Calendly Leadership

Our team is customer-obsessed, mission-oriented, and believes anything is possible.
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Tope Awotona
Founder, Chief Executive Officer
Prior to Calendly, Tope spent the majority of his career in enterprise software sales, working for companies such as IBM, Perceptive Software, and Dell Technologies. He grew up in Lagos, Nigeria and came to the US in 1996. Tope graduated from The University of Georgia with a degree in Management Information Systems, and currently resides in Atlanta and New York City. When not fine-tuning and perfecting Calendly, he’s probably LOLing at a standup comedy club, (occasionally) showing up for CrossFit, or dreaming about a tropical vacation.
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Stephen Hsu

Chief Product Officer

Prior to Calendly, Tope spent the majority of his career in enterprise software sales, working for companies such as IBM, Perceptive Software, and Dell Technologies. He grew up in Lagos, Nigeria and came to the US in 1996. Tope graduated from The University of Georgia with a degree in Management Information Systems, and currently resides in Atlanta and New York City. When not fine-tuning and perfecting Calendly, he’s probably LOLing at a standup comedy club, (occasionally) showing up for CrossFit, or dreaming about a tropical vacation.

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Roy Duvall

Chief Technology Officer

Roy is responsible for designing and scaling a solution to give users two of the most precious resources available: more time and improved collaboration. This mission drives his undying passion and focus on excellence. Prior to joining Calendly, Roy built high-performing engineering teams for multiple high-growth organizations including Sharecare and The Weather Channel. He studied computer science at the Georgia Institute of Technology and calls Atlanta his home. Roy is an outdoor enthusiast with a running problem that often compels him to run ultra distances through forest trails as a hobby.

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Jessica Gilmartin

Chief Marketing Officer

With decades of B2B and B2C marketing experience, Jessica leads all aspects of marketing. Previously, she was Head of Revenue Marketing at Asana, where she exponentially grew its global marketing enterprise engine. Prior to that, she was the CMO of three high-growth, venture-backed startups, including Honor, one of the largest privately-owned home care companies in the U.S., and Piazza, an online college recruiting platform. She also co-founded Fraiche Yogurt, a successful chain of yogurt stores in the Bay Area. She 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. Outside of work, Jessica volunteers her time as a board member with senior dog rescue Muttville and at her sons’ schools. She has two boys and spends her weekends watching, attending, and hearing about sports.

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Tina Dobie

Chief Customer Officer

Tina holds 25+ years of experience in the SaaS and management consulting industries. Previously, she was Chief Customer Officer at WP Engine, where she built and scaled the customer experience team to serve hundreds of thousands globally. Before that, she was VP of Client Services at Bazaarvoice and Director of Client Services at Inquisite, where she grew sales nearly 110% in two years. Her teams have earned 13 Stevie Awards for customer experience and service. She holds a BBA and an MBA from the McCombs School of Business at the University of Texas at Austin. She enjoys traveling, cooking, and exploring with her two daughters and husband.

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Frank Russo

Chief Information Security Officer

Frank brings over 20 years of security and infrastructure experience to his role as CISO. Most recently, he was the vice president of information security and CISO of XRP II at Ripple. Before that, he spent nearly a decade at Salesforce as the director of enterprise security. Frank began his career working in customer support engineering positions at several companies including Cisco. He has a Bachelor of Arts in Liberal Studies from Boston University. Frank enjoys spending time with his young son, mountain biking, skiing, and taking apart old pocket watches.

Kate Ahlering

Chief Revenue Officer

A seasoned and passionate leader, Kate has proven success in building and scaling high performance revenue teams. Most recently, she was the Chief Sales Officer at Glassdoor, where she helped grow the company from less than $10 million in revenue to several hundred million and through a $1.2 billion acquisition. Previously, Kate held multiple positions in sales leadership at ACTIVE Network, where she helped grow the company to more than $500 million in revenue and achieve an IPO. Earlier in her career, she held sales roles at Blackboard. She holds a Bachelor of Arts degree in Political Science and a Master of Education in Leadership, Social Foundations, and Policy from the University of Virginia. A retired athlete, Kate now enjoys riding a bike that doesn’t move, amateur home improvement projects, and chasing her two children at the beach.

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John McCauley

Chief Financial Officer

A veteran finance leader, John has spent his career scaling financial operations for global businesses. Before Calendly, John was the CFO of Seismic, in addition to holding senior financial strategy positions at Illumina and ServiceNow, where he helped orchestrate a successful IPO in 2012. He began his career in assurance services at Ernst & Young. He holds a Bachelor of Arts in Accountancy from the University of San Diego and a Master of Science in Accountancy from San Diego State University. Outside work, John enjoys photography, spending time on the water, or adventuring with his four children.

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