The Struggle Huddle

Struggle Huddle #4: AJ Kissh


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Director of Marketing at Parakeet, AJ Kissh, joins Struggle Huddle to talk about turning CRO instincts into a brand voice people actually want to hang with. We dig into why semantics matter (“say it so a 10th-grader gets it”), how AJ treats websites as a 24/7 ad, and the headline that finally clicked for Parakeet: “We write, test, and send better cold emails.” We also get real about experiment discipline (what to measure, how long to wait), pushing LinkedIn tone without going cringe, and why AI risks creating a “new vanilla.” In the Struggle segment, AJ opens up about imposter syndrome and shipping with conviction even when the data’s not there—yet.

Listen for: practical copy tweaks, channel-by-channel tone, and a simple framework for deciding when to pivot vs. let it run.

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The Struggle HuddleBy Em Thomas