There are a lot of new faces around “The Grid” lately. Two of these faces—Chiara McPhee and Jen Kessler—have such a striking story that we just had to share it with our readers. The entrepreneurial duo is out to solve some of marketing’s growing challenges. And they’re doing so by bringing drastically different perspectives to each problem they decide to take on.

The pair joined SendGrid in early 2017 when SendGrid acquired their marketing automation software company, Bizzy. They’ll continue to drive improvements for email marketers and developers now under the SendGrid portfolio.

Bizzy founders Jen Kessler (left) and Chiara McPhee (right) settling right in at the SendGrid headquarters in Denver, CO.

Converging, complementary personalities

Chiara and Jen’s personalities and background at first seem a bit at odds—a good thing the two both agree. Chiara is both soft and well-spoken, assertive, and a visual thinker driven by arts. Jen comes off a bit bolder, speaking with intrepid intensity (ask her about predictive modeling!), while remaining thoughtful, and grounded by mathematical logic.

Those differences intersect at a common desire and aptitude to solve marketing problems that satisfy both the art and science component of marketing issues. When Jen and Chiara formed Bizzy the weekend before receiving their MBAs from Stanford Graduate School of Business in 2013, they made a pact that they would tackle every marketing problem they faced with an answer that satisfies both the art and science component of the issue.

“We knew we always wanted to work together” says Chiara. “It was a matter of coming up with that idea that we were both excited about.”

The two admit that their different perspectives sometimes resulted in heated and exciting discussions, but that it also paved the way for an open and honest relationship built on respect and trust. Not to mention success.

Before Bizzy

Jen and Chiara met on the first day of Stanford Business School. They struck up an instant bond and even went school supply shopping together after their first day of classes—an unnecessary errand the two, years later, agree–turns out you don’t need many/any supplies while getting your MBA. That bond turned into a friendship throughout their years during business school despite their very different backgrounds.

Prior to business school, Chiara studied a combination of media policy, economics, and animation in undergrad. She says she was most interested in learning 1) how people consume media and 2) how people make decisions. After she graduated, she even tossed around the idea of working in the film industry at Disney or 20th Century Fox.

Shortly after, she dove into the digital marketing consulting world working on large CRM projects for Fortune 500 clients. As a result, she’s used every major marketing tool under the sun—Marketo, Salesforce—you name it.

Jen, on the other hand, has degrees in cognitive neuroscience and math. She is an expert at measuring risk, value, and building models that predict behavior. She says that studying math allowed her to break down problems into logical structures.

“I liked math because it just kept getting harder and harder continuing to present different types of challenges,” says Jen. “It almost felt like it was stretching my brain.”

She, like Chiara, worked in the consulting world after graduating, but she focused on quantitative finance and measuring risk and value across a variety of industries. She then joined the pharmaceutical company, Merck, where she developed models that would determine which drugs the company would invest in.

It was at Merck where an idea for a marketing portfolio sparked. Her job was always trying to build the most accurate models to value things that couldn’t be measured in “traditional” ways.

“What was cool was that nobody was really doing that with marketing,” says Jen.

The Bizzy years

So…the two decided to build their own platform that would help ecommerce email marketers determine when to send email recipients an email and when. With funding from Silicon Valley incubator, Y Combinator (they were the first all-female founder team), the two went to work with a small team of engineers, breaking down the art and science of email marketing automation. In its first year, Bizzy amassed an impressive 1,000 customers.

When SendGrid acquired Bizzy, Jen and Chiara said they were especially excited because it meant they would continue to work together.

“We were looking at various next steps for Bizzy and this was the most attractive option—continuing to work with each other was a big portion of that decision,” says Chiara.

Chiara, now Director of Product for SendGrid Labs, will explore opportunities for SendGrid to solve cross-channel, attribution, and large data problems that ultimately help marketers be smarter communicators. Growth marketers today have to strike a balance between art and science in their work daily, and she is excited to help make science more accessible.

Jen, Director of Product for Marketing Campaigns (SendGrid’s email marketing platform), will be driving improvements within the product. But, she reiterates that despite being on different teams,  all teams at SendGrid are really working on the same thing—building an email marketing product that is fundamentally different from other tools, and that also makes room for other channels.

