Transforming Education, Tackling Inequality, and More: Meet Diane Hessan, CEO of Startup Institute

Diane Hessan is a successful entrepreneur, marketer and author. She is currently CEO of Startup Institute, which is dedicated to helping people transform their careers and find jobs they love.

She is also Chairman of C Space (formerly Communispace), where she was CEO for 13 years. Diane led Communispace to 13 years of exponential growth, and it now has over 500 employees, and offices in over a dozen countries. She has spent her career as a business executive & is co-author of the book Customer-Centered Growth: Five Strategies for Building Competitive Advantage. The book, a Business Week best-seller, was published in 11 languages.

Diane serves on many boards, including Tufts University, Panera, CoachUp and Horizons for Homeless Children. She is an active angel investor and an advisor to Datapoint Capital. She received her M.B.A. from Harvard Business School and her B.A. in Economics from Tufts University. She has 2 grown daughters, and is founder of The Sound Bytes, an a cappella group that sings about business.

Why are you doing what you are doing today?

I absolutely love how Startup Institute is transforming education, and it is a blast to be building another company. We have all of the challenges of any early-stage company, but it is so inspiring to be helping people to reinvent their careers.

If you had no constraints, what problem would you like to start tackling tomorrow and why?

I think that inequality is the biggest problem facing us. When people feel that they don’t have a chance to succeed, it causes all kinds of problems, and we lose our American Dream. I am also very passionate about Youth Voting: how only 18% of people ages 18–29 voted in the last election. If they all voted, they have the power to change everything about our country, and so I am passionate about getting people engaged.

Tell us about a story when someone won you over. How did they do it?

When I was CEO of my previous company, Communispace, I decided not to see any more “vendors”. They were mostly salespeople, pitching their wares, and coming to me to see how they could be a better partner, which was code for “How do we get more business from you?”

One day I was at my desk early in the morning, and I got a call from a man who was amazing.

“Diane, he said, please don’t hang up on me. It’s my first day in sales and I am going to remember this call for the rest of my career. I have been reading everything about your company and I am in absolutely crazy about what you are doing.”

He went on to tell me which of our case studies he liked the best, which of my tweets he thought were the funniest, and on and on. And, it didn’t feel like a sleazy pitch. He was just plain interested and authentic — and he did his homework — and I wanted to give the guy a break. I saw him the following day and we ended up buying from him. I hope he is sitting on a panel somewhere talking about how I gave him his first break!


SheWorx is a global collective of ambitious female entrepreneurs and changemakers redefining the next wave of leadership.

RSVP for the next SheWorx breakfast with Diane Hessan on Wednesday, April 20th, 9–10:30 AM. We will be discussing how to build strong organizational structures for an early stage startup.