Episode #19
#19 - He Closed an $8.5M Deal on the Last Day of the Year | Rob O'Keefe
Imagine working an 8.5M deal for an entire year, and still having the paperwork unsigned going into the last day of the fiscal year! That would rattle anybody, but Rob O’Keefe fully trusted that the deal would close on Friday January 30th, and that’s exactly what happened. He knew this because he had personally brokered 18 meetings between Senior Executives at his company (Docusign) and his customer, and he had a direct line to all key decision makers to ensure it would close on time. This deal was the largest net new revenue deal of the year at Docusign, and helped Rob nearly triple his earnings from $350,000 to $970,000 W2 his second year in our coaching program, finishing at 248% of quota! But Rob’s story isn’t just how he closed the big deal. It’s a story of persistence, determination, and resilience. Before he “boomeranged” back to Docusign, Rob struggled with three and a half years of underperformance at startups. Then he decided to go back to Docusign, and didn’t sell anything for two quarters straight before landing his biggest deal on the last day of the fiscal year. Most Enterprise reps would have called it quits during that “ valley of despair .” But not Rob. He kept walking the hallways and building relationships with executives at an account which had been neglected for years. He kept meditating twice a day and fully trusting himself and the process. And when the deal finally closed, he could breathe a sigh of relief, knowing he had made the right decision returning to Docusign. On the latest episode of the Untap Your Sales Potential podcast, I sat down with Rob to discuss how he closed one of the biggest deals in Docusign’s history. He gave a Masterclass on how to quarterback and close a massive Enterprise deal, crack into the C-suite, and fully leverage his executive team to win. Here is what we covered: How he brokered eighteen C-level meetings for a single deal, and why that level of multi-threading protects a deal when things get shaky at the end His advice on how to quickly connect with Executives and be seen as a peer at that level How to use the org chart as a “treasure map” The two quarters of goose eggs, and exactly how Rob kept faith without the results. The value of meditation, breath work, and simplifying his morning routine The handwritten thank you note and small gift habit that sets him apart from others What happened behind the scenes as the $8.5 million deal came down to the wire Learn more at: https://www.untapyoursalespotential.com/podcast
