Interview with our CRO: Gary Littlefair

You have held sales roles with some very impressive technology companies. Besides great technology, what made those companies so successful?

I think two things set these companies apart. First, all of these companies, including Sun Microsystems (acquired by Oracle), BEA Systems, (also acquired by Oracle) Oracle, Jive Software and Swrve, were not just product companies but they had a vision for changing things. With Sun it was the ‘Open Systems’ approach to computing, with great slogans like “The network IS the computer.” BEA had the ‘Service Oriented Architecture’. Jive had a vision for Social Collaboration and Oracle had a vision for database technology. The second thing these companies had was great sales leadership. Scott McNealy at Sun was a natural sales leader, as was Larry Ellison at Oracle and Bill Coleman and Alfred Chuang at BEA. These were all very much ‘sales first’ companies.

What changes have you seen over the years in sales?

I think sales has fundamentally remained the same. What has changed is the attitude towards sales people, especially in Europe. While sales has been a respectable profession for a while in the USA, it wasn’t always the case in Europe. But thankfully we have caught up and European companies are making a much bigger investment in recruiting for the right sales skills and continually training existing resources. I think that this lag partly explains why Silicon Valley got the edge over Cambridge Science Park, for example. We were late to understand the enterprise sales cycle and invest in sales tools and training the way Silicon Valley did.

Today it’s common to see specialization in sales, especially with sales development roles. What are some of that challenges that the shift has created?

When I was a younger salesperson, I did it all, including lead development, lead qualification, demos, opportunity management and close. Today there is a lot more specialization, with most recent college grads getting their feet wet with lead development and passing along deals to Account Executives once they have been qualified. While this allows companies to acquire sales talent at a lower cost, the trick is to evolve these people to Enterprise Sales over time. There is definitely a ‘hire and fire’ mentality now since it’s hard to know if SDRs will be effective until they get some experience under their belt. But it is sales management’s job to give them the sales tools, coaching and the skills to succeed.

How have prospects changed since you began your career?

Prospects have a lot more information at their disposal than ever before. By the time the prospect gets to sales they know a lot about the solution and the sales rep has less time to develop a personal relationship and build the political alignment between organizations. The compressed sales cycle is one of the key reasons to have a technology solution, like ClosePlan, in place to ensure that the right sales events occur at the right time in the sales cycle, even if they’re in parallel to save time, so that steps aren’t missed which might impact the close.

What are some of the characteristics your most successful reps shared?

The best salespeople that I have worked with have a high level of personal integrity and are able to garner trust, in any scenario. They also have an ‘edge’ or something that sets them apart. Some call is charisma but it’s more than that and it’s hard to define. It might be personality or intellectual curiosity. They are also team players since their success depends on orchestrating internal resources (ie legal or product) to get everyone working together to close a deal.

Do you have a sales methodology that drives your management style?

I have looked at many of them, including Holden, Blue Sheets, TAS, SPIN, Challenger and Sadler and all have some good things about them. For example, I use the 3 key qualifying questions from TAS. (Is there a compelling event? Can we provide unique business value? Is there, or can we create, political alignment?) But what I like most about all methodologies, when used effectively, is that they all establish a common language that the whole team can use when selling.

How do you manage a sales team that might be different from your peers?

I’m not sure that I do anything differently but I do try to coach more than ‘do’. I realized early on that I can’t scale so it’s critical for me to hire well. It’s very rare that you can hire the perfect sales person, but if you can get someone that is prepared to listen and learn from colleagues and management, then you can work with that. I like to say that I hire ‘sponges’, not ‘rocks’. Second, I believe in leveraging the experience on my team. One of the things I say a lot is, ‘the answer is in the room,’ meaning that almost any problem we come across has likely already been experienced by someone on the team, so collaborating amongst the team and talking through challenges is key.

What frustrates you the most about sales management?

I genuinely enjoy every aspect of sales but do recognize the inherent pain in forecast meetings, which I know you wrote about in your blog. Sales management is asking, ‘When? If? How?’ The sales team doesn’t always have the answers, which leads to conflict. I see technology, like ClosePlan, helping here by providing better visibility into the deal to the entire team, so that there are no surprises in the last stage of the deal.

We have all managed ‘lone wolf’ salespeople. How do you ensure these rogue sales individuals follow sales processes?

