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Today, CTOP is one of two major initiatives that Dalio oversees tohelp young people and public education in Connecticut. CTOP investsin helping nonprofits work effectively, reliably, and sustainablyto get young people at risk of dropping out of high school—andthose who have already dropped out—through secondary education andinto satisfying, family-supporting jobs. CTOP supports a smallnumber of grantees with large, unrestricted, multiyear grants andlots of non-financial support. Dalio has come to believe thathelping nonprofits become stronger is key to helping young peoplesucceed in school and life.
Barbara Dalio vividly remembers the meeting when she realized shehad to pivot the Connecticut Opportunity Project (CTOP) to generatepositive outcomes. David Hunter, an experienced consultant onphilanthropic and nonprofit performance, told her that there was noway her giving through CTOP at the time was having a lasting impacton the young people whose lives she wanted to help change. If shewanted to improve their life prospects, he explained, she needed tochange her strategy and provide a whole other level of support.Hearing it was painful. And she knew he was right.
When Dalio first started her education philanthropy more than adecade ago, she felt that Dalio Philanthropies’ significantresources would allow her to achieve anything. She’d visit schools,talk to teachers, understand what their needs were—and fund oneproject after another, from the school library that needed morebooks to the community-based mental health center. “Everything feltimportant. I’d hear about great programs and think, why wouldn’t Ido that?”
But Dalio quickly saw that there are many more educationinitiatives than any one philanthropist can meaningfully support,and she began to learn that saying no to some projects allowed herto focus her efforts in ways that enabled her to have a greaterimpact. She had made changes to her philanthropic approachgradually, and when she met Hunter, his advice about CTOPresonated.
An Initiative of Dalio Education Mission: To invest in and helpstrengthen youth-serving organizations in Connecti- cut so they canwork effectively, reliably, and sustainably with young people ages14 to 22 who are disengaged or discon- nected in order to help themre-engage in and complete secondary education,
then transition successfully to the pursuit of post-secondaryeducation, such as a
technical certification, military enlistment, or an academic degree– with the ultimate
goal that all young people will achieve satisfying employment thatsupports their
agency and self-sufficiency. Location: Connecticut
Year Established: 2017 Staff: 4
2020 Grants: $5M Average Grant Size: $1M
Hands-On Learning
Dalio began her education philanthropy after her four boys weregrown. Her husband, Ray Dalio, had built Bridgewater Associates,the world’s largest hedge fund, and the couple invested part oftheir fortune in founding Dalio Philanthropies in 2003. Thefoundation invests in the family’s home state of Connecticut, andeach family member focuses on grantmaking in areas of specialinterest to them. Dalio’s special interest is supporting strugglinghigh- school-age youth. As a mother, she knows that plenty offactors can make it hard for a teen to succeed, even if that teenhas two parents and the benefit of stable resources. Thecomplexities of poverty and racial inequities make it evenharder.
“I’ve always been hands on,” Dalio says. “That’s how I learn.” Oneof her most cherished early experiences involved volunteering at analternative high school in Norwalk. She
remembers it as “an immersive experience, being so close to thestudents and seeing firsthand how challenging their circumstanceswere.” She firmly believed that the students, who had struggled intraditional school settings, could succeed with sufficient support.Providing that support was expensive, and Dalio’s supporteventually helped to secure significant additional resources forthe school from the State of Connecticut, leading the schoolcommunity to embrace the transfer school model and develop a planfor adopting it.
In a stakeholder meeting at the school, she met Andrew Ferguson,then working on the turnaround of low-performing schools for theConnecticut State Department of Education. Ferguson, who had been apublic school teacher earlier in his career and shared Dalio’spassion for giving every student a great education, would becomeDalio’s first staff member as Dalio Philanthropies’ chief educationofficer in 2014. Together, they started looking for the mosteffective ways to help struggling young people succeed.
Untapped Potential
To improve their understanding of the needs and experiences ofstruggling high-school-age youth and carve out their strategy tohelp, Dalio and Ferguson commissioned a statewide analysis. Theresulting 2016 report Untapped Potential made plain that the scopeof the problem was staggering: One in five Connecticut teens ofhigh-school age—39,000—was disengaged (enrolled, but at riskof
dropping out) or disconnected (not in school, younger than 21, andwithout a high school degree). Without a high school diploma, theprospects of a satisfying job with a living wage areminiscule.
Halfway in, problems became apparent. Not every partnerorganization was serving the most struggling students, yet manymore of the most struggling students needed support. Moreover, manypartner organizations couldn’t produce data to show they weremaking a difference. “We were data-driven, we knew the importanceof data, but this field was different,” Dalio recalls, comparing itwith the school system, where she had more experience. “It washarder to see how much services kids were getting and what happenedto them. We knew instinctively that something was lacking, but wedidn’t know how to address it.”
The youth workers were doing heroic work, but their organizationsfaced complex challenges, and it was about much more than data.They had limited access to the kinds of funding streams and outsideexpertise that could best support them in strengthening theirpractices and systems, and they had to cater to many differentdonors, which sometimes meant deviating from their missions tosecure funds. On top of that, it’s far from easy to help youngpeople who are disengaged or disconnected to succeed.
