Michelle Calcagno

VP, Solution Engineering & Revenue Enablement | GTM Strategy | Revenue Productivity | Demo Excellence | Technical Sales Leadership

ParentSquareex-PowerSchoolex-Paycom

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I lead Solution Engineering organizations that help sellers win complex deals. As a VP of Solution Engineering and GTM enablement, I build and scale high-performing pre-sales teams that drive revenue through strong discovery, value-based demos, and technical storytelling.

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My focus is aligning Solution Engineers tightly to the sales motion, so SEs aren’t just supporting deals, but actively influencing outcomes. I’ve led: -Multi-disciplinary Solution Engineering teams supporting mid-market and enterprise sales -Demo strategy and sandbox environments that increase win rates and deal velocity -Transitions from feature-led demos to outcome-driven, persona-based storytelling -SE hiring, onboarding, certification, and competency frameworks tied to performance I partner closely with Sales, Product, and RevOps leadership to ensure SE efforts are measurable and scalable, tracking SE-influenced revenue, win rates, pipeline impact, and attach rates. I’ve also owned tooling and process decisions that improve how SEs prep, demo, and engage customers across the funnel. What differentiates my approach: -Treating Solution Engineering as a revenue function, not a support role -Coaching SEs to lead conversations, not react to them -Building repeatable demo frameworks that scale across products and personas -Developing SE leaders who can think commercially and technically I’m most excited by roles where Solution Engineering has a seat at the table and the mandate to shape how the business sells.