GTM 71: Writer CEO Tells All: Securing Enterprise Customers with a PLG Motion | May Habib (Revisited Bonus Episode)

May Habib is CEO and Co-Founder of Writer, the full-stack generative AI platform for enterprises. Writer empowers your entire organization to accelerate growth, increase productivity, and ensure compliance. 

May has worked in NLP and ML for 10 years, and before Writer, she founded and built Qordoba, a localization software company. She is an expert in AI-driven language generation, AI-related organizational change, and the evolving ways we use language online.

She sits on the board of TechWadi, an organization that bridges MENA-based entrepreneurs with Silicon Valley-based VC and talent networks, and is a MELI Fellow with the Aspen Institute.

May graduated from Harvard University and spends her time between San Francisco, where Writer is based, and London, where her two children live.

What You Will Learn:

  • May’s perspective on the economy now compared to that of 2008/2009. 
  • Writer’s decision to make PLG table stakes and how they leverage their motion to secure enterprise customers. 
  • AI use cases – what they are and how they continue to progress. 
  • Tips for recruiting the best possible team members and how patience factors into that. 
  • Career insight from years of operating. 


(6:12) May’s learnings from Lehman Brothers and the economic crisis of 2008/2009.

(14:11) How much attention the average business leader should spend thinking about AI and how much of a near-term impact AI will have.

(25:17) Writer’s PLG motion, including self-serve and sales-assisted, and how it’s used to turn small downloads into big enterprise accounts.

(31:07) A consultative sales process and messaging considerations. 

(36:56) May’s strategy for recruiting A players. 

(42:55) Personal career learnings distilled by May.

Guest Speaker Link:

Host Speaker Links:

Today’s episode is sponsored by Flex, a finance super app built around a credit card with unique Net-60 day terms that enables businesses to make an investment today and pay it back 60 days later with zero percent interest. If your business growth is constrained by the cashflow you need for inventory, advertising, or something else, Flex could provide you with an interesting growth lever.

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Before helping found GTMfund, Scott spent 4 years at Outreach as Director of Strategic Engagement. He was in charge of aligning key relationships with VCs, BoDs, ecosystem partners and community members to drive revenue and strategic initiatives across Outreach. Scott initially ran revenue/partnerships for Sales Hacker (which was acquired by Outreach in 2018). Prior to Sales Hacker, he led and built outbound Business Development teams at Payfirma and MediaValet. Scott also advises for a number of high growth start-ups and is the host/author of The GTM Podcast and The GTM Newsletter. At GTMfund, Scott leads all fundraising efforts and runs the media arm of the firm. He’s also responsible for assessing investments, team management, LP/community relationships and GTM support for founders.

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