But understanding the challenges didn’t help Dalio and Fergusonfigure out how to overcome them. “As a funder, we don’t want toforce them to work in certain ways, but we want them to be strong,”Dalio says. “There’s a fine line between having high standards andbeing too controlling.” If there was one thing she didn’t want tobe, it was controlling. She wanted to be supportive. And she wantedpositive outcomes for young people.
As a funder, we don’t want to force them to work in certain ways,but we want them to be strong. There’s a fine line between havinghigh standards and being too controlling.
Barbara Dalio
“ “ From an equity perspective, it was no less alarming. Low-incomeand minority students represented 38% of the state high schoolpopulation—but double that percentage of the young people weredisengaged and disconnected; 15% of students had disabilities orwere English-language learners, but twice that percentage made upthe disengaged and disconnected population.
After crisscrossing the state to learn how others were working withthis group of youth, Dalio and Ferguson launched a statewideinnovation challenge to plant the seeds for the CTOP pilot. Aimingto improve outcomes for as many disengaged and disconnected youthas possible—and help close the achievement gap—they invitedproposals from almost 80 organizations. Nine public and privateorganizations ran programs that met the criteria and were fundedfor a two-year pilot phase, starting in 2017.
Strength From Clarity
Dalio and Ferguson were always looking to learn from the best.Hector Rivera, COO of Our Piece of the Pie (OPP), one of thegrantee partners, recalls that already in the early pilot phase,“Barbara and Andrew would often ask whom they should talk to andwhat we needed.” He suggested they talk to Roca, based in Chelsea,Massachusetts, and added an ask: “I said, ‘We’re missing thesocial-emotional model that Roca is using. I need you to get thatmodel from Roca.’”
Roca, which has had stellar results serving young adults involvedin gangs and the justice system, had adopted—and adapted—CognitiveBehavioral Therapy (CBT), an evidence- based practice traditionallyused in a clinical
setting, for community-based work. While OPP’s population was alittle different, the leadership had no doubt that their existingyouth development model could be strengthened by adding thetargeted CBT component to regulate emotions and build resilience.OPP CEO Enid Rey and her predecessor had tried to get Roca’s CBTmodel for years. But it wasn’t available as a neat package thatcould simply be dropped into another organization without elaboratetraining and coaching. So when Dalio and Ferguson asked what theyneeded, access to Roca’s model was a high priority.
Rivera wasn’t the only one to recommend Roca, and Dalio andFerguson had already visited the organization after therelease
5 Photo courtesy of J. Fiereck Photography
of Untapped Potential. They did so again several times. CEO MollyBaldwin blew Dalio away. “To see how clear and disciplined she is,and how simple her execution is—it was beautiful. Some things thatseem very complex, which I’ve always struggled with, she’s made sosimple.” When Baldwin raved about a Connecticut-based man namedDavid Hunter and credited him with having had an outsized influenceon Roca’s success, Dalio and Ferguson had to meet him.
“We wanted his fresh perspective,” Ferguson says about their firstmeeting in 2018. They got it. In a nutshell, it would take largegrants for general operations rather than ones restricted tospecific programs, and deep non-financial support over the longterm, for nonprofits to overcome systemic barriers to their successand become able to produce outcomes with consistency. And CTOPwould have to build its own capacity to provide it. “David spokethe truth, and he spoke it bluntly. We appreciated that, becausefew people speak truthfully and bluntly to philanthropists.”
Dalio and Ferguson hired Hunter to lead what would become anintense—and deeply emotional—process to develop a new investmentstrategy for CTOP. After one meeting, “It was like having had anexhausting workout, because my brain was working so hard, and Istarted questioning everything we were doing,” Dalio says.
Amanda Olberg, the only one of three current portfolio directorswho was with CTOP at the time, remembers the team’s process ofdeveloping a theory of change as a powerful experience. (Hunter’smethodology is outlined in Working Hard and Working Well.) Havingdeveloped a deep passion for
youth development and education policy as an AmeriCorps VISTAvolunteer, she had just joined CTOP from the position as managingeditor of Education Next, a national journal based at Harvard, andit was a “dive into the deep end to learn so much about programdesign and what it should look like if you want to beeffective.”
Hunter’s relentless drive for discipline stuck with her, and sherecalls how narrowing down the target population was emotionallydifficult for the group. Clarity about whom to serve was importantbecause it would determine how to work to produce results, but italso meant deciding to say no to those who fell outside that group.And six of the nine pilot grantees did.
Developing the new strategy “was like destroying everything andstarting from scratch,” Dalio says. “It was hard, but now I loveit.” The beautiful clarity she craved is spelled out in asophisticated, 32-page Investment Strategy, which is worth a read.Ten social investment principles articulate the investmentphilosophy (see next page). While clarity gave Dalio strength,parting with six grantees she knew and respected wasn’t easy. Shetried to do so thoughtfully, giving them time to plan ahead.
