- 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.
And when I think about marketing — when I think about really good marketing, it really is about that personalization and creating a very tailored message. It’s so much harder, but I think in the end, it’s really worth it.
Related Article: CMO Circle: Christopher P. Willis on Community, Sales-Marketing Collaboration
Staying Ahead of the Marketing Game: Slack-Fueled Secrets and Tech Tales
Torres: How do you stay up-to-date with the latest marketing trends and technology because you know, there’s a lot these days to keep up with, and how do you keep your team informed of them?
Gilmartin: So, I actually love to join marketing Slack groups and other types of marketing groups. I’m actually involved in a lot of them, and I swear 90% of the conversations are how have you used this, or what have you used, or what do you think of this or this or that? So, it’s clearly something that all marketers think about. So that is the number one way that I keep track — I love to see the latest things that that people are using.
I’m also very fortunate to get invited to a lot of dinners and other very small events with other marketers. And I find that that’s a really great way to get to dig in a little bit deeper and understand how people are using technology and how they’re thinking about it. I mean, that really is like the number one thing for me is just hearing from other marketers — and with my team, I’m just passing it down. I actually was just on a call this morning with someone from the venture capital firm that we invest in, and I asked him, what are the tools that I should be thinking about? And I made a list and as soon as the meeting is over, I’m going to send out a Slack to my whole team letting them know. So, I just think that it’s just a constant, you know, asking questions and learning from other marketers and just trying to pass it down to my team.
Curiosity Is Key: Recipe for Aspiring Marketers and Future CMOs
Torres: Okay. Well, last question. What advice do you have for someone aspiring to get into the marketing industry or become a CMO one day? What qualities do you think are essential for this field?
Gilmartin: I love this question because I think about it a lot, and I really invest a lot in my team in thinking about how they can be successful. We actually just launched a “Making Great Marketers Academy,” and I actually posted something on LinkedIn if you want to check it out. I think one of the big things that I think a lot about as a great marketer is — you have to ask a lot more questions than you speak. Right? So, you have to be really intellectually curious and you are constantly in investigation mode. What that means is you’re constantly asking questions about who your customers are, and what are their needs, and what can you do to make sure that you are speaking to their needs.
You have to be talking to your salespeople and asking them questions about what they like, what do they not like? What more can you do for them? Why are they winning deals? Why are they losing deals?
You have to be tough, you’re asking questions like what do you care about and what are you concerned with? What information do you need for me to give you so you can understand what I’m doing? You have to ask questions of the data, that’s really important — like what are we doing now and how can we do things better? I think in marketing, in particular, things change so quickly, the things that you were doing yesterday are definitely not the things that you want to be doing today. So, for me, it really is about just being very intellectually curious, very humble, and very empathetic to all of your customers and stakeholders.
Torres: That’s a great response and I really enjoyed speaking with you today, Jessica. This has been Jessica Gilmartin, CMO for Calendly, joining us today, and I appreciate your time.
Gilmartin: Thank you very much.
Torres: All right, great. This is Jennifer Torres with CMO Circle, and we’ll see you next time.