One of the just-named 40 Over 40 Women to Watch for 2015, Diane Hessan is a successful entrepreneur, marketer and author. She is currently the CEO of Startup Institute, an organization dedicated to helping people transform their careers by providing immersive education for the innovation economy. Via SI’s programs, people gain the skills, mindset and networks to succeed in the exciting startup world. Since its inception 2 years ago, over 800 students have gone through Startup Institute program in Boston, New York, London, Chicago and Berlin.
She is also the Founder and Chairman of Communispace, a leading next-generation market research company that recently rebranded to C Space and boasts “a Blue Chip client list that would make a Madison Avenue giant jealous,” according to Ad Age. A pioneer in creating online communities to help nearly 300 global corporations generate consumer insights around their brands and services, Communispace launched in 1999 – when few knew what social media was — and was sold to Omnicom in 2011.
Diane is also co-author of the book Customer-Centered Growth: Five Strategies for Building Competitive Advantage, a BusinessWeek best-seller that was published in 11 languages. She has received many honors for her leadership, including The Pinnacle Award from the Greater Boston Chamber of Commerce, Most Admired CEO Award and Boston Power 50 from the Boston Business Journal, Ernst & Young’s Entrepreneur of the Year, the Greater Boston Chamber of Commerce Entrepreneur of the Year, and a range of Best Boss citations. The Boston Globe listed her as #3 on its Top Women in Technology List, and Communispace was listed as one of 25 Top Places to Work in Boston.
Diane has a B.A. from Tufts and an M.B.A from Harvard. In addition to serving Tufts Board, Diane also serves on the board of Panera, the Advertising Research Foundation, and Horizons for Homeless Children. Based in Boston, she is the mother of two grown daughters, an avid Red Sox fan and co-founder of The Sound Bytes, an a cappella group that sings about business. She shares some of the lessons she has learned in growing businesses and brands and the best advice she has received.
brandchannel: Diane, you’ve had an admirable career and success as a serial entrepreneur. Did you plan this kind of career trajectory? How did you get your start?
Diane Hessan: If you think of a career as a journey, mine has really not had an itinerary. I have had many phases, and each one has been pretty serendipitous. I have made more decisions based on a conversation with one person or a chance meeting than anything like a big plan. Early in my career, I worked in larger companies, and over time, I started to love the thrill that you get with smaller fast-growing companies: the feeling that you are indispensible, the rush of creating something and watching it grow, the challenges of building something from scratch, and so on. I became an entrepreneur because of that love of adventure – and because of the chance to build the kind of company I always wanted to work in.
bc: Startup Institute is a fantastic resource for people who want to get into that space and launch their own careers. What made you decide to take the job and where do you see the organization going in the future?
DH: I took the job at Startup Institute because I just fell in love with the mission. You know, not everyone wants to be a founder, but there are lots of people who dream about working in an exciting startup or scaleup. They want to do work that matters, with an inspiring team — and all they need is a lift in their skillset and a network to help them find the right company. Startup Institute helps those people in eight short weeks and they get what they need to transform their careers. At the same time, we help growing companies find the talent they need. It is exciting and meaningful, and we have a really diverse group of students, with ages ranging from 18-62. Our future is mostly about expanding to new cities. We already have nearly 1,000 alumni, and our dream is that some day there will be tens of thousands of Startup Institute alums globally, having a tremendous impact on the innovation economy.
bc: You’re also a huge champion for women in the workplace, especially in startups and technology. How has your own experience shaped or influenced the mentorship work you’re doing now? Has it changed your leadership style?
DH: I am a huge champion of diversity in the workplace, and of course, part of that means making it a priority to help women. The reason I emphasize diversity is that I believe 100% that a diverse team makes better decisions, innovates faster and thinks more creatively. I have seen it again and again in my career. There is nothing more boring than a company full of people who all look the same and have the same backgrounds, and that doesn’t just mean gender and racial diversity. It also means that when you have people in their 20s working with people in their 40s and in their 60s, everyone is enriched. My leadership has changed over the years because I have gotten really insightful feedback from co-workers, including many men. I have learned major things that I try to share with women, like how to dream bigger and how to have thick skin, and I have picked up lots of smaller things like how to net things out, how to stop apologizing and how to not worry about what you can’t control.
bc: The challenges women face in their careers are a huge topic of discussion. What’s the biggest challenge you’ve encountered in your career? How did you overcome it?
DH: I think that my biggest challenges came when I saw life as a series of tradeoffs. This notion of balancing competing priorities was drilled into me. Would I be a great mom or a great leader? Would I do that project or go to the gym? Would I work for a company that made a ton of money or one that did good for society? Would I be a tough boss or would I be the kind that people liked? I overcame this by throwing out the word “or” and substituting it with “and.” We cannot necessarily have it all, every day, but we can do so much more than the advocates of tradeoffs tell us. We can be tough AND be well-liked, and so on. The word “and” has helped me do things that I never thought possible.
bc: What is the best piece of advice you’ve ever gotten? And what’s the one thing you would tell your younger self today?
DH: Yes, I have had great advice over the years. One of my favorites was from my daughters, Lindsay and Amanda. I have a bit of a fear of heights, and one day, at the top of the Eiffel Tower, I found myself in between the two of them, squeezing their hands really tightly. They both shouted, “Mom, don’t look down! Just look across!” This has been invaluable in my entrepreneurial journey. People would ask me if the risk bothered me, and honestly, it didn’t. I never really felt I was on the edge of the precipice. I looked out there and I wanted so badly to build the kind of company I always wanted to work in, and so I ignored that big chasm below. Don’t look down!
In terms of my younger self, I think I would say that life is long. We have so many chapters. I have been in jobs I hated, jobs where I was a mediocre performer—I was fired once before I even started a job—and so on. And I have also had success that was unimaginable for me when I was growing up in Norristown, Pennsylvania with two parents who had never gone to college. We learn and we change, and now I also hope that I have many new chapters ahead of me.