Photo courtesy of Andre Wagner
1. Maintain an ethical duty to do no harm;
2. Invest to create social value above all else; in other words,social investing is not charity;
3. Hold the grantee organization and the investor accountable forcreating social value; the investor (not just the grantee) needs tocontinuously improve in order to create social value;
4. Make investments within a well specified and delimited domainwithin which the specific outcomes and impacts that will count associal value are clearly identified;
5. Make investment decisions based on rigorous selection criteriaand due diligence assessments based on them;
6. Provide long-term, unrestricted capital aligned to performancemetrics for helping organizations build their capacity to delivereffective services reliably and sustainably at high levels ofquality;
7. Track performance and provide non-financial supports to helporganizations succeed in helping people they serve actually improvetheir lives and life prospects;
8. Diminish transaction costs to help organizations stay focused onachieving their missions;
9. Protect investments through restructuring and/or non-financialsupports as needed and stay committed if grantee organizationsdemonstrate the will to create social value so they have the timenecessary to develop the capacity to benefit the people they serve;and
10. Help organizations build reliable revenue streams that willsupport them sustainably at the appropriate level of scale.
The Connecticut Opportunity Project’s
Ten Social Investing Principles
Depth, Duration, and the Performance Imperative
CTOP has three goals for the next 10 years. First, grantees willcreate 2,500 program slots providing disengaged and disconnectedyouth with the quality and dosage of services believed necessary toproduce positive outcomes (as defined by each grantee’s theory ofchange). Second, this work will result in measurable improvementsin “their [participants] re-engaging in and completing secondaryeducation and successful and sustained participation in the labormarket.” And third, because disengaged and disconnected youth aredisproportionately Black and Latinx, CTOP aims to contribute toadvancing ethnic and racial equity through its direct work withgrantees and their resulting outcomes for youth.
The strategy to achieve these goals is a long- term one based, inlarge part, on lessons Hunter learned as director of assessment andknowledge development at the Edna McConnell Clark Foundation (EMCF)in the 2000s. Under the leadership of Michael Bailin and laterNancy Roob, EMCF pioneered an engaged, venture-philanthropyapproach to help the best nonprofits build up their organizations’capacity to deliver outcomes as intended and increase the number ofyoung people they served.
“One of the big things we didn’t know was how underdeveloped theability to manage performance was, even though we were being veryselective,” Hunter says. “We thought the leaders knew how to do it,which seemed reasonable at the time, and
Building on those lessons—and the fact that most local granteeswill be much less advanced—the CTOP investment strategy is longerand deeper. “From the very beginning, we imagined a 10-yearinvestment, with the first five years in each organization yieldingnothing more than organizational capacity in the form of increasedcapacity to manage performance,” Hunter says. “It’s only once youhave that, and you’ve had an implementation evaluation that showsto what degree it’s been successful—and fixed whatever isn’tworking—that can you expect positive youth outcomes. That’s fiveyears into the future.” Only when organizations have theinfrastructure to support continuous improvement will they receivesupport to scale. An exception—one expected to produce outcomesquickly—is the plan to support advanced organizations to replicatewhat CTOP considers proven
From the very beginning, we imagined a 10-year investment, with thefirst five years in each organization yielding nothing more thanorganizational capacity in the form of increased capacity to manageperformance.
David Hunter
“ “
that turned out to be a naïve assumption.” The most successfulinvestments were in the few nonprofits with the best track recordsat the outset. Even then, the amount of capital needed to scale wasfar larger—and the time horizon far longer—than EMCF hadexpected.
programs in Connecticut. The first such grantee was recently addedto the portfolio: Roca will begin running its Young Mothers programin Hartford in mid-2021.
The level of investment and the type of non-financial support ismatched to each grantee’s tier rating, which indicates the level ofrisk that the investment won’t work out as planned (1=highest risk,5=lowest risk). While grants—$1M annually over five years for eachof the current grantees—are unrestricted, they are tied to“performance metrics for helping organizations build their capacityto deliver effective services reliably and sustainability at highlevels of quality,” as expressed in one of the social investingprinciples. The grantees develop these in collaboration with CTOP,and CTOP commits to helping achieve them. The non-financialsupport—from CTOP and external consultants—is valued at nearly $1Mannually for the three grantees.
The conceptual framework for the work, from due diligence tocapacity building,
draws heavily on the Leap Ambassadors Community’s PerformanceImperative. According to Ferguson, it’s “part of our language andmindset, how we organize internal data, systems, and priorities.”The seven pillars of the Performance Imperative are the disciplinesnonprofits must master to become high-performing organizations,ranging from board and executive leadership to externalevaluation.
There are many frameworks out there but, to Ferguson, whatvalidated this one was that “it wasn’t developed in an ivory towerabstractly but came from people who were actually in the fielddoing work that led to good outcomes.” Baldwin and Hunter wereamong the 50+ Leap Ambassadors—nonprofit leaders, funders,consultants, evaluators, academics, and intermediaries—whocollaborated on its content. All had a common passion for improvingoutcomes. As a result, every pillar and principle ties back to thePerformance Imperative’s definition
of high performance as “the ability to deliver—over a prolongedperiod of time— meaningful, measurable and financially sustainableresults for the people or causes the organization is in existenceto serve.” This is precisely what CTOP wants to help granteepartners do.
Tipping Point Community CEO Sam Cobbs, a Leap Ambassador andadvisor to CTOP who reviewed the initial investment strategy, says,“They are being very true to the role of engaged funder or venturephilanthropist.… They make deep investments in terms of dollaramount and investing in the capacity of the full organizationrather than just ‘buying’ programs. This is still pretty rare inthe foundation space.” Georgetown research professor and formerpresident of MDRC Gordon Berlin, who is also a Leap Ambassador andadvisor to the initiative, thinks CTOP may be truer to the role ofengaged funder than any other. “If we are going to improve thissector, we have to have a game plan for continuous improvement, andI view CTOP as one of the most systematic and comprehensiveapproaches to nonprofit improvement and the unique challenges ofscaling an intervention that I’ve seen. It was really designed andstaged to address all seven pillars of the PerformanceImperative.”
