Leadership is not about perfection. It can be tough and messy. This journey of being a better leader has a lot of hills and valleys, and we have to be able to take those punches as we go and continue to be there for the people we are leading.

Our guest for this episode is Sarah Bierenbaum. Sarah leads a section of the Customer Success team at Olo, a SaaS company in NYC; she’s a Senior Director overseeing a team of 20. Her leadership career has ranged from theatrical stage management, to general management, to her current role in tech.

She believes if we take the time to understand each other as human beings, we will build a better world.

Today on the podcast we talk about her leadership style, where her drive comes from, the importance of empathy and how she creates safe spaces for failure.

Click the play button below to listen to the rest of the episode!

The Space to Fail

An extreme interest in other people is what drives Sarah to be a leader. She has always felt that understanding each other as human beings is how we build connections, find creative solutions and do great things.

If you’re trying to solve a problem or trying to accomplish something, you are doing so with other humans. For her, a big part of leadership is understanding the people she’s collaborating with and figuring out how to use their different skills and unique qualities to accomplish something they couldn’t do on their own, or with a different set of people.

Her work history is somewhat unusual for someone working in the startup world. She spent 15 years or so working as a professional stage manager. She had a Masters in Fine Arts in Stage Management and so she spent a lot of time working with artists and supporting them artistically.


A huge part of a stage manager’s role is to create an artistically safe space for all of the different people in the room and outside of the room, to try and fail, and try again, until they create something amazing.

There’s a lot of supporting space for failure, which has always been at the heart of leadership for me. Click To Tweet

Sarah’s leadership style

As much as possible, I try to lead by asking questions and listening. When I hear what my team – or whoever it is I’m talking to – has to say, I try to repeat that back in a way that helps that person understand what I’m hearing, what they said, and hopefully can also guide them to coming up with solutions.”

I like to understand and help the person I’m talking to understand, and ideally help them come up with a solution and support them in the solution that they want to try. Click To Tweet

Ask for feedback when things go wrong

Sometimes, leaders mess up. But when they do, they’re quick to become aware of it, and they ask feedback from their team about where they went wrong and what they can do to improve. Click To Tweet

When Sarah handled a meeting in a way that made members of her team feel frustrated, she asked them to give her feedback and how she could do better.

It’s empowering for team members when leaders ask for feedback from them, because they know that their words are going to mean something to you. Click To Tweet


Connect with Sarah on LinkedIn