Fewer Goals, Bigger Growth: Math Circles of Chicago, Enrichment at Scale, and the Strategic Plan Behind It
A Morales Consulting Client Spotlight, featuring Doug O'Roark, Executive Director of Math Circles of Chicago
Math Circles of Chicago (MC2) served 8,600 children last year through single-day math festivals, weekly math circles, and summer camps across the city. Its weekly math circles alone enroll 1,600 students, more than three times the size of the next-largest math circle program in the country. More importantly, MC2 is deliberate about what it is not. The organization does not do tutoring or test prep. Its programs are built on enrichment: spherical geometry, game theory, graph theory, the kind of math that lives outside the standard curriculum and gives children a sense of belonging in the wider community of people who do math.
That scale is recent, and it is not an accident. Since partnering with Morales Consulting in 2024 on its third strategic plan, MC2 has exceeded its annual fundraising goal by 50%, roughly doubled its staff, grown summer camp enrollment by 70% in a single year, and surpassed a West Side equity goal set for 2028 by more than 40%, years ahead of schedule. The organization that once managed a strategic plan of more than 100 milestones now runs on manageable and measurable goals, and it is preparing a hub-and-spoke model to take its work national.
We sat down with Executive Director Doug O'Roark to check in on implementation, talk about what changed when MC2 traded the checklist for clarity, and why he believes a shorter plan is a stronger one.
Tell us about Math Circles of Chicago. You are careful to say MC2 focuses on enrichment, not tutoring. What is the difference, and why does it matter?
We run three levels of programming: single-day math festivals that bring kids and families in the door, weekly math circles that run through the school year, and summer camps. Last year, it added up to 8,600 children, and our weekly circles are now about three times the size of the next-largest math circle program in the country.
The distinction between enrichment and tutoring is fundamental to who we are. We are not reteaching the school day, and we are not test prep. Our kids do spherical geometry, game theory, graph theory: math that is not in the Common Core. When a child gets to explore a problem no one has told them they are behind on, something shifts. They start to feel a sense of belonging in the larger community of people who do math. That is the outcome we are after.
It also shapes our model. Our after-school programs are led by school teachers, which is unusual in this field, and it means the adults guiding the work already know the kids and their communities. Our job is to bring that experience to children and neighborhoods that enrichment programs have historically overlooked.
MC2's first two strategic plans were built in-house, and the second produced more than 100 milestones. What was happening inside the organization when you decided to partner with Morales Consulting on the third?
The first plan worked because I was the organization's only employee, and a plan for one person can live in one person's head. The second plan did not scale. I ended up with a laundry list of more than 100 milestones that took me very far from strategy. Every board meeting became a status update on a checklist that never ended, and I felt like I was constantly failing no matter what the organization actually accomplished.
So for the third plan, we knew we needed professional rigor. But rigor alone was not the deciding factor. Our mission runs through specific communities, and I needed a partner who actually understood them. I had a real sense of trust from the beginning that you knew the communities. You knew different cross-sections of Chicago, whether it was organizations on the Southwest Side or the West Side. You knew the funders working in those communities.
That mattered because MC2 and Morales Consulting were equity-committed from day one. We did not need a consultant to align us on values. The value of the partnership was translating those values into goals with real accountability behind them.
Were there recommendations from Morales Consulting that pushed the organization in a direction that felt uncomfortable at first?
Yes, and the most uncomfortable recommendation turned out to be the most important one: cut. We came in carrying more than 100 milestones, and plenty of them were ideas I was personally attached to. The push from Alberto and the team was to let go of anything we could not measure and were not prepared to be held accountable for. A short list felt like exposure. When you commit to a handful of goals with hard numbers attached, in writing, in front of your board and your funders, there is nowhere to hide.
The same was true of our equity targets. Aspirational language is comfortable. Naming the number is not, because if you name the number, you can miss the number. Morales Consulting pushed us to name it anyway, and that discipline is exactly what has driven our growth since. Looking back, that is what I was actually looking for in a partner, even if I could not have articulated it at the time. A good consultant documents your ambitions. A great partner holds you to them, and that is what this team has done at every step of implementation.
The strategic plan we co-created in 2024 centers on a concise set of specific and measurable goals. What has that changed?
Nearly everything, honestly. Two of the impact goals focus on the children we serve and one focuses on the teachers we develop, and each one is genuinely measurable. We committed to serving 2,100 children a year in our sustained programs, including 1,400 Black or Latino children and 1,400 children from lower-income families. I'm confident every member of my staff, if asked, could tell you what those impact goals are.
That clarity transformed my relationship with the board. The goals never change; only the tactics do. So when a tactic falls short, I no longer walk into a board meeting reporting failure. I come with a new strategy for the same goal. That is a completely different conversation, and a far more honest one.