I haven’t had to work with too many lone wolves. This type of salesperson is usually pretty short-lived in enterprise sales, where following a process and collaborating with colleagues are critical to success.

People often classify salespeople as either relationship or process people. Can a relationship salesperson be process-oriented? Can a process-oriented salesperson be a relationship sales person? How do you ensure both qualities are displayed?

I look at it a bit differently. Relationships are built on trust and trust is built on action, doing what you say you are going to do and professionally and methodically leading the sales/buying process. I think these two characteristics are tightly linked and you can’t really have one without the other. In my view you cannot be a good ‘sales relationship guy’ unless you have the sales process piece. It’s Important here to differentiate between a ‘relationship guy’ and someone you like spending time with. “Everyone loves a clown, but no one wants to lend him money”. In the end, serious business is done between serious people.

You often talk about the “Zone of Doom.” What is it?

I stole this phrase from an old manager, who used it in a totally different context. The Zone of Doom happens to every salesperson at some point in their career. It’s when all of a sudden, everyone goes quiet. Your calls and emails go unanswered. It’s dangerous because during the Zone of Doom, you start to panic about the situation and can make some bad decisions. You typically end up in Zone of Doom because you haven’t been able to expand your influence within the account, perhaps stopping at a single coach, hoping they can pull the sale through. Of course hope is not a valid strategy so it is important to have several activities planned with different people within the target organization. Sales tools such as ClosePlan can really help here. Laying out various events to complete within the sales process, such as a reference call, a breakfast briefing, a demo, an executive visit, a social event, a project planning session, etc. All these events canmove the sale forward and, more importantly, involve various personas from the prospect organization. A tool like Closeplan is essential for implementing these events and tracking them. It also enables multiple participants to collaborate to ensure we widen the touch points on both sides.

In your experience, what are the main reasons that deals push? What tools or approaches can prevent this?

The main reason that deals push is because they’re poorly qualified, meaning the ‘close date’ probably wasn’t realistic in the first place. Regardless of sales methodology, it’s important that a scorecard of some sort is used by the deal team, not just the AE, to help qualify the deal and to ensure the best likelihood of a close. Another reason I see deals pushing is because sales is focused on the signed contract as the ultimate deliverable. The best close plans are collaborative with the prospect and take the prospect’s goals into account. The prospect is probably not focused on the signed contract but rather the go live date or the project start date. Once the deal team and the prospect are focused on a common goal, then receiving a PO is just one of the milestones that needs to be met in the process.

You also talk about the “Sales Immune System.” Can you describe what that means?

You see the Sales Immune System when you are focused on calling in high to a CXO and not involving the lower levels of management. If you’re just focused on the C-Suite, you might find that a director or VP catches wind of the conversation and tries to kill the deal. I have seen great CXO pitches and positive CXO decisions get overturned by middle managers that were not part of the deal team. Like an immune system, they club together to suppress an unwelcome intruder. A good close plan will ensure that key individuals are not excluded from the selling process.

What are your thoughts on the use of a close plan?

Close plans are essential tools in the sales cycle because they involve the larger team and get everyone on the same page with a clearly defined process. I expect my teams to use them and I have seen them in every form imaginable - paper and pen, spreadsheets, docs. Automation and transparency is important so I am happy to see ClosePlan bring a powerful solution to the market. It’s ironic because I think it’s your tagline but I really think of close plans as sales execution plans because it allows sales teams to follow a process that drives the deal to close.

As a sales leader, what excites you about ClosePlan?

So much thought and innovation is going into automating parts of the sales process but all the focus seems to be at the top of the funnel, around lead generation, lead qualification and follow up. The bottom of the funnel has been largely ignored. While there are systems today for managing the close, most of them are built for management to monitor and forecast sales. ClosePlan is the first app that I have seen in the Salesforce App Exchange that helps sales team members close business faster. And, I truly believe that when used by the entire deal time, ClosePlan will lead to less work for sales people, not more.

How do you think ClosePlan is going to benefit the teams using it?

Because ClosePlan brings visibility to opportunities, it will mean less reporting and more forecasting accuracy in the end. Everything from legal to deal desk will be easier because the events around the deal will be clear to the entire team and there will be fewer surprises. So much time today is spent on internal conversations and wranglings to get deals done and ClosePlan will alleviate some of that pain. Finally, sales teams will have all the relevant sales data and deal information in one place so it will be a huge time saver.