Women make up just over a quarter of the workforce in the tech industry. The truth of the matter is that the underrepresentation of and inherent bias toward women stacks the odds against women who want to pursue careers in this space. Equally capable and intelligent women have to work harder than their male counterparts to achieve equal positions.

Women’s History Month gives us the opportunity to bring attention to these disparities on a larger scale. Since this year’s International Women’s Day theme was “Embrace Equity,” we’re breaking down the experience of a female leader in tech who heads up operations at an organization that truly embraces equity.

Without further ado, let’s dive in with Olivia Friedlander!

Who is Olivia Friedlander?

Olivia Friedlander is the VP of Operations at Maestro, a white-label streaming solution for brands and solopreneurs. 

Olivia studied psychology at Hunter College. During college, Olivia had her first taste of the hustle of the corporate world. In addition to being a full-time student, she worked a part-time job and had a marketing internship at the Times Square Alliance, where she helped organize some of the most iconic events in Manhattan.

Before coming to Maestro, Olivia worked with a women-run business called FundedBuy, a tech start-up that paired service providers and businesses. From there, she partnered with a business consultant who advised tech startups in the entertainment industry, and Maestro was a client of this consulting firm. 

Olivia was inspired by Maestro’s mission, so when given the opportunity, she went all in with Maestro and has helped grow the company to where it is today.

When she isn’t working, Olivia is trying out a new wine and cheese pairing or reading her latest book club novel. 

Q&A with Olivia

Olivia was kind enough to take some time out of her busy schedule to answer some questions and talk about her journey as a woman in the tech industry. She shared about her trials and triumphs as a woman in tech.

What has your journey looked like as you’ve stepped into a leadership role in tech? 

Working with women-led businesses before coming to Maestro helped shape my perspective that women can stand independently. I didn’t even recognize this at the time, but I subconsciously absorbed the fact that women can do whatever they set their minds to. 

With that said, I stepped into Maestro very early in my career, which also happened to be the very early days of Maestro. I wasn't involved when the company was started. However, I was part of the founding team of Maestro as we know it today.

I didn’t actually set out to be a leader in tech, but I have a knack for identifying gaps in systems and creating solutions for bridging those gaps. I brought that talent to Maestro, and I wore many hats before I got to where I am today.

For example, when I came to Maestro, I recognized that nobody was doing customer success. Sales was handling customer relationships, which was less than ideal, so I stepped up, took charge, and created repeatable processes and standards to set the foundation for the department. I’ve repeated this process countless times throughout my experience at Maestro.

Throughout my journey, there’s been a consistent theme: I've had to fight through imposter syndrome and believe that I knew what I was doing, which has forced me to step out of my comfort zone.

Another part of excelling as a professional woman, especially in tech, involves finding a woman-friendly work environment. This includes working with a team of both men and women who truly support women and appreciate what a strong woman can bring to the table. I’ve been fortunate to help create a workplace where misogyny is not tolerated by anyone, and the women truly support each other.

What skills or experiences have propelled your career as a leader in tech?

A few skills that have proven extremely valuable in my career are communication, curiosity, and confidence. 

Being an effective leader requires being able to communicate with all different types of people and personalities. You can develop your communication skills by increasing your exposure to and interactions with different types of people across the company. 

You also have to be curious. Don’t be afraid to dig deeper and explore areas in which you might not be as experienced. Don’t be afraid to ask questions, be challenged, or challenge someone else. Pushing your own boundaries by communicating and collaborating with people from different departments will help you grow and open the door to greater opportunities. 

Confidence is also majorly important, even if you have to fake it ‘til you make it. Not only do you have to believe in what you say, but you have to inspire confidence from others in order to build trust. Do what you say you’re going to do, and be prepared to back up your claims when you’re called to do so.

As women, we’re not always taken seriously, especially in the tech space, where some biases prioritize men's thoughts and opinions. I’ve had calls with clients when they ask for a member of my technical team to join to offer another explanation, but I know that really means they want to talk to a male member of my team. I know that request is often guided by subconscious biases, so I just bring on a male engineer to validate what I already shared.

As for experiences, the best teachers have been my mistakes and failures. As a leader, failures will teach you very quickly there is no “I” in “team.” We succeed together, and we fail together. You will learn and grow when you learn to take ownership of your mistakes. You’ll only open yourself to this growth when you become okay with failing.

It can be intimidating to be wrong or make a mistake as a woman in a male-dominated space, but you have to have the courage to stand up and say something you believe in to move forward 

What unique qualities or perspectives do you think you and other women bring to the tech field?

Women often bring a level of empathy that is necessary for a high-performing environment. At our core as humans, we want to feel like someone is there for us. Since women are naturally nurturers, we tend to provide that comfort for our teams.

Empathy is built over time, and it is also recognized and received over time. Let people know that you care about them, want to listen to them, and want to understand them. When you have empathy, your team feels like you have their backs, and therefore, they are able to be their best selves and do their best work. Your goal as a leader is always to inspire people to be their best.

What advice would you give to young women who have their sights set on a leadership role in the tech industry?

It may sound cliche, but if you’re a young woman wanting to land a leadership role in tech, you must believe in yourself. 

When you’re working in a male-dominated space, you may be made to feel like your voice or thoughts don’t matter, but they do. In order to find success in a male-dominated space, you need to have the self-confidence and self-assurance that your ideas matter. 

The next guy might know more than you, but you also might know more than him. Be willing to go out on a limb to voice your idea, even if it might not be right or best. Mistakes are always a possibility, but they don’t have to be negative experiences. Know they can happen, take the learning, and move forward. You can only go up as long as you continue to step up and try.

Another important piece of advice I have for women is to know the difference between being aggressive and being firm. Men are quick to label strong women as “bitches,” even though their equivalent behavior would never be questioned and might even receive a pat on the back. 

Not only are you allowed to be firm, but you need to be firm. You’re allowed to express what’s important to you without fearing the backlash. However, finding the balance between firm and snarky is extremely important and takes practice. 

When you’re firm, it’s also important to make sure you can back up your claims and do the legwork required to make sure your firm stance supports a rock-solid claim. 

Some other great actions for growing into a leadership role are putting yourself in a position to grow, always doing your best, remaining accountable, taking action when necessary, and requesting more responsibility as you’re ready for it.

Do you have any good resources or tools for continued learning and growth in the industry?

There are tons of great creators that provide resources for different areas of the tech industry. I recommend reading blogs and watching videos to see how other people are solving problems. Take what you want, and just try it out. You'll become your best resource through your own trial and error. 

I also recommend leaning on your team. I mentioned before how valuable communicating with different departments is. Never be afraid to ask questions within your organization because your team members are the experts.

The Women of Maestro

Having a strong woman like Olivia enter the picture at the founding level has helped shape Maestro’s company culture to be woman-friendly. In fact, women represent 40% of Maestro’s leadership team. This is nearly four times the industry average.

Olivia is accompanied by a slew of other badass women at Maestro. Some of the women who keep the ship afloat include:

• Olivia Jones, Senior Director of Customer Success 
• Amy Brown, Customer Success and Operations Manager
• Bárbara Dórame, QA Automation Lead
• Alejandra Landavazo, QA Manual Engineer

Thank you, Olivia, for giving us an inside look at her journey as a woman leader in tech and providing actionable tips for women who hope to follow in your footsteps!

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