Long Story Short
Co-leadership isn’t the norm, so it can feel risky and uncertain. The key is finding someone with shared values, complementary skills, and both of you doing the personal work you need to keep your egos out of it.
Why We’re Sharing This
Jess Skylar here. (Our contributor’s name is Jess/Jessica also, so we’ll be using last intials throughout to help!)
I’ve been in co-leadership myself — and it gave me some of the best years of my working life, right up until it gave me some of the hardest.
We were so aligned at the start. And then, somewhere in there, the specifics of where we were going and how we’d get there shifted and looked different for each of us.
I’ve thought a lot since about how much of that was my ego (it seemed to get bigger over time!!!), and how my identity was so woven into it all — how tightly I was holding onto who I was at work, especially in a stretch when so many hard things were happening in my personal life. Professional identity was something I clung to (which I am pretty sure wasn’t good for me or the work or anyone I was working with…).
While my own story had all the people layers, these would have existed whether I was going it alone OR with someone else. But because co-leadership isn’t the norm, it somehow feels caught up in that.
Bringing someone else in to lead with you — or joining someone else — can feel risky and uncertain. But maybe things are always that way? And while adding a second person and all their things into the mix is a risk, when co-leadership is good, it is so good.
While chemistry is obviously part of all of this, there is so much else to know and understand about how to find the right fit. There is work we can and probably should be doing personally (read: how to separate your professional identity from your personal one), foundations and processes we can put in place to support an aligned team (e.g. a joint strategic plan/vision), and key criteria to help us find who can be a good fit.
There’s no such thing as THE way to do it, but maybe instead of asking “Is partnership better than going solo?”, we might want to ask ourselves, “What leadership models are we willing to explore?”
Jessica Allen and Andrea Chen gave me a clear look at just how incredible co-leadership can be. Shared values underneath everything. A genuinely shared vision of where the organization was headed. Skills that weren’t the same, that balanced each other out. And the hard one: not much ego about whose idea won. The part that humbled me most was hearing Andrea talk about the years of personal work she did to hold her identity as her own person, not just as the founder and CEO. How many of us are willing to do that before we have to (asking for myself!!)?
This is a story about what co-leadership can be when two people do their own personal work, come to it for the right reasons, and find the right person to do it with. And it’s a case for staying open to new models, because whether or not you ever share the seat, the leaders who keep exploring how they work, and with whom, are the ones who find the thing that fits.
The Co-CEO Gut Check
Before you rule out co-leadership, run this on yourself and a possible partner. If most of these are true — or could be, with some work — that’s a green light to explore.
- Shared values. You might approach the work completely differently, but you don’t argue about what matters.
- Complementary skills — not identical ones. You cover each other’s gaps instead of doubling up on the same strengths.
- A shared vision you built together. You both actually agree on where the organization is going.
- Low-to-no ego. It doesn’t matter much to either of you whose idea wins.
Jessica Allen and Andrea Chen’s Story
This is Jessica Allen’s and Andrea Chen’s story — co-written with Helia and told from both their perspectives.
Jessica Allen serves as CEO of Propeller, a social enterprise innovation hub in New Orleans, and has been with the organization for almost nine years. She didn’t come to it from an entrepreneurial background, but rather via public health, which brought her to the city in 2012 for a graduate degree at Tulane. She joined Propeller in 2017 on the program side, coaching entrepreneurs through the Impact Accelerator and helping them solve whatever puzzle was in front of them. “It always kept things really interesting,” she says.
Becoming a co-CEO and then sole-CEO wasn’t the plan. “I am not somebody who had on their vision board, I’m going to be a CEO of an entrepreneur support organization,” she says. But staying open to things she hadn’t pictured is a through-line in her life — it’s how she got to Propeller in the first place, after ignoring the job posting a few times because she was sure she didn’t have the right background. “I’m so happy that I finally applied.”
This co-CEO partnership wasn’t luck, and it didn’t fall from the sky. Andrea Chen had been trying to share the load for years. She tried a “deputy model” and a few other setups, but none of it clicked. “Nothing felt very smooth in those other iterations,” she says. What finally worked wasn’t a perfect job description. It was someone already inside the culture, with real relationships and peer trust: “People had already worked with Jess. They knew Jess is a person of her word.”
It started, of all times, in the early days of COVID. Andrea was carrying everything alone, and Jessica A. just began helping. “Can I take the staff meetings, the retreats, the touchpoints that keep some normalcy?”
Andrea noticed something bigger. “Whatever Jessica touches, it goes smoothly,” she says. A pattern of what it takes to do this well emerged: “emotional intelligence, collaborative decision-making, putting the structures and processes in place, communicating things, tracking things. It’s not easy for everyone to do.” Propeller got through COVID without the chaos a lot of organizations hit in large part due to the way Jessica A. stepped up.
From there it grew — Jessica A. became chief of staff, then COO, then took two turns as interim CEO. They now call this a kind of stealth onboarding. To truly take the day-to-day off Andrea’s plate, Jessica A. had to understand Andrea’s decision-making intimately, so that Propeller’s vision and voice would hold up even when Andrea wasn’t the one making the decisions. Andrea was learning in reverse, too. She calls it the best professional development of her working life: “to be that close to someone else’s brain who you respect.”
So by the time they formally became co-CEOs in 2024, not much changed in practice. The team’s reaction was basically, “Wait, so what’s new?” The role got real long before it got a name, which is exactly why it wasn’t a dramatic handoff. What the title did do was let each of them lean into the work they loved: Jessica A. on operations, team, and programs; Andrea on fundraising and finances, at which she’d always excelled.