Active Service Slots and Other Ways to Measure Progress
Central to CTOP’s philosophy is that funder and grantee shareresponsibility for results. But if outcomes aren’t producedreliably and consistently for five years, how will they knowthey’re on track?
First, each organization can assess progress toward itsorganizational- improvement goals. Using a guide based on thePerformance Practice—which operationalizes the seven pillars of thePerformance Imperative—consultant and Leap Ambassador Ellen Bassassessed each organization’s capacities. OPP’s Rivera, also a LeapAmbassador, was already familiar with the framework, but theprocess was new. COMPASS Youth Collaborative CEO Jackie Santiagodescribed it as “taking an objective view of how the agency isdoing in all these areas. Then you have all that data in front ofyou and you get to make decisions. Nobody was telling us what towork on, just raising tough questions.” The resulting work plan orroadmap for improvement is what Santiago’s refers to as “the biblethat guides the daily work.”
Increased organizational capacity is, in turn, expected to improvea set of key performance indicators—which measure progress towardimproving outcomes—year over year. A unique example is the conceptof active service slots, which Hunter developed in the early 2000s,because he’s no fan of “number of people served”—used inpractically every grant application in the nonprofit sector. Peoplecould be counted as “served” if they only receive services once,but how many times does it take to achieve outcomes? Instead, CTOPlooks at the “number of people from the target population, enrolledin outcome-producing services and getting the right dosage to getthose outcomes,” Hunter explains. “If the number of active serviceslots increases each year, even if the number of people you’reserving remains constant, you’ll be much more likely to get tooutcomes, because you’ll be matching the
Critical Friends
For support on the journey, each grantee has a portfolio director,whose role is very different from that of a typical foundationprogram officer. Olberg, the first CTOP hire and portfolio directorfor Domus Kids, describes it as one of helping the grantees by“being a colleague, providing a second pair of eyes, and sharingthe responsibility for moving the work forward.”
Currently, each portfolio director has only one granteerelationship to manage, and their frequency of contact ishigh—several times a week. There are scheduled meetings
with different leaders of the organization to discuss differentprojects moving forward in parallel and lots of informal contacts.After working in finance with Citigroup, Aimee Rincon switchedcareers to something that was more aligned with her passions:helping under-resourced students access college. She continues thatwork as portfolio director for COMPASS, whose leaders like to useher as a sounding board. “I appreciate being a thought partner withCOMPASS leadership, joining critical conversations around staffingand programming changes,” she says.
The frequent contact is necessary to build the kind of trust thatis the foundation of good working relationships. Adhlere Coffy—whohas a consulting background in aerospace engineering and was laterinvolved in evaluation, data analysis, technology, and capacitybuilding with the many grantees of the Fairfield County CommunityFoundation—is portfolio director for OPP. He thinks the hands-onapproach allows the portfolio directors “to get into the weeds andunderstand what are the right levers to pull for advancing thedevelopment of the organization and making headway in establishingthe relationship, because a lot of the work is about the peoplemore than the processes or system. The people will enable you tohave an impact on the processes and systems.”
There’s one qualification a portfolio director needs to have aboveall: passion for learning. Dalio and Ferguson had little luckfinding a CTOP director, and in mid- 2020, they managed to getHunter out of
retirement to take the job. With Hunter at the helm, Olbergdescribes each meeting as a “professional-development session.”Hunter’s approach to supervision is to “use every discussion ofevery relationship with every grantee as a teachable opportunity tohelp [portfolio directors] learn about the distinction betweenbeing a social investor and a funder who takes over anorganization.”
This is critical, because while the payoff from this work doneright is enormous, so is the fallout if it’s done wrong. “If you godeeply into an organization in a bad way, you can wind up playingtoo big of a role in the organization. And that’s terrible, becauseyou undermine their ability to develop their capacities at thehighest level,” Hunter explains. The relationship can’t be one inwhich grantees keep asking their portfolio directors what to do andthe portfolio directors tell them. The portfolio directors can helpthem see different sides of an issue, identify options for solvinga problem, and be straight when they think the grantee is goingdown the wrong path—but they should never tell them what do to. “Ithas to be a critical friendship relationship, not anI-will-take-over relationship,” Hunter says.
Hunter also wants the portfolio directors to keep increasing theirsubject-matter knowledge. They can act as consultants in someareas. For example, they already call on each other’s expertise andhelp each other’s grantees. But they should also become able to dowhat he can after 30 years in the sector: spot what isn’t workingoutside their areas of expertise, so they can call on an expert tohelp solve the problem when necessary.
Hunter is trying to work himself out of a job—and back intoretirement—after all.
Transformational Theories of Change
The portfolio directors’ capacity-building work is based on eachgrantee’s roadmap for improvement, rooted in the PerformanceImperative, and their organization-wide theory of change forproducing outcomes, also developed during the due-diligenceprocess. For COMPASS, creating a theory of change was atransformational experience. Narrowing down the target populationwas every bit as agonizing as it had been for CTOP. With whom couldthe organization most effectively achieve outcomes?
