Rusty Cole

Enterprise Customer Success Manager

After living in Siberia for six months teaching English, I launched my career in direct and partner sales at Microsoft, Informix, and Genesys. Across these roles, I was able to do many exciting things, such as managing a $600K marketing budget, building 40+ channel partnerships, meeting with customers from around the world about a brand-new product, and working with global ISVs.

That commercial background is why I treat every renewal like a deal that needs to close, and why my portfolios run at 110-120% net revenue retention.

Enterprise Customer Success

My book of business ranges from $3M to $6M in annual recurring revenue, with individual accounts from $30K to over $1M ARR. I work with Fortune 500 enterprises and high-growth companies across telecom, media, retail, technology, and more, on every continent except Antarctica.

On any given day, I go from a technical implementation call with a Solutions Architect at 10 am to a budget conversation with a CFO at 11 am. Engineering leads want specifics about implementation. C-suite sponsors want three slides and a number. Each one needs a different version of the same story.

AI & Customer Success Management

I started building with AI tools in 2024, during a career break. The first project was Customer Success Retriever, a custom GPT designed as a working co-pilot for enterprise B2B CS workflows. It generates lifecycle emails, success plans, QBR prep documents, and executive summaries based on real account scenarios. Eleven iterations to get it producing output I’d actually send to a customer. That process taught me more about prompt engineering and workflow design than any course. You always learn more by doing.

Since then, I’ve started exploring AI agent systems that can handle the repetitive operational work in CS, things like summarizing support ticket trends, flagging adoption changes, and drafting internal handoff documents. The goal isn’t to replace CSM judgment. It’s to clear away the busywork so there’s more time for the strategic conversations that actually protect and grow revenue.