How the LeadBoston community helped one alum connect affordable housing residents to essential services

Trevor alumni profile

When Trevor Samios, LeadBoston alum of the Class of 2019, and his team at WinnCompanies recognized how complicated it was for many residents at their company’s mixed-income properties to access the services they needed, Trevor set out to find a better way to connect residents with available resources as part of his LeadBoston leadership commitment. Trevor’s fellow LeadBoston alums assisted him on his leadership commitment by contributing to an online portal, Connect by WinnCompanies, which helps affordable housing employees and their residents find social services available to them, such as housing, legal, and education assistance.  

LeadBoston, YW Boston’s inclusive leadership program, connects leaders with the networks they need to drive equitable change. Toward the end of the 11-month program, LeadBoston participants reflect on what they have learned and what resources they have access to, and commit to an action plan furthering equity and inclusion in their workplace, which LeadBoston participants refer to as their Leadership Commitment. The Leadership Commitments they develop utilize their new knowledge and connections into creating direct equitable change. Trevor committed to strengthening the newly built Connect platform with the support of others in the program. By working with his fellow LeadBoston alums, Trevor received critical feedback on the design of the portal and expanded the number of services available. We recently spoke with Trevor to learn about his LeadBoston experience and its impact on his work and leadership.

At WinnCompanies, Trevor incorporates six key areas of equity into his work with affordable housing residents.

Trevor Samios serves as the Vice President of Connected Communities at WinnCompanies, “a family owned and operated affordable and mixed-income housing development group and property management company.” As he described, the “bread and butter” of their work has always been providing affordable housing, of which they are the largest provider in the nation. In his role, he leads the company’s resident services across the United States. He stated, his team “develops programs that exist within housing itself and then connects residents to resources based on what they might need or be interested in in that moment for themselves or their family.”

He explained that WinnCompanies’ Connected Communities department is “unique in housing in that we are not a human service organization: we are not healthcare; we are not a workforce development agency; but we dabble in a lot of that.” Essentially, they seek to support families in affordable housing to ensure that as their rent increases in tandem with their income, they don’t lose out on their savings or the programs available to them. His team focuses on connecting residents with six key areas: housing, healthcare, employment, economic mobility, community engagement, and education. In doing so, he said, his team “show[s] that when you invest in those types of programs and services that are community-based, they lead to better outcomes in health, employment, youth development and more broadly, for the economics of the City at large. Ultimately though, and most importantly, they lead to better outcomes for the folks who call our communities home.”

In a new position and a new city, LeadBoston provided him an opportunity to learn about Boston and connect with community leaders.

When Trevor applied to LeadBoston, he had recently started in a new role in WinnCompanies and was working to build the department. He heard about the program from a former colleague who had not attended but had heard great things about LeadBoston. He did his research and found it to be a “perfect fit,” because as he explained, in his work he knew “enough to be dangerous in each one of the six areas” listed above. He saw this is an opportunity for him to “dive thoughtfully” into the six areas of his team’s work and examine their complexities and how system inequities came to be.

Trevor in a small group discussion with his LeadBoston classmates.

A transplant from New York City, Trevor moved to Boston a few years before joining LeadBoston. In the program, he learned about history that is unique to Boston, such as its history with redlining, transportation, criminal justice, healthcare, and more. He found that “each speaker at each program day thoughtfully delved into [each topic’s] historical context and how [it] came to be in an effort to then say how do we […] solve this in the future.” As he explained, the depth of knowledge he gained is rarely achieved without spending a large amount of time reading or by taking a series of graduate courses. He found it motivating to hear how the program day speakers are advancing equity and how they were willing to hear others’ ideas.

He was able to directly incorporate the topics he learned about into his work at WinnCompanies and his personal life. For instance, Trevor found the program day on criminal justice and the judicial system to be “particularly impactful”. In particular, he learned about the barriers to reentry from the prison system, and how these barriers lead to high recidivism rates. He noted that while WinnCompanies are helping thousands of returning citizens, “there are millions, [and] it became a more personal than professional interest of how can we do that better.”