They concluded that their expertise was working with middle- andhigh-school-age young people (11-18). Though new to the CEO role,Santiago had worked 20 years with COMPASS, and the organization hadalways served children from 5-21. It was hard to let go of theyounger kids. “I kept saying those are the babies; they need us,”she says. “We had to look at ourselves very candidly in the mirrorand ask how well we were doing with that population. We were doingwell in terms of funder requirements, but it wasn’t the best workthat could be done for these kids.” Others could serve the youngestbetter, and COMPASS eventually made sure all the children they nolonger serve had somewhere else to go.
Then they focused all their efforts on their target group of teens.Santiago summarized the theory of change experience likethis:
“We recognized that our duty as a nonprofit is that the youth areprogressing and meeting milestones—and not that COMPASS isexcelling on a grant application or performing to the funder’sneeds. That’s what I think we were doing. It was a powerfulmindshift.”
Domus went through a similarly difficult process to narrow theirtarget population. When the target population changes, programshave to change accordingly. In Executive Director Mike Duggan’stelling, “David said in the beginning, ‘You’re trying to get thesekids to outcomes. Do you think you can do that running charterschools?’ We listed all the reasons why we couldn’t, and he lookedat us and said, ‘Then why are you doing it?’ We had noanswer.”
Domus decided that Hunter was right. They couldn’t achieve whatthey wanted through charter schools, so they got out of thatbusiness and focused on their core programming: tailorededucational opportunities, out-of-school-time programming, andsupport in relation to the justice system.
Building Capacity in Partnership
Rivera describes CTOP’s capacity-building as “the whole caboodle,an environment for improving a nonprofit in its totality.” Thatmeans having a funder involved in all areas of the organization.Given the power imbalance, Berlin asked, “These organizations havebeen around a long time and have something of a track record. I’msure they have room to improve, but is it a partnership, or is itone- sided?”
We asked the grantees: Is it a true partnership? According to allof them, the answer is “yes.” Santiago describes it as a marriage—agood one, with constant communication, information sharing, andtroubleshooting. It’s also hard work and has its ups and downs.Julie DeGennaro, associate executive director at Domus, says, “Mostfunders have the philosophy that ‘I gave you the money, and if youdon’t get to the outcomes, you failed.’ CTOP says, if you failed,we failed, and we don’t want to fail, so what do you need tosucceed?”
She recalls a disagreement about a collaborative project that wouldrequire staff to enter the same data on two platforms: “We got to apoint where I said, ‘I’m not moving forward. … I, as a programperson, am not subjecting my staff to this.’
CTOP circled back, and fixed it. That has rarely been my experiencewith funders in all these years. They do a very good job oflistening. It’s like we’re equals in this, and together we’re goingto get to this point.”
We recognized that our duty as a nonprofit is that the youth areprogressing and meeting milestones—and not that COMPASS isexcelling on a grant application or performing to the funder’sneeds. That’s what I think we were doing. It was a powerfulmindshift.
Jackie Santiago
“ “
Rivera describes the portfolio director’s role like this: “Adhlere[Coffy] is a strategic thinker. He’s taken our expertise and liftedit. He’s helping us take advantage of our strengths.” Enid Reyvalues that CTOP appreciates the need to build internalcompetencies: “I want CTOP strategically embedded in thehigh-leverage, organizational change areas for the agency.” So theydecide together how Coffy can be most productively involved,whether as a facilitator, sounding board, coach, or in some otherrole—always with an eye to staff competency development as the keyto sustaining improvements.
From Coffy’s perspective, the work “isn’t wishy-washy. It’sstructured and guided by the Performance Imperative, and thatallows us to be more effective capacity builders.” It’s alsoholistic. “It’s not just emphasizing one area in a silo and thenanother, but understanding the interaction between the sevenpillars, and how that is the path to meaningful growth andsustainable organizational development,” he says. Using the lens ofthe first pillar, “courageous, adaptive board and executiveleadership,” CTOP prioritized supporting their partners early on inthe often overlooked area of board development, for instance.Because the board can—and should—influence progress in otherpillars.
At OPP, Rey is pleased with the results so far. She knew the boardwanted to support her as the new CEO, but they were struggling withhow to do so. “This process and Pillar 1 have given us anopportunity to figure out how to operationalize all this,” shesays. “It has heightened board members’ awareness of their role andchanged the dynamics.” In
the past, staff reported to the board without much feedback. “Nowwe do formal write- ups and pose specific questions about policy orprogram. We share trends, explain what we see, and tell the boardmembers how they can help. We’re working through the process ofbuilding a high-functioning board at the next level.”
But Rey notes that one important piece needs to be strengthened inthe Performance Imperative (the Leap Ambassadors Community isplanning to do so in its third iteration): “When looking at thepillars, I always wonder where race, ethnicity, and equity fit in.That’s part of leadership and part of performance. What does itmean to be an agency that is diverse, serving youth of color,funded by funders who wield a lot of power in the community—how dothose pieces influence the work?”
