From Investment Banking to Marketing Mastery

The Gist

• Unconventional Beginnings. From investment banker to marketing maven.
• Lessons in Collaboration. Navigating stressful campaigns.
• Personalization Prevails. Gilmartin’s tailored triumph in marketing.

Jessica Gilmartin is the Chief Marketing Officer at Calendly where she’s responsible for leading all aspects of marketing including brand awareness, creative, demand generation and product marketing. Gilmartin brings nearly 20 years of marketing and leadership experience to Calendly.

Most recently, she was head of revenue marketing at Asana where she led demand generation, marketing operations and product and sales-led growth business integrations for the Americas, EMEA, Japan and APAC businesses. Before Asana, she served as CMO of three high-growth, venture-backed startups, building their global enterprise marketing engines during rapid growth periods, including Honor, one of the largest privately-owned home care companies in the US, and Piazza, an online college recruiting platform where she also led sales to build it into a multi-million-dollar revenue-generating company in one year. Previously, she co-founded Fraiche Yogurt, a successful chain of yogurt stores in the Bay Area.

Jessica received a Bachelor of Science in Industrial and Labor Relations from Cornell University and a Master of Business Administration in Marketing and Strategy from The Wharton School at The University of Pennsylvania.

We caught up with Gilmartin for a five-question Q&A on her role as CMO in our latest edition of the CMSWire CMO Circle series.

Editor’s note: This transcript is edited for clarity.

Journey to Marketing Success

Jennifer Torres: Hi, I’m Jennifer Torres, reporter with CMSWire and this is CMO Circle, our chance to get together with a different CMO each episode and ask questions.

Today I’m excited to welcome, Jessica Gilmartin, chief marketing officer at Calendly. Hi Jessica, thanks for joining us here today.

Jessica Gilmartin: Thank you very much. Great to be here.

Torres: Well, we appreciate you being here as well and we’ll get right into it. So, what inspired you to pursue a career in marketing? How did you get your start in the marketing industry?

Gilmartin: So, I actually started my career as an investment banker, and I did that for four years. I know, not a traditional start into marketing. I went to business school because I knew I wanted to switch careers, but I had no idea what I wanted to do. I took my first marketing class, and I fell in love. I realized that was that was for me. I went to Wharton — and not surprisingly, the marketing at Wharton is very data driven, and so, what I loved about it was this combination of using my right brain and my left brain, right? So, you can be really creative but also grounded in data. I ended up majoring in marketing and then was lucky enough to get a job in marketing in Austin and that was that.

Related Article: Unlocking the Secrets of Effective Marketing: Real-World Experience and Success Metrics

Going From Campaign Chaos to Collective Collaboration

Torres: It does seem like everyone I talk to in marketing — a lot of them do come from different areas. It just a very dynamic field with people from a lot of different professions that just kind of find their heart in marketing when they get started. So that’s amazing. Question No. 2: can you describe a particularly stressful marketing campaign or project that you led and what you learned from it?

Gilmartin: Well, I think they’re all particularly difficult in their own way. So, I think the hardest ones tend to be where you’re doing something for the first time and you’re rallying the team for the first time, and you’re kind of struggling through things, and I think one of the biggest challenges is really overcoming people’s fears that they’re going to fail. Right? And I think one of the biggest things that I always talk about is psychological safety — and really making people comfortable with the idea that things are going to fail and nothing’s going to be perfect the first time.

So, I’d say one of the difficult campaigns was Academy (Calendly’s “Making Great Marketers Academy”). I’d only been here for four months, and I think a difficult campaign was the first campaign that we all ran together, where we were all learning about each other — and learning from each other. And, you know, we hadn’t quite figured out our patterns. We hadn’t quite figured out how we all work together. I think it was stressful for the team because they didn’t know when to bring me in or how to bring me in and really know my working style. And I didn’t really know the team and I didn’t really understand their strengths and what they were interested in and what they could do.

And so, I think that just understanding how do we work together? How do I give them autonomy, but also have some control and understanding of what they do and sort of that trading. It was definitely really challenging.

Revolutionizing Lead Generation: A Tailored Triumph

Torres: Can you describe a successful marketing campaign or project and what you learned from it?

Gilmartin: Yeah, so we actually just launched Calendly Routing a few months ago, which was our first big product launch that we have done in many, many, years. And basically, what routing is, is it enables prospects when they come to a website — instead of filling out a form and waiting weeks to hear back from a salesperson, they can actually schedule a meeting with a salesperson right from the website. So, it eliminates all of the messy middle that we typically see with leads. So, we just launched that, and I think it was very, very successful.

And I think the reason it was successful is because my team took a really highly personalized approach with how we marketed. Instead of just doing a blast email and messaging everybody in our database, we looked at each of our segments, and we created very tailored messaging to each of those. So, for example, if we already knew that you use HubSpot, we would send you a very specific message talking about how our routing integrated with HubSpot, and we knew that you were this type of customer with this type of needs. And so, we had dozens of these different sorts of paths.