MarTech Interview With Jessica Gilmartin, Chief Marketing Officer at Calendly

Jessica Gilmartin, Chief Marketing Officer at Calendly catches up with MarTechSeries to talk about her new journey as CMO at Calendly while taking us through a few marketing best practices she swears by:

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Tell us about your marketing journey. Specifically, more about any key lessons you’ve learned throughout your marketing journey, we’d also love to hear about your new role as Calendly’s Chief Marketing Officer…

I’ve taken a very non-traditional career path to CMO, from investment banker to brand manager to yogurt store owner to salesperson to tech marketing! I’m so glad I did because each of these experiences have made me a stronger, more well-rounded, and empathetic leader. Every marketer needs to be an entrepreneur, a data geek, a sales expert and an expert communicator, and I apply these disparate skills every day in my role as a marketing leader.

I’m particularly excited to be at Calendly right now because of the tremendous opportunity we have as a company. We already drive so much value for the millions of individual and small team users that use Calendly to streamline their scheduling, and now with our investments in sales, marketing, and product, we’re seeing significant traction in becoming the scheduling and routing platform of choice across sales, customer success, marketing, and recruiting teams within enterprise companies.

Your five “best practices” for modern-day marketing professionals?

Good marketing relies on keeping your team focused and accountable:

• Listen to your sales and product peers and make sure you’re on the same page around the value you believe your team is driving, and the value they perceive from your team. Their support is critical to your team’s success – treat them like your most valuable customers.
• Build 2-3 specific and measurable team OKRs and ensure that every one of your team has 2-3 OKRs/goals that ladder up to team goals. Make sure they’re staying on track with those OKRs and not getting distracted by new opportunities that pop up.
• Strategy is the art of prioritization. If new ideas come up throughout the year, be ok with saying no if they don’t align to your key priorities.
• Co-create your roadmaps with your sales and product partners and ensure their OKRs are the same as yours so you’re aligned on priorities from the start.

Even with bad or incomplete data you can still measure results. Even 60% measurement and fidelity is better than nothing, and creates a culture of data-orientation and accountability.

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In your opinion, what are the essential skills and tools B2B marketers today should use to help them push boundaries (martech, data knowledge, training, etc.)?

Marketers need to be nimble, curious, and risk-takers. What worked yesterday doesn’t work today, and what works today won’t work tomorrow.

I love when my team deeply understands our customers’ needs and buying patterns, and uses those insights to take calculated risks and try new content and channels to reach them. The last few years of economic turbulence has made it very obvious how critical agility and creativity is to successful marketing.

What can B2B CMOs today do differently to further business impact and drive better ROI-driven marketing performance at their organizations?

Build your plans with your sales team and make sure you are 100% aligned on the key metrics your team will be driving, and what success looks like to your sales counterparts. You also want to make sure you fully understand their sales strategy before building your marketing strategy, so you’re not throwing balls when there’s no one there to catch them! Make sure you’re aligned on everything from regions and industries sellers will be focused on, your ICP, expectations on lead volume, routing and follow up, and positioning in the market, so you’re investing every dollar in leads that sales are excited to work.

Can you share your predictions for B2B marketing in 2023?

B2B marketers will have to be very thoughtful about our marketing spend and maniacally focused on campaign ROI. We’ll also be grounding our content in the hard metrics of what economic value our solutions drive, since our buyers will be scrutinizing their spend. Being relevant to the “buying committee” – procurement, finance, IT – will be more important than ever.

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Calendly helps individuals, teams, and organizations automate the meeting lifecycle by eliminating the back and forth of scheduling. Today, over 10 million users across 155 countries use Calendly to simplify meetings, collaborate more effectively and efficiently, and drive business forward.

Jessica Gilmartin is CMO of Calendly. She leads all aspects of marketing, including brand awareness, creative, demand generation, and product marketing. Jessica has over 20 years of marketing experience, most recently serving as Head of Revenue Marketing at Asana. Before that, she served as CMO of three high-growth, venture-backed startups including Honor and Piazza, as well as co-founded Fraiche Yogurt, a successful chain of yogurt stores in the Bay Area.