Pete Heslop 12 May, 2025 4 min read

Lessons from Stripe's Community Lead; Ashley Williams

For years, community teams have wrestled with a familiar question: How do we prove our value in a way the C-suite actually understands?

Ashley Williams, Community Lead at Stripe, and formerly of Wix, Airbnb and ClassDojo, has built a career answering that very question. On the latest episode of the Digital Community Leaders Podcast, she shared exactly how community leaders can position their work as a core driver of business success.

“Learning to paint a picture with data”

Ashley’s advice is clear, if you want to secure buy-in, data is your strongest ally.

“I can't emphasise enough like learning. Getting yourself into the data, being data savvy, learning to paint a picture with data,” she said.

While at Airbnb, Ashley faced a challenge familiar to many community leaders. She was running high-touch, full-day events for hosts, and leadership began to question the investment.

“I think got a lot of feedback, so you're saying this will increase host success, but can't we just send them some push notifications or some emails and that'll increase host success?”

Rather than argue, she partnered with the data science team to find out exactly what was happening.

“We saw, oh, okay. Actually while these two metrics… we are like moving the needle wildly through these events.”

Why? It turned out that certain behaviours simply couldn’t be nudged by in-app notifications or emails.

“Our hypothesis was it's like there were certain things hosts needed to hear from other hosts.

If they heard it from Airbnb, it was like, oh, you don't understand my business, like you don't get me. You're not a host.

But if they heard it from another host being like, Hey, I did this thing and it increased my revenue, other hosts were like, oh, I'm gonna go do that tomorrow.”

“What is the business impact that only you are driving?”

Ashley made it clear that proving value isn’t just about showing any impact; it’s about showing the unique impact of community.

“You wanna ladder up to the company's metrics, but you need to figure out like where will, how community have outsized impact? Where will Community be valuable? Where other things have failed?”

She encouraged community professionals to ask: Where is Community solving a problem that no other channel can?

“If you can drive that same metric with an email, you're gonna do that. Because it's a lot more efficient. So what is community driving that's unique?”

“Become best friends with the data scientist”

Ashley stressed that one of the most valuable things a community leader can do is become comfortable with the numbers; and the people who hold them.

“If you're joining a new company and a new community role. Become best friends with the data scientist that's relevant to you. Get really familiar with the data tools.”

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And if you’re lucky enough to be hiring?

“I highly recommend hiring a community ops person on your team if you have the resourcing and support somebody who can like really own that. Like, how are we making sure we're distilling and capturing data from the things we're doing and then exporting it in a way where we can translate into business impact?”

“You are the expert”

To close, Ashley offered some encouragement for anyone feeling imposter syndrome when stepping into conversations about business impact.

“Just remember. You are the expert on this. Nobody else at Stripe knows this. Like you, you are the expert.”

And when it feels like you’re constantly having to explain what you do?

“Instead of getting defensive, oh, they don't understand me. It's the saying actually oh, I'm gonna own this role as a teacher and an educator, and that will position me as a thought leader.”

If you want more insights on making community matter at the highest level of your organisation, listen to the full episode with Ashley Williams on the Digital Community Leaders Podcast - available now on all platforms.

Listen on Spotify