Photo courtesy of J. Fiereck Photography
This is something they’ve been able to discuss with Coffy who, inRey’s experience, brings a critical understanding to theirconversations about equity. While representing a funder, he canalso identify with the OPP youth. Born into a Haitian family inBridgeport, he describes himself as a “first-generation American,first- generation college student, growing up in a working poor,single-parent household in a very violent community, exposed toviolence... I feel an almost organic identification with what theyouth face on a daily basis.”
A Delicate Balancing Act
Playing the role of critical friend—without taking over—will alwaysbe a delicate balancing act for portfolio directors. On the onehand, they have to actively manage to milestones that determine acontinuation of the investment. That means stepping right in, asRincon did at COMPASS. “What helped me was the experience asfrontline staff,” she says. “I rolled up my sleeves and said let’sdo this together.”
On the other hand, they aren’t part of the organizations and haveto allow dynamics to play out, give the partners room to learn, andmake decisions in their own ways. That means stepping back withoutbecoming a passive observer, which was an early challenge. “Thatsends signals too,” Rey says. “It makes us wonder, are we beingobserved? What’s happening? Are we on track or not? At OPP, we liketo know. Adhlere engages and helps us move the work forward withoutbeing overbearing or interfering. … He has brought tremendouselasticity to our thinking. He’s an external partner who’s lookingin, even though
he’s sitting at the table with us. He has a certain level ofgravitas with the staff, because he’s built thoserelationships.”
Awareness and empathy also go a long way in an unequal powerrelationship. “They can’t just stop all operations and cater to ourdesire as a funder,” Coffy says. “They still have things they haveto do. They still have staff, who are human beings dealing withCOVID-19, homeschooling, family members, and their own mental andphysical health. It requires a good deal of empathy, and thatempathy has to be manifested in the power dynamic.” That meansunderstanding, for example, that sometimes there will be slow-downs—what matters is positive aggregate development over theyear.
In Coffy’s view, the crux of the issue is this: “Grantees need tostep up, acknowledge, and challenge the power dynamic, andphilanthropy needs to tone it down, take a back seat sometimes, andrealize that our outcomes are entirely dependent on the nonprofitorganization. We are in service to them; they are not in service tous.” And the grantees have stepped up.
Challenging Power Dynamics
“The challenging side has been that relationship building takestime and doesn’t necessarily follow the project timeline,” Reysays. It can be hard to let outsiders in, especially in a role thatinvolves framing issues, asking questions that stretch thinking,and testing assumptions. As a new CEO, she didn’t
want to come in and direct everything. “I was trying to elevate myteam, to let them lead the work ... and create a real environmentwhere, through this process, we were cultivating internalleadership and our ability to step into roles differently. In thatvulnerable situation, we had partners in the discussion. It’s hardto be vulnerable and move the work when you’re sussing things outat the same time. … That mix of us learning and CTOP also findingtheir way was a challenge in the launch.” It took time and practiceto learn what support looked like from each side of thetable.
At Domus, Duggan and DeGennaro feel that, though it’s been adifficult process, they’ve found the balance after openlydiscussing power dynamics. “We’ve had conversations about how tomake this a collaborative effort, as opposed to them just sayingyay or nay,” Duggan says. “It’s much better now, because I thinkwe’ve had the conversation.” DeGennaro sees how hard Olberg and theother portfolio managers work to build a trusting relationship,and, in return, she’s transparent. “If I disagree, they’re askingme to move my position, which I’m unwilling to do, I ask ‘So now,what do we do?’” she explains. “And it’s never been, ‘If you don’tdo that, then you lose the funding.’ It’s been, ‘In the end, it’sDomus’ program and Domus’ decision,’ which I appreciate.”
Rincon tells her partners at COMPASS what she thinks but alsoencourages them to push back. “Through that productive disagreementwe come to the best decisions,” she says. Santiago vividly recallsone of those “productive disagreements.” Among COMPASS staff, aconcern about program
design had been coming up repeatedly: Staff felt that theshort-term outcomes wouldn’t lead to the long-term outcomes. “Ithought by the time they’re in year four, our kids should have thekind of leadership skills that would allow them to advocate at theCapitol in Hartford,” Santiago says. She was confused when Rinconasked if she wanted to change the outcomes in the program model.Because, Rincon said, that kind of leadership skill wasn’t amongthem. “‘We’re not aiming for them to be that successful,’ is what Iheard in my brain,” says Santiago. “It sounded horrible.”
Photo courtesy ofAndre Wagnar
(CBT) model for years? They weren’t the only ones interested.COMPASS had experienced “heartbreak after heartbreak,” inSantiago’s words, and were wondering what they were doing wrong.The teens were doing well, but, after graduating the program, theyweren’t ready after all. One young man with previous justice-systeminvolvement was doing exceptionally well, earning licenses andcertificates, even doing public speaking on COMPASS’ behalf. “In amoment of conflict, to make sure he wasn’t hurt, he went into ahome, got a gun, and shot up into the sky. He was rearrested andgot a lot of time. We thought we had made it with him,” saysSantiago. Making the wrong decision in that one moment changedeverything.
When the young people had to make quick decisions in difficultsituations, they weren’t in control. Some would be disrespectful toan instructor and were returned to the program. Some were expelledfrom school. Some were arrested.
