5 questions with Calendly’s new CMO, Jessica Gilmartin

Today, we’re beyond excited to announce that Jessica Gilmartin is joining Calendly as Chief Marketing Officer. With her decades of B2B and B2C marketing experience — most recently, she served as Head of Revenue Marketing at Asana — Jessica has a ton to share about marketing enterprise software. We sat down with her to chat about that, and to get to know her better as a person and a leader.

What drew you to Calendly? What are the biggest opportunities you're excited to tackle? 

Calendly is a beloved product that solves a need that absolutely everyone experiences and can relate to. I loved the idea of building on Calendly’s existing success and helping to evolve the perception of Calendly as a scheduling platform for departmental teams and enterprises, beyond being the world’s best scheduling link or tool. 

I spent the past few years at Asana during its successful evolution upmarket, selling to enterprise companies and becoming the default work management platform for executives down to individual users. I see the same potential for Calendly to be a critical productivity solution for large deployments within enterprise companies. 

Looking into your marketing crystal ball for the year, do you have any predictions for how the marketing landscape will evolve?

It’s been fascinating to see the evolution of go-to-market strategies, from traditional top-down sales and marketing to bottom-up organic adoption, and now to the hybrid of the top-down and bottom-up motions. I speak with many marketers and founders, and this blending of the two motions is clearly the future of marketing. Traditional enterprise sellers are trying to figure out how to create virality and user adoption to shorten sales cycles and improve close rates, and the companies that have relied on organic adoption are adding on enterprise marketing and sales expertise to improve their storytelling and ability to be relevant to decision makers within larger organizations.

I love seeing this evolution because in both motions, a company must be innovative, responsive to its users, and able to provide a product that users love and are willing to adopt and champion within their organization. It’s one of the big reasons I joined Calendly. It’s a gift to market a product that users love and advocate for its expansion throughout their company. Calendly has amazing customers, and I can’t wait to help tell more of their stories.

What's your favorite Calendly feature? 

I used to run sales and sales development, and I know how every minute counts when it comes to responding to scheduling meetings with prospects, whether they’ve responded to an email or reached out to you on your website. To have a single tool that cuts out the back-and-forth friction, allows prospects to schedule a meeting within seconds, integrates with your go-to-market tech stack, and automates the rest of the meeting lifecycle, is absolutely game-changing. It’s the difference between capturing your prospect’s demand right at their moment of interest, versus your competitor. 

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What are some of the greatest lessons you've learned from your marketing career to date? 

I’ve been doing this for a long time so this is a hard question to answer! I’ve had the privilege of learning from some incredibly talented coworkers and managers, and it’s hard to pick just a few things. As a marketer, one thing that I try to remind myself and my team is that even though we’re marketing enterprise software, we’re all just human beings speaking to other human beings. We have to resist the temptation to sell products and features, and instead focus our marketing on what problem we solve and how we can make our users’ lives better. And even if we’re a serious product, we can still be a fun, relatable brand and show our personality and humanity.

As a leader, the thing I care the most about is that my team feels safe to take risks, make mistakes, and give and receive tough feedback. Marketing is a rapidly evolving discipline and what worked yesterday won’t work today, and what works today won’t work tomorrow. Because we’re always trying something new, there will be some campaigns that are wildly successful, and some that don’t work out, and I want my team to be generous in sharing the best practices from the successes and the learnings from the failures so that everyone is constantly learning and improving. 

The last time you were in a state of flow — where you were so focused you lost track of time — what were you doing?

With a busy job and an even busier household to manage, I’ve found that I need balance in my life to keep me physically and mentally healthy. Following a few sports injuries over the past few years, I discovered yoga which has been life-changing for me. It’s the only time my wildly over-active brain shuts off and I just allow myself to focus on my breathing, my posture and the poses. I know after class ends I’ll still have to put the kids to bed and answer my mountain of emails, but for those 45 minutes I’m in a perfect state of focus and flow. 

Follow Jessica on LinkedIn.

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