Women in B2B Marketing: Q&A with Marketing Leader Caralyn Quigley Stern

March 17, 2023

ViB Editorial Team

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Women still face plenty of obstacles in the corporate world, especially when it comes to achieving equal representation in leadership positions. And, often the path to career advancement isn’t as clearly defined for women as it is for their male counterparts.

Recently, we sat down with a few women who have navigated those challenges – including Caralyn Quigley Stern who works as VP of Americas and Global Channel Marketing at Sophos.

Stern offered insight into her work as a mentor, how she believes we can all advocate for women, how to prepare for negotiations and interviews, and much more. Today we’re sharing a few highlights from our recent webinar with Stern, Women in B2B Marketing: Career Advancement Strategies & Advice.

Q&A with Caralyn Quigley Stern

Q: How do you advocate for and mentor other women?

Stern: The best way we can do this is by being good role models and good examples of what a female leader looks like — and it doesn’t necessarily have the word “female” in front of it. Living that sense of leadership as a strong example for everyone within the organization, people who are senior to you as well as people who are within your team or starting up their career.

One of the easiest or fastest ways to drive change is when people are coming up earlier in their careers. And as we’re building people who are coming into the organization who aren’t bringing with them a history of seeing things as overly gendered. Bringing in a diverse, open, transparent, and engaging new workforce is one of the best ways a leader in an organization can help to create that dynamic.

Look for ways to market yourself inside your company as being available for mentorship. It wasn’t until we actually created a formal mentor program inside Sophos that I started getting inquiries from people in the product management department, people in the sales department, and people outside my direct sphere of influence who were reading my profile and saying, “I’d like to engage with this individual.” So, look for ways to advertise yourself as being available to help women come up through the ranks and address those challenges they might be facing.

And third, share your experience — good and bad. Recognizing and sharing your failures and your setbacks, as much as the things that you’ve done that have been successful, can help to really inspire and help young people, male and female, advance their careers themselves.

Q: What advice would you have for someone who is starting out or trying to advance their career?

Stern: I’m lucky enough to have several opportunities to mentor individuals, and, usually, they’re much earlier in their career. So, first, I think that’s one of the most important and helpful things you can do: identify someone either within your company or within your network that you feel comfortable with and respect to build a mentoring relationship. It doesn’t have to be terribly formal; it just has to be someone you can trust.

In my personal experience, it helps if they have years in front of you because they’ve walked through a lot of situations you’re going to be facing. They won’t be identical, but they’ll be able to give you some perspective and advice.

For me, when I started my career, I always found myself working in environments where I genuinely liked the people I reported to, and created really strong relationships with them and could talk about what I wanted to do, what I needed to improve, and how I could put myself in a position to continue to advance.

Secondly, and this is something I came to appreciate later in my career, is to spend a little bit of time understanding yourself and what makes you tick. I think the more you genuinely understand what you like about the work you’re doing, and what motivates you, and what intrinsically and genuinely gets you enthusiastic about the work that you’re doing, the better you can direct where you’re going to head from your career’s perspective.

I’m not saying you’ll always only do stuff you love — there is a lot of grind and work that you have to do along the way in your career. But if you have a sense of what you genuinely enjoy, it makes it easier to find out what kind of career you want and start to drive towards that goal.

Q: How can women be better negotiators?

Stern: Do your budgets, look at your time, look at your goals, and ask yourself what you want. What do you need? What would you be really happy?

I think that’s one of the things that often ends up as a stumbling block, especially for people when they’re new in their career they’re like, “Well, I don’t know, what does the job pay?” And I always wanna say, “What do you need?” Think about that for yourself. Because what we’re looking to do is develop you from a place where you’re comfortable. No manager, I can assure you, wants you to be underpaid and feel like you’re under that kind of stress all the time. So you have to have a good sense of yourself.

Very often, I see females who want to wait till they’ve done the next level job and proven that they can do it and played it through a couple of times before they’ll raise their hand for that promotion. And I often see men say, “No, I’ve thought a little bit about doing that one time; I’m the person for the job.” So, that confidence and, you know, willingness to be uncomfortable and put yourself out into that role, I think, is how you’ll drive those growth goals for it.

If you’re sitting in a job and you think you’re underpaid, and you want to stay with that job, and you’re negotiating for a salary increase, my advice is, go to your manager and talk to them about it. Say, “How do we go about building a business case for this? Do you agree with me?”

Get a good sense from your direct manager of, “Am I way off-kilter here, or do you agree with this? And what can I provide you to help put you in a position to go advocate for this additional investment for me?”

Q: How do you build your expertise when you want to switch careers?

Stern: I ask two first questions through the course of an interview. One is, “Can you tell me your story?” So be prepared to talk about your story. And when you’re telling me your story, start showing me that you understand the transferable skills you’re bringing to the table. In the pandemic, I’ve interviewed and brought several people over who worked in completely different industries. They worked in restaurants, they worked in retail, even healthcare, even nurses who were interested in working in technology, technology sales, and marketing positions.

The most successful ones were the ones that said to me, “I know I don’t have this direct experience, but let me talk to you about how the experience and strengths I bring to the table will directly apply to exactly what you said you’re looking for for this role.” I mean, all day long, we were able to open up those opportunities for people who are popping over from completely unrelated industries.

The second question I ask them is, “Tell me what my company does?” And you can’t believe how many times people are stumbling and bumbling to answer that question. Then I ask them, “Why do you think you’re talking to me today?” And if they don’t know who I am, they haven’t done the basic research on LinkedIn. If they don’t know enough to tell me what my company does and they haven’t figured out to tell me a transferable skill, then that’s not a bet I’m going to make.

But if you’re nailing all of those, and you’re coming from a completely different industry or a completely different kind of job, I’m absolutely open to a discussion and feeling much better about bringing you on to the team.

By working together, we can achieve equality in the workplace. To learn more, be sure to check out our webinar, Women in B2B Marketing: Career Advancement Strategies & Advice.

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