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Leadership Edge with NerdWallet CMO Kelly Gillease

I had the pleasure to interview Kelly Gillease, CMO at NerdWallet.

Kelly Gillease is NerdWallet’s Chief Marketing Officer, bringing a consumer-first focus to the company’s product and brand marketing strategy. In this role, she oversees the company’s national brand campaigns, marketing team job architecture, and measurement strategies to drive product growth and consumer value. She brings to the table 20 years of experience at startups in travel, EdTech and search, even supporting strategic startup acquisitions at Hotwire, Viator, and StudyBlue. Kelly is passionate about building a high performing department culture that prioritizes employee retention. She graduated from UC Berkeley with dual BA degrees in Economics and English.

Thank you so much for doing this with us Kelly! Before we dig in, or readers would love to learn a bit more about you. Can you tell us a story about what brought you to this specific career path?

I’ve always been drawn to companies that improve people’s lives and send a positive message. Before joining NerdWallet, I worked in the edtech and the travel industries, both of which have the power to make a tangible positive impact on the world. When I was researching NerdWallet, its mission of helping people manage their finances resonated with me immediately. I liked that the message was positive and focused on what good can come from understanding personal finance, rather than focusing on the negatives of what will happen if you don’t manage your money correctly.

I never intended to have a career in marketing — my first job out of college was working as an economist for the federal government. I was fascinated by the rise of the consumer internet and how it could positively change our lives, and I wanted to be a part of that journey. When I started in digital marketing it was a natural fit for me because it brought together my quantitative, analytical experience as an economist and my experience in creative thinking and writing (I also have an English degree).

Can you share a story about the funniest marketing mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Once, before there was automated bidding, I was doing SEM and accidentally set a bid for $3.00 instead of $0.30 (which was A LOT in 2002). Luckily I caught it before I blew the monthly budget, but it taught me that the devil is in the details and to check my work! I am now an obsessive double-checker.

Are you able to identify a “tipping point” in your career when you started to see success? Did you start doing anything different? Are there takeaways or lessons that others can learn from that?

The tipping point for me was taking a job at a smaller startup where I could build a marketing function from the ground up. Because there wasn’t a big team, I had to teach myself about almost all areas of marketing, and a ton about data and attribution and technology. It was so valuable to get that breadth of experience across different areas. Even today, that hands-on experience helps me advise my team and have empathy for their work.

What do you think makes your company stand out? Can you share a story?

NerdWallet’s unwavering dedication to helping consumers is what makes us stand out. Everything we do is in service of our mission to help Americans understand their finances and make smart money moves. Whether that’s by creating a firm divide between our editorial team and our product recommendations, or by turning down partnerships that aren’t in consumers’ best interests, our users are at the forefront of all decision-making.

NerdWallet has been profitable since its early days, and we reinvest a significant amount of that profit back into our product. Having that sense of security in a stable revenue flow means we’re even more empowered to make the best business decisions for consumers.

Are you working on any exciting new projects now? How do you think that will help people?

At the end of December 2019, we launched our first-ever national brand campaign and we’ll be scaling those efforts by tapping into new media channels and continuing to invest in establishing NerdWallet as a go-to resource for all your money questions.

We’re continuing to leverage popular social channels like Facebook and Instagram to reach our core audience. We’ve produced new animated, channel-first creative to highlight how NerdWallet’s shopping tools and advice can help answer frequently asked / searched money questions about savings, investing and more.

What advice would you give to other marketers to thrive and avoid burnout?

I’d argue that marketers need to be more comfortable with taking risks. When your company is doing well, it’s easy to fall into a routine because it’s safe and backed by proven results — but that won’t help you achieve your mission any faster. It can be hard to convince people to think bigger and take risks, even when there is a safety net.

I try to encourage my own team to think about the worst-case scenario, the probability of it happening, and how we would address it. This eases their minds and allows us to think big picture by answering questions like: What’s the risk of us not taking this action? What does it say about our culture? From there it’s easy to be comfortable taking calculated, strategic risks and it keeps the work fresh and exciting to try new things and push ourselves to do new work.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I will always be grateful to my former CEO, Barrie Seideberg. I worked with her for over eleven years in my first leadership role, and she was an incredible mentor for me. She empowered me to make decisions, take risks, try new things, and work independently. She had a lot of trust in my abilities, but still gave me valuable feedback about where to focus my growth. As a CEO and a mom, Barrie set a great example for how to balance work and family life.

One moment that I’ll never forget is when I came to Barrie with a pivotal recommendation about our marketing strategy. I had put a lot of thought into this and spent time weighing the pros and cons of this decision. As I was walking her through my recommendation, she stopped me and said, “Kelly, no one knows more about this than you. If you say this is what we need to do, then this is what we need to do.” And our discussion was over. I walked away realizing that she’s right — I should be more decisive and own my decision without looking to others for validation.

Ok super. Let’s now shift to the main part of our discussion. There are hundreds of memorable marketing campaigns that have become part of the lexicon of our culture. What is your favorite marketing or branding campaign from history? Can you explain why you like that so much?

