Breaking into Enterprise: How Anagram Landed Disney with Cold Outbound

In the latest episode of Founded & Funded, Madrona Partner Vivek Ramaswami sits down with Harley Sugarman, founder and CEO of Anagram, to unpack how one pivot, a flood of cold outreach, and relentless focus on behavior change transformed a niche tool into an enterprise platform serving companies like Disney and Pfizer. From landing enterprise logos off of nothing but wireframes, to outmaneuvering the 800-lb gorilla in a legacy industry — Harley's tactics are a masterclass for any founder trying to stand out in a crowded market. Transcript: https://www.madrona.com/how-anagram-landed-disney-with-cold-outbound-security-awareness-training Chapters: (00:00) Introduction (01:53) Harley Sugarman's Background and Journey (03:24) Founding Anagram (04:21) Initial Vision and Pivot (05:50) Challenges and Market Realities (06:54) Customer Feedback and New Direction (09:25) Executing a Startup Pivot (11:31) Cold Outreach Success (14:20) Security Awareness Training that works (18:52) Competing in a Crowded Market (24:48) Enterprise Sales Strategy (27:04) Fundraising Journey (28:54) Choosing the Right Investors (33:32) Advice for Founders (36:33) Future of Security Training

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This episode was published on June 26, 2025.

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