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She's So Suite: The Attorney turned Chief Revenue Officer of Calendly

Updated: Apr 3



  • Pivoting from one career path to another

  • Leaning in and leaning out in in your career

  • Learning Mindset vs. Fixed Mindset

  • Being authentic and being true to yourself

  • Navigating imposter syndrome as a senior leader

  • Focusing on business impact over titles and compensation

Thank you to our Sponsors: ClientSuccess and Wednesday Women

Produced by: Manali Bhat

Listen to the She's So Suite Podcast:

Podcast Episode Overview:

Welcome to another enthralling episode of the She's So Suite podcast! I'm your host, Kristi Faltorusso, and today, we delve into the inspiring story of Jessica Gilmartin, the CRO of Calendly and a beacon for women in leadership.

In this episode, Jessica opens up about the pivotal twists and turns of her career, from her initial pursuit of law to conquering the finance industry, and ultimately becoming a tech-marketing maestro. Jessica shares her philosophy of 'leaning in' and 'leaning out'—a balancing act of prioritizing career and personal life based on her values. Hear her insights on why a traditional 9 to 5 may not cut it if you're shooting for the stars in your career, along with the lessons she's learned from integrating sales and marketing to create a unified powerhouse team at Calendly.

From her days in Cornell to running a successful fast-casual yogurt business, and embracing the tech world, Jessica's journey is nothing short of incredible. She also opens up about overcoming impostor syndrome, staying authentic, and the importance of failing forward. There's so much to unpack—the hidden challenges of work-life balance, empowering women through mentorship, and why focusing on impact rather than titles and money can vastly change your career trajectory. She hasn't just climbed the ladder; she's built her own. So tune in, as we discuss everything from personal growth to making your mark in the corporate world. Make sure to rate, follow, and connect with us after the show, and let's get ready for an episode filled with lessons, laughter, and leadership with the remarkable Jessica Gilmartin.

About Jessica Gilmartin:

With two decades of B2B and B2C go-to-market leadership experience, Jessica leads all aspects of sales and marketing at Calendly, the world’s leading scheduling automation platform. 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 Honor, one of the largest privately-owned home care companies in the U.S., and COO of 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.


00:00 Importance of post-sales experience for customer retention.

05:45 Forced into labor relations, found alternative careers.

09:54 Creating healthy, fast casual food concept successful.

11:45 Transitioning from fixed to learning mindset challenge

13:46 Embracing authenticity at work led to happiness.

18:46 Grateful for sharing struggles, work with men.

22:59 Overcoming fear, achieving success through self-belief.

25:28 Executive sponsor supports and mentors women professionally.

28:41 Prioritize hard work for future success.

30:29 Influenced by others, but now follows self.

35:01 Advocating for company over self is key.

37:06 Acknowledge, empower, and reward based on merit.

40:25 Thank you all, please rate and follow.

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