• Signing the largest new business deal
  • Selling to multiple lines of business
  • Breaking down the buyer/seller paradigm 

When I joined In early 2015, Kahuna was a Series A Sequoia Capital-backed mobile marketing automation company. At that time, Kahuna had the most advanced push-messaging technology with well-recognized customers like The New York Times, The Weather Channel, and DraftKings. The technology exposed me to the world-of-mobile and provided a technical understanding of SDKs (software development kit), database structure, and messaging architecture. Additionally, Kahuna was a product that in order to sell successfully, one had to engage Marketing, Engineering and Product Development teams.  

The largest deal is company history

I brought on many successful customers during my time there. One of my favorite experiences was signing-up a large travel app customer who was based overseas. The following is a walkthrough of the deal and how we ended up winning a competitive contract:

At that initial meeting, the first thing I said to the Senior Director (Sr Dir) and his associate was: “hi this is David Schooley and this is my fifth day at Kahuna.” Naturally they both laughed, and the early awkwardness that is so common on a sales call disappeared completely. This approach of being totally transparent is a big theme of my sales. Admitting the vulnerability that ‘I’m the new guy’ helps set the stage for an honest relationship to grow.

By the end of that first 30-minute call, the Sr Dir was starting to push on the gas by asking more detailed questions. This was a great sign and even though I knew almost nothing about our product, I understood my job as a salesperson was to shepherd this prospect through the sales cycle just as fast as he wants to go. We ended the call, with each of us having next steps and a scheduled follow-up call two days later.

Selling to multiple lines of business

On this second call, I brought my manager to the meeting. I think it’s important to get managers and other executives involved early in the process for two reasons 1) it increases the likelihood that the prospect will involve people of power from their side (in this case the CMO and CTO) and 2) it allows your manager to have a better insight on deals---the old sales adage “you win and lose as a team.”

It’s critical, however, to ensure that your manager is prepared properly. In this case I knew my manager was on many sales calls every day; was managing five other reps; and overall was very busy. To prep him I used my standard Sales Call Plan template and had a 15 minute prep meeting. Once this prep work was complete, we could go into our meeting with everybody on the same page.

Looking back, I believe that this second meeting was the turning point that put us in position to win the deal. We had three main topics to cover: 1) Integrations 2) End-user experience 3) Pricing. Because this was the second time I had spoken to the prospect, I still didn’t understand much about their business. Knowing that I was selling a very expensive product, involving a brand new technology, to a prospect based in another country, there was a tremendous amount I needed to learn in order to see if we could help them. In this situation, I thought it called for more discovery before we got into the agenda...and I was right.

Instead of starting off the call by walking through the bullet points, I started with the customer---because it’s always about the customer. And, through my research I had a specific question for the Sr Dir.

“I was using your app today, and I saw that I can book a flight from SFO to Bangkok, Thailand, round-trip for $800. I have to tell you, I love to scuba dive and I flew to Bangkok last year for a dive trip, and it cost me almost $2000. I’ve got to ask: how the heck can you offer a flight for that price?”

Even more than during the first call, the Sr Dir laughed and said: “well that does sound like a good price.” he then proceeded to look up that exact flight right there while we were on the phone.

Removing buyer/seller paradigm

By my asking questions about his product and his company first, it changed the entire dynamic of the call. The Sr Dir, for the next 20 minutes went into detail about how his company works, how they’re different from the competition, what their focus was for 2015, what’s important to him personally; what’s at stake if they don’t execute on engaging their end users; etc. It was a wonderful place to start a sales call and provided an excellent launching point to then discuss our product.

Over the next three months, my Sr Dir contact and I worked closely together. He introduced other departments as part of the evaluation; he built out feature-spreadsheets; we worked together in building an ROI analysis for his CFO; and in the end he signed the largest new- business contract in Kahuna’s history. When I asked his feedback months later about the sales process? He said: “You being interested in our business, you taking the time to care about what was important to us. That really helped us build better rapport and combined with your having the best product, made you the winner.”

This story was a great example of selling an enterprise deal. There were multiple stakeholders; it involved a mid-six-figure deal with a brand-new vendor; there were numerous competitors in the mix; and in the end the client chose us because he had determined that we had “the best product” and that we had built the best relationship with his team.