Leader to Leader: Jordyn Lexton

One of the most difficult decisions for any nonprofit leader, particularly a founding executive director, is figuring out when and how to step down.

Jordyn Lexton, the founder and CEO of Drive Change, recently made the decision to step down after nine years of leading the organization. Drive Change grew out of Jordyn’s experience working as a teacher on Rikers Island, an experience that underlined how difficult it was for formerly incarcerated young people to find meaningful employment. The organization began by providing participating young people with jobs working in a food truck offering locally-sourced meals. It has since evolved into a multi-faceted organization that does advocacy work pertaining to justice reform and the hospitality industry. Drive Change also operates an industrial kitchen that provides job training to dozens of participants every year.

One of Jordyn’s goals in leaving is for Drive Change to transition to “proximate leadership,” that is to say find a new executive director that more directly shares life experiences, and a sense of identity with the Black and brown participants that the nonprofit primarily serves. Leadership transitions are crucial in the life of any agency. They are a time of possibility and vulnerability. For some organizations, they are the start of a bright new chapter. For others, a harbinger of decline. 

There is no shortage of consultants and experts urging nonprofits to think about sustainability, succession planning, and the dangers of founder’s syndrome -- a syndrome that afflicts many organizations with charismatic leaders who end up getting in the way of institutional change. However, the typical nonprofit is usually under-staffed and under-resourced. For these organizations, getting the daily work done almost always takes precedence over engaging in rigorous planning for the future. Given this reality, it is often difficult for a founding leader to exit gracefully and thoughtfully.

Lexton wants to be an exception to this rule. 

NYN Media spoke with Lexton about Drive Change’s leadership transition and the lessons they have learned that might be applicable to other organizations.

The following interview has been edited for clarity and brevity.

How did you reach the decision that it was time to step down? 

About two and a half years ago, it started feeling really clear that the organization would benefit from more proximate leadership. I was also ready for my own next chapter professionally. I didn't get into the work to be a fundraiser but I became a fundraiser. I was really feeling the grind. Drive Change is a pretty small organization. Our full-time staff is about seven, eight people. And our board is small too, about five people. We didn't have a full-time development person. I started feeling like my relationships professionally had this transactional element that was a little bit difficult for me. And my wife and I were thinking about new things in our life. She's from California so we made the decision to move back there.

What do you mean when you say that your professional relationships were starting to feel transactional?

I think it is sort of inevitable when you are responsible for fundraising. I really tried hard to be a vulnerable and authentically connected leader in fundraising. I tried to be honest and to talk about the hard stuff with funders. So much of fundraising work is about relationships. I think the power dynamics around money, and the way that nonprofit organizations are set up, contributes to there being a kind of transactional quality to many of those relationships. I would be feeling like, "Oh, I really need to call this person back." Not just because I care about them and I want to hear about their life but because they also are a funder and I need to sustain that connection in order to support the sustainability of the organization.

Tell me where you think Drive Change is in its developmental arc. 

I think it's a toddler. I think it's a finding-its-feet toddler.

How have you changed as a leader since the organization’s inception?

I think I have really grown a lot. I was involved in starting the organization because of personal experience I had teaching on Rikers Island. I really witnessed the negative impacts of the system on young people, particularly Black and brown people, firsthand. I was constantly hearing students say, "We need access to quality employment." In thinking about what that could look like, I started working with other people to develop a food truck business that could also be a platform for industry skills, education and be an advocacy engine.

A lot of the initial push for Drive Change was me leveraging my personal privilege. I was in a position, as a young person with access through my family to resources, to not have a full-time job for a while. That enabled me to become a social entrepreneur. And it enabled me to just have a lot of gumption in terms of being someone who was encouraged to ask questions, to be curious. I think that's something that carried me through – being curious and learning. Before starting Drive Change, I worked on another food truck. I also worked for three other reentry organizations to try to learn a bit more of the landscape and where Drive Change could fill a gap.

In the early stages, the organization was really tied to my identity, my sense of self, and my sense of purpose. I was a green manager. I was 27, when the organization started. I had never really been a manager before. I think that led to me be overly involved in certain decisions and outcomes. I was so fortunate in my professional life to then get connected to other social entrepreneurs, particularly through the organization Echoing Green. I think Echoing Green helped me start to think about what I could do as a leader to create a team, an infrastructure, and a culture that was more distributive. 

In 2017-2018, there was some staff turnover at Drive Change. For me personally, it was also kind of aligned to my own growth, and sense of confidence, as a leader. I'm a queer person. I'm a trans person. And that moment was also a moment where I was ready to claim my own identity and step into my leadership a little bit more. I made a commitment at that moment that I was going to be intentional about stepping back and creating infrastructure where other people could come in and develop true ownership and leadership, which is not something I think I had done well before. I think that that was the moment where the organization took on an identity beyond me. 

Were you doing all those things with an eye toward succession planning?

