The First Deal That Changed Everything
Our Breakthrough Enterprise Deal
Hey, it’s Vince, and I’m back with another edition of Red Zone Selling, my newsletter that delivers actionable insights and lessons to help startups and sellers close enterprise deals, achieve market fit, and confidently scale.
Everyone remembers the first big deal they closed. You remember where you were, who you were with, the adrenaline, the relief, the feeling like we actually did it. It sticks for a reason—because closing a meaningful deal just feels damn good.
For me, one of the most memorable came during my time at Cheetahmail when I was the SVP of Sales. Back then, we were still clawing our way into the enterprise world. Cheetahmail was an up-and-coming ESP in a very crowded space, fighting to get noticed. Every deal was a slugfest, with multiple vendors jockeying for position. Honestly, most of our competitors didn’t even see us as a real threat—and I can’t really blame them. At the time, our biggest client was literally Joke of the Day.
But what they didn’t know was that we were building something real. A machine. Great people, solid tech, and a team that was hungry to prove itself.
The deal was with Sears which was at that time one of the biggest multi-channel retailers in the US.
It was being led by their procurement team (yep—always a fun crew). From what we could tell, we were up against at least three other providers, all much bigger and better known. We were definitely the underdog. But we had a few things working in our favor:
A killer cross-functional team (sales, CS, product, leadership, everyone showed up)
A rockstar rep leading the charge (@Jeff Olander)
A clear, aligned sales process
A differentiated product
And a serious chip on our shoulder
We wanted it more than anyone else. We wanted to show the market—and ourselves—that we belonged in the enterprise conversation.
The big moment came down to what was basically a “pitch-off.” Each vendor was invited to pitch, back-to-back. We prepped like crazy. We assigned roles, built a sharp deck, rehearsed the story, refined the value prop. We walked in tight, aligned, and confident.
We showed up at Sears HQ and waited in the lobby while a competitor wrapped up their pitch. Then it was our turn. Afterward, we walked out and saw the next vendor waiting for their turn. Four total pitches that day. Funny aside, when we walked out of the pitch and saw the competitor I turned and said to them “Good luck, you’re going to need it”. The look on their faces was priceless. Talking a little trash is appropriate at times 😀
Ours went well—really well. Great engagement from the business team and procurement. (I know, shocker.)
Then came the waiting game.
About a week later, Jeff and I got the call. Procurement on the line. You know that awkward pause before they tell you the decision? Like 1.5 seconds of dead air that feels like 15 years?
“We’ve come to a decision annddddd… we’d like to move forward with you all.”
Boom.
We beat out the bigger players and landed one of the largest deals of the year. And back then, Sears was a big-time, multi-channel retailer. It was a statement win—for us, for the company, and for every underdog trying to break into the enterprise.
That win was a catalyst for dominating the retail sector over the next five years.
Lessons from Our First Big Enterprise Win:
Underdogs can absolutely win. If you’re aligned, sharp, hungry, and have a differentiated solution, you can beat the bigger players—especially if they underestimate you.
Process matters. A clear, rehearsed, role-based pitch isn’t just theater—it shows you’re serious and ready to execute.
Enterprise buyers are looking for more than just logos. They want partnership, value, and confidence that you’ll deliver. Show up with the full team and a shared message.
Procurement isn’t the enemy. Treat them like part of the decision-making team, not a roadblock. If you win them over, you’re halfway there.
Momentum is earned. That win gave us credibility—and opened doors to more enterprise deals down the road. You only need one to start the snowball.
Featured Early Wins Podcast Episode
In this spotlight, Robbie Allen compares audio books and founder-led sales. "Audiobooks are always better when read by the author. Similarly, It's almost always better for the founder to lead the sales efforts for the first 10 customers or so and not punt to someone else early on.
Watch the Full Episode on our YouTube channel. Ping me if you’d like to be a guest.
Whenever you're ready, there are 5 ways I can help you:
Advisor: Strategic GTM guidance to help founders build scalable growth plans and achieve impactful results.
Fractional CRO: Hands-on sales leadership to drive rapid revenue growth, setting teams on a path for long-term success and potential exits.
Sales Coach: Targeted coaching using my Red Zone Selling framework to increase win rates, streamline closing strategies, and develop repeatable sales processes for lasting growth
Workshop: Hands-on training designed to help sales teams take control of deals, eliminate stalls, and close with confidence using my Red Zone Selling framework.
Speaker: SKOs, quarterly team meetings, and sales training sessions to equip sales teams with the mindset, strategies, and execution tactics needed to win more deals. Using the Red Zone Selling framework, I help teams learn how to control the sales process, build momentum, and close with confidence.
Vince Beese, vince@salesatscale.com, Book a FREE Consultation,
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