I love the Mastercard Priceless campaign. It is such a great example of marketing that connects with consumers on an emotional level while also messaging a practical benefit. There’s a reason it was incredibly successful and has been running for over 20 years. Great campaigns have legs! I also love a positive, optimistic campaign that shows how people’s lives can be more fulfilling.

If you could break down a very successful campaign into a “blueprint”, what would that blueprint look like? Please share some stories or examples of your ideas.

First, connect with your customers on a broad, emotional level, then get more specific about how your brand supports that emotional connection on a practical level. I think NerdWallet’s Money Questions campaign does a great job of this. In our flagship brand ads, we surface all the tough, emotional money questions everyone has, like, “How do people buy a house?” and “Am I supposed to be investing?” Then in our second wave of ads, we get more specific about how NerdWallet can help you answer these universal personal finance questions. There’s both an emotional and practical benefit in the campaign.

Companies like Google and Facebook have totally disrupted how companies market over the past 15 years. At the same time, consumers have become more jaded and resistant to anything “salesy”. In your industry, where do you see the future of marketing going?

I really believe that if a brand is feeling too “salesy,” it’s a sign they aren’t marketing effectively to their audience. Effective marketing feels appropriate — the media, the message and the audience are at an intersection that feels natural and appropriate. When marketers force that, it feels inauthentic and “salesy” to the audience. I see brands in the future getting more and more rigorous about being authentic and appropriate in their marketing, rather than taking an “all things to all people” approach and aiming for the broadest reach.

Can you please tell us the 5 things you wish someone told you before you started? Can you please share a story or example for each.

Be more confident — even if you have to fake it. I project a lot of confidence, but I don’t always feel it on the inside. Just the other day, I was at a company lunch for Women in Data & Engineering and an attendee asked, “When did you last feel like you had imposter syndrome or weren’t qualified to do something?” My answer was, “Yesterday.” I’ve worked on my confidence a lot, but I wish I had started giving it attention much earlier in my career.

  • Worry less. I am naturally a worrier who imagines the worst-case scenario for everything and makes backup plans on backup plans. When I was first starting out, I wasted a lot of energy worrying pointlessly, when I could have focused my energy on something better!

  • As much as you’d like your organization to be flat, it won’t be. You will have to work continuously to not only make yourself seem approachable, but to make your team comfortable approaching you. I make it a point to interact with everyone on my team — I eat lunch with them, sit in an open office with them, and have happy hours. But still some people don’t utilize me because they feel intimidated by my C-suite title, are afraid of wasting my time, or don’t want to appear imperfect around me. I have to constantly reassure my team that I am here to help them do their best work, and that they can talk to me any time. I forget about this sometimes until I hear comments like, “You’re the CMO, I didn’t want to bother you with that.” It reminds me that there’s a barrier preventing my team from fully engaging with me that I don’t always perceive.

  • Don’t get too comfortable where you are, and be open to change.In the past I’ve stayed too long at some companies, which had its benefits, but also had its downsides. I now think a lot more about my natural life cycle within a company and am very honest with myself about when it’s time to move on to something new.

  • Always have compassion and kindness for your colleagues and partners. Work is tense sometimes, and everyone is just trying their best. In stressful situations, compassion and kindness are a much better approach than harsh words and demands. In a previous role, I was on a call with a vendor and one of my directors. My team was not getting the support they needed from our vendor and we needed to share this feedback with them. At the end of the call I sincerely thanked the vendor for taking time to talk to us and being open to addressing these issues. Afterward my director said she would have never thought to thank the vendor, and that it was a great way to end a challenging call.

What books, podcasts, documentaries or other resources do you use to sharpen your marketing skills?

I keep up on marketing news via a variety of email newsletters, and sites like MediaPost, Ad Age, and Search Engine Land.

Most of the podcasts I listen to aren’t marketing specific, but they help me think more creatively, or think more broadly about growing our business. I love “99% Invisible” and “Dolly Parton’s America.” Dolly is an amazing creative talent and a personal branding genius! “Masters of Scale” is another of my favorite business podcasts, and I am always up to date on NerdWallet’s “Smart Money” podcast!

I also take courses on management and leadership on Lynda, a website that offers video courses from experts on software, creative, and business skills. I have taken several manager and executive online courses through Lynda that were extremely valuable.

Who is your hero? Can you explain or share a story about why that person resonates with you?

It’s hard to choose one person because I’ve learned a lot from so many people. I studied physics initially in college, so I am a big fan of Albert Einstein. He was a genius, but he was also unapologetically nerdy and didn’t take himself too seriously. I love the idea that you can be at the top of your professional game, but also have a ton of fun! I often think about him when I am stumped by a problem. Einstein was incredibly creative and is famous for saying, “Imagination is more important than knowledge.” I remind myself of this to encourage more creative problem solving and alternative approaches.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

As a person who works in personal finance, I think a lot about the financial lives of Americans and the real financial struggles families face today. I would love to see financial literacy be a required part of all school curriculum, and I’d love to see a living minimum wage for all Americans. I think that would make a huge impact on people personally and on our economy as a whole.

How can our readers follow you online?

You can find me on Twitter @kellpickles and on LinkedIn.

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