Before the plan, you wrote grant proposals reactively. Last year, MC2 exceeded its strategic plan fundraising goal by 50%. You describe the plan's effect as a flywheel. Walk us through it.
I used to improvise a tactic for every grant application. Now the goals come first and the proposals follow, and funders can see exactly what their investment moves. Last year we exceeded our fundraising goal by 50%.
That is the first turn of the flywheel. Clear goals made our case easier to make, which attracted more funding. More funding let us hire, and we have roughly doubled our headcount since the plan began. More staff capacity means we hit more goals, and hitting goals strengthens the case for the next round of funding. You can see it in the programs: our summer camps grew from 260 children to 440 in a single year, a 70% increase.
The flywheel runs through our staff culture too. Every staff member's annual goals now tie to the organization's strategic priorities, not just their individual role. One of our program assistants is bilingual and deeply connected to the Southwest community we serve, and her goals around family communication and retention connect directly to our strategic targets even though her role is not classroom-facing. The point is not to critique how someone does their work. It is to support their growth in service of goals the whole organization shares.
The plan sets explicit equity targets tied to geography, race, ethnicity, income, and gender. How are those targets performing, and what happens when a goal misses?
For the most part, we are ahead of schedule. Our West Side growth goal was set for 2028, and we have already exceeded it by more than 40%. Those targets drive concrete decisions, including where we open new program sites. We know exactly which ones we want. That's where the clear targets have really helped, because in reaching the goal there, everything else just follows behind.
And when a goal misses, we recalibrate without drama. Our teacher development goal got ahead of our hiring timeline, so we rewrote it. I do not treat that as failure. If we achieved 100% of our goals, then maybe we weren't ambitious enough.
The plan's influence extends into the boardroom, where MC2 is shifting from an advisory board to a governing board. How did the plan support that transition?
It is what made the transition possible. The board now receives quarterly progress reports tied directly to the plan's goals. It's liberating for me because I know exactly what I'm supposed to report on.
The timing helped as well. Our founding board chair, who served the organization for years, passed the role to a new chair right as the plan took hold. Instead of inheriting years of informal habits, the incoming chair walked into a documented direction on day one. We're sort of losing all the baggage of the way in which the informal board used to operate. Our upcoming board retreat is focused on strategic growth and operational excellence, which is exactly where a governing board should spend its time.
MC2 is preparing to grow beyond Chicago. What does national expansion actually look like, and how does the strategic plan make it possible?
We are running two tracks at once. Internally, we are strengthening the foundation: board governance, evaluation, and standard operating procedures. Externally, we are designing a hub-and-spoke model in which future city partners apply to join under a shared set of equity standards, rather than MC2 recruiting them directly. There is already interest from other cities, including Houston, which has already launched an unaffiliated program based on our model. But it's very dangerous for the organization to expand nationally tomorrow if things rely on me too much. We're doing the hard work now to try and set it up.
Chicago is the first hub and our proof of concept. Houston is likely next. From there, the model is deliberately different from how most organizations grow: cities will come to us through an RFP process and apply to join the network, and every partner will have to meet the same equity standards we hold ourselves to here. We are not going to franchise enthusiasm. We are looking for partners who are as passionate and committed to their communities as we are to ours, because the equity commitments at the center of our plan are non-negotiable, in Chicago or anywhere else.
I want to be direct about what made this conversation possible. Before this plan, national expansion was a dream that lived in my head, and you cannot scale what lives in one person's head. The work with Morales Consulting changed that. It gave us goals we can measure, a board built to govern, and a case that funders trust. What we built together is not just a plan for Chicago. It is the thing we will hand to every city that joins us. Over the next few years, that is how we reach more students and deliver greater impact: the same clear goals, the same equity standards, the same accountability, city by city.
What is your advice to other executive directors beginning a strategic planning process?
My advice to other EDs is simple. Keep your list of goals short and genuinely measurable. If we put too many things into our plan, we'd end up feeling like we're not accountable for anything. It's more powerful to reduce the list and hold ourselves to it.
Fewer Goals, Held Tighter
Morales Consulting is deeply grateful to Doug O'Roark for his time, his candor, and his partnership. What began as a partnership to match MC2's ambition with a plan equal to it has become a shared discipline that touches every part of Math Circles of Chicago, from the classroom to the boardroom to the balance sheet. The impact goals have not changed since the plan was built; only the strategies to reach them have. For an organization preparing to scale nationally while staying rooted in the communities where it began, that kind of clarity is not a planning exercise. It is the foundation everything else gets built on.
Math Circles of Chicago partnered with Morales Consulting on the development of its strategic plan. If you are ready for a strategic plan your team can implement, with goals you can actually measure, contact us for more information.