Framework
The 'Core group of 10' is the heart of a community business
Chief's model centers on curated 'core groups' of 10 executives who meet monthly with an executive coach in the room; everything else (programming, network, clubhouses) orbits that core. The takeaway: anchor a community business on a small, recurring, curated peer group, not on content or events.
“probably the heart of what we do is what we call our core groups. It is this group of 10 individuals. We go through a very curated process of finding the right group of 10 to come together. They meet every month. There's an executive coach in the room, and that's called Core for a reason. It is the heart of, of the service that we provide.”
Steal thisBuild your community around a small, curated, recurring peer group (e.g. 10 people meeting monthly), and treat everything else as add-ons.
Number
15,000 members, 60,000-person waitlist
Chief has close to 15,000 paying members but a waitlist of nearly 60,000, which the founder cites as proof of how badly the community is needed.
$60K
Waitlist size · people
“now, yes, we're close to 15,000 members, but we have a waitlist of close to 60,000, which is kind of incredible.”
Story
Cold emails to Fortune 500 C-suite landed the first members
When VCs assumed Chief's early members were just friends, Carolyn pushed back: they cold-emailed C-suite executives at Fortune 500 companies and people were excited to join, partly because referencing the known YPO model created instant credibility.
“It was amazing, a cold email to C-suite executives at Fortune 500 companies and people were excited to join. I think being able to also reference the YPO model, which a lot of people understood, helped to create some of that traction.”
Steal thisCold-email senior buyers and borrow credibility by referencing a category leader they already understand (the 'X but for Y' anchor).
Story
Cold emails to Fortune 500 C-suite landed the first members
When VCs assumed Chief's early members were just friends, Carolyn pushed back: they cold-emailed C-suite executives at Fortune 500 companies and people were excited to join, partly because referencing the known YPO model created instant credibility.
“It was amazing, a cold email to C-suite executives at Fortune 500 companies and people were excited to join. I think being able to also reference the YPO model, which a lot of people understood, helped to create some of that traction.”
Steal thisCold-email senior buyers and borrow credibility by referencing a category leader they already understand (the 'X but for Y' anchor).
Take
Community must lead, not curriculum
Carolyn argues community-led businesses beat education-led ones: even with business school, people return for the network, not the curriculum. Sam agrees that leading with education makes the model hard.
“for us, community has always led. And even, you know, you could extend that to many other paradigms of like, does community lead or does space lead? Like, what is the actual service that you are providing? And for us, we knew that community had to be the thing that always led.”
Steal thisWhen building a paid community, make the peer network the lead product and treat curriculum or content as a supporting feature.
Fact
YPO uses unpaid member-facilitators, juicing margins
Unlike Chief, which pays ~400 executive coaches, YPO trains its own members to facilitate the peer groups for free, which Sam calls 'a racket' and likely makes it one of the most profitable nonprofits around.
“For YPO, they actually don't have paid facilitators. They train members to be the facilitators of a lot of those groups. So it's an interesting model to think about. And what a racket. I would imagine that as a part of that, they do pretty well.”
Framework
The A-to-C-to-B sales model: sell to her, she gets the company to pay
Chief sells the membership directly to the individual executive, who then gets her employer to sponsor it. Carolyn frames this as an A-to-C-to-B motion, and notes the sponsorship is easy to get once she asks.
“right now it is an A to C to B business, right? Like we develop the relationship with her. She then goes and gets it sponsored. And what we have found is that when she asks, the sponsorship has actually been pretty easy to get.”
Steal thisSell to the individual who wants it, then arm them to expense it to their employer; the company sponsorship is an easy yes once the user asks.
Take
A denied membership is the trigger to quit, not a perk to chase
Counterintuitively, companies don't lose people because membership opens new doors; people leave when a company says NO to sponsoring it, reading the denial as 'you don't value me.'
“What we have found is when a company says no on the sponsorship, it is a really clear signal to a lot of these people that, okay, you're not investing in me, you don't value me. And so that is actually the trigger of somebody thinking about going and leaving and finding other opportunities.”
Tactic
Use mandatory monthly touchpoints to pull members into the app
Chief sustains engagement on its own platform by building in 'known touchpoints' (like the monthly core meeting) that require logging in, then surfacing utility (hiring help, finding an employment lawyer) so members get pulled into the broader community.
“there's these known touchpoints that are going to come up. You're going to, every month, you're going to have a core meeting that's going to pull you into the product in order for you to go and get what you need to get to go and have that conversation.”
Steal thisEngineer recurring required touchpoints (a monthly meeting, a key utility) that force members into your product, then convert that visit into broader engagement.
Take
Build a 'vetted' brand, not 'warm white wine and name tags'
Carolyn says the old image of a 'women's professional network' was 'warm white wine, name tags, and pantsuits,' so Chief deliberately built an aspirational, vetted (not elitist) brand that celebrates members, and skipped most social media to keep it tight.
“if you heard the term a women's professional network, you would not think of something aspirational. It would be like warm white wine, name tags, and pantsuits. Like, that is what would be like in your mind of what a women's professional network was.”
Steal thisIdentify the tired default image of your category and brand deliberately against it to make membership feel aspirational.
Story
Lawyers refused the deal, calling it a 'lifestyle business'
In the early days Carolyn couldn't even pay a lawyer to incorporate Chief as a VC-backed company; they insisted it should be a 'very nice lifestyle business,' which makes the later billion-dollar valuation sweeter.
“I literally could not get a lawyer to work with me because they were like, this should not be a VC funded business. This is a very nice, you know, lifestyle business. I was like, I can't even get a lawyer. That's stupid. I'm going to pay to do this.”