And when personal reasons eventually pulled Andrea away and she needed to relocate, moving back toward a sole-CEO model meant they didn’t have to onboard a stranger. After 10 years, Andrea knew every nook and cranny of Propeller; through her stealth onboarding and co-CEO model, Jessica A. knew them all now, too. This made for one of the smoothest founder-to-new-leader transitions Andrea had ever seen. “It just worked for everyone.”
What Made This Work
“The more we talked about it,” Andrea says, “the more we could see it wasn’t just luck.” When they trace why it worked — and why they’d both do it again, “depending on the person” — it comes down to the same handful of things in the gut-check up top.
They were opposite on every style test and identical on every value. A work-style assessment once put them at opposite ends of every spectrum — “not even in the middle,” Andrea laughs. But on values, there was never a question of alignment: “It’s not the how that matters here — it’s the why.” When you’re aligned on the why, you can disagree hard on how the work gets done and stay on the same team.
They built a practice for the moments they were far apart. They didn’t have conflict in a bad sense, just two people with different reads on how to move forward. What they committed to was either finding a new option neither had thought of, or agreeing to back the decision fully and be a united front for the team. This often showed up around timing: Andrea would get excited about starting something new immediately and Jess A. would be the one saying “that can’t land by next week” or “realistically that person won’t start until June.” This is a classic operations / visionary conflict, but they made it work by always coming together to ask, “Okay, so what do we do?”
They shared a real vision — because they built it together. The strategic plan Jessica A. ran around 2020 set clear targets and laid the groundwork for how Propeller has grown since, including a reaffirmation to center the needs of Black, native New Orleanians across programming, team, board, and operations. When two leaders genuinely share where the organization is going, a whole category of friction never shows up.
Neither of them led from ego. “It was never a huge deal whose idea got advanced or who made the call,” Jessica A. says. They were aligned on the work, on where the organization was going, and on how they wanted the team to feel day in and day out. That, she’s quick to note, isn’t always the case — especially for founders asked to share this part of the work.
Andrea did the work to separate her identity from the org. “When I started Propeller, it was all-consuming — my whole life. Friends told me there was a point where they never saw me. Being at Propeller was my identity. And realizing that’s not healthy… it took a lot of years to get to where I can say, No, it’s not my identity to be CEO. You’re a better leader if you’re not clutching it.”
NOTE: If you’re reading this as the founder who can’t picture letting go — the one for whom being the leader is the identity right now — that’s not a disqualification. It’s the starting line. It’s the same work Andrea did, and it took her years. (I’m in it too.) You don’t have to have finished that work to begin.
And they didn’t go hunting for this. They were in the work, they found each other in it, and they grew. You can try different models, stay open, and let the right partnership reveal itself — as long as you keep paying attention and doing your own work. Jessica A. runs Propeller solo now, and that’s right for this moment. It doesn’t make the co-CEO years any less real, or the openness that made them possible any less worth practicing.
On why they’d do it again. The CEO seat is lonely. “People warn you, but you don’t know loneliness until you’ve sat there.” You’re the one everyone brings the hard thing to, and there’s rarely anyone to bring your hard things to. What co-leadership gave Andrea and Jessica A. was exactly that person. Someone to share the load with. Someone, as Andrea puts it, to say “Oh no!” with — and then find the way forward together.
“The most fun time I had running Propeller was when I was running it with Jessica.” That’s a pretty solid pitch for co-leadership if we’ve ever heard one.
If You Want Help
Andrea is exactly who you can call about this. She founded and led Propeller for 15 years, has lived the whole co-leadership arc, and now coaches other leaders through it. She’s also part of the Helia Collective (she wrote Fundraising That Runs Itself (Almost)).
She’s a good fit if:
- You’re a founder sitting with whether — and how — to share the seat, and want to talk to someone who’s actually done it
- You want to explore a shared-leadership or co-CEO model and don’t know how to socialize it with your team or board
- You want to talk honestly about ego, identity, and holding the work without clutching it
- You’re thinking about succession and want it to strengthen the organization, not destabilize it
Connect with Andrea!
Try This Yourself
- The Partnership Questionnaire: Co-Leadership Alignment Questions: Eleven questions that cover your vision for the partnership, how you’ll support each other, and what you’ll do when you disagree.
- The Co-Leadership Decision-Making Matrix: Use it once you’re aligned and ready to formalize your model and bring your board along.
Questions to Sit With
- Run the gut-check for real: on the four criteria — shared values, complementary skills, shared vision, low ego — where are you (and a possible partner) already strong, and where’s the work?
- If you’re a founder or long-time leader: what’s tied up in being the leader that would be hard to set down — and what might open up if you did?
- Is there someone already inside your organization quietly growing into more than their title? What would it look like to name it?
- When you and a partner are far apart on a decision, do you have an actual practice for getting aligned — or do you improvise it every time?
- Have you ruled out sharing leadership because it felt risky or “not how it’s done” — before you’d really looked at whether it could work for you?
Not sure Andrea‘s the right fit? Talk to Helia directly!
This story comes from a conversation with Jessica Allen and Andrea Chen in July 2026. These conversations form the heart of the Helia Library — because we’ve learned the most from doing and from talking with other doers willing to share their wisdom. We don’t need to start from blank pages or do everything alone.
About the Contributors
Jessica Allen came to New Orleans in 2012 for a graduate public health degree and never left. She joined Propeller in 2017 to help entrepreneurs solve their puzzles, and — after a role she kept ignoring, a job she never pictured, and nine years of staying open — now leads the organization. She’s proof that the best roles are sometimes the ones you don’t apply for the first three times you see them.
Andrea Chen founded and led Propeller for 15 years, growing it into a New Orleans institution for entrepreneurs building businesses as catalysts for change. She’s also spent years doing the quieter work of learning to hold her identity as her own — which, it turns out, made her a better leader and a better partner. She no longer checks in on Propeller, and she means that as the highest compliment.
Work with Andrea