“We are all working in a very cohesive manner from a product perspective across the company,” says Jen.

Never easy

With all of the successes that Jen and Chiara have had thus far, they do acknowledge that their founder story came with a lot of support from every angle: friends, family, classmates in business school, and YES those investors. But no matter how much support your business stands on, starting your own company is never going to be easy.

“In the beginning, starting your own company is like carrying a backpack with bricks and then there’s also a trail of bricks and you’re moving forward with this weight,” says Jen. “You’re just pulling this thing with you and the only thing that will keep you moving forward is sheer willpower and persistence. If you don’t keep lugging everything forward, it’s not going to happen. It’s hard.”

Jen adds that having a partner you can count on helps tremendously in moving the business forward because you equally share the burden.

Chiara also emphasizes the importance of picking the right co-founder. “I saw a lot of friends coming out of business school going at it alone,” says Chiara. “That’s such a big emotional weight when you are responsible for everyone and unfortunately, relationships out of work can start to suffer.”

Jen and Chiara say they keep each other accountable for many aspects of the business—including not working because it’s easy to let your health and personal relationships slide.

“If you have a good partner, you can hold yourself accountable,” says Jen. “Having the right partner keeps you healthy.”

And personal health is a crucial component of the Jen and Chiara’s success. The two value and prioritize exercise because they both say it clears their minds, helps them prioritize, allows them to work through stressful situations, and ultimately get more done throughout the day.

On female entrepreneurship and building teams that last

Although there had been solo female founders backed by Y Combinator, Jen and Chiara were the incubator’s first all-female founding team. But the two don’t dwell on that important milestone (we’re still impressed!).

“I wish it would have happened sooner and that we hadn’t been the first” says Chiara. “Those solo female founders really deserve an award.”

But the two both admit that there is something different about being an all female founding team—and that the effects were clearly felt during scenarios such as pitch meetings.

Investors and entrepreneurs alike have historically been mostly male. And while investors are trying to determine and measure the risk of business ideas, they need to know how to read people’s signals. So they develop a framework to apply to each individual. The thing is, you can’t apply an identical framework to females because, well, females and males communicate in different styles.

“Investors look for pattern recognition and females don’t fit those patterns,” says Jen. “We were breaking the normal signals and you could definitely feel it during the pitch meetings.”

As far as hiring and building out their own teams, Jen and Chiara look for people with a natural curiosity, ability to figure out their own answers, and those who people wanted to work with over and over again. Chiara adds that those who tinker with side projects or those who have a “side hustle” are “seriously, by far the best.”

The two agree that formal training only goes so far and you really need to have an inherent curiosity to get to the bottom of things.

“Don’t be afraid to sound dumb, it’s much more important to understand, which is how you learn,” says Jen.

SendGrid and beyond

So far Chiara and Jen are transitioning into SendGrid seamlessly whether they are socializing with other Gridders over breakfast in the SendGrid kitchen, presenting big picture ideas at our monthly all-hands meeting, or just appreciating all the extra office space they have to work with.

And it’s quite a lot of extra space! Bizzy’s first office was Chiara’s apartment. After that, they upgraded to a room in a WeWork office with six desks and adjoining phone rooms the size of a closet.

“I walked into a meeting room at SendGrid on my first day that was a 1-person room and all I could think about was how enormous it was,” laughs Chiara.

Despite the size and space, Jen says that the offices feel cohesive and tight. “I love that everyone sits together at lunch and makes breakfast and chats during the morning,” says Jen.

“It was just a really comfortable environment right off the bat.”

Whether they are working in closets or at SendGrid’s 52,000 square foot downtown Denver office, Jen and Chiara are already accomplished and set up to to do great things for marketers around the world. I’m excited to see how they shape the future of SendGrid. Stay tuned!

Kelsey Bernius
As a senior content marketing manager at SendGrid, Kelsey oversees the SendGrid Delivery blog. Her downtime is dominated by either her mountain bike or skis (depending on current weather forecast)–and mixing up a salty marg afterward.