Highlights

• How I initiated a $32 million sale with a cold outbound email

• The evolution of start-up sales team to Enterprise team

• Field sales

Microsoft’s acquisition of Yammer closed in October 2012. With the purchase official, it helped clarify some of the ambiguity for our customers and prospective customers regarding what was to happen to Yammer as part of a larger organization.  Additionally, it provided the Yammer sales team an opportunity to focus on continuing to sell our product directly as we had done prior to the acquisition news breaking.

For the next nine months I focused the majority of my time on SMB accounts, while partnering with an experienced field rep on 10 Enterprise accounts. This partnership was another step in the career development of younger reps and proved very rewarding for myself. The field rep with whom I was partnered had a proven track record and you always want to be surrounded by winners

Of the ten Enterprise accounts where I partnered with my field rep, all had prior knowledge of Yammer, though to varying degrees of consequence. At this stage, Yammer was over five years old and had a tremendous marketing engine (a critical element in a successful startup) that helped drive demand generation. However, simply because we had conversations with potential accounts by no means indicated that we were actually close to signing a new customer.

The Nordstrom Deal

With Nordstrom, there had been two conversations over the past year with little traction gained. In early December, my field rep invited me to the follow-up call with the Director of Communications--someone who had expressed mild interest in Yammer. I listened to the call and quickly inferred a few things. First, the Dir of Comms appeared to have little authority in making a decision. Second, his IT department was close to buying a competing vendor’s because it had more bells and whistles for IT’s enjoyment. When we got off the call, my field rep said to me: “well, this one’s in trouble.”

Working together we devised a strategy: we would give the Dir of Comms the rest of the week to respond. In the best case scenario, he might broker a meeting with his IT team where we could discuss how we stacked up against the vendor they were leaning towards. Clearly this was not a favorable position for a rep to be in.

The following Monday, after we had heard nothing from the Director of Comms, I suggested to my field rep a different approach. “Let’s go around these guys. Let me try to prospect above the Dir of Comms and see what happens.” He was all for it. After all, what did we have to lose? IT was about to buy a competitor, the Dir of Comms had demonstrated little interest in being a champion for Yammer and we had no executive level engagement. So with that, I was off to do my research on the company and send some personalized messages to people of consequence.

After doing some research I identified four senior executives to target. Below was the winning message that changed the direction of the deal and started what would be one of the largest Office 365 deals in Microsoft history.

This email changed the game immediately. That Tuesday afternoon, the Dir of Comms responded to the field rep and set up a meeting with himself and the IT team that was evaluating the other vendor. There was also a new VP involved in the conversation, one who had keen interest to “improve employee communication.”

That afternoon’s meeting was a drastic change in tone from the 1:1 with the field rep and the Dir of Comms. Everyone from the prospective customer was engaged. They inquired about ease of implementation, integrations with their other tools, and an on-site meeting at their corporate office.

Over the next 15 months I watched this deal evolve. First from a “we’ll evaluate Yammer” and then to “we want to try this out” and still later “how might this help us transition to the cloud?” In the end, an opportunity that started with a cold email to the President of the company, finished with Yammer “leading the charge” to a $32million O365 contract.

I learned so much from this deal. Everything from determining when a prospect is hiding something through their cryptic language, to reaching high into an organization, and finally to getting on-site and watching the deal progress. Enterprise sales is not a sprint, it’s a marathon. And in this instance, we came in first!

Moving to Microsoft 

Starting in July 2013, the Yammer sales team was mapped over to the Microsoft sales team. This transition, paired each Yammer rep with an existing Microsoft sales-team. My new team was based in Boston. Over the following year I worked exclusively with this Boston-based team and learned how to sell into existing accounts, how to sell a new product (O365), how to work with channel partners, and how to conduct proper face-to-face customer meetings.

Selling into an existing account was new wrinkle for me because most of Yammer’s sales were all new business. Selling into a company that had been a customer of Microsoft for years--and sometimes decades--involved a slightly different approach.

The biggest difference with an existing customer sale was the dynamic of on-premise vs the cloud. Traditionally, Microsoft had sold to the Information Technology (IT) department who bought the on-premises software and then, after extensive customizations and integrations, rolled out the technology to their business units. Because of cloud technology, more departments--e.g., Marketing, Engineering, Sales--were buying cloud-based solutions without asking for IT’s blessing.

The key for me in my new role as an Office 365 sales professional was to understand 1) the business-drivers for each department, and 2) talk to each department about what we were seeing from other companies moving toward the cloud. This approach involved speaking across lines of business about Microsoft products (which had seldom been successful up to this point) and starting to open the doors for a larger footprint of Microsoft tools.

The second shift in my new role involved my relationships with my fellow sales reps. With Microsoft selling a variety of products, there were always other reps selling into the same account. The key to success was collaboration across the team so that we had a holistic understanding about the account.

Field Sales

Being a remote-field-sales-team, we achieved this collaboration in three ways. First, weekly meetings where reps could discuss specific accounts. Second, we used Yammer as a collaborative tool to share knowledge about each customer and to crowdsource ideas. Third, I relied heavily on the phone to stay in touch with my fellow reps. It was always a team effort.

The third change with selling Microsoft Office 365 was working with channel partners. Channel partners are separate companies that sell a number of different software platforms. The partners typically had long-standing relationships with the accounts in question and could help facilitate a conversation around O365 with the right contact.  

I found the most successful way to work with channel partners was to manage the partners just like I was managing a team of sales reps. Quickly I understood who were my best partners and focused my time to work on the opportunities they brought me. By taking this approach I kept things focused “on point.”

The final large-learning from my year selling O365 involved face-to-face meetings. Unlike selling Yammer, which mostly consisted of using the phone, I spent 30%-40% of my time in the field visiting customers. This helped me develop a tighter relationship with the customers, increased my close-rate, and gave me a deeper understanding of what Enterprise sales is all about.

There is no substitute for in-person customer meetings. Those moments of walking in the hallways before you enter the conference room are often where one learns about the customer, their desires, their personal needs, etc. Moreover, changing the scenery with something like taking customers out for meals helps break down the buyer/seller paradigm quickly and leads to a more valuable teacher/student relationship.

My Microsoft experience provided invaluable experience that has helped paved the way for me to continue to grow my sales career. From seeing the conception of a multi-million 15 month sales cycle to working with partner sales team across the country, the experience was rewarding, educational, and productive.