Executive Highlight

Susan Westwater

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AI Strategist | CEO/Co-founder | Author, Pragmatic Digital
Business Founded: 2018
Phone: (312) 933-6090
Email: [email protected]

Address:
205 68th Street
Darien, IL 60561

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How long have you been in your industry?29 years
Why did you choose your industry?My partner and I have always been drawn to moments when emerging technology forces business transformation. AI is one of those rare moments. We chose to focus on AI and innovation because we saw too many companies either overwhelmed by AI or missing the opportunity entirely. Our background leading digital strategy, voice interfaces, and CX made it clear: AI wasn’t just a technology, it was the next business imperative. We wanted to help organizations implement it practically and profitably.
Who are your typical clients?Our clients are CMOs, COOs, CTOs, and Innovation Leaders in healthcare, manufacturing, and consumer packaged goods (CPG). They’re forward-looking decision-makers who believe AI can give their company a competitive edge—but don’t have unlimited budgets or years to experiment. They’re looking for a trusted partner to help them move fast, smart, and with confidence.
What do you like best about being in this industry?We love the moment when an executive realizes that AI doesn’t have to be abstract or overwhelming and can actually solve their business problems, right now. Whether it’s reducing production downtime, improving patient experience, or launching more personalized campaigns, we’re energized by making AI useful, actionable, and aligned to strategy.
What are common problems you see?Too many companies chase AI tools without a strategy or with the wrong advisor. They’re doing disconnected pilots, investing in platforms they don’t need, or ignoring organizational readiness. On the other side, some teams are frozen in place—paralyzed by uncertainty or over-analysis. The result? Missed opportunities, wasted time, and siloed innovation that doesn’t scale.
What advice/tips do you have for clients?Start with business outcomes, not AI features. Identify the problems worth solving, then work backward to the right technology. Align early with your stakeholders, focus on quick wins, and don’t wait until your competitors pull ahead. Most importantly: AI isn’t just for data scientists. Your brand, marketing, and operations teams need to be at the table.
When is your busy season?We see a spike in interest at the start of Q1 when leaders are setting priorities, and again in late Q3/early Q4 as companies look to allocate budget or prove progress on innovation initiatives.
What keeps you up at night?Knowing that smart, capable teams are falling behind; not because they lack resources, but because they lack a clear path forward with AI. Our job is to close that gap and make sure innovation doesn’t stall due to uncertainty, misalignment, or internal gridlock.
How do you market yourself to grow/expand your business?We speak at industry events, contribute to thought leadership publications, and host educational workshops. We’ve authored two books (one with a foreword by Philip Kotler) and frequently partner with associations and accelerators to offer executive guidance on AI. Our website and webinars are designed to lead with education because trust starts with clarity, not a sales pitch.
How involved are you in the community?My partner and I co-founded the AI in CHI Meetup to bring AI literacy to Chicagoland businesses and professionals. I am also active in my local community through the junior high music boosters to support the choir and band programs. As a family, we support many outdoor clubs and organizations.
What is your favorite not for profit or charity?Turks & Caicos SPCA, Arabian Horse Association, Streetwise GiveaShirt, hand the National Park Foundation
What advice would you give to someone thinking of getting into this business?Lead with empathy and practicality. Executives don’t need another consultant talking about the future or theory—they need someone who can help them deliver results now. Build trust, communicate clearly, and stay curious. And make sure you know how to translate tech into business value, or you’ll lose your audience before you’ve even started.
What do you enjoy doing in your free time?As a family, we enjoy being out in nature so we try to book several fishing trips a year to Michigan and Wisconsin and elsewhere. I have been riding horses, first eventing and jumpers then Arabians, for over 40 years. We also love to travel throughout the US and Europe when possible.

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