Client Stories

Q&A with CMO Rebecca Biestman

By October 27, 2020 No Comments

Lessons Learned on My Journey from Retail to Tech Chief Marketing Officer, Rebecca Biestman, on what she learned on her journey to tech’s C-level, the secret that makes great leaders, and the importance of setting clear expectations in both your work and home lives.

When she worked in merchandising and brand management for Gap Inc., Rebecca Biestman had no idea she would one day find herself in the tech industry. And before she got to tech, she was told that leaving one of the world’s most well-known retail brands would be the biggest mistake of her career. But Biestman, chief marketing officer at and a BOCA client, would have it no other way. She much prefers saying “YES” to challenging new opportunities, as opposed to what most would consider a “traditional” linear career path. Her approach has most definitely paid off. Biestman is a forward-thinker when it comes to diversity and inclusion, and proves that when organizations make a proactive effort in diversifying executive management teams, it makes for a greater organization. BOCA recently chatted with Biestman on these and a number of other topics — here are some highlights:

BOCA: Based on your experiences, is there any advice you would give women looking to carve a journey to the C-Level in tech?

Biestman: One thing I would say is, your life will always look different than your male counterparts. You need to be clear about boundary-setting and communication. I’ve found that you must be direct and clear about responsibilities both in and outside the workplace. Being able to set those expectations early on is so important, and it’s something women, in general, are sometimes afraid to do. Our lives typically look different — I don’t think I’ve worked for a man whose partner also worked full time. Like many women who work full time, I’m that person who does laundry, makes the kids’ breakfast and lunch, and joins 10 meetings a day. 

I’ve had last-minute happy hours for work come up, and one of my co-worker’s wife would bring him a change of clothes for the evening — I don’t have that person. At times I’ve asked myself, “am I going to see my kid at all today?” My male counterparts typically have a partner who maintains that familial role for them. It makes both their work and home life more straightforward. So, unless women have those conversations with managers and leaders, who are typically men, they often feel like they’re not giving enough at work or in their personal life. I think that piece is really important.

I’ve also found that being unafraid to take on opportunities that may look like a strange fit — being comfortable with the uncomfortable — has served me well. A lot of people chart out their careers in a linear path. But when someone gives me an opportunity to do something new, I’m very likely to say yes. The worst thing that can happen is it won’t go well. But it’s beneficial because it gives you a more holistic skill set and makes you more appealing as you move up in your career. 

I started my career in brand marketing at Gap, a highly coveted spot very few people leave. I then received an offer to become a regional VP of sales in field marketing for a smaller consumer packaged goods company — and in no world was that as appealing as what I was already doing. But I took the job, with no real qualifications, because I knew I would have had to stay at  Gap for 25 years to manage a team of 30 people. I was told I was making the biggest mistake of my career. But I did it anyway. Later, I challenged myself again by attending business school at UC Berkeley’s Haas School of Business. I’ve run across people who are either uninterested or afraid to take a chance in their career because they fear it’ll be a setback. I’ve found it to be the opposite — the breadth of experience has served me well. 

BOCA: What is something you’ve learned running a department and business unit?

Biestman: It’s pretty simple: hire the best people and let them do their thing. To me, being an advocate and evangelist for their work is the definition of being a great leader. I’ve been lucky enough to work for a few outstanding mentors who have taught me well and also allowed me to hone my craft. I’m now focused on passing those lessons down to my team members. 

BOCA: Your style of communication has been described as “coach-like” — would you agree, and what is it about that approach that has worked for you in the past?

Biestman: I would call it candid and direct. That has been both a benefit and detriment at times. As a woman, it has absolutely meant being noted as “overly opinionated.” I’ve been called that many times. But overall I really appreciate candor and transparency. Anything else can turn minor challenges into big tangled messes. Who has time for that? 

However, there are cons to my direct approach. Some people work better with that style than others, and I’ve had to learn to appreciate the communication styles of those around me. I coach when necessary and always provide concise feedback. I’ve learned that by creating an open forum where employees feel they can have a safe and honest exchange, we can learn from each other. 

BOCA: What are some of the most common challenges female executives face? Are there others that tend to fly under the radar?

Biestman: I started my career in retail, where there are mostly women in the room. Tech is the exact opposite — I’m often the only woman with a seat at the table. From a gender perspective, not having a comparable barometer for your behavior is challenging. You can feel alone at times.

For me, I’m usually also the youngest, which compounds the challenges. I often have to prove I’m right instead of it being presumed. It forces me to bring my best self to every meeting, and every interaction. That said, it’s a fine line because people may perceive me to be more aggressive, opinionated or over-eager — something negative. It really forces you to be more thoughtful.

BOCA: What are some of your leadership techniques when it comes to diversity and inclusion? What are some keys that leaders should be thinking about, particularly in the wake of recent events?

Biestman: The “Tech Bro” culture does exist, and many people in this industry, especially women, will tell you that it’s a problem. There’s no shortage of guys who think they’re the smartest in the room and never miss a chance to remind others of their superiority. And often, they are the people in leadership roles. I’ve found that while they’re really good at building products, they’re either bad or mediocre at running a company. If they’re smart, they staff their companies with strong operators. 

I strive to create a culture that fosters diverse opinions  — and there is so much data that proves why it matters. Differences such as race, class or geography are also very important because homogeneity is bad for business. It’s ironic because the tech sector comports itself to be this liberal beacon of ideation, where all ideas are welcome. But intellectual privilege, education, gender, skin color — there is a lot of implicit bias going on, and it’s a shame.

BOCA: What drives your competitiveness?

Biestman: I’m competitive with myself. I’ve seen my fair share of mediocre, incompetent men rise to the top in my career, and nothing makes my blood boil more. At the C-level, there is one woman for every six men, but there are not six times more men in the workforce. That one woman you see will be a rockstar, but with some of those six to eight men you’re thinking “how did you get this job?” 

There are plenty of mediocre women out there too, by the way. But we’ll know we made it when we see more women in top positions and we question whether they’re rockstars or just mediocre at their job. I’ve worked with some of the smartest guys out there, and they deserve everything they get. But I’m talking about the men that are a part of every staff I’ve been on that haven’t necessarily earned a seat at the table, yet there they are in a leadership role.

BOCA: You are now leading marketing at a company that markets to marketers — describe what was appealing about that to you.

Biestman: When I started in brand marketing before the Great Recession, the internet and e-commerce wasn’t nearly as ubiquitous as it is now — I worked for Gap Digital when it first started. When I was there, the conversation between brands and customers was very one-sided. Brands controlled the narrative. That dynamic made it fun, but over the past 15 years, the brand/consumer relationship has shifted in a very positive way. The consumer really owns the conversation now, and that’s because real-time customer feedback is easily accessible, actionable, and with tremendous scale. 

I think this dynamic shift is incredibly valuable — it makes for true conversations between brands and consumers and drives transparency, accountability and innovation. Consumers can now quickly ascertain whether a business is being well managed, if they care about their customers’ experience, and if there’s a problem whether they quickly respond and fix it.’s platform helps with the full lifecycle, including the fix.

Listening to customers is great, but equally important is a business’s willingness to learn — that’s the big piece that separates the executives who have evolved with the era of the feedback economy and those who are approaching their final chapter. It’s, “I hear you, but also show me and tell me how to do better by my customers.” Those are the executives who thrive.

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