About Kerwin
Progressive Strategies Services exists for one reason: to help small businesses use AI without the overwhelm. No jargon, no rip-and-replace overhauls — just practical automation that fits how you actually work, built alongside you instead of handed to you.
At Avalara, my job was putting the customer first — translating the complex backend of tax compliance software into plain language so people could actually get their goal done. AI does the same thing for me now, just wider: I hear constantly what small businesses are drowning in, and AI can take a real chunk of that off their plate. And we're still early — what it can automate for you next year won't look like what it does today.
I spent 8 years in Customer Success at Avalara, managing enterprise accounts worth up to $250M in combined ARR with a 98% retention rate — which meant one thing above all: understanding exactly what a business needs before recommending anything. That's the same approach I bring to AI.
I've lived in the Bellevue/Newcastle area since middle school, and I still shop and eat at the small businesses here. Watching them thrive isn't abstract to me — it's what drives this work.
"Built alongside you" isn't just a line — it's why I call this approach Learning Together. That means regular communication, taking the time to actually explain things, and answering every question along the way. I know AI can feel intimidating; my job is to take that weight off your shoulders, not add to it.
Day to day, that means the same tools I use with you: Microsoft Copilot, Gemini, Claude, Google Docs and Salesforce — hands-on, not just theory.
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