Trevor gained a sense of the barriers affordable housing residents face in accessing resources, and brought that knowledge to the Connect platform.

In his work, Trevor recognized how difficult it can be for residents to find available resources in WinnCompanies’ six key areas. As he explained, resident service coordinators are helping “people find what they need and it’s often times deficit- or challenge-driven,” and reacting to people’s current barriers to access. For instance, a person may need help applying for rent assistance but then face a 10-page form that may not be in their language or which can be dismissed if not filled in correctly. And, searching on the internet for resources can turn up an overwhelming number of results, many of which the searcher may not be qualified for. Residents often end up too frustrated to continue.

So, he set out to create Connect with the goal of leveraging technology “to help our team and to help people directly navigate resources [for] access to the programs and services they need when they need them and in a more efficient way.” The platform collects information about a resident, such as their area code, income level, and more, in order to solely connect them with resources they qualify for. He gave an example of a hypothetical person looking for health insurance. If that person Googled health insurance, it would take them a while to find results they qualified for. But if a resident services coordinator can work with them, knowing their income and asset level, veteran status, or other relevant information about their needs, the results would be tailored to meet the person.

His LeadBoston classmates and alumni provided crucial support for the launch of the platform.

As he neared the end of his LeadBoston experience, Trevor dedicated his leadership commitment to leveraging his class connections in order to expand the services available through the Connect by WinnCompanies platform. A number of his classmates worked in housing or at organizations who refer clients to services. He worked with them to get their feedback on the platform’s design and usability. He utilized those connections to onboard his classmates’ organizations to the platform. Boston Medical Center, Action for Boston Community Development, and Metro Housing Boston, for example, agreed to accept referrals through the platform, which greatly streamlined the process. Trevor explained that, “when you look back at the past decade-plus, pretty much every major health center, human services group, or youth development organization in the city has had someone in a leadership position go through LeadBoston and so being able to use that network to help get all of those groups connected on the platform was both affirming and definitely eased the process of doing so.”

With this help, Connect by WinnCompanies just completed their pilot year. They found the platform particularly useful in the face of the COVID-19 pandemic and decided to send it to every housing organization in every state they operate in, including Massachusetts. They offer a resident-facing version that anyone can use, in addition to their internal-facing website for staff case management. In rolling it out in a mass way, he explained, they are also helping to keep the information updated.

Ultimately, LeadBoston strengthens alum’s ability to lead within their workplace and their community

As a result of participating in LeadBoston, Trevor found he better understood how systemic inequities are interconnected. That, in turn, led him to expand his thinking at work, including considering which organizations his team partners with. He made an effort to hire more people who come from fields other than housing, such as education and financial services, to round out the expertise on the team. Because of this, he has found that he is listening more and explained that “it’s amazing to be constantly learning within your own team.” Trevor’s goal is for each member of his team to cycle through LeadBoston in the next five to six years, in an effort to deepen each member’s understanding of the systems and institutions of Boston. He even said he’d go through the program each year, if he could.

He still keeps in touch with his LeadBoston class regularly. Before COVID-19, they were meeting up for coffee. They continue to connect virtually and through their listserv, sharing articles and information to expand on the knowledge they learned as a part of LeadBoston. As Trevor explained, LeadBoston gave him the space to meet new people while learning, building, and growing together.

The LeadBoston Class of 2019 at graduation.


About LeadBoston 

Become a part of YW Boston’s LeadBoston program and join a network of over 1,000 inclusive leaders in Boston. During this 11-month program, participants explore and learn how to address barriers to inclusion through facilitated dialogue, expert speakers, and peer learning. Through experiential activities, participants delve into the social, political, and socioeconomic realities of Boston and explore innovative solutions to inequity. Interested in learning more? Reach out to Rachael McCoy, LeadBoston Manager, at with any questions about the program.