Walking through SFO in early 2021, I couldn't escape ClickUp's "Save 1 Day Every Week" ads plastered everywhere. As someone running a growing company, the message resonated. Today, sitting across from Melissa Rosenthal, ClickUp's former marketing leader and current founder of OutLever, I'm struck by how that campaign exemplified her revolutionary approach to B2B marketing.

"Our addressable market was everyone," Melissa explains between bites of empanada, describing how ClickUp's universal appeal demanded breaking away from traditional B2B marketing approaches. When your ideal customer profile includes teams of all sizes across every industry, you can't rely on conventional enterprise playbooks. You need to think bigger.

But the real revelation isn't just about market size – it's about bringing humanity to B2B. Under Melissa's leadership, ClickUp created SNL-style ads poking fun at competitors, a stark departure from the stoic world of enterprise software marketing. The results? Their irreverent campaigns not only drove growth but attracted talent, with competitors' employees jumping ship to join their mission.

However, success at this scale comes at a personal cost. Melissa candidly shares her experience working 20-hour days, six days a week. "I wasn't working out, wasn't going to the gym... I was really passionate and very driven about this one singular focus," she admits. It's a level of dedication she acknowledges isn't for everyone, but her perspective on work-life balance is refreshing: when you're genuinely passionate about what you're building, work becomes life in the best possible way.

The conversation turns to scaling teams during hypergrowth, where Melissa's insights challenge conventional wisdom. Rather than chasing big names from established companies, she advocates for finding people who can handle the chaos of startup life. "A startup is a fire, all hands on deck, pivoting a thousand times a day," she explains. "It's super tough for someone that's been at a 5,000-person company to understand."

Perhaps most compelling is her perspective on brand building. In an era where startups rush to spend millions on flashy websites and conferences, Melissa argues that brand means something different at each stage. "Brand isn't throwing fancy conferences or building a really fancy website," she insists. "It's having your motion work and having your customers really excited and able to give referrals... brand is nothing if it's empty."

This philosophy extends to her new venture, OutLever, which aims to transform companies into their own media platforms. It's a bet against the commoditization of outbound sales and a belief that human relationships will always matter in business – a fitting next chapter for someone who's made her career bringing humanity to B2B marketing.

As our conversation wraps up, dodging crows trying to steal her lemons (yes, really), Melissa leaves me with a powerful insight about innovation: sometimes not knowing how hard something should be is your greatest advantage. In marketing, as in life, the willingness to ignore conventional limitations often leads to breakthrough results.