Diana Olympia

I help small businesses and scaling teams cut operational friction using AI and automation. I have leverage my 17 years of GTM, strategy, and operational experience to make sure these systems actually work and actually scale as you grow. I've introduced hundreds of professionals to practical AI implementation through workshops and 1:1 coaching, with a focus on helping solo operators and small teams automate the work that's eating their time. My approach: start with what's broken, build the simplest system that fixes it, and only add AI where it earns its place. On the CS side, I led Foursquare's customer success function to 5-year retention highs managing enterprise accounts including Meta, Walmart, and American Express. In addition to B2B SaaS, my experience spans traditional media (Viacom), ad tech (Inscape), and content partnerships (Hulu). Most impactful for: * Small business owners automating operations for the first time * Teams that want to implement AI tools that actually get used * Founders building CS systems without full-time hires * Enterprise onboarding, churn prevention, and expansion strategy Specific expertise: AI workflow design, automation platforms (Zapier, Make, n8n), health scoring systems, QBR frameworks, churn prevention playbooks, expansion identification, enterprise onboarding. What I love about mentoring is helping founders skip the costly trial-and-error phase and implement frameworks that actually work. As a woman of color who's navigated leadership across corporate and startup environments, I especially enjoy working with founders who value diverse perspectives.