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Emily Tsitrian

Emily Tsitrian


Head of Enterprise Implementations

Chicago, IL

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My Role

At Stripe I lead the team of implementation consultants that work with our enterprise customer base, helping them realize their business goals with Stripe's product suite. I also help define strategy, priorities, and goals for this customer segment. I've been working in tech for about 11 years, and the past 7 I've been in management positions.
Outside of my day job at Stripe, I write and produce a podcast about people-management in the modern era. In fact, I recently published a book specific for first-time people managers called Make Me the Boss, which is the book I wish I had had when I first became "The Boss" - and is full of hard-won lessons, checklists, and situations that first-time people managers encounter in their first 6 months.

What I love most about my role

I love building teams, coaching people to greatness and most of all - developing the next generation of leaders in business. The business world has changed a ton in the past couple of decades, and now in this strange post-pandemic era, it's a different game entirely.

I'm convinced that the generation that is coming into the workplace and leadership roles has a different set of priorities and life experiences than the current status quo - and this is a good thing. The world needs leaders that embody change, radical inclusivity, and show up with authenticity and boldness to do what is needed to meet the moment.

How I define success

Success is a moving target, and I think that really good leaders never totally feel like their work is done. That doesn't mean that we shouldn't celebrate wins - the small ones and the big ones. Rather, it is more that the great leaders are holding themselves to the same standard of ongoing growth and evolution that they are asking from their teams.

As managers, we have good days, great days, and rotten ones just like everyone else. We have days we feel we are letting down our team, and days where we feel we can do no wrong. That's all normal - and success over time really just looks like continual improvement - in my opinion.

The best piece of business advice I ever received was

You have two ears and one mouth for a reason. Whatever industry you're in - listen to your customers, your team, your competitors, your own leaders. Just...listen. Don't listen to respond, listen to understand. Then, when it's your turn, speak with clarity and empathy - and your words will land more forcefully because of the time invested in understanding others' perspectives.

What would I tell my younger self

I would tell my younger self invest in a leadership coach and my mental health sooner. Especially in my first couple of years, I had a hard time creating boundaries around my empathy for my team members - and would frequently burn myself out. I would have worked with a therapist to better understand my own motivations in the workplace and learn to accept occasional failures with more grace.

What 2B Bolder mean to me

It is said that fortune favors the bold, and that is a mantra I tend to embody. One of my most influential mentors would frequently tell me: "Emily, be bold!" -- I can still hear him saying that to me. It's served me well and I want to pay that forward to encouraging the next generation of business leaders to take some risks and step up to the plate.

Years of Experience


I recommend you focus on developing these 3 skills to succeed in a role like mine

public speaking, writing, management

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