7 Startup Leadership Lessons from Former Constant Contact CEO Gail Goodman



Gail Goodman was the president and CEO of Constant Contact for nearly 17 years before stepping down after the company became a unicorn, selling for $1.1 billion last year.

She helped grow Constant Contact, which provides email marketing software to small businesses and nonprofits, from a pre-revenue startup without a product to a publicly traded company with 650,000 customers and revenue of $367.4 million in 2015.

I’ve had the pleasure of meeting Goodman in person on a few occasions. She is a small business advocate, is the author of “Engagement Marketing: How Small Business Wins in a Socially Connected World” (2012), and now sits on the board of Shopify, MassChallenge, and MINDBODY.

Among her honors and awards:

  • “Executive of the Year,” American Business Awards, 2008.
  • 2008 Ernst & Young Entrepreneur of the Year award, New England region, 2008.
  • MITX Innovation Hall of Fame, class of 2011.
  • Named a Top 30 Boston Innovator by The Boston Globe.

Here are seven lessons startups can learn from Goodman.

1. Genchi Genbutsu

This means “go look, go see” in Japanese. Goodman wrote that the true secret of growing a successful business is to get to know your customers and actually view your own business through the eyes of your customers.

By doing this, Constant Contact found out that one of the big ways their target audience learned new things was from the radio. So Constant Contact – an online company – used old-school broadcast media reach its target audience. And it worked!

“Get to know them. Visit them where they live or work. Find out how they spend their days. What apps do they use? What sites do they visit? When and how do they search for what you offer? What is important in their buying decisions?

Once you have a marketing hypothesis, run a small test. If it works, scale it and fine tune it. Then do it again.”

2. Listen to Your Team

Want insights that can help grow and change your business for the better? Then listen to your team. In her words:

“You have people around you who can give you insights, if you ask and then REALLY listen. Listening to feedback is hard. It’s so easy to feel (and act) defensive. Instead, take a deep breath and thank them. Then think about what they told you.”

It doesn’t have to be done face to face, as this can be intimidating to your team. Find out what your employees are thinking by soliciting feedback anonymously.

3. Wowing Your Customers = More Referrals

“Wow” is the biggest driver of referrals.

You need to create a “wow” moment in your early experience that inspires your customers to tell others about how great your product or service is, she said in a Business of Software talk in 2016.

If people love something, they will tell their friends about it. Marketing your product to people who like it will lead to a lot of revenue.

4. Experiment Constantly

When you’re a startup CEO, you’re “hunting for the model” in the early days of your company, according to Goodman.

To find and perfect your business model, you need to constantly experiment. Success is driven by a million incremental improvements to your business model.

However, it’s important to give things enough time. While “failing fast” gets a lot of praise, failing fast can lead to false negatives or positives.

Did you fail because you didn’t do it right or did you fail because it’s the wrong thing to know? Give your growth initiatives enough time to gather data that answers this question.

5. Coach, Don’t Sell

If your product is great, you don’t need to sell to customers.

Your sales team needs to help customers understand why they need your product and then how to use it.

Make sure your sales team stops selling and starts coaching your prospects and customers on how your product can make them more successful.

6. Remember Who Your Customer Is

Never forget who your customers are.

Very early on, Goodman said Constant Contact started holding company meetings every week. At these meetings, they told a customer story, whether it was reading letters or bringing a small business owner into the office.

The point of doing this was so that everybody in the company remembered who their customers were and why the company was doing what it was doing.

7. How to Keep Innovating

How can companies continue to innovate? According to Goodman:

“It actually starts with making sure everyone knows they’re paid to think and to innovate. It all starts with an attitude: what else cool can we do?”

Another thing that helped Constant Contact: employees used 10 percent of their time focused on innovation.



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