Updated on April 1, 2024
Left to right, Cynthia Huang, CEO of DTravel, Sue Jones, CEO of HR4VR, and Margot Schmorak, CEO of Hostfully
1 in 10 vacation rental CEOs and founders are women
Long before Vanessa de Souza Lage founded and became CEO of Sustonica, an environmental certification for vacation rentals, she noted in a speech at the Vacation Rental World Summit in 2019 that there were not enough women on stage at vacation rental events or leading vacation rental tech companies and large property management firms.
“In fact, I’m hosting a podcast called the Secret Sauce of Large Property Managers, and I haven’t yet found a female CEO to interview,” said Vanessa, then the chief marketing officer at Rentals United, “so if there’s anyone out there that has more than 1,000 properties, please, let me know. I would love to interview you.”
In 2023, Fortune reported that women ran 10.4% of Fortune 500 companies, an 18% increase from the previous year.
The vacation rental industry exceeds that statistic just slightly. According to a Rent Responsibly analysis of about 370 vacation rental companies, including property management firms, support services, and tech companies, 11.1% have female CEOs, and 10.7% have female founders.
Female CEOs in action
Sue Jones, CEO and founder of HR4VR, a human resources consultancy for vacation rental businesses, once gave a group of 40 female founders in the industry a DISC assessment and found some common traits among them.
She said most of the group scored high in dominance (the D is DISC). “Most were extroverted, people-friendly, and driven,” Sue said. “They have a sense of urgency to get stuff done. And that drive is not just limited to their jobs. It extends to their lives and homes. Most of them are volunteering in other organizations. That was really fascinating.”
Cynthia Huang, CEO of DTravel, has been a founder and CEO of multiple companies. When she and her husband founded AltCoin Fantasy, a cryptocurrency trading simulator game, they agreed that she would be CEO.
“He’s actually much more comfortable in a non-front-facing role. Whereas I love going out and talking about our mission and vision,” Cynthia said. “I’ve always really loved being the driver. I think I realized that if I wasn’t in charge, I wasn’t going to be happy.”
Cynthia said she sees being a woman in leadership as an advantage rather than a limitation.
“To me, it’s actually a huge strength because fewer women are in leadership roles,” Cynthia said. “I think, if you show up and you’re very strong, and you’re articulate, especially if you’re doing public speaking, you actually get noticed more, and you have many more opportunities that I think men maybe don’t have as much. Right. I think there’s this misconception that there aren’t enough talented or smart women to fill those leadership roles. And I think that’s actually the big problem because it’s not necessarily a pipeline issue. It’s a visibility issue.”
The visibility issue
When Margot Schmorak co-founded Hostfully, she vowed to document her journey as the company’s CEO in several online articles. As one of the first women to lead a vacation rental software company, Margot felt responsible for sharing her story and filling a void in the news on female CEOs in the larger tech sector.
“When I started, there was just no news about female CEOs, especially women who are moms,” Margot said in a March 2024 interview with Rent Responsibly. “I just wanted women to see other women doing this.”
Back in 2016 when Margot started documenting her life as a CEO, Marissa Mayer, then-CEO of Yahoo, was the only female tech leader who regularly grabbed headlines.
In news reports, “it was a side note that she had twins living next to her in her office,” Margot said.
“Since I started Hostfully, I’ve seen a huge change in the amount of news, stories, products, and services geared towards women who are entrepreneurs,” Margot said, “and I’m really excited about that. I know there’s a huge way to go before we’re close to equal, but the first step is amassing these stories.”
“We just need more women to speak up and be more visible with their successes,” Margot said. “That’s inclusive of property management firms as well.”
For example, “When we call for speakers at the Vacation Rental Managers Association or when we ask, ‘Who wants to be on the board?’, we usually get more male applicants,” Margot said. “I think that will change, but it’s an unfortunate reality.”
Funding for female-led businesses
The statistics on the capital that goes into women-led businesses are dire: Just 3.5% of equity investment for the first half of 2023 went to female-led businesses, while 85.1% went to male-led firms and 11.4% went to startups founded by co-ed leaders, according to Accelerate to Excel, the latest annual report from the Female Founders Forum.
