GTM 136: How Asana & Calendly Scaled: PLG to SLG Playbooks That Work | Jessica Gilmartin

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 organizationThe difficulty of selling to both midmarket and enterprise customersCultivating a culture of creativity and approachabilityHow to hire your first marketerHighlights: 06:29 How Asana moved from product-led growth to sales-led growth18:00 Why refining your ICP is paramount for product-led growth33:37 Fostering a culture of experimentation40:23 Hiring your first marketer as a startup founderGuest Speaker Links (Jessica Gilmartin):LinkedIn: https://www.linkedin.com/in/jessicagilmartin/Host Speaker Links (Scott Barker):LinkedIn: https://www.linkedin.com/in/ssbarker/Newsletter: https://thegtmnewsletter.substack.com/Where to find GTMnow (GTMfund’s media brand):Website: https://gtmnow.com/LinkedIn: https://www.linkedin.com/company/gtmnow/The GTM Podcast (on all major directories): https://gtmnow.com/tag/podcast/Sponsor: PursuitThe 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.If you're hiring for sales or marketing roles, reach out to Pursuit at pursuitsalessolutions.com/gtm or message a GTMfund team member.The GTMnow Podcast The GTMnow Podcast is a weekly podcast 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.