After agreeing to sit in the discomfort for a while, the disconnectbecame clear. Rincon wasn’t saying that the young people didn’tdeserve the best. She was pointing out that COMPASS’ job is to makesure the youth coming in with risk factors make progress and don’treturn to violence. COMPASS is only part of the journey. After fouryears, they should be ready for the next phase with anotherprogram, which—depending on the young people themselves—might helpthem develop that level of leadership skills or go in a completelydifferent direction. “By keeping the old name of the program, weinadvertently kept the old outcome expectations. All we had to dowas align our outcome expectations with all the other changes wehad made,” Santiago says. “I felt so good afterward.”
Thoughts, Emotions, and Behaviors
Remember how Rey and Rivera had asked for Roca’s CognitiveBehavioral Therapy
Photo courtesy of J. Fiereck Photography
One died. When Santiago, who had been fascinated with brain studiesfor years, heard Roca speak about CBT, she thought it was theanswer. “They were talking about executive functioning, the limbicsystem, and how we need a system that is mobile, that can be usedanywhere to help youth ‘press a pause button’ and make betterchoices,” she says.
Impressed with Baldwin’s description of CBT as one of the mostimportant things they had done in Roca’s history, Dalio andFerguson delivered. CTOP partnered with Community Psychiatry PRIDE(Program for Research in Implementation and Dissemination ofEvidence-Based Treatments) at Massachusetts General Hospital, whichhelps community- based organizations employ evidence-basedpractices with youth facing adversity. Founder and director LuanaMarquez had helped Roca adopt CBT with their participants. Roca’sImpact Institute became another partner in providing training andcoaching support.
Thanks to feedback from young people at Roca, the community-adaptedapproach got the friendlier name Thoughts, Emotions, and Behaviors(TEB). Staff of the three grantee partners are trained using anopen-source evidence-based curriculum, which CTOP makes availableon its website, to address emotion dysregulation. Three cohorts ofstaff are being trained and coached for eight months per cohort inhow to apply TEB skills and how to react, encourage, and refocusyoung people when needed. The goal is to learn to “press the pausebutton” and apply skills to make better decisions beforeacting.
At OPP, Rey says, “TEB has given a name for some of the things wedo innately, and it’s given us strategies to perfect how we workwith youth—and with each other.… We have staff who are not in thefirst training cohort who are chomping at the bit to get in. Wecan’t do it fast enough.”
It’s a Lot of Work—For the Right Reason
It won’t surprise anyone to learn that the nonprofit leadersgreatly appreciate the multiyear, unrestricted grants. Berlinwondered whether CTOP would be too demanding of the grantees, but18 months in, it turns out that the non-financial support tops thelist of favorites (along with the dollars).
When reimagining their data systems, OPP needed different supportthan other grantees. As one of the more advanced organizations indata collection, finding recognition for the expertise it alreadyhad and working with CTOP to calibrate its support to OPP’s stageand desire to move to the next level were among the areas of early,joint learning. There have been plenty of challenges for everygrantee, but they insist it’s worthwhile. “If we only had thefunding, I can say with certainty that we couldn’t have doneanything different from what we knew how to do already,” Santiagosays. “We’d be spending money to build capacity only in the waythat we know how. I think we would have been stuck in a rut.” Inthe beginning, for example, she thought buying a new
If we only had the funding, I can say with certainty that wecouldn’t have done anything different from what we knew how to doalready. We’d be spending money to build capacity only in the waythat we know how. I think we would have been stuck in a rut.
Jackie Santiago “ “
building should be a priority for COMPASS. Now, she shakes her headand smiles at the thought. Her perspective is entirelydifferent.
Even when a leader knows what to do, support is key. Domus hadindependently assessed their organization using the PerformancePractice earlier, but Duggan said, “Truth be told, it kind of saton the shelf after that. There are a lot of things you know youshould be doing, but then the day-to- day gets in the way. It washard on our own to drive it forward.” As Rey says, “We forget thatadults and agencies need a supported learning environment to makechange. That has been phenomenal.” Rivera agrees that having astrategic thinking partner has great value: “This has allowed usnot only to assess ourselves against the pillars, but to developstrategies for how to improve across all of them. You couldn’t buythat. Especially for someone to support it resource-wise is justunheard of.”
It’s a lot of work, though. “We almost needed to hire anotherperson just to do the CTOP work,” Duggan says with a laugh. “Whenwe talk about how much work it is, they just say, ‘Yes, you gottaput the work in.’ They’re holding us accountable, and it’s makingus a better organization. But it’s not easy.”
While the workload is heavy, all the grantee partners agree thatthere’s a major difference between doing a lot of work as a CTOPgrantee and doing a lot of work for the average funder. InDeGennaro’s words, “With most funders, you do lot of work for them,and it doesn’t get you anywhere. I never feel like that with CTOP.”Quarterly reporting, for example, includes a cover
digital system shared with the portfolio manager. It isn’t aboutdoing work for CTOP at all, Santiago explains, but about eachorganization building the strength it needs to move as many youngpeople as possible into education, employment, and better lifeprospects. “I don’t feel like it’s CTOP’s demands or expectations;they are my own. It’s not extra work; it’s a support to us in thework. Having funding and guidance through this process is a doublegift. It’s super intensive, but it’s what our agency needs.”
