Enterprise Account Executive Strategy

Just closed a $2.4M deal. 11 months from first conversation to signed contract. Here's the timeline nobody talks about: Month 1-2: Discovery Hell Initial meeting with VP of Operations. She loved the demo. "Let's move forward quickly." Reality: 6 more stakeholders needed to weigh in. Month 3-4: The Economic Buyer Hunt Finally got to the CFO (real decision maker). His response: "Interesting, but not budgeted for this year." Deal should have died here. Instead, I asked: "What problem, if solved, would make you find budget?" Month 5-6: Building the Champion CFO introduced me to Director of IT (future champion). Spent 8 weeks building relationship: - Weekly check-ins (not about our product) - Shared industry insights - Connected her with peers at other companies - Became trusted advisor, not vendor Month 7: The Business Case Champion and I built the ROI model together. Not our standard template - custom for their business. Showed $4.8M value over 3 years. That's 2X return on investment. CFO approved budget review. Month 8: Committee Purgatory Now 9 people in "evaluation committee": - IT security (worried about compliance) - Legal (contract concerns) - Operations (implementation disruption) - Finance (payment terms) - End users (change resistance) Each one could kill the deal. Month 9: The Executive Sponsor Champion helped me get 30 minutes with CEO. Not to pitch. To understand her strategic priorities. Found the angle: Our solution directly supported her public goal to "reduce operational costs 20% by 2026." CEO became executive sponsor. Month 10: Procurement War Contract goes to procurement. They want 40% discount and ridiculous terms. My response: Brought customer success data showing companies that cut implementation services (to get discount) had 3X higher failure rates. Framed it as risk management, not cost. Month 11: Finally Closed Signed at $2.4M over 3 years. $240K year 1, growing to $1M year 3. What actually made this close: 1. Multi-threading: 12 different stakeholders mapped and engaged 2. Champion development: Invested in relationship before asking for anything 3. Business value focus: ROI model in their language, not ours 4. Executive alignment: Connected solution to CEO's strategic goals 5. Risk mitigation: Addressed every stakeholder's specific concern 6. Patience: Stayed engaged through 4 "no budget" responses The part nobody tells you: I had 6 other deals die during these same 11 months. For every closed enterprise deal, 3-4 fail. That's the game. Enterprise sales isn't about closing fast. It's about knowing which deals are real and staying in them longer than your competitors.