What I’d say to me back then - Stacey Epstein, CMO at Freshworks, on not self-limiting your ambitions

Madeline Bennett Profile picture for user Madeline Bennett April 5, 2022
The first in an occasional series in which women in tech discuss what's changed in their careers to date and explore what advice they’d give their younger selves as well as to women entering the sector today.


Stacey Epstein’s career in tech has spanned 30 years, but the IT industry was definitely not her initial dream job.  When the now CMO at Freshworks entered the US workforce in the early 1990s, her heart was set on being a sportscaster.

But back in those days, there were no female sportscasters, she recalls:

If you were watching sports, you were hearing about what was going on from a man. It's something that has bothered me my whole life. I was really interested in sports, I grew up playing sports with my older brother and his friends. We'd play tackle football, and it was never a problem. I grew up with this mentality of, 'I can do whatever they're doing'. Nobody ever really gave me the message that I couldn't.

Having always been an athlete - she was a four-time all-conference soccer player at university -  Epstein couldn’t understand why women weren’t able to give a perspective, one that might even be different and unique. However, needing to pay the rent after college, she took a job as an executive assistant at Oracle:

It was literally, ‘Where can I find a job so I can pay the bills?’, that's how I got into tech. I had a perception that you had to be an engineer to be in tech. It never occurred to me that you had to be a man to be successful. I just thought, ‘I'm an English major, why would I be in tech?’.

When Epstein arrived at Oracle in 1992, she soon realised her perception of requiring an engineering background to work in technology was wrong:

There was sales and marketing and all these things I had never really had exposure to, and it didn't seem like anyone was any smarter or any more ambitious than I was, yet they were in much bigger, higher paying jobs.

She made the decision to educate herself outside of work hours to progress her career, and signed up for a SQL programming class at UC Berkeley Extension:

If you asked me to tell you about programming and SQL, I don't think I could tell you one single thing. I don’t think any of the skills I learned were useful. But the fact I had taken the course was impactful. When I was competing to move up in Oracle in sales, marketing, partner, the fact that I had gone and done that and supplemented my English degree with an attempt to understand technology was, no question, a huge edge for me and I was able to move up pretty quickly.

Where are all the women?

Although Epstein found it quite easy to move up from her very entry-level job to increasingly more important and higher paying roles, there were not a lot of examples of women in more senior leadership positions at the time. Just like sportscasting, it left her confused as to why there weren't more women around. Diversity initiatives were also in short supply, she observes:

When I got out of college, I was told, 'Put on a suit, and dress and act like a man. That's the only way you're going to get ahead'. I didn't understand it. We're just as smart - in fact, we have some unique skills that a lot of men don't have. It seemed foreign to me.

When Epstein used to watch the lone female VP from her division speak at big company events, it spurred her on to progress her career and get a speaker slot:

I always had something to prove, but it wasn't easy. And it wasn't hard because people were squashing me down;  it was hard because there were no examples of it. There was no-one to be inspired by. It was almost like you could self-limit by the perception of what was going on.

This goes to the heart of what Epstein wishes she could tell her younger self entering the technology sector back in the early nineties – don’t live your life thinking about the bias or obstacles against you. It’s something she carries with her today:

We have to be very careful about not limiting ourselves because of what we see. You have to keep your eye on what you believe you are capable of and the opportunities that you believe you deserve, and go for them. We should all be thinking about our careers not as - ‘Will I ever get that role because I'm a woman?’, or ‘I haven't seen another woman in that role, so are they really going to consider me?’.  The focus should all be on being a high performer and the opportunities will absolutely come.

Setting an example

Today  Epstein lives by her own advice, participating in various industry event panels, offering herself up as a role model off the back of her own successful career. Before joining Freshworks as CMO last year, she led the marketing functions through 6 years of triple digit growth at both SuccessFactors and ServiceMax. She went on to become CEO of Zinc, a real-time communication app for field service workers, which was acquired by ServiceMax in 2019, returning her to the CMO post there.  She currently also serves on the board of Litmus and CircleCi.

Epstein takes her role in encouraging and enabling other women very seriously:

Now I'm at this stage where I can set an example of a woman who's been a CEO, a public company CMO, a board member and investor. I do a lot of writing, advising and mentoring. I do speaking, a lot of encouraging.

She still remembers being encouraged in her own career by the then CEO at ServiceMax, Dave Yarnold, who told her, ‘You owe it to women to go be a CEO’. She says:

At the time I thought, ‘What do you mean I owe it to women?’ This is my life, I’ve got to decide if I want to be a CEO or not'. But in retrospect, I realize that the more women that are in these roles, the more women that can see themselves and aspire to it in the future, I understand what he meant by that - and I take it very seriously.

The tech sector has many more examples of visible and prominent female role models now compared to when Epstein joined the industry, but the business world still has its biases. Epstein recounts a story of the men's soccer team at a US college being flown out to New York in a private jet and introduced to all the college alum hedge fund companies:

They usher them into these sweet jobs in New York. It's not an organized school thing, it's the alums that played on the soccer team who are now running hedge funds. They just keep this pipeline. And they don't do it for the women's team.

Don't they understand how valuable the women's team could be too? Even though we've made a lot of good advances and it is more in vogue to have more diversity, everyone is still not convinced that it really does make for better business. We still have a way to go.

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