As part of our Lead(H)er series, we have had the great privilege of interviewing so many incredibly talented women who are founders or executives at some of the fastest growing companies in Boston's vibrant startup scene.
They’ve told us about everything from the challenges, successes, and surprises of their careers to how many cups of coffee it takes to get through a day, so take a look at our list of the talented women we’ve spotlighted this year.
“I think that was a useful experience because it's a completely different set of skills that you get when working at companies of different sizes,” Ladiwala said. “My sweet spot is between 200 to 1,000 employees. That’s where I have, in the past, come in and be able to add value and make a difference.”
“I was blown away by just how hard the postpartum recovery period was, even with help from family, friends, and good health care,” Westervelt said. “I started to think about single moms everywhere, and others with fewer resources than I. How, if this was so hard for me with all of my available helping hands, were other women with fewer resources getting on?”
"It was so outside of my wheelhouse,” said Shaikley, who had dreamed of building United Nations resettlements for people who had been displaced by conflict or natural disasters. “It was insane, and I fell in love with technology and the idea of working within technology while I was there.”
“My decision to jump over and do a startup was the culmination of having worked in more innovative and entrepreneurial settings and really liking that, but also finding a vision and a partner that shared my values and wanted to bring more data into the hands of students and families so that they can make better decisions,” Manville said.
“When I think about a new challenge, I assess what I've got to work with and where I see gaps, and then I ask for things to enable success, whether it's people or skills or a new office or software,” she said.
“When you're talking about an early stage or start-up organization, you have an opportunity to really make an impact and see the results of your team's efforts,”
“What’s most important to me is constantly improving as a manager and leader to make sure that my team is running effectively and feeling fulfilled in their work,”
“What’s important to me is that I continue to learn,” Rose said. “And the more time I spend with customers, the better. I hope to always be working in a role in a company where customers are truly seen as the lifeblood of the company and where a customer-first strategy is our compass.”
“What I find most rewarding is really being able use my position to focus on the people that work here,” Ames said.
“I always look for the problems that are going to be exciting, interesting, and satisfying, and for the people that I’m going to be pumped to work with,” Morway said. “It’s about, where can I be learning and growing? ”
“Going back to that smaller, earlier stage startup is what really got me excited,” she said. “I love to build something from nothing.”
“It’s really been an awesomely fun career, and while you certainly never master something like advertising, jumping into something where there are parts of it that you know nothing about is both terrifying and exhilarating,”
“From a really broad sense, it’s about taking all of the different sales channels that we have and people who are customer-facing within our own company and improving their understanding of our solutions. How can we better educate and enable people that are working within our marketing services division to drive revenue and improve customer service?”
“When you think about the future, that’s really today,” Smith said. “It’s been exciting to embrace every new capability that comes into marketing, and now it’s faster and more exciting than ever. Imagine a day when all you have to do is say, ‘Alexa, schedule my oil change,’ and she goes, ‘Okay, contacting Openbay!’”
“Somebody said to me in a very casual conversation that I was creative and should look into this web design thing,” said Rice, now the Head of Product Design and Research at Toast. “I had no idea what that was, but I did look into it.”
“What I thrive on is the energy, ideation, and willingness for people to test things, try them out, and then dust themselves off and start over again when they have to,”
“I was managing a team at that point, and I realized that I loved helping people,” she said. “I loved growing people’s careers and finding out their strengths and weaknesses to help them thrive within the company.”
“It’s an incredible opportunity to apply process improvement and account management strategy at a fast-paced, high-growth company, like Applause.”
“I don’t believe HR can be of value in an organization unless you understand the business,” she said. “For me, that means helping business leaders figure out the puzzle of, how do we take what the business wants to do and tie that to your people initiatives?”
“We saw families who were trying to do something like this through Craigslist or Yahoo,” Gubin said. “That’s how much they wanted this type of care. The whole point of CozyKin is to bring peace of mind to families.”
