How to Close $1.1M in One Week

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It was the last week of June 2017 which happened to be the last week of our second quarter as well (funny how all the deals come in the last week of the quarter in SaaS, right?). It was an amazing week. Per the usual dance, the week was filled with the ups and downs of negotiating custom pricing, order form terms, redlines on MSAs, and of course, getting internal approvals on all the asks from the prospects. It was a week of very little sleep but come Friday afternoon, I was fortunate enough to have closed $1.1M in ARR (annual recurring revenue) in one week, netting myself a pretty handsome commission check, before taxes of course. What’s really amazing about this last week is that it all started in December of 2015.

We just rolled out a new sales process called MEDDPICC which stands for Metrics, Economic Buyer, Decision Process, Decision Criteria, Paper Process, Identified Pain, Champion, Compelling Event. I’d never heard of it before but always eager to be a student, I gave it a try on the first prospect I could which happened to be a Product Manager at a major media company (one of the largest in the world) based in LA. We got on a call and after learning about his interest, I started running the MEDDPICC sales process. He was super humble and basically said “I really don’t have the answers to these questions but my VP does.” To which I happily replied with “great, I’ll be in LA next week anyway so how about we set up a joint meeting.” The intro meeting was set-up and from December 2015 to August 2016 the VP and myself worked together to get a small “land” deal done for one mobile app. Once this VP started using the product, he immediately became a Champion introducing us to the C-Suite folks based in NYC which led to a global MSA being inked in May 2017. A series of Order Forms from the various business units under this company’s umbrella kicked off in June 2017 at $400K ARR and didn’t end until October of 2017, amounting to a total of $2.1M in ARR. The $400K from that first business unit was the first traunch on the way to the $1.1M week.

Next, we have an online real estate business that our company had been trying to sell to for years. In fact, I had a small land deal on the table with a satellite team in the Fall of 2016 which got killed by an incoming CTO who needed time to think through the company’s overall strategy. Serendipitously, in January of 2017, a Champion at a previous company I sold to in July 2015 moved to this company along with the new CDO who not only knew the product but loved it. While we had to conduct a very difficult and technically challenging POC, which lasted 2 months and was a real nail-biter, we satisfied the POC requirements and closed the deal at $300K in ARR. Now we’re at $700K ARR in total.

One of the oldest retailers in the country reached out in November 2016 telling us they were replacing their legacy technology with a modern tech stack and they had already decided it was either us or our biggest competitor. On one hand, this was a great sign as they weren’t window shopping and plan to make a decision one way or the other. On the other hand, it was incredibly competitive; one of the most competitive deals I had ever faced in fact. Our Economic Buyer would often flip flop and was very hesitant to commit to anything. Fortunately, we had an amazing Champion who sold on our behalf when we weren’t in the room and gave us the heads up when we started to lose the battle. He even took the time to walk us through the procurement process. I finally asked permission to take the “kid gloves” off with the Economic Buyer and give it to him straight. He said, “Well, so and so competitor is telling me they are becoming like you.” To which I responded, “it’s one thing to try to become like us, it’s another to be us!” Let’s just say, that was the clincher and we closed on a multi-year deal at ARR of $160K per year bringing our total at this point to $860K.

While the previous deals highlighted very long sales cycles, there were two deals with shorter cycles proving that bluebirds do exist, just don’t bank on them.

In January 2017, I took a call with an extremely technical leader at one of the oldest automotive retailers in the country. In fact, he was so progressive I was wondering why he was working at a company not known for innovation or moving quickly. I soon learned that was the exact reason they hired him and his mandate was to shake things up. He was looking at us and a competitor with a plan to run a POC with each in parallel to prove to his bosses which technology was the best. It was a pretty basic POC and while we did run into some small hurdles, overall it was a fairly smooth evaluation and considering our Champions predisposition to select new, cutting edge technology, we were fortunate to win their business at $180K ARR; allowing us to break the $1M ceiling and land us at $1.04M in ARR with one deal left. The all so elusive bluebird deal flew right into our nest!

This last one, while only $60K in ARR, was a real gem. They happened to be a partner on our platform so they knew us well and basically already decided they were going to buy. Yes, this does happen sometimes and when they do I implore you to cherish every dollar you make off such deals as this is literally a salesperson’s dream. This particular company, which is a support ticketing software, reached out in early May 2017. They ran a 2 week POC to ensure we’d be able to meet their use cases and once complete, immediately moved forward with the procurement process in time to close the last week of June, bringing the grand total to $1.1M in ARR and topping off the best week in sales I’ve ever had in my life… so far.

Well, folks, that’s Enterprise sales for you. Stick to the process and have some patience. Most deals have a 12–18-month sales cycle. Typically the larger dollar size deals, which include ups and downs, twists and turns, politics, competition, and even delays that indicate you’ve actually lost the deal, take time. Every now and again you’ll get a bluebird, but those typically aren’t that large in dollar size and not as complex. Anyone who tells you differently either doesn’t have sufficient experience in true Enterprise sales or is lying to you.



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Chris Surdi

Chris Surdi

I’m a serial entrepreneur and angel employee with a passion for disruptive technology and sales. More info on me can be found at