2018 Ones to Watch: Cindy McLaughlin, CEO at Envelope City

Name: Cindy McLaughlin

Title: CEO

Company Envelope City

Address: 233 Broadway, Suite 2170

Year that you entered your current field? 2000

Who or what do you attribute to your success? 

Part is personality. I’ve got lot of tenacity, a high tolerance for risk, and a high degree of confidence in my vision for the business. It helps me sell the vision to others. Part is experience. I’ve learned that once I set a course that feels right, I need to put blinders on and execute. It’s too distracting and confusing for everyone involved to shift direction without overwhelming evidence. Finally, I’ve been wildly lucky. I have an incredibly supportive family, lots of terrific mentors, and came of age in a time and place that allowed for female entrepreneurs.

What are your professional goals for 2018? 

We are thrilled to be past the point where we struggle to survive. We are lucky to have great investors and enough money to plan ahead. I’m settling into a groove this year with a greater focus on management, culture-building, operations, and strategic partnerships. 

How do you manage the work/life balance?

How does anyone? I get up, try to do my best, try to forgive myself–and others–for not being perfect, and then try to remember how lucky I am.

 to have this life, this work, and these responsibilities.

How did you get your start in your current field?

I start tech companies for a living. I was in my third semester at MIT/Sloan in 1999, when my favorite strategy professor asked me to help him launch a company with a bunch of his engineering advisees. We all dropped out of school that January, and the company promptly failed in March when the market crashed. Luckily MIT has an open-door-for-life policy, so I was able to go back, finish my MBA, and wait out the market while figuring out what to start next. 

How do you contribute to the future of your industry?

First, I’m working hard to be a role model for other women with similar ambitions. It IS possible to be a successful entrepreneur-mother-wife-friend, and to do it all with integrity. I’m especially interested in changing hearts and minds within my current industry, real estate tech, which (surprise!) is male-dominated. There’s a loose cabal of female investors and entrepreneurs who band together to support and create opportunities for each other. It’s exciting to know these incredible women break the mold, each in her own way.

How do you motivate or inspire your colleagues?

My team makes Envelope the incredible company it is – they inspire me! My only work is to try to make their lives easier by bringing in money, hiring them phenomenal colleagues, setting a clear strategy, and getting out of the way so they can shine. I then ensure proper communications, resolve questions about direction or conflicts, offer help where needed, and represent their interests with the board and investors. My current team is amazing – they’re all smart, kind, motivated, and excited about what they’re building for its own sake. Business success with them flows much more easily. 

Where do you see yourself in five years?

I hope to be investing in other great companies to pay it forward. With luck, many of those will be founded by great women or people of color.