Kevin Woolley Consulting

Kevin Woolley Consulting specializes in helping government contractors win more RFPs in less time through the strategic application of generative AI. The firm combines go-to-market strategy and operations expertise with technical capabilities in RAG (retrieval-augmented generation) pipeline design—from building enterprise knowledge libraries to implementing fully automated RFP response systems with embedded graphics and tables. Kevin Woolley brings a vendor-agnostic approach informed by his experience as a Vice President at two technology unicorns (Geotab and Suhai), an MBA from Columbia Business School, and extensive work on international expansion initiatives including cross-border tenders. Services span commercial strategy development, capture-phase insights, go/no-go analysis, and hands-on enablement through group training and real-time collaboration with proposal teams.