspective of our strategic execution."
Building It Right
Our QuickStart Implementation got Step Up For Students operational quickly, covering project management with financial tracking, status reporting, and risk and issue management, along with resource management, roadmapping, and hierarchies.
The OKR layer came next. Broadcom had a framework within ValueOps, but it needed to be tailored to how Step Up For Students actually worked. We built it out together with Broadcom, incorporating Imperatives into the standard OKR structure so that every project could map to a Key Result, which rolled up to an Objective, which tied to a strategic Imperative set by leadership. The solution also brought risk management up to the Objective and Key Result levels and enabled financial roll-up, allowing the team to analyze costs by strategic priority, not just by project.
From there, we introduced additional phases and OKR-specific enhancements incrementally to support adoption without overwhelming the team.
What It Looks Like Now
The shift wasn't just operational. It changed how the organization thinks about its work.
Every project is now explicitly tied to strategic outcomes. Progress against OKRs is visible and measurable. Risks and issues are identified and addressed earlier. Roadmaps reflect true organizational priorities. And what used to require hours of manual compilation is available with a click.
The growth in platform adoption tells its own story. A platform that launched with around 50 users now supports more than 500 users across the organization, reflecting how deeply the solution has taken hold and how much the team has continued to build on it over time.
Gonsalves reflected: "Winmill PPM has been the conduit to our digital transformation success in this space. Their approach, patience, and expertise have shone as they expertly guided us through our launch. Their cautious approach and thoughtful design of the system provide a testament to the professionalism, experience, and work they do. I am so glad they are our partners."
The Bigger Picture
Step Up For Students is a reminder that sophisticated portfolio management and strategy execution aren't reserved for large enterprise IT shops. Education organizations, nonprofits, and institutions managing complex portfolios of programs and initiatives on stretched budgets face the same challenge: ensuring the work being done is the work that matters.
The right tools, implemented the right way, make that possible.
If your organization is managing more than your current tools can handle, or struggling to show leadership how projects connect to the goals that matter most, we'd like to talk.
