GTM 136: How Asana & Calendly Scaled: PLG to SLG Playbooks That Work | Jessica Gilmartin
Mar 4, 2025
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In a captivating discussion, Jessica Gilmartin, a seasoned go-to-market leader and former CRO/CMO at Calendly, shares her journey through tech giants like Asana, Google, and Microsoft. She dives into the challenges of transitioning from product-led to sales-led growth and emphasizes the need for clear ideal customer profiles. Jessica also highlights the importance of fostering a culture of experimentation, building trust within teams, and the strategic role of marketing in startup growth. Her insights on hiring and nurturing creativity are invaluable for aspiring leaders.
An entrepreneurial mindset fosters ownership and accountability within a business, motivating every team member to contribute towards success.
Transitioning from product-led growth to sales-led growth requires strategic resource allocation and understanding customer demands for effective market expansion.
Creating a culture of experimentation encourages innovation and adaptability, allowing teams to explore new ideas without fear of failure.
Deep dives
The Importance of an Entrepreneurial Mindset
Having an entrepreneurial mindset is crucial for success within any business. This means taking ownership and being proactive in all aspects of the company, regardless of one’s designated role. The focus should solely be on making the business successful and not remaining passive or waiting for direction. Cultivating this mentality fosters a culture of accountability and encourages everyone in the organization to contribute actively towards achieving common goals.
Navigating the Shift from PLG to SLG
The transition from product-led growth (PLG) to sales-led growth (SLG) is essential for companies aiming to expand their market reach. As a company sees success with intuitive products that users enjoy, they may feel pressure to cater to larger enterprise accounts. This shift necessitates different marketing and sales strategies, requiring careful allocation of resources and clear objectives. Understanding customer demands plays a vital role in determining whether to enhance PLG features or adopt SLG tactics.
The Role of Data in Strategic Decision-Making
Data is a fundamental aspect of making informed decisions within a business, despite being a challenging and complex component to manage. Organizations often struggle with disorganized data streams from different teams, hindering effective analysis. Creating a centralized source of truth for data ensures that everyone has access to accurate information, which ultimately leads to improved decision-making. Investing in robust data management practices from the outset is critical for driving growth and understanding market dynamics.
Cultivating a Culture of Experimentation
Encouraging a culture of experimentation allows teams to innovate and adapt to rapidly changing markets. Leaders should create a safe environment for employees to explore new ideas without fear of repercussions for failure. Open communication about past mistakes can foster trust and promote learning throughout the organization. By emphasizing the importance of continual change in tactics and approaches, companies can remain agile and responsive to new opportunities.
Investing in Brand Development
Brand development should start early and involve creating a strong, positive reputation through product excellence and customer experience. Companies do not need to spend heavily on traditional advertising to build their brand; instead, focusing on product quality, customer satisfaction, and community engagement can be effective. Investment in brand may become essential when seeking to reposition the company or launch a significant new product. Overall, a positive brand is built on authentic interactions and supportive customer experiences.
Jessica Gilmartin has nearly 20 years of go-to-market leadership experience, most recently serving as both the Chief Revenue Officer and Chief Marketing Officer at Calendly. Prior to that, she led marketing teams at an impressive array of companies, including Asana and Calendly. As the cherry on top, Jessica also built and sold a successful frozen yogurt chain in San Francisco.
Discussed in this Episode:
Taking an entrepreneurial approach to ownership in an organization
The difficulty of selling to both midmarket and enterprise customers
Cultivating a culture of creativity and approachability
How to hire your first marketer
Highlights:
06:29 How Asana moved from product-led growth to sales-led growth
18:00 Why refining your ICP is paramount for product-led growth
33:37 Fostering a culture of experimentation
40:23 Hiring your first marketer as a startup founder
The best talent isn’t actively job hunting. Pursuit helps companies hire elite go-to-market talent on a non-retainer basis. As a key GTMfund partner, they equip sales and marketing teams with top performers.
The GTM Podcast The GTM Podcast is a weekly podcast hosted by Scott Barker, GTMfund Partner, featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
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