Calendly Taps Asana Executive Jessica Gilmartin as CMO

Scheduling automation leader appoints Gilmartin to accelerate market awareness and enterprise revenue growth

Calendly, the modern scheduling platform for high-performing teams and individuals, announced the appointment of Jessica Gilmartin as Chief Marketing Officer, reporting to Founder and Chief Executive Officer Tope Awotona. Gilmartin brings decades of B2B and B2C marketing experience to Calendly to help drive adoption across sales, marketing, customer success, recruiting, and other high revenue-generating teams within mid-market and enterprise companies.

As CMO, Gilmartin will lead all aspects of marketing to partner with sales and grow Calendly’s annual recurring revenue business and drive its move upmarket. “Calendly’s proven it’s a beloved brand to its customers, making the opportunity to redefine our market position and build our enterprise marketing motion all the more exciting,” said Gilmartin. “We’re an easy solution to a massive industry problem that lets workers schedule for faster, impactful connections that improve organizations’ bottom lines.”

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“Calendly’s proven it’s a beloved brand to its customers, making the opportunity to redefine our market position and build our enterprise marketing motion all the more exciting”

Prior to Calendly, she was Head of Revenue Marketing at Asana, where she spearheaded demand generation, marketing operations, and product and sales-led growth business integrations for the Americas, EMEA, Japan and APAC businesses. She also 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 U.S., 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’s extensive background in product and sales-led growth motions moving upmarket, as well as building B2B marketing programs and teams in support of our customers, is exactly what we need to achieve our next stage of growth,” said Tope Awotona, Calendly’s founder and CEO. “Her expertise will help us define a new category in technology and get Calendly into the hands of every departmental team within the enterprise.”

Jessica’s addition follows a momentous year for Calendly. In 2022, Calendly accelerated its ambition to deliver deeper solutions for enterprise teams and organizations with the acquisition of Prelude and the release of new features and integrations like Calendly Routing Forms, Calendly Analytics, and Calendly LinkedIn browser extensions. Calendly’s Teams and Enterprise Plan customers continued to be its fastest growing cohort: the company bolstered its customer roster with Twilio, Staffmark Group, and Cintas, and customers spending greater than $100 thousand per year increased 100% year-over-year.

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