Vol 27. Insights from ResortPass’s VP of Marketing

Case Studied Experts
Meet Nicole Maddern

Each week, we sit down with a marketing leader to learn more about their career, insights, and accomplishments. This week, that marketing leader is Nicole Maddern, VP of Marketing at ResortPass.

Nicole started out her career as a competitive dancer. She learned how to market herself in New York’s performing arts scene and eventually built a track record of scaling mission-driven startups across education, healthcare, and hospitality. Along the way, she’s become known for building growth marketing engines from scratch.

Here are the need-to-knows about Nicole:

• She scaled Flatiron School from one location in New York to 10 campuses across the nation, driving the growth that eventually led to WeWork’s acquisition of the school.
  

• She grew the growth marketing team at Calibrate from 1 to 17+ within one year, exceeded aggressive month-over-month growth targets, and cut the company’s CAC in half.
  

• In her first VP-level role, she increased qualified lead generation by over 2x and built a partner program that scaled to 10%+ of monthly recurring revenue.

From Performing Arts to Marketing Funnels

Nicole’s path to marketing starts in the dance world. She grew up as a competitive dancer, moved to New York to attend NYU Tisch School of the Arts, and was set on becoming a professional performer.

“That’s when I learned how to sell myself. I had a website with videos of me dancing. I was constantly hustling and figuring out how to be the most marketable version of myself to get gigs. I learned that I actually enjoyed it. And I had a knack for it.”

To support herself, Nicole became a brand ambassador for companies like Nike, pulling together community workouts and recruiting hundreds of students to events. The thrill of inspiring people to take action was her first taste of marketing.

When an injury ended her dance career, Nicole pivoted into PR, then New York City startups. At Likeable Local, she learned the foundations of funnels, paid ads, and marketing programs. But beyond tactics, she also gained the belief that most purchases, whether it’s a coding bootcamp or a sweater, are more considered than they look on the surface. 

“There are conversations with spouses, research that happens offline, signals you can’t track. And recognizing that is a strategic advantage.”

Scaling School and Navigating WeWork

Nicole took a huge growth leap at Flatiron School aka a coding bootcamp that came onto the scene as bootcamps started booming. She joined to help scale online programs and ended up managing a 25-person marketing team and helping the school expand from one New York City location to 10 campuses across the U.S.

“We drove consistent 10% month-over-month growth in online programs. That momentum fueled the WeWork acquisition, and then from there, I had the opportunity to actually just scale out the business. It was my biggest crash course in growth—managing teams, building community at a local level, and learning how to operate in hyper-growth and, later, hyper-efficiency.”

At first, the mandate was “grow as fast as humanly possible.” Later, after WeWork’s collapse, the focus flipped to cutting costs and maximizing utilization. Nicole learned to flex different muscles: big-bet growth in one season, lean optimization in the next. 

“I realized that I had worked at one company that had four seasons,” she said. “I think operationally, it’s valuable to look back and recognize what muscles were flexed during each season.

From Healthcare to Hospitality

After Flatiron, Nicole sought out high-growth, mission-driven challenges. At K Health, she helped launch AI-driven care programs, long before AI was a buzzword. Then at Calibrate, she built an 18-person team and scaled revenue 10x in a year, and helped normalize GLP-1 weight loss treatments well before the treatment was a household name. 

The trend of high-growth roles was very intentional for Nicole. “I'm a growth chaser. I don't want to go somewhere I don't think I can grow a lot. So if it's already a saturated space, it's probably not right for me. I want to work on things that are disruptive and defensible—categories where I can build the machine, not just optimize it” she said. 

“I’ve also been a bit of a snob for mission-driven companies that I'm personally interested in. With as much time as I spend working, it has to be on something I can get behind.”

In her current role, Nicole is back in category-creation mode, this time in hospitality. Her company ResortPass lets people book day access to luxury resorts and spas, without overnight stays.

“The idea of giving people a one-day escape they can actually afford is powerful, especially as people are increasingly overworked, not taking their PTO, and rethinking if they can afford to go on vacation” Nicole said. “Growth here has been fueled by really incredible word of mouth. I came in looking to juice that and scale out the performance marketing program.” 

In the process, Nicole has learned more about the brand marketing engine. “This product has broad appeal so we’re thinking about how to create more brand awareness to the masses. There's so many creative ways we can enter the zeitgeist with ResortPass so I’ve spent a lot more time thinking about brand marketing than I have in previous roles.”

A Standout Campaign

At Calibrate, Nicole drove and concepted a campaign that became an annual cornerstone for the brand: The Results Report. 

“We were the first mover in GLP-1 care and as the category was starting to get busier, we had to show how our program was driving results. So I advocated for this larger campaign that laid out people’s health metrics into a comprehensive report—weight loss outcomes, cholesterol, inflammation markers. The medical team worked really deeply on it and it was validated by third parties. And then we made a huge push to show the efficacy of the program. It became a full funnel asset.”

Nicole said her idea for the campaign came from a real customer problem/question. “We heard from prospects that they were unwilling to put down the money and convert because they were unsure about the efficacy of the program. And what better way to solve that than by putting stats and money behind it to create that trustworthiness?”

The campaign gave Calibrate an edge that competitors couldn’t easily replicate. “This may be a bit of a controversial take but I think campaigns that are only centered at the top of funnel are a mistake. To me, it’s much more beneficial to think about how it moves down the funnel and its implications at different stages.”

Advice and Takeaways

1) Talk to your customers (really).

Nicole has seen data-driven growth reach its limits as tracking gets murkier. Her answer is to identify the external channels that are actually influencing purchase behavior. “For example, are people really turning to reviews online? Is that a strong decision driver? Or are they visiting a specific Reddit thread on a monthly basis? You have to go through a discovery process to learn what channels really matter.”

Take a critical look at the outlets you monitor to track consumer sentiment. How do you talk to your customers? Are there external outlets you can keep an eye on that aren’t on your radar right now? Consider going through the discovery process to find out. 

2)  Recognize when it’s time to pivot.

Like most leaders, Nicole came into her role at ResortPass with a strong perspective based on her background. But after experimenting with a lot of different ways to optimize, she wasn’t seeing as much growth as she expected. “I think if you find yourself in that situation, you have to be honest about the realities and recognize that certain channels just aren’t right for the business.”

For your own work, map decision points. Test your hypotheses and be open to recognizing what works and what doesn’t. Too much pride or preciousness can block growth so instead, prioritize self-awareness and be open to trying something new. 

3)  Build new muscles when the role calls for it.

Nicole describes herself as a data-driven growth marketer at heart. But stepping into ResortPass meant leaning into brand-building—PR, out-of-home, podcast ads—the very things she once rolled her eyes at. “It’s been healthy unlearning parts of the old playbook. Sometimes you need to build a new one.”

Tempting as it may be, don’t box yourself in by past expertise. Each company, category, and season calls for different muscles. Be self-aware about where you’re strong, but open enough to surround yourself with people and experiments that stretch you. Growth often comes from the discomfort of trying the things you don’t fully know or trust yet.

Think long-term: What could help make your campaigns more successful over time? The right agency partner. And Vendry can help you meet yours, for free. Get started.