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Women in Enterprise: Stefanie Syman at

This series features profiles of some of the top women leaders within our enterprise technology community here in NYC. We hope by highlighting the terrific work, stories, and career trajectories of these women at top venture-backed startups and operating roles will continue to encourage more women to consider careers in enterprise software.

As a follow up to our sold-out Navigate 2018: Women in Enterprise Tech Summithere at Work-Bench with Salesforce Ventures, we are continuing to recognize and amplify these impressive women in NYC enterprise tech.

Stefanie Syman is the VP of Customer Experience & Communications at

What were you doing before this current role in enterprise tech, and how did you get to your current role?

I was working at a boutique consulting firm that focuses on early customer acquisition, branding and positioning. Basically, we were helping our clients, which included startups and more mature companies launching new products & services, find product market fit.

I had met Dennis ( Founder & CEO) before joining that firm. He stood out to me as entrepreneur because he was so good at what most entrepreneurs fail at: customer development. We stayed in touch, and I became an early Beta user of Amy + Andrew (July 2014!).

For me, consulting was a good way to see how the same problem manifests in multiple businesses, but I am at heart an operator. I also wanted to be part of business that I thought could be massive. I thought had (and still does) a real shot at scale. So I reached out to Dennis in spring of 2015 and began my campaign to get hired by At some point it became clear that needed help around communications and content, and from my previous life I had those skills. I jumped on board figuring that if we succeeded, I’d probably expand beyond that narrow role. It worked ;-)

What pain point is your company solving, and what gets you excited to go to work every day?

We’re solving the pain of meeting scheduling. All knowledge workers waste hours every week scheduling their own meetings. Our AI scheduling assistants Amy + Andrew take over the job in full, so that you can focus on more meaningful work. They’re autonomous AI agents that operate over email or Slack. All you have to do is cc Andrew in email or wake him up (via /andrew) in Slack. And because Amy + Andrew are AI agents, you interact with them using plain English. It’s vey intuitive, and now I’m completely spoiled. I can’t go back to scheduling my own meetings.

What do you wish you had known earlier in your career?

I have had a fairly nonlinear career that has crossed media, online community, and enterprise software. Plus I wrote a book on the cultural history of yoga in America. Looking back, it might have been helpful to understand how critical story telling is within this enterprise tech realm, as I might have considered it earlier on. Most people focus on how data is the key to understanding customers and their needs; however, in enterprise tech where you have fewer, bigger customers, you need to be able to translate their needs, pain points, feature requests and questions into a coherent narrative that your product can address — rather than rely on masses of data. That process — of listening, researching, and synthesizing information — drives the best non fiction writers as well so it’s not a big leap.

Give us one piece of tactical advice (small or large), as a page from your enterprise tech playbook — that you would give to another woman considering a career in enterprise tech?

Because I span both marketing functions and customer success, I see the whole customer journey. For me, I need to be able to tell a coherent story about our product and its core customers. Until I have that, I can’t move forward. And sometimes you think you have it but it’s the wrong story. Focus on digging into the data — quantitative and qualitative — until you really figure out the true story. Once you nail that narrative all the other decisions become much more obvious.

What do you love about enterprise tech?

There’s a ton of opportunity here now in NYC. I remember an era before enterprise tech was at all visible. The ecosystem has really matured, and that means women can enter enterprise tech at many different levels. I also appreciate how grounded in real world problems this tech has to be. If you’re not helping real companies right now, no matter how cool your product is or how on trend it is, you’re not going far.

What do you wish would change?

More women all through the ranks. We’re getting there but still have a long way to go. Here being in NYC makes me hugely hopeful. As they grow enterprise tech companies are hungry for talent, and because NYC is not a one industry town, there are talented women who have built up relevant skills in other industries who can help grow this one.

Connect with Stefanie on LinkedIn and Twitter.

Our inspiration for this series comes from Digital Currency Group’s terrific profiles of Women in Blockchain — thank you!

Know a woman leader in enterprise technology whose story we should feature?We’d love to hear from you.



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