Closing My Biggest Deal in SaaS, Right Before End of Quarter

The result after that call? Two new asks that have never been discussed. So pissed off it made me look like a donkey. What was after the donkey? Here's a story about how I closed one of the largest deals in my career on March 31st at 9:38pm I'd actually sent out the DocuSign the previous night and I thought it was going to get signed. And as the hours crept in Friday morning on the 31st hour by hour, my biggest sales fear came to life. I got an email from them late Friday morning sharing that they were not able to sign and with a very vague note that they wanted someone in our leadership to give their CEO a call as soon as possible. The result of that call was two more asks from the potential customer that I hadn't yet even been made aware of during the cycle and candidly, it made me look really bad. But fortunately my team had my back and what ensued was us working into that night to make the deal a reality. Calls, texts, email reminders. Later it finally came through at 9:38pm Central Time. My favorite type of email completed with DocuSign. A few really key lessons from this deal. Number one is that goal posts can continue to shift. Never make assumptions off of what you learned, maybe weeks or even months ago as you head into the final days of the inauguration. Number two, we did a good job early on in the cycle getting exact to exact level connections. But there's a really big difference between getting to power and actually staying with power. Number three, the larger your deals are that you're working, the more blockers are going to be involved. Always push to get time one to one live and don't try to convince. Try to understand where they're coming from. Number four, while power might have in the past been like a director or a VP level, more CEOs and CFOs are getting involved in deal cycles than ever before, so continue working as high up at that organization as you possibly can. Number five, create out a business case that's specifically designed for a CEO and a CFO that might know nothing about your category or your type of technology. That one pager business case that removed all all the jargon was absolutely critical until it was eventually signed at 9:38pm if deal lessons and deal stories like these are valuable, go to my LinkedIn profile and subscribe to my newsletter at closed1xyz. Would love to hear from others in the comments. If you've had any other crazy stories where you sent out a docusign and it didn't end up getting signed right away.