Founded & Funded podcast

Breaking into Enterprise: How Anagram Landed Disney with Cold Outbound

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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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