Kaya Sheppard

Background

About Kaya Sheppard

I have 10+ years of experience leading enterprise transformation across fintech, edtech, and HR tech. I specialize in bringing clarity to complexity, aligning cross-functional teams, enabling C-suite decision-making, and embedding operational rigor. From high growth startups to Fortune 500s whether it’s scaling systems, driving M&A integration, or launching new platforms, I help organizations move faster, smarter, and with purpose.What I’ve Delivered• Led a two year, cross-border acquisition integration of Morningstar Health into TELUS, aligning teams across the enterprise in the U.S. and Canada to ensure seamless transition, regulatory compliance, and stakeholder trust, resulting in accelerated synergy realization and sustained operational continuity.• Mobilized a 60 person Go-to-Market cross functional team to deliver the company’s first new B2B2C SaaS offering reaching 1.5M + users.• Led end-to-end discovery and implementation of centralized product management platform for product, design, and engineering teams projected to result in 20% efficiency gain, saving 1.4 FTEs• Developed and launched custom leave program offerings in partnership with clients, product, and engineering; built new onboarding infrastructure for implementation teams, driving $1M+ in additional annual revenue. Known for:• Driving strategic execution across complex, cross-functional environments• Leading operations infrastructure that accelerates decision-making and delivery• Orchestrating enterprise wide programs that align stakeholders and drive business outcomes• Enabling change through scalable systems, process optimization, and executive partnershipCliftonStrengths: Achiever, Discipline, Responsibility, Analytical, Focus