Entering a new paradigm, while other funders are still in the oldcan pose some difficulties. Each of the grantee partners haveseveral other funders. “It would be awesome if CTOP was the solefunder, but they aren’t, so balancing with what the other funderswant is challenging,” DeGennaro says. At COMPASS, they made bigchanges to their program model, and it
When we talk about how much work it is, they just say, ‘Yes, yougotta put the work in.’ They’re holding us accountable, and it’smaking us a better organization. But it’s not easy.
Mike Duggan
“ “
letter summarizing the work, challenges, and areas needingadditional attention, along with the same financials submitted tothe board. Aside from that, progress on the workplan needs to be upto date in the
will take a while before it pays off in better outcomes. Then,funds may be easier to raise, but, in the meantime, Santiago has toconvince funders used to quantity of youth served to support higherquality, intentional work with a smaller number of teens.
Dalio’s passion is plain for all to see, and the grantees know shewon’t lose sight of the end goal. “One of the best parts is thewarmth, care, and participation of Barbara and Andrew, and theirenthusiasm for the work,” Rey says. “It is so unique to have suchgreat access to a funder who is … thinking all the time what couldwe do better, what could we do more of. Funders have the privilegeof distance and Dalio doesn’t act from a place of distance in thatway.”
Challenges and Innovations in Scaling
In pursuit of its goal to create 2,500 program slots providingdisengaged and disconnected young people with the quality anddosage of services needed to produce outcomes, the team hasconducted its first landscape analysis to identify prospectivegrantees. Ferguson sees a funding system that in many ways worksagainst nonprofits’ hard efforts, as the main reason why theuniverse of potential grantees consists of relatively smallorganizations. “In Connecticut, the work isn’t about finding tier 3organizations with 10 to 20 years of good track record and helpingthem become tier 4. It’s all about tiers 1 and 2 (or even pre-tier1) and helping them build capacities over time—and listening andlearning about communities’ unmet needs. In a few cases, we try tohelp by supporting
the replication of high-performing tier 5 nonprofits with greattrack records elsewhere to meet those needs in Connecticut,” hesays, referring to CTOP’s investment-risk tiering system.
That it’s all about identifying lower-tier organizations withpotential became particularly evident in CTOP’s efforts to sourceprospects equitably. Cobbs warned about the need to avoid what hecalls “network bias,” the tendency to search within our ownnetworks. The difficulty doesn’t lie in finding organizations withleaders and staff of color, CTOP found, but
It is so unique to have such great access to a funder who is …thinking all the time what could we do better, what could we domore of. Funders have the privilege of distance and Dalio doesn’tact from a place of distance in that way.
Enid Rey
“ “
rather in choosing to fund them. Because funders have longneglected them, they’re small and have “very little, except anincredible passion for helping the young people in the community dobetter,” Hunter says. From the lens of a traditional funder, theyare likely invisible “because they don’t look like they couldpossibly benefit from an investment. They look too weak, too under-resourced, too fragile,” he says. “These are
very high-risk investments, but if they succeed, the return is thebiggest one you could ever get.” And that makes the risk worthtaking.
For now, Ferguson hopes CTOP can lead by example. In the long term,he says, “The capital streams need to become more robust, sothat
when these organizations become higher performing, they will beable to compete for something.” On the flipside, the fewfoundations that currently aim to fund scaling of effectiveprograms on a national level, like Blue Meridian Partners, have adearth of nonprofits with sufficient capability to choose from.Berlin believes CTOP’s major contribution in the long term could bebuilding a pipeline: “By taking a group of nonprofits that want toget to a really different place, strengthening them over time, andhelping them expand in scale and quality at the same time, theywill build the kind of pipeline that would fit what Blue Meridianwants to invest in.”
Cobbs believes CTOP is doing something else that’s much needed inthe field. Some foundations have helped nonprofits scale programsnationally, but “when we start to talk about equity and proximity,maybe some organizations are so good because they are so locallygrounded. Maybe they don’t want to be in five different states;they just want to be able to serve more people and serve thembetter in the communities they are already in,” he says. “Nobodyhas defined scale at the local or regional level and actually doneit. Maybe CTOP will create the blueprint for what that lookslike.”
Ferguson thinks one of the biggest challenges moving forward willbe to remain focused. “There’s this fierce urgency…. The needs ofyoung people are so high, yet the capacity is so low relative
Photo courtesy of J. Fiereck Photography
to the needs. We want outcomes to be better today, but we realizethat isn’t possible until we help organizations become higherperforming and produce organizational outcomes.” It takesconsistent focus on a long-term strategy and patience because thatstrategy will take time to yield results. “Five to ten years is along time, when people are hurting today,” he says.
It was neither a desire for recognition, nor a need for theimmediate validation that charity brings, that led Dalio andFerguson to social investing. It was humility, exploration,
and never losing sight of the end goal. That, it seems, may also bewhat makes them stay the course. “It was heart-breaking when Davidsaid we weren’t making a difference. I loved and respected all ourgrantees. We cared about their programs, we had relationships withthem. But when David said we had to invest more in eachorganization to change anything, I saw it,” Dalio says, thinkingback to their first meeting. “There’s a saying: ‘When the studentis ready, the teacher appears.’ If I had met David earlier, maybeit wouldn’t have resonated. After 10 years in this work, it madetotal sense.”

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