In a young industry like vacation rentals where there is a disproportionate number of startups, the percentage of capital going toward women-led businesses is likely even less, said Merilee Karr, founder and CEO of UnderTheDoormat Group and chairperson of the UK Short Term Accommodation Association.
“Fundraising as a woman is very different from fundraising as a man, not just in terms of how VCs might react to you or view you but even in your own psychology, and fundraising is all about your own psychology,” Cynthia said.
Cynthia belongs to Female Founders in Hospitality (FFiH) where members meet regularly to discuss these challenges and ways to overcome them.
“Having people you can talk to about these things, who understand where you’re coming from and can validate your feelings, that’s really important,” she said.
Margot realized this as well. In January 2022, she founded VC Backed Moms, a forum for venture capitalist-backed founders who happened to be moms. The organization provides a forum where these female entrepreneurs can discuss leadership and motherhood topics and support each other. The organization has gone global and has over 420 members and regional chapters holding in-person gatherings.
Opening the door for more women
Women have made significant progress in spreading their voices in the vacation rental conference circuit, but this and many other areas of the industry still need improvement in gender representation.
Margot and other female leaders in the vacation rental industry have contributed to encouraging, supporting, and developing women in the leadership sphere.
Merilee is encouraged by the increase in women’s voices at vacation rental events and the influx of women starting vacation rental businesses, and she makes a point of helping other women doing so.
“It’s a tough journey whether you’re a female or a male to start a business,” she said. “And so I think having an open door and willingness to support others is almost incumbent on us if we want to see that number [of women in leadership] grow.”
“That collaborative approach to leadership is certainly my leadership style. It isn’t everyone’s. Sometimes there can be almost a sense that women compete with each other, rather than collaborating, and there’s just no need for that,” Merilee said. “The more we support each other and the more that we can bring more women into this space, the better.”
Ashley Ching, CEO and founder of Inhaven, organized a founders’ group for about 40 female short-term rental entrepreneurs at Amy Hinote’s Vacation Rental Women’s Summit in December 2023 so that these women could support each other and tell each other’s stories.
Stacey St. John, owner of a vacation rental management company, started a mentorship program for female STR entrepreneurs. Additionally, she invites only female entrepreneurs and experts on her weekly podcast, the STR Sisterhood. She also holds an annual STR Virtual Summit for Women that features female-only panelists and speakers.
“I’m on a mission this year to help women unleash their inner boss lady,” Stacey said in an interview with Rent Responsibly. “It’s very much a passion project. Because I see that time and time and time again, women want to do their best and are absolutely dedicated to their business. But sometimes the feeling of overwhelm and analysis paralysis get in the way.
“Women have got to understand how to run a business and delegate tasks to be great business leaders,” she said. “I see that women have that desire to be leaders. So I hope to bring the skills into play to help match that desire.”
Fran Maier, founder and CEO of BabyQuip, echoed that sentiment in a March 28 LinkedIn post to mark International Women’s Month.
Reflecting on her successful career as an entrepreneur, she recounted how she had co-founded Match.com in 1994 and sold it for millions of dollars five years later.
“I know my work has had an impact,” she wrote. “But that doesn’t mean I don’t have moments where I think about how different my career would have been if I were a man.”
“One of the reasons I undervalued Match.com in our 1999 sale is that I simply didn’t know better. I didn’t have the kind of support or network that would have helped me accurately assess the value of my product.”
“At the time, no one looked at women as potential powerhouse founders, people who could take their companies to the next level,” Fran continued. “There’s no question that a man in my position would have had a different journey. That’s why it’s so important to make sure female founders are getting the resources they need to meet their full potential. Not just money but guidance, connections, and good faith. The same resources that would be afforded to any man.”
“It’s incredibly exciting that more women are entering the entrepreneurial space, but we have a long way to go in making sure these women have everything they need,” she said. “This International Women’s Month, I’m excited that every generation, fewer and fewer women are living with ‘what ifs.’”
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