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Lessons from One of the Top Female Leaders in Tech: Gail Goodman

January 24, 2020

In our first Curated Conversation of 2020, HubWeek Co-founder and Managing Director of The Boston Globe Linda Henry hosted Gail Goodman to chat about her many years of experience as CEO of Constant Contact, her decision to join startup Pepperlane as Chief Product Officer, and her lessons learned as one of the most successful female leaders in tech. 

The two women share something unique in common: both are the fourth child of immigrant parents. For Goodman, that meant she and her older siblings were taught to value hard work. After starting her career on the technical side of things, Goodman put herself through business school and gained the foundation of her leadership skills by learning to ask the right questions and honing her skills of focus and alignment.

Read on for a few of the life lessons we gained from Gail Goodman and her impressive career during this Curated Conversation:

The biggest change often comes from the smallest businesses - After graduating from UPenn, Goodman began her career at IBM. Afterwards, she chose to join companies that were increasingly smaller in size. “I like moving the needle, she said. "I like seeing change, leading change, and so I kept going to smaller and smaller companies.” Her desire to create change and influence led her to companies including Open Market and Constant Contact, which had only six employees when she joined.

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Sometimes all you need is an extra push to be your best - After working for Open Market, Goodman interviewed for CEO as well as VP positions, unsure if she was ready for the top job. As an outcome-oriented person, learning to understand her inner dialogue has been an important part of her leadership journey. A male friend gave her the final kick she needed to stop pursuing anything but CEO jobs, something Goodman considers a good example of what men can do to support women: pushing them to be everything they can be. 

Feedback, while tough, can be a gift - While Goodman acknowledges we live in a world where people would rather give feedback than receive it, she learned early on that allowing and accepting it from the people you work with is the only way to grow. “You can’t change what you don’t know, and most of us don’t know what people really think,” Goodman said. At Constant Contact, this resulted in hosting "feedback speed dating" at leadership offsite meetings to encourage a standard of candor.  

There's no better place than Boston to build a business - “I am a huge fan of the Boston ecosystem," Goodman said. Constant Contact was built entirely in Boston, and while it was a bit more difficult to partner and integrate with companies in Silicon Valley, the extra effort was worth it. Boston's biggest benefits, according to Goodman? Talent and employee loyalty, through thick and thin.

Small businesses are the bedrock of the American economy - Goodman shared that supporting small businesses in America is one of the things she cares most about. She became heavily involved in the nonprofit Entrepreneurship for All (EforAll) as a mentor, philanthropist, and now board chairwoman after falling in love with the power of helping someone who has an idea and an energy but is completely un-networked. She considers EforAll one of her anchor initiatives because it genuinely makes a difference. "We are literally transforming communities through entrepreneurship," she said. Through Pepperlane, Goodman's helping moms become entrepreneurs with tools, training, and a supportive community that allows them to build and grow a business on their own terms.

We thought attendee Jay Ash (@JayAshMACP) summed things up nicely:

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