“My real skill is being able to look at companies when they’re going into a real growth mode and trying to figure out how to go from startup to scale while still driving the same level of service,”
“When we talk about attracting, developing, and retaining talent, it’s about coaching them through a series of experiences and providing them with enough support that they can use all their experiences as a series of touchpoints they can grow from,”
“What I've learned is that I love problem-solving, and what's interesting is, no matter the size of the company, there are always new challenges and problems to solve,”
“What I loved about Wayfair and now love about Takeoff is that we’re solving problems when there’s no blueprint,” Scott said. “You can’t call anybody or look this up online, because nobody knows how to do this. I don’t know how to do it either, but I know how to put the right people into the room to dig into problems and figure it out.”
“Our customers are very large enterprises, so it can be a lengthy process to acquire new customers and onboard them,” Bohne said. “We give them lots of TLC along the way, working in close partnership with the sales and customer success teams, to make sure potential customers feel confident that AppNeta can help make them successful.”
“You can work anywhere, but more importantly, what are the compelling factors that differentiate where you work compared to any other company in the marketplace?”
“It’s been a constant series of evolutions over the course of two decades from web design to information architecture to user experience design, to now managing the entire process.”
“I want to be in a position where I feel really proud of having built a team that understands how each person contributes to the overall results and feels really good about the impact we have on the business,” Cunnane said.
“As a data scientist, it’s important for me to work in companies where the value proposition is the data,” Schreiber said. “I wanted a company that didn’t compromise, and strives to be the best in that field.”
“I felt like I could have an impact within an organization of this size,” Esten said. “My last two companies have been founder-led, and I think working with the founders and executive team at this level is something really special. Everyone knows everyone’s names and what they’re working on.”
“Everyone’s focused around our customers,” she said. “We’re a pretty small, agile company, so we’re able to bend over backward for our customers.”
“You go from having zero to five leads to then building an engine, trying new things, and seeing the impact of that happen so quickly,” she said. “You can build your own path and experiment.”
“I’ve always been able to work with a smile on my face, no matter how challenging things were, and most often found a resolution,”
“I’m proud to be part of the company’s history of financial stability and financial strength that allows us to make investments that are all self-funded.”
“You have to know what problems you need to solve, but also what’s the most effective tech and how to integrate it with your marketing,”
“I can trace all of my big career moves to a time that I raised my hand and said I’d do what no one else wanted to do, which was either travel 60 percent of the time or move to another location,”
Lauren Melton, Vice President of People Operations at Ellevation Education
“I very quickly learned a lot of employee relations skills that I’ve seen people go their entire career never having encountered,” Melton said. “I dealt with everything from unfair labor practices and contract negotiations to investigations around some really challenging situations.”
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“I really fell in love with the startup environment,” Mallett said. “I especially love the hypergrowth atmosphere.”
“Selling technology to large enterprises was a sweet spot for me,” says Melissa, who managed sales teams at IBM, BMC and Oracle before joining Tamr. “But I was nervous about moving to a smaller company because I’d always had the mindset that I was a ‘big-company gal.’”
“As a female executive, I feel strongly about a lot of topics, including equal pay, diversity and inclusion, and making sure different voices are heard.” Making sure these issues are addressed in her own company, and then at others, “that’s really gratifying.”
“There’s always something you could do better. So you have to find a balance, figure out where to focus your time and apply limited resources. Sometimes you realize something isn’t perfect, but doing it perfectly also isn’t the best use of time.”
“I saw this job working with collaboration software, Lotus Notes, and I thought it looked interesting. I wasn’t sure if I was qualified, but I figured I could learn it. So on a whim, I applied!”
“I like helping people grow. Whether they’re fresh out of college or an MBA program or very experienced, I want to figure out what makes them tick, what their career goals are, help them create their path. I strive to be someone others trust.”
Vitri Bhandari, VP People Ops & Strategy at Klaviyo
“I want everyone who comes into contact with Klaviyo to have an awesome experience,” she says. For example, if someone interviews at the company, “even if it’s not the right fit, I want them to feel like they’re better off for having coming into contact with us.”
What do you enjoy doing in your free time? 
What do you consider one of your greatest accomplishments? 
