Who I am

I'm Chummy Prestowitz, a senior technology executive with 25+ years building and scaling enterprise software platforms across fintech, insurtech, and healthcare.

I founded Inside Edge Advisory to give founders, investors, and boards access to the kind of senior technical judgment that's typically locked inside large organizations — practical, unbiased, and focused on what actually matters.

My work spans technical due diligence, fractional CTO leadership, and AI advisory. Whether you're evaluating an acquisition, navigating a platform inflection, or determining where AI creates real leverage in your business, I help you move forward with clarity and confidence.

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Contact us

I work with a small number of clients at a time. If you're evaluating a technical decision, considering an engagement, or just want to explore whether there's a fit, reach out.