Lead(H)er: Stefanie Syman, Vice President of Customer Experience and Communications at x.ai
Stefanie Syman sees the world through a literary lens.
After studying literary theory at Yale, Syman began writing about the things that interested her to understand them better. In those first few post-grad years, she wanted to understand technology most.
“I was fascinated by the way technology was changing the culture fast, and I made career decisions based on what I thought was going to happen,” said Syman, who is now the Vice President of Customer Experience and Communications at x.ai.
She quit her first job at a documentary film production company after concluding the technology would likely advance so much that it cost less to make a film, which would change dynamics around fundraising as well as other parts of the industry. True to her storytelling instincts, she began writing and pitching stories to publications about how technology was impacting society instead.
Her stories got the attention of an editor at the Wall Street Journal, who hired her as a semi-
regular columnist to continue writing about her perspectives on technology. Then a former classmate introduced her to Steven Johnson, who was similarly writing about technology for The Guardian of London. She and Johnson would found one of the first online magazines in 1995.
Syman took on a major operational role at the magazine, managing everything from the editorial calendar to audience development and ad sales while contributing a significant amount of written work to the publication until it was forced to fold six years later when the dot-com bubble burst. “It was too early on the Internet to build a real audience, so we didn’t survive the bust,” she said. After 9/11, the so-called Internet industry in New York fell apart for several years.
With many of her skills and contacts in a temporarily dormant industry, Syman decided to write a book on the history of yoga in America. She worked on the book for five years while also helping build various digital media companies, including a multi-platform media company called Lime.
“It wanted to be Goop, but it was a little bit overly ambitious for the time,” Syman said. “This was 2005, and YouTube had just launched. We were trying to combine satellite radio, online video, online community, and a cable channel.”
Despite having financial backing from AOL, Syman said that such an integrated media approach was simply too much, too soon for one brand to be successful. She turned to consulting, finished her book, and had her first child before choosing to return to the startup world full time.
“As much as I loved writing, I didn’t feel that I wanted to invest the energy in the way you need to in order to make a successful writing career.”
Syman then carried her storytelling skills to the business side of company building at Atavist, where she was responsible for customer development and helped the company focus on who their customers would be, what value they would get out of Atavist’s software, how much they would likely pay for those products, and more. It’s an area that many startups fail to consider, Syman said, much to their detriment. (Atavist recently sold to Automattic, the company behind WordPress.)
“One thing people don’t realize is that a lot of succeeding at business is being able to tell a good story, and I don’t mean regarding selling. I mean understanding what is going on with the market and your customers vis-a-vis your product and then narrating it back to them in a way that they feel connected to it and want to purchase,” she said.
She continued telling stories to customers in 2015 when she joined x.ai, a startup that has developed a pair of artificial intelligence scheduling assistants named Amy and Andrew. In addition to the technology involved in the product, Syman said she was drawn to the company because she felt it had the ability to grow exponentially, and that she had skills to help it do just that.
She ran the majority of the company’s content and public relations operations during her first seven months there, seeing it through its Series B funding round before turning to customer acquisition and success. She and her team researched how to price and roll out x.ai’s product, why customers were attracted to the product, and what product features may be necessary to retain more customers. Through it all, being able to tell a story to describe each situation has been essential.
When Syman looks to the future, she sees several possibilities, from remaining an operator to taking a more portfolio-centered view of the startup scene. She’d also like to see what it’s like to work at a more mature company.
“I’ve been in the ‘build early and get to liftoff’ stages, but I’ve never worked inside a really mature organization,” she said. “At some point, I’d like to participate in a company that’s gone beyond its massive growth stage into early maturity. That brings an entirely different set of challenges.”
Whether or not that happens at x.ai, which has raised $44.3M in funding to date but is still quite young as companies go, Syman will undoubtedly have plenty of stories to tell along the way.
Rapid Fire Questions
What do you like to do in your free time?
As a mother of two kids who are still pretty young—middle school and grammar school—I have very little free time, so mostly it’s hanging out with them and then Ashtanga yoga.
How do you typically deal with stress?
Yoga. Moving my body is really the keyway. And then I have good friends, hanging out with my family, and unplugging. I try to unplug on the weekends. I know there’s a little bit of machismo around being on your phone and working all the time in the startup world, but I just don’t think it’s fair to my family or good for me. There are times where I’ll come in on a Saturday if I absolutely need to get something done or do the work for a deadline late hours, weekends, whatever. Still, by and large, I really try not to engage with work on the weekends as much as I can.
How many cups of coffee do you drink in a day?
Two, but it’s mostly tea.
What is one of your favorite spots in the New York City area?
Prospect Park is high on the list. Luckily, we live really close by.
Aside from family, what do you consider one of your greatest accomplishments?
Running my first startup for those six years was incredibly gratifying. My book also ranks also among my favorite accomplishments; it was well received by the people whom I cared about. And then building the team here at x.ai definitely counts. I’ve been really proud of the team here and the work they’ve done.
Where did you see yourself 10 years ago, and how does that compare to where you are now?
I was still far enough away from the publication of my book to imagine I still might be writing much more. Also, I had a two-year-old and assumed I’d have another child, so I was a bit mired in the present. I expected that my career would continue to be as it was when I was running my first startup. I was writing a ton at the time, and I was running operations and making sure that the teams got along and that ad sales were going well and that things were getting published on time. I imagined my career to be this kind of company building on the one side but also doing quite a bit of writing under my own byline, possibly with more books, and that somehow I would weave that together in a very obvious way.
So I may have been a bit surprised that I’ve favored pure company building with nearly zero writing. That’s the only thing that would be surprising.
What advice would you give to recent college graduates?
I graduated into a world where it was still possible for mid-list authors—mid-list, nonfiction authors—to succeed in writing alone. That’s not possible anymore. If you’re writing, you have to pretty much be at the very top of published authors to make the economics work. So there’s very little room to be romantic about taking up any creative pursuit. If you’re going to go do that, you’d better have a backup skill set, like programming or writing in a corporate setting or some other way of engaging with large organizations that can pay you a decent wage.
On the flip side, the great thing that I’ve witnessed in the last 25 years is that there’s a real ecosystem of company creation in New York City now (and a much more thriving investor community as well). Startups come and go, like they always do, but the young women and men employed there are acquiring solid skills really quickly. That means they’re able to build these nice careers, and move between startups and more significant companies if they wish. Particularly for women, including those I’ve hired and watched grow, there’s a ton of opportunity to have a business career that’s not limited to investment banking or the big consulting firms. And there are options for creatives in those startups as well—it’s not so binary.