“I said, listen, I will recite the Jets’ season record from the last 5 years.”

“I said, listen, I will recite the Jets’ season record from the last 5 years.”
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The first thing that strikes you about Dheerja Kaur is her energy. She’s like a highly focused tornado that can spin an audience into a state of excited attention within moments of starting to speak. We were thrilled when Kaur agreed to join our New York-based class for a fireside chat as part of Matter’s “The Drunken Walk” series.

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When you take a job at age 21 with a top sports broadcaster and stay for 7 years, it’s not easy to make the leap and start something new. But Dheerja Kaur had done everything she could have dreamed of, and more, at ESPN. She started there as a web developer in 2008, after sweet-talking her way into a job she didn’t technically know how to do: “I’d never touched anything on the web. I was like, I’ve heard of HTML. I’m a big sports fan, I’ve taken programming classes, I pretty sure I can learn this stuff.”

Her detailed knowledge of the Jets’ season record won the recruiters over, and learn she did. Kaur’s career at ESPN spanned creating the site’s London and Vancouver Olympics sections to helping build some of the company’s flagship mobile apps to spearheading a complete redesign of ESPN.com. She was also the first engineer to work on Grantland, the sports and pop culture blog founded at ESPN by veteran sports journalist, Bill Simmons. It was, in effect, her first taste of startup life. “I was the only engineer coming in from ESPN. It was just me and editorial,” she says.

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“He would fight to the death for them.”

Her experience at Grantland taught her two important lessons. The first was about empowerment. As a young, female engineer in the male-dominated environment of the tech team at a sports media company, she had struggled to feel confident in her own skin. A series of highly supportive bosses helped her find her “inner rockstar” and recognize her value. At Grantland, she found happy staff with deep loyalty to their leader: “The people who were working for [Simmons] — he would fight to the death for them. [I saw] how important it is to empower people under you and help them come to life and grow and blossom.”

The second lesson was about audience loyalty. Kaur says that sports fans are “dream customers to build for” because of their passion for the content, but that their primary allegiance is to their teams, not to media companies. Simmons, though, has been able to nurture a platform-agnostic following, and take those people with him from AOL to Grantland and, now, to HBO and The Ringer. He knows, she says, how to take care of his tribe.

“Everyone knows their s**t, but comes in truly humble.”

At theSkimm, co-founders Carly Zakin and Danielle Weisberg have similar priorities around building community, starting with a great workplace culture. “We have a collaborative, driven team that believes in what we’re building.” When looking for new hires, they privilege humility: “Everyone knows their s**t, but comes in truly humble, and wants to learn from people around them. That takes collaboration to another level.”

theSkimm is also deeply concerned with designing for, and collaborating with, its audience. The team has a well-defined target demographic — female working professionals aged 22–34 — and keeping the 3.5+ million active subscribers engaged lies at the core of its strategy. They run a “Skimm’bassador” program of 14k+ brand ambassadors who help spread the word in their own communities. “We’re really focused on building trust and loyalty,” says Kaur.

“Thinking about building a strategy from scratch was terrifying.”

theSkimm recently launched Skimm Ahead, a service on theSkimm app “that makes it easier to be smarter about the future.” It integrates with a user’s smartphone calendar, and populates it with important upcoming events. It’s also theSkimm’s first paid subscription product.

Kaur says she “had no idea what a product role at theSkimm could be” when she first met Zakin and Weisberg, but was motivated by curiosity and respect for their newsletter, which she’d been reading for more than a year. When Zakin and Weisberg explained their vision for making theSkimm a multi-platform company, she thought it was “brilliant.”

The next step, the co-founders explained, would be to figure out how to take that audience and build products for them — and she was the woman for the (daunting) job. It was time to learn fast all over again: “Thinking about building a strategy from scratch was terrifying. But I was talking to some of my mentors and they said, ‘this is what you’ve been waiting for. You spent 7 years thinking about content.’ Then I got really excited about it.”

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Dheerja Kaur maps out the product journey of theSkimm’s calendar app

The new app launched on April 19th, priced $2.99, with the Skimm Ahead calendar feature as “the first service within the app”. Kaur says she learned at ESPN that launching a suite of apps can dilute a brand, so the team intends for this one app to become the hub of its mobile experience. As theSkimm diversifies further, launching video with the introduction of Skimm Studios, they will continue to shape the product around the routines and rhythms of its female millennial audience. The ultimate aim is to create a seamless experience for other busy working women, women whom Kaur’s intelligence, energy, and confidence may also inspire as they learn to channel their inner rockstars.

The Drunken Walk is a series of live fireside chats, blog posts, and podcasts (coming soon!) from Matter Ventures, the world’s only independent startup accelerator for media entrepreneurs. We dive into the personal stories of founders, experts, and innovators in media to uncover the moments in their careers that changed everything. Our goal is to inspire and empower the next generation of media entrepreneurs to get from A to B without a map.