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413: Creative Destruction at Calendly with Chief Revenue Officer Jessica Gilmartin

In this episode, Alan and Jessica talk about the evolution of Calendly from serving solopreneurs to mid-market and enterprise organizations, the success factors that have made that shift possible, how she thinks about the RIO and effectiveness of marketing spend, and balancing the need to drive results and be creative through “creative destruction.”. 

Jessica Gilmartin is an amateur baker, an ex-yogurt mogul, and the new Chief Revenue Officer at the scheduling automation platform Calendly. When Jessica started her career as an investment banker, she knew it wasn’t the right role for her, but she didn’t know what else was out there, so she went back to school. After her first marketing class, she knew she had found her passion. She took her first marketing job at Dell, which prompted a move to the Bay Area, where she also started and sold a chain of yogurt stores. Before joining Calendly as their CMO in 2023, Jessica was Head of Revenue Marketing at Asana and had also served as CMO of three high-growth, venture-backed startups, building their global enterprise marketing engines during rapid growth periods. 

Calendly started with a basic scheduling link for individuals, but then business users told them they needed more team features, and enterprise users told them they needed more admin and security features, so the product grew to meet those needs. Despite the complexity of its user base and multi-faceted personas, the individual user experience remains a top priority as Calendy grows. Jessica tells us they are building for scale but are sure to never lose sight of the individual user’s success. Her team is focused on how to tell a complete story with comprehensive features while maintaining simplicity in the product and the messaging.

To do that, Jessica and her team have to experiment. Marketing changes all the time, and what worked then will not work now, so marketers have to be creative to drive results. She refers to this as “creative destruction” and encourages her team to make 70–80% of what they are doing every quarter new. However, to make this work, her team must trust that failing is not career-ending as long as they learn from it. Jessica also outlines how her approach to segmenting and communicating expectations around marketing spend facilitates experimentation. AI is a place where many companies are experimenting, but Jessica feels there are some misrepresented expectations around the capabilities of AI in its current state. Within their product, the Calendly team sees a huge amount of opportunities they are pursuing, but they are taking a measured approach to keep their users’ interests top of mind.

Alan and Jessica wrap up by talking about how she learned to accept and embrace hard feedback, the importance of listening to her gut feelings, why markets have to learn sales, and the shifts coming from the consumerization of B2B tech. 

In this episode, you’ll learn about:

  • How Calendly developed through user feedback
  • What “creative destruction” is and the culture needed to make it work 
  • How Jessica segments out her budget to maximize RIO and the effectiveness 

Key Highlights:

  • [01:55] A love of baking born out of necessity 
  • [03:10] From investment banker to CMO
  • [04:40] Wait… a yogurt shop?
  • [06:20] Where Calendly started and where they are now
  • [08:00] Comprehensive solutions rooted in simplicity
  • [09:20] Success factors in shifting from serving one to many
  • [11:00] ROI and effectiveness of marketing
  • [14:00] Fulfill your commitments and build trust to get more wiggle room. 
  • [14:45] Balancing the need to drive results and be creative 
  • [17:10] The AI portion of the show is a little different this time.
  • [19:45] How Calendly is using AI
  • [21:30] Learning to accept and embrace really hard feedback
  • [24:25] Advice to her younger self
  • [25:20] Advice to other marketers 
  • [26:05] Trends and subcultures
  • [26:45] Marketers basically have to be magicians. 

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