In the Lead: With Caren Maio

Group of women confidently standing together

In this month’s edition of “In the Lead,” we speak to Caren Maio, an accomplished founder and thought leader in the PropTech industry.  She is currently the President of Moved and the Co-Founder of Funnel Leasing (formerly Nestio).  In addition to building businesses, Caren also mentors aspiring female leaders as Entrepreneur-in-Residence at Camber Creek, and as part of New York University’s Female Founders Fellowship program.

Caren has many accomplishments under her belt, but arguably, one of her most impressive achievements is how she thoughtfully and intentionally creates positive working environments that foster growth for her teams. The intentional part is essential.  Many founders can get lost in the concept and neglect the people management part of a company. Perhaps this is why more than 90% of start-ups fail.

I ask Caren to explain her team-building approach to better understand her leadership style. Caren emphasizes the importance of defining a company’s set of values that are important and non-negotiable early on and ensuring it’s clearly communicated.

“Culture is really important. It is very critical to be clear in that so that people can self-select into the culture or self-select out of it. It’s important to know what your North Star is and what you stand for, what you celebrate and what you won’t tolerate.”

Caren believes the most essential part of creating a healthy company culture is for leaders to focus on their people as much as possible.

“It’s about priorities. Prioritizing the important over the urgent. Investing in your people might not feel urgent, but it’s so important.”

Investing in people can look many ways, but according to Caren, it starts with her leadership style.

 “I really try to coach to the individual and find out what makes them tick. What are their priorities, what is their communication style?  I ask them, what makes you feel good? What pumps you up? What motivates you? What makes you shut down? It sounds so silly but it’s so important. It’s even beyond the Golden Rule of treating others the way you want to be treated; it’s the Platinum rule: treat people how they want to be treated. It’s really easy and so simple, but so many leaders don’t do it. It’s so impactful.”

Another important point about culture and values is to empower people to bring their whole selves to work. This can be achieved through promoting positivity, inclusivity, and healthy work expectations.

“Ask your team what they care about, what makes them feel good, what their values are. And actually live them.”

“Ask your team what they care about, what makes them feel good, what their values are. And actually live them.”

Caren gives an example of an education initiative they started at Nestio. Every year, a certain amount of money was allocated as an education stipend to allow the team to learn something new, no matter what they were interested in learning. Beyond being a great company perk, this enabled individuals to explore their interests outside of work, which in turn, helped them feel fulfilled and appreciated.

Being a woman in Tech isn’t an easy path to choose, but Caren has never been one to shy away from challenges. After all, being an entrepreneur is in her blood.  Caren grew up watching her father run his own business, and even as a kid, she knew she wanted the same thing for herself. “It’s how I’m wired; I really like the idea of building.”

I ask Caren if she’s experienced any particular barriers as a woman in Tech. She nods and explains that although she prefers to focus on what she can control in any given situation, she has experienced barriers and has had to work hard to get a seat at the table.

“I remember when we were out raising money for Nestio, I had an investor talking to my male COO the entire time and the last question he asked sent me over the edge. He asked my COO, why did you start the company? I said, “Hey, over here, I started the company.“ Lots of scenarios like that. This is why women supporting women, mentoring other women, and paying it forward is so important.”

I asked Caren how she overcame these barriers to entry and whether this contributed to Imposter Syndrome. She explains that she didn’t overcome impediments as much as she combatted with resilience.

“Putting one foot in front of the other and saying, I’m in this, I have passion, conviction, I believe this is going to work; that this needs to exist, and I’m going to see it through. Having a strong sense of conviction in the work you’re doing and combining that with the “fake it ‘til you make it” approach helped. And being able to talk to people you trust and let your guard down.”

Caren had a lot of female mentors when she was starting. They helped guide her through some complex parts of the job and ultimately helped her create her coaching style. She is still a part of this strong network and enjoys helping other women starting.

“Now I get to pay it forward.” She explains.

When it comes to the advice she’d give new leaders, it doesn’t disappoint.

Caren encourages people to be truly clear about their “why.” Keeping your “why” at the forefront helps keep people focused on what is essential and prevents getting distracted by things that aren’t important. Caren also encourages people to always prioritize themselves and their needs.

“This is the hardest one. I thought for a really long time that I had to outwork everyone. I had to work harder than anyone I knew. I had something to prove and believed the people who loved me would have to understand. ‘I’m sorry I missed that birthday, I have to work.’ Now I know that what feeds me is time with people I love.”

This circles back to the concept of having your whole self show up for work and leading by example. You’re better equipped to lead and inspire a team when you are fed emotionally and physically.

Before we sign off, I want to know Caren’s pump-up song.

Hey, Ya by Outkast. It works for all occasions!” She laughs.

We’ll be back next month to chat with another inspiring female leader. In the meantime, make sure to check out all the amazing content on Bosstrack! We offer leadership courses to help empower you and reach your goals. Leadership courses can be found here.


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