Dan Clifford joined lingerie brand Pepper as chief marketing officer late last year, attracted to being a part of growing a founder-driven company.
“I think founder-driven brands have a huge advantage because the founders are the ultimate brand directors,” says Clifford. “The challenge is, how do we not lose sight of that? That’s a real superpower.”
Pepper’s mission is to offer a line of lingerie, swimsuits and more for small-chested women. The company was born after its two founders – Jaclyn Fu and Lia Winograd – had a successful Kickstarter campaign in 2017. The company has been growing ever since and is now available through the brand’s global ecommerce store, as well as in Nordstrom and on Amazon.
“The opportunity always existed out there, and this customer, this consumer, this community was always largely ignored by retail brands in this space,” explained Clifford. “One big opportunity we have is it’s so much easier for our brand to build when they are facilitating a community instead of trying to create a community.”
Brand Innovators caught up with Clifford from his office in Boston to talk about brand building around the community, establishing trust and cultivating loyalty. This interview has been edited for length and clarity.
What is your approach to storytelling?
it’s really about being authentic and transparent and customer-first values. This customer has been largely ignored.
What we want to do is make sure that they understand where we’re coming from, that our story is true and authentic. One of our co-founders had the same issue that many people in our community have. There’s a sense that the retail and fashion communities looked past them.
There is a sense that it becomes a personal issue. Is it a confidence issue? It goes back to authenticity and transparency around the challenges that this customer group has always had.
Bringing it forward to where we’re at this year, one big thing that we talk about all the time is trust. The rise of algorithms, the growing overall consumer skepticism towards things like big business, big pharma, big brands, and the increasing integration of AI in all of our experiences—I really think trust is becoming more of a fragile commodity.
Consumers are really questioning the authenticity of what they see or what they hear from brands they once really relied on. I used to think that the return to brand would be driven by our over-reliance on Meta and Google and paid acquisition—putting a dollar into the Facebook machine and hopefully getting $10 back. And while that’s true, our dependency on platforms like Meta and Google often over-distort our strategies and skew our conversations about what we really should be talking about.
I believe now that the real catalyst that’s going to take us back to making sure brand is at the heart of our conversation—and our customers at the heart of our conversation every day—is really trust, and to build meaningful and lasting connections.
Brands have got to prioritize authenticity and transparency, customer-first values, and a personal touch, because I think brands have just lost the conversation on what trust means with their customers.
You mentioned community. Can you tell me how you’re showing up in this community? Are you working with influencers? What does that look like for your brand?
Community is absolutely at the heart of what we do every day. It’s one of our key strategies. We’re showing up in all the right places where she’s trying to find, discover or talk about solutions or connecting with Pepper. We are definitely prioritizing our community and our influencer strategy and our ambassador strategy as we think about what’s ahead for us.
We’re really investing trust, investing in our community, but then finding the right tools that we can ensure help us connect on a personal level and where we can scale that. Like all brands, we’re integrating AI and those solutions to help us work and think and execute more efficiently, but we absolutely do not want to lose sight of a personal touch within our community strategy.
As a DTC brand, how is your customer finding you within the marketplace?
Not only are we in all the basics, in all the places we need to be as a DTC brand, but we’re thinking more broadly around our distribution strategy in order to reach our customer and audiences that maybe a paid or organic channel is too difficult for us to reach.
Distribution strategies have proven out at this point that DTC brands can’t just pour more money into advertising in order to scale. That’s a pretty big race to the bottom. Your distribution strategy needs to go hand in hand with your community strategy and your growth strategy at this point. That would definitely be a huge consideration in how we are growing and reaching our community in 2025.
What kinds of marketing trends are you expecting to see in 2025?
Trust hits home for us because a bra is a little more intimate than just a t-shirt. As brands like ours scale, it’s so easy to just plug and play some tools from some vendor. But when you think about it, what we’re really selling here is giving somebody self-confidence that for a good portion of her life probably felt like she had been overlooked.
A big trend for me is really trust and prioritizing customer needs and really building on that promise. Looking for small human-to-human moments and experiences where she feels heard, seen, and valued—a thoughtful interaction, a personal touch, a gesture that shows we care and understand her challenges. Those are the moments that build emotional connection and lasting loyalty.
Another big trend is AI. Obviously, everybody’s going to say that. It’s about going from experiment to application in an interesting way. We’ve moved past the playtime stage. We were enamored with AI. We weren’t sure where it was heading. But now, the bright shininess factor is off, and we can put it in perspective—it’s an enabler, not a replacement for our relationship with the customer.
