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I was fortunate enough to join Constant Contact in the early days, (before the email marketing industry “crossed the chasm“) and spent 10+ years inside the tornado it would become. Since moving on and launching Alignable, I’ve continued to watch the evolution of SMB email marketing with a close eye. So when I read Constant Contact’s recent announcement that it would be acquired by EIG, it got me reflecting on the past 15 years and how much the industry’s evolution has taught me about what it takes to effectively sell to small and medium-sized businesses (SMBs).

I joined Constant Contact in 2001 at a time when SaaS was called ASP and when SMB email marketing didn’t exist. Constant Contact had 10 customers, $100 in monthly revenue, and about 20% market share. We had no way of knowing when the land rush would commence, but we knew we were going to fight our way to the front of the pack as Battle Round One commenced.

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Battle Round One (2001 to 2008)
In 2001, four major players vied


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Source: Street Fight