Gwenevere Crary

Gwenevere Crary is a future-forward HR executive, founder, & award-winning strategist (NHRA Executive of the Year Award, 2020) with over two decades of experience transforming People Operations into a driver of growth, scale, & enterprise value. She’s led across startups, mid-market, & Fortune 500 firms, bringing deep expertise in hypergrowth, organizational transformation, & AI enablement.

Most recently, Gwenevere served as Chief People & Infrastructure Officer at LILT, a VC-backed AI SaaS & Services company. She architected a fully scalable operational foundation across HR, TA, IT, Payroll, & Facilities, achieving 50% reduction in departmental spend, +13-point increase in quality of hire, & drove cross-functional adoption of AI platforms & workflows. Her AI strategy encompassed department & companywide implementation of tools such as ChatGPT, Gemini, Notion AI, Zapier, Workato, & REKAP, redefining how teams approached learning, onboarding, performance, & change management.

A recognized thought leader in AI for HR, Gwenevere has integrated intelligent agents and automation into core HR functions—streamlining help desks, compensation, career paths, and employee communications. Her work reduced overhead, improved compliance, enhanced employee experience, and enabled real-time, data-driven decisions.

As founder of Guide to HR, launched in 2021, Gwenevere delivers full-spectrum HR strategy through an AI-enabled lens. She advises high-growth companies, non-profits, & scaling startups on building resilient people infrastructures with modern tech stacks. In 2024, Guide to HR was recognized as a “Top HR Strategy Services Partner” by Manage HR Magazine for its cutting-edge work in enabling clients to future-proof their people function through intelligent systems, tech integrations, & change leadership.

Gwenevere holds SPHR & SHRM-SCP professional certifications, a Master’s in Human Resources Management from Chapman University, & dual B.S. degrees in Actuarial Mathematics & Management Engineering from Worcester Polytechnic Institute.

Gwenevere challenges outdated playbooks, blending strategic vision with operational precision to help organizations scale smart. She designs compliant, cost-effective systems that are dynamic, inclusive, and human-centered—reflecting a bold, tech-savvy, and people-first approach to modern HR leadership.