Founding Member Of GTM - Solutions Engineering at poolside
New York City Metropolitan Area United States
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Summary
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Rockstar
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Jason Massey is a seasoned solutions engineering leader with 11 years of experience building and scaling high-performance technical sales teams across startups and large enterprises. As a founding member of Poolside's GTM solutions engineering org and former Head of Sales Engineering at Plaid, he specializes in aligning technical pre-sale and post-sale strategies with revenue and product expansion goals. At GitHub he led enterprise and SMB SE teams responsible for a $40M+/year region and tripled team capacity through recruiting and coaching. Known for translating deep engineering fluency into persuasive customer outcomes, he began his career as a hands-on software engineer and has repeatedly shipped integrations, POCs, and complex demos. Based in the New York metro area, he blends startup grit with enterprise rigor, advising early-stage GTM efforts like Stainless while maintaining a strong developer-first perspective from time at Plaid and GitHub. A subtle differentiator: he pairs technical product contributions with commercial strategy, enabling multi-product, vertical realignments that drive measurable topline efficiency.
11 years of coding experience
18 years of employment as a software developer
Bachelor's, Computer Science, Bachelor's, Computer Science at Colorado State University
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Jason Massey - Founding Member Of GTM - Solutions Engineering at poolside