Not really.I knew that the organization needed to be bigger than any one person.I think somewhere in the back of my brain I was always thinking, "How do we get to that next chapter? Am I actually getting in the way of us getting to that next chapter? What do I have to do to let go of my own ego, and my own control?"

What has happened in the years since you started to take this more distributive approach to managing the agency?

We are the kind of place where people bring a lot of themselves to work. It is part of our core identity as an organization. When COVID and the movement for Black lives happened, it was really clear that we were going to be thinking about power structures and racial justice inside of our own dynamics as a team. And we were going to be asking how we can do even more to embody the values that we stand for in terms of our own organizational structure.

During 2020, we realized our programs needed to shift and change. We're an organization focused on quality employment, and historically a lot of the jobs that we helped people get access to were in the restaurant industry, which is an industry that needs an entire overhaul. And so the organization was in this mode of saying, "We need to rethink.”

It became clear that the team was ready for new leadership. They were recognizing that the organization needed a new chapter after nine years of me being the founder and CEO. And that was tied to my blind spots as a white leader. And it was tied to the unrest that people were feeling coming to work during the pandemic.

And so, there was a clear internal desire for a shift. I was also in a position where I was ready. Then the question became what's the role and responsibility of all of our teammates to actually effectuate this change in a way that's going to be healthiest for the organization.

So, what are the best things that you did? What do you feel good about as you look back on the transition?

I feel best about the way our team has responded. My colleague Kim DiPalo, our COO, assumed the interim CEO position. We created a transition team that consisted of two additional staff members and three board members. And we worked together to create a structure and a calendar around what we would need to do. Both the desire that I was having and the team's desire for new leadership became clear in January of this year. We really started effectuating the transition in early March. And so from March through July, Kim and I probably had over 100 conversations with different stakeholders. She was meeting a lot of people for the first time. I think if we had done some of that relationship building sooner that it would've really served the organization well.

Are you going to have any ongoing role with the organization?

I'm not playing a formal role. We made the decision that I wasn't going to stay on the board because we want the new leader to come in and really assume that authority. We heard feedback from other folks that it was just really tough, especially with a founder, to do that. I'm very much in a, "I'm here for you" mode, but I'm not formally in any kind of advisor role right now.

Have you thought at all about what it will feel like the first time that Drive Change does something that you disagree with?

I have. I think this is a bit like grief, and I'm open to the knowledge that it's not linear. So I am prepared that I may have moments where my attachment, my emotional energy, tightens. There have already been moments like that. In January and February, it was becoming clear to me that this transition was something that other members of the organization wanted. That was hard. It was right – they knew what was best for the organization. But it was also hard. Now that I'm away from that acute moment, I think it actually helped me to get to a place of emotional detachment sooner. 

Do you have a sense of what comes next for you?

My wife and I are moving to California, which we're really excited about. No longer being the CEO and founder of Drive Change has opened up space for me to be expansive in my thinking. I have no real sense of where that exactly is going to take me but I know that I really dislike the structures of philanthropy and I think there's a lot of opportunity to change things, in particular around wills and estates, end-of-life giving, and the redistribution of wealth. I'm really curious about what's out there, what gaps need to be filled and whether I could play a role in making some impact. 

You described yourself as a social entrepreneur. Do you think that your instinct would be to create another new entity?

One of the things that I've said is that there's no way I'm going to ever do anything again as a sole founder. Because the isolation is just really hard. I am curious to see how I might respond inside of a more structured environment. I’d be curious to kind of try that out for a little bit before potentially building something again. But at the same time, there is a reason that I haven't let myself be inside of those kinds of structures and systems because I don't fully buy into that or believe in that. I've always seen my entrepreneurship connected to my queerness and to my trans identity. I have a lot of practice reimagining things and demonstrating to people that something they thought was one way doesn't always have to be that way. 

If you were to start another enterprise, how would you do it differently?

There's so much I think I would do differently. I think that one thing that I never did well as a leader was to demonstrate real clarity around organizational structure. It doesn’t have to be rigid or hierarchical, but I think people are looking for clarity of roles, responsibilities, and expectations. They want to really understand, "This is what my job is, and this is how I do it well." And they want to know that there is an element of collective accountability in place. 

One of the themes of this conversation is that you have a pretty strong critique of philanthropy. I'm wondering if you have ideas for how to improve philanthropy?

I think we need to reset expectations. I truly think that it is wild that such a small amount of endowments or assets are annually distributed. So much money just sits in bonds and banks and accumulates more wealth. When there's so much need, it's just beyond my comprehension. I think we should be rethinking what is an appropriate amount for foundations to be distributing.

And then there is the process. There is often a lack of trust that the people who are doing the work really know what needs to be done. I think there's so much room for more creativity that should be grounded in trusting people who are actually closest to the challenges. A lot of the problems have to do with bias, and structures, and who holds the money versus who's doing the work. I'm hopeful that it's going to shift, but I think there needs to be some willingness to let go a bit.