“Top Three Lessons That Landed My First Big Deal” – B2B Sales Mentors Sample Story

“Top Three Lessons That Landed My First Big Deal”
By: Jamal Reimer

Making the transition from selling for a small solution vendor to a huge global software brand can be a jolting experience. The first four years of my enterprise sales career we spent with three early stage software companies have no more than 150 employees. My experience was fairly typical. I was one of a handful of reps who banged it out on the phones every day. Progressing conversations through the typical set of hoops, pitch, demo, follow up meetings, negotiate, closed. The typical deal size was 50 to 250K, nice enough. Then I got my first job with one of the largest enterprise software companies in the world, over a hundred offices and 10,000 reps just in the U.S alone. Layers and layers of management, territory changes every year. It felt like moving from a small town to a big city. It was my first experience with a completely self-service culture. I remember sitting in a cubicle on a vast office floor trying to navigate our internal online HR system just to confirm my banking details for payroll. I wanted to ask somebody for help, but it felt like they’re studying in a big library, there were a few people around, but I knew none of them because they were all in different business units. I just stumbled through the process and finally figured it out on my own. The biggest change was the selling process. I remember going through my usual sales cycle routine for about the first four months and then I got an inbound lead that would ultimately change my life in terms of understanding how enterprise sales really work in the biggest companies. The inbound call was from a software company with 2000 employees who are looking for a new CRM system. When we did some initial calculations, the value of the opportunity was somewhere between 2 to $3 million. That would be roughly 10 x the size of any deal I had done in my short four-year career up to that point. Immediately there was a great deal of attention paid to this opportunity and me as the rep. My manager, my VP of sales and my presales director all started asking lots of questions and wanted constant updates. The prospect issued an RFP with the goal of inviting a shortlist of vendors to a series of onsite meetings to vet each product from top to bottom. The prospect said this would be the biggest internal investment software that the company had made in the past decade and would require approval from their board of directors.

Preparation.

In a large software company, even when a small 2 to $3 million opportunity appears. The preparation for the RFP responses and the onsite sessions are totally projects in themselves, CRM purchases or a big decision for any company because it’s a core system that will be used by many stakeholders, lots of features and functions for lots of stakeholders means lots of questions and the questions did come. The RFP was the size of a Russian novel. Fortunately, I had a very experienced team who had been in many similar opportunities and it’s seen most of the multitude of RFP questions before. We set about the RFP response with Gusto. It was true war room stuff, eight people sitting in a room banging out question after question until every box had been checked. Every question had a detailed explanation. After the RFP was submitted, we soon learned that we had made it to the shortlist of vendors and we’re invited to the onsite presentations with the prospect CRM project team. In another round of preparation, the war room was again filled with product specialists coaching my presales resource who was going to be driving the actual Demo and my manager coaching me as the salesperson who was to be delivering the intros and color commentary during the demo to point out value points and tell relevant stories. The results of the preparation were amazing. During the onsite sessions, we were asked to demonstrate how our software would handle 20 use cases for stakeholders in sales, sales operations, sales management, and marketing. As we discussed each use case, the project team would pelt us with questions. What if we wanted to do an action like this? and can your software do that? This went on for hours. We were able to answer virtually every question with a credible response. I recognize many of the questions from the prep sessions. Someone in the war room had seen that question before and made sure we not only had an answer, but we could contextualize that answer the prospect’s business. By the end of the session, it was clear the project team had considerably warmed to us. Several times throughout the session, I would spot two or three project team members looking at each other with excited expressions as my presales resource described how our software would handle a specific situation. By the end of the session, it was clear that they were simply no meaningful objections left. At worst they like this and it best they preferred us.

Visit a Customer.

One of the most powerful tactics we used, which ultimately won the deal is that we had worked with one of our existing CRM customers to host our prospect for a half day visit to discuss their experience with our CRM solution. This was an absolute game changer on a number of fronts. It got 20 people from the prospect to travel with us, huge bonding experience to the customer site by flying to another city, having multiple meals together and traveling by bus from the hotel to the customer site and back. The moment we stepped out of the prospect’s offices and began our journey, everything changed. There’s an immediate redefinition of a relationship when if the physical journey is involved, you see being just a salesperson and become a travel companion. In the airport, you might say, “I’m going to go get a bottle of water for the flight. Do you want one?” Later the prospect just might reciprocate. Small interactions like this are powerful events that change, improve and deepen any relationship. The visit itself was highly impactful. We arrived at the customer’s site and were greeted by our host, the head of business operations and owner of their CRM system. We were ushered into a large conference room and were served coffee and donuts, which I had prearranged and catered. The customer then led the session by having leaders in business operations, sales and IT. Make 20-minute presentations about their use of an experience with our product. While the overall feedback from the customer was good, it was definitely areas of dissatisfaction or disappointment. I remember cringing and thinking comments like those would sink our chances of a win, but subsequent conversations with the prospect told a different story. The prospect’s project team knew that no solution was perfect and the candid feedback from our customer, positive and negative had given them a clear understanding of where the pitfalls and weaknesses lie. This is a key point for them because none of the other vendors offered such a complete and candid view into their customer’s experience, so they felt committing to any other vendors carried greater uncertainty and this greater risk.

Informal Conversations.

The customer visit yielded third learning, which was the value of informal conversations. As the trip helped deepen relationships with the project team members. It also provided settings which helped change the nature of the conversations we had with them. Sitting next to project team members on a plane or at dinner and a boisterous restaurant or at a late night out at the Riverside Tavern opened the door to a totally new level of frank conversation about the realities of the project, the players, their executives, and the decision drivers. More than any phone chat or conference room meeting could ever produce. Social environments in gender interactions which are strongly influenced by social norms, which often includes sharing little known details or speaking plainly and without pretense or defenses. Informal conversations during and after the customer visit revealed the concerns of the project team had about our product and in several cases, they also suggested the support we could offer to help alleviate those concerns. Through these conversations, we were able to develop to coaches within the project team who we worked with to refine what became our final offer. In the end, we were awarded the prize and won the deal. The feedback from the prospect’s GVP of sales who was the executive sponsor for the project was that his team confirmed their strong impression that our software could do what they needed it to do and much more. Further, some of the project team members added that after interacting with my team in several environments on and offsite, they came to understand that we were the people they wanted to work within the long term. He also said, “what really drove it home for us was visiting your other customer who’s also a software provider like us.” That gave us the comfort that what we saw in your demos actually works in production, which was the proof we were looking for before making a decision. What I learned from this deal that has stayed with me ever since. Number one, preparation is the best way to avoid uncertainty in you and in your customer. Uncertainty kills deals. Number two, visiting a customer with a prospect is a huge differentiator. It gives the prospect living proof your product works and gives you many chances to interact with your prospect offsite. And number three Informal conversations, deepen relationships and tend to be the best forum for getting the real story on the prospects, the players, and details on how to win the deal. If you’d like to discuss and learn about sales techniques like those in this story, join us in our LinkedIn group The Sales Tribe, the LinkedIn group for enterprise salespeople.

Want more from Jamal Reimer? He was the star of episode 61: Jamal Reimer – Doing Mega Deals at Oracle (3X $50M+)