Jessica Gilmartin on Adapting Your Marketing Mindset to Thrive in the Face of Change

A Content Disrupted podcast with Jessica Gilmartin, CMO of Calendly

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Join us for a fascinating conversation with Jessica Gilmartin, the CMO and Chief Revenue Officer of Calendly. In this episode, Jessica explores the challenges and benefits of transitioning from startups to larger organizations, as well as her role at Calendly following a large funding round. She discusses her advocacy for a product-led growth strategy and the importance of segmentation and prioritization. Jessica also traces the constant evolution of marketing strategies. 

Episode Highlights:

• • [10:01] The Power of Product-Led Growth - Jessica explores the advantages of a product-led growth (PLG) strategy, focusing on how Calendly leverages its viral nature to drive adoption. Unlike traditional models where sales and marketing target a single decision-maker, PLG enables widespread user adoption from the ground up. This strategy allows for organic growth, where individuals within an organization adopt the product independently before influencing broader team or enterprise-wide adoption. 
  • [26:35] From Startup to Scale-Up - Jessica discusses the unique challenges companies face when transitioning from the scrappy startup phase to a more structured scale-up phase. She highlights how the shift requires a mindset change, both for leadership and employees. In the early stages, flexibility, rapid iteration, and wearing multiple hats are key to survival. But as a company grows, processes, consistency, and clear ownership become essential for sustainable growth. Jessica points out that many early employees may need help with this shift because it often means moving away from the fast-paced, dynamic environment they initially thrived in.

• [28:32] “Creative Destruction” - Jessica discusses a concept she has coined “creative destruction", which she’s integrated into her marketing philosophy. This approach emphasizes the importance of continually reevaluating strategies and processes to foster innovation. Gilmartin explains that every quarter, her team assesses 70% of their work to determine if it’s still effective. The key isn’t about creating chaos or abandoning everything; it’s about having an objective lens on what’s working and what needs improvement. This approach has allowed her team to stay ahead of market shifts and remain engaged by continuously tackling new challenges.

• [31:06] Transitioning from Traditional Marketing to Influencer Marketing - Jessica says that initially, influencer marketing started as a small experiment, but eventually grew into a core part of their marketing strategy as they observed its positive impact on customer engagement and KPIs. Gilmartin emphasizes that this transition was gradual rather than abrupt, allowing her team to build on small wins and allocate more resources to strategies that showed promise. As influencer marketing became more successful, they reevaluated traditional PR, shifting resources to support this focus. 

Follow and subscribe to Content Disrupted on Apple Podcasts, Spotify, or Google Podcasts. Every other week, we host candid conversations with pioneering CMOs and researchers on the topics most relevant to enterprise marketers, from the psychology behind today's digital buying behaviors and how to craft more relevant creative to maximizing internal trust in the marketing team.