Making Enterprise Work

​How operators prepare their teams, systems, and priorities to land (and survive) enterprise deals.

​Going after enterprise clients changes everything. Longer sales cycles, higher stakes, more decision-makers, and no room for dropped balls. But most startups start the chase before they’re operationally ready.

​This session is for the operator stuck between a high-stakes sales push and systems that aren't built for enterprise demands. When the CEO says “we’re going upmarket,” what needs to change across product, ops, and leadership?

​We’ll break down what gets missed when startups pursue big clients too early, and how strong operators build credibility, coordination, and execution strength behind the scenes.

​🔧 You’ll walk away with:

• ​A clear picture of what “enterprise-ready” really means: before and after the deal

• ​Tools to pressure-test your internal systems against enterprise expectations

• ​Strategies to align leadership, product, and ops under long-cycle complexity

• ​Lessons from real enterprise deals that failed or got saved in the final mile

​🎯 About the Series

​Startups don’t scale on great ideas alone. They scale on great execution. And behind that execution are operators.

​Each session in the Strategy & Operations Masterclass Series is a 90-minute deep dive into a real challenge startup operators face, from aligning execs to managing trade-offs to scaling messy systems.