Scottsdale, Arizona, United States
People executive operating at the intersection of growth, capital constraints, and organizational design within venture-backed and regulated environments. Trusted partner to founders and boards, aligning workforce strategy with runway, revenue realities, and long-term scalability. Experience spans early-stage buildouts, MGA and insurance structures, cross-border compliance, multi-scenario restructuring, and transaction windows including acquisition exploration and strategic alternatives. Built Talent and HR functions from zero, scaled engineering and go-to-market teams rapidly, and led workforce stabilization efforts during high-volatility phases. Comfortable operating where burn, risk, and execution intersect. Focused on building resilient infrastructure, attracting and retaining high-impact talent, and ensuring organizational design supports both growth and durability. Thrives in high-ambiguity environments where decisive leadership, calm execution, and disciplined workforce planning matter. https://jeangallaghermccauley.com/ https://www.passionfroot.me/jean-mccauley
Executive partner to CEO and board during structural realignment tied to capacity risk, runway preservation, and strategic alternatives. Created and launched LEEO's enterprise AI strategy from zero, leading tool discovery, Claude Team deployment, AI policy development, and cross-functional enablement across underwriting, broker relations, product, and engineering. Led multi-scenario workforce planning aligned to revenue projections, capital constraints, and capacity partner dependency. Directed organizational restructuring across 5 countries (US, India, Israel, Poland, UK), reducing global headcount by 72% and decreasing operating burn by 66% within 6 months. Partnered with board on capital preservation strategy, workforce modeling, and scenario planning in advance of potential acquisition and vertical expansion. Designed and executed compliant multi-country RIFs across complex regulatory environments. Recruited and placed 25+ senior and executive-level hires, including VP and functional leadership roles across underwriting, engineering, product, and go-to-market. Owned compensation strategy, equity modeling, and retention frameworks during high-volatility transition period. Consolidated international operations to a streamlined US and Israel footprint. Led People strategy during acquisition exploration and strategic alternatives proces
First People and Talent hire in a private equity-backed insurance analytics company; built the People function from zero through rapid scale and acquisition. Designed and implemented end-to-end Talent and HR infrastructure, including recruiting operations, compensation frameworks, performance management, compliance systems, and PEO/vendor oversight. Partnered directly with CEO and executive leadership on headcount forecasting, budget planning, and organizational sequencing aligned to PE growth objectives. Doubled company headcount within 12 months, leading executive and technical hiring across engineering, data science, underwriting, and go-to-market functions. Built structured recruiting processes and agency strategy to support rapid scaling while maintaining capital discipline. Developed foundational compensation and leveling frameworks to support sustainable growth under PE ownership. Supported company through acquisition process culminating in April 2025 exit.
First People and Talent leader hired following Series A financing; built the function from zero to support rapid post-funding scale in a data-driven insurance technology company. Scaled organization from 18 to 40 employees, leading hiring across engineering, data science, product, and go-to-market functions. Designed and implemented foundational People infrastructure including ATS selection and implementation, structured hiring processes, compensation benchmarking, performance frameworks, and compliance systems. Partnered directly with CEO and executive leadership on headcount planning aligned to Series A capital deployment and growth milestones. Built executive hiring processes to expand leadership bench during early-stage scale. Supported company through strategic acquisition following Series A growth phase.