Startup Institute kicks off new era of honest conversations with power quartet of female tech leaders

The scene at the Startup Institute.
The scene at the Startup Institute.

The Startup Institute hosted an event on Tuesday called Amazing Women, Honest Conversations, with Diane Hessan, the career accelerator’s dynamic new chief executive serving as moderator for the evening.  Meredith Davies, a Startup Institute student in the “Web Development” track came up with the idea — a way to let women leaders in high-growth companies talk about the challenges and opportunities they face.

Speakers included Emily Green, chief executive and Chief Lunch Lady at Smart Lunches, Nataly Kogan, chief executive and co-founder of Happier, Jen Reddy, vice president of marketing at IdeaPaint, and Zenobia Moochhala, vice president of consumer marketing and co-founder of

All the panelists had spot-on advice for the large crowd that was made up of mostly women and a few men.

Everyone offered very simple advice about how to win as an entrepreneur. Each panelist told stories of the difficulties they’d confronted in male-dominated companies in the past, but, overall, they made everyone feel that there are some great opportunities awaiting women on the road to success — and fewer potholes (like rampant sexism in the workplace).

Emily Green, the chief executive of Smart Lunches, told a story of her first engineering job as the lone woman on a team with 300 male engineers back in the late 1980s. “I felt like an animal in a zoo,” she said. “Guys would come by just to see ‘the girl’ as I sat at my desk.”

When a large group was discussing performance appraisals with the boss, she realized she hadn’t been told anything about it and asked when she would be getting her appraisal. “I’ll give you a performance appraisal any time you want, if you come in a bikini,” her boss answered in front of the roomful of  men. Later Green talked to HR about what had happened and ended up getting transferred out of the department. As the CEO of a successful startup, she still wonders what she might have done differently.

Her advice now to aspiring young women, “Show up, look up, stand up, suck it up, and sometimes, shut up and listen harder to others.”

Nataly Kogan from Happier recounted her early job at a venture capital firm where she invested in a woman-led company against most of the male partners advice — a decision that later resulted in a big win for the firm.

Early in her career, she found out that one of her newer, less experienced male colleagues was making $50,000 more in base salary than she was. After a confidence-building lunch with her administrative assistant (a lady of a certain age who knew what went on at the firm and told her not to put up with it) and two Cosmopolitan cocktails, she got her nerve up and marched into her boss’s office, confronted him with the facts, and told him she was leaving unless they fixed the discrepancy.

They fixed it.

Now Kogan is a co-founder with a small team, which is mostly female, and an app with a huge female customer base. Her advice for other woman entrepreneurs, was to be a strong advocate for yourself if you’re not being treated fairly, and have what she called her  “4 a.m. team”  of friends.

“I can call them when I feel like giving up or don’t know what to do. I can freak out with them and then get back to business and back in balance,” she said.  Her biggest challenge lately: Avoiding burnout by taking time for herself to do yoga, walking, and even finding time for some off-the-grid days. 

Jen Reddy from IdeaPaint recounted early days on ad agency teams where the lead partner would tell her, “We need a girl on the team” or before a big presentation would look at her seriously, as if needing her savvy advice and then say, “What are you wearing tomorrow?”

Reddy’s reaction? “I decided to focus on being the smart girl in the room, which I figured was sexier than any outfit I could put together.” Like the other speakers, she thinks that the “Mad Men” era of overt sexism is behind us.

Zenobia Moochhala, co-founder at looked refreshingly puzzled when asked if she’d experience any sexist corporate behavior saying, “We’re a women-led company, that just doesn’t happen.”

But Moochhala was honest about another negotiation ambitious women must schedule. “Women need to be sure they talk out the reality of being committed to a career with their partner and get their support,” she said. “I told my husband that I wasn’t going to be home making dinner for either of us. We knew we could both have jobs, but one of us would have a ‘job’ and one of us would have a ‘career’ and that meant staying late at the office and traveling more than being at home.”

“As a co-founder of a startup, I’m the one with the career, and he understands that,” Moochhala said.

Diane Hessan was the perfect moderator for the event, even offering sage advice of her own.

As a founder of a successful startup, Communispace, which she sold to Omnicom in 2011, she is an inspiration to women and men in the Boston entrepreneurial community. She is vehemently against women apologizing for themselves every time they speak, something she noticed in meetings all the time.

“Stop saying things like ‘I’m not sure if this is on topic, but — ‘ or ‘You probably already thought about this, but what if we — ” or ‘I know you’re very busy, but just wanted to run this by you.'”

Hessan was emphatic: “Just state your opinion and own it!  Stop apologizing for having an opinion. And watch your friends in meetings, and if they do this, tell them to stop it!”

If the Amazing Women, Honest Conversations event is any indication of the new energy Diane Hessan will bring to her role as CEO at Startup Institute, you won’t want to miss any of her upcoming events.

So show up! Get ready to stand up! Since most of Startup Institute’s events are likely to be standing room only.



Halley Suitt Tucker is an author, entrepreneur, TechStars alum, and two-time successful Kickstarter campaigner. She lives in Arlington.
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