Women in Marketing: Q&A with Marketing Leader Caralyn Quigley Stern

Q: What best practices have you employed to grow your career?

STERN: My honest answer is I don’t know that I proactively grew my career. Rather, I found myself in situations where I was challenged and able to align to the goals of the business.

My career developed somewhat organically because of two factors. One is the problem-solving of technology I just loved. When I first started working in technology, I was planning on biding my time before I headed off to law school. I learned really quickly the satisfaction of being able to talk to a customer and have them say, “This is all of the stuff I’m struggling with,” and being able to say, “Oh, I’ve got an answer to that problem.” 

From there, it was about the teams. I have quite a few companies on my resume. But what’s hidden inside that view of it is it’s almost always certain members of teams that I’d worked with before. And that worked really well for me for a long time. I hooked myself up with really smart and intelligent and challenging people who were looking at complex problems that the world was facing and how technology could help to solve it, and grew organically with that group. 

At some point, though, I did have to really start to actively manage my career. The best advice I got about that was to step out of a passive engagement of my career development and move into an advocacy step. I thought I could just sit in a large company and work away and let my results speak for itself — and someone was going to tap me on the shoulder and say, “Here’s your next most amazing job.” I received some great advice that said, “That’s just not how it works.” 

That is step one: do your job. And exceed your performance. Know exactly what is expected of you by your management team and how they’re going to be looking at your performance. If you’re not getting that engagement with your manager, ask for it and look to build that.

And once you have a really clear understanding of what the company and your team is looking for you to perform, as you’re hitting and exceeding those goals, look for effective and authentic ways to advocate and share those successes within the company. 

When you’re learning something — either failing fast or learning something that works —  you’re also sharing that success within the company. It’s therefore giving you advocacy and raising your profile, but also putting you in a position where you might be able to have influence and impact beyond the core of your role.

I think that advice was the most effective for me. Once I had sort of run to the end of the rope of, “Hey, if I just do an amazing job and work really hard and become that person that everybody always wants on their team, how do I get to the next level?” That advocacy, and that intentionality, made probably the biggest difference for me.

Q: How do you advocate and mentor for other women in your company and industry?

STERN: Once we find ourselves in positions of leadership, what is our commitment and our cadence about managing the teams in such a way that leaves that fluidity for different types of personalities to be able to be recognized and comfortable? 

From a mentoring perspective, we have a program inside my company which I’ve been thrilled to be a part of. The exercise I went through with one individual was to spend a little time auditing her story. How did she get to where she is today? What is it about the job that she does today she thinks she is uniquely strong at? What is it that she does about the job she uniquely enjoys? And we talked a little bit about her whole career progression. 

Once a picture begins to form about where an individual’s strengths are, start looking at the business and engaging in conversations with people in your direct organization. Or if you don’t have a relationship with your manager that feels really natural to do that, find those allies outside your direct line of command.

The one piece of advice I give: try to work through your manager. Instead of saying, “I’m uncomfortable with my manager. I’m going to reach out to this other person and engage in a side conversation,” try to say to your manager: “I’m really interested in exploring my career path. I’ve got some questions. I want to learn a little bit more about the company. My thought is I wanted to reach out to person A, B, or C. Does that sound good to you?” 

Because what you’re doing there is you’re just providing a healthy amount of respect to your chain of command so that the person that is currently your direct manager can be in a position to be your advocate and pull you through. But you’re also exploring the fact that there might be other relationships you’re more comfortable engaging with.

Q: What are your recommendations for breaking into the “boy’s club”?

STERN: I’ll share some advice I was given in my past on this. If you’re finding yourself in a room all the time where you feel like the only one — whether you’re the only female, or you’re the only person of color, or you’re the only person who’s transgender — when you find yourself the only “other” in that room, one of the things that you might be able to do is identify who could be an ally for you. 

When in a club of people that you don’t feel like you belong to, what can be very helpful at breaking that down and finding your voice and finding your comfort is: can you identify a person in that room who could be that ally, that you could build that relationship with? When you feel your voice has been taken from you and you look across the room and you don’t see anyone, you can see that set of eyes that helps you to restore and find that confidence. That was something that I thought was really helpful for me in those cases.

Q: How can you advocate for minorities, for women of color, and also transwomen as well?

STERN: I think that having a really strong advocacy at the senior management level, someone who’s willing to be the sponsor of an ERG [or employee resource group] — and put their name and face and business reputation behind the effort and the initiative is hugely important. 

If you’re not sitting on the senior level of the staff that can enforce [diversity and inclusion] initiatives from the top-down or start to build it from the top-down, be bringing ideas and bringing that sense of information and exposure and resources into the company from the ground up as well. 

And be the advocate in the moment — find the strength and the confidence in yourself to say, “Hey, I’m sure you didn’t mean anything by this, but I just wanna give you some feedback about how that felt for the people in the room.” You can do it in a way that brings them into the effort and brings them into the conversation.

One of the things our company has done is send out an anonymous survey for self-identification because, you know, in marketing, we live by the adage, “Those things that are measured naturally improve.” And diversity can be one of those things that is difficult to measure. The survey asked, “Tell us who you are. Tell us how you like to be recognized. Tell us something about yourself.” It was anonymous and it was designed to create a baseline for us to look at ways we could, first of all, judge ourselves. How are we doing? How are we meeting our commitments? And how far off are we? What could we do to improve?