Eyes on the prize: How 2 sales VPs motivate their teams through slow sales cycles

by John Siegel
January 2, 2018

The last few months of the year can be an incredibly stressful time for tech companies, with potential and current clients finalizing budgets and sales teams grinding to hit their fiscal targets in order to end the year strong.

We recently connected with two VPs of sales departments to learn how they keep their teams motivated and focused, in order to close out the year successfully. 


PatientPop Team Members

The last two years have been quite hectic for Santa Monica-based PatientPop, with the team growing exponentially, moving into a new office and seeing demand for the company's health care marketing software boom. For VP of Sales Justin Welsh, the year's slow months come in the middle of the summer, when many prospective clients take a vacation. 

Can you describe any periods during the year in which closing sales is particularly difficult? 

The toughest time of year for us here at PatientPop is the beginning of each quarter, and the months of June and July. The beginning of each quarter is generally a pipeline rebuild. For summer months, most of our customers — health care providers — are taking vacations, so that is something we prepare for in advance. 

What makes the end of the fiscal year so tough for sales? 

The end of the fiscal year is tough for two reasons: The first is that the pressure is on to hit your yearly goals. The second is that you're depending on the months of November and December to be strong, even though the holidays take a large chunk of sales days off of the calendar. 

How does your team prepare for the slower end-of-year sales cycle? 

Our team generally prepares by having an action plan in place to shorten our sales cycle, increase referrals from existing customers and incentivize providers to make decisions inside of the last month of our fiscal year. 


SnackNation Team

As VP of Sales at SnackNation, Dan Salazar is familiar with the ebbs and flows of the sales cycle. While some teams are proponents of creating artificial deadlines for prospects to get them to sign on the dotted line — a method that can be successful in the right situations — Salazar shared that instead, he prefers preparing for slow periods in advance by building out prospect pipelines to make up for the lack of responses. 

Can you describe any periods during the year in which closing sales is particularly difficult?

There are a couple of tough stretches that virtually all sales teams face, no matter what product or service a company is selling. 

The first comes around July or August, when people take summer vacations. This often means that a point of contact within the company — or more importantly, the primary decision maker — is out of the office, which can make winning deals very difficult. 

The other tough stretch for most sales teams is the end of the year — late November and December. Like the late-summer months, people vacation during the holidays, but you can also encounter companies that have already exhausted their budgets. 

What's so tough about the end of a fiscal year? 

It's common to run into situations where companies have exhausted budgets by September or October. 

In addition to competing for budget dollars, you're also competing for mindshare. Remember, companies are focused on hitting their own goals and planning for the next fiscal year, which means they might not have time to evaluate what you're offering. 

The other major factor, of course, is the holidays. People generally shift focus to consumer purchases around this time, which means search volume for enterprise products tends to decline. This makes it harder for marketing teams to provide sales with the inbound lead flow that your team is accustomed to. 

How does your team handle slower sales periods? 

The first step is to be aware of when these periods take place and plan for them. I'm a big believer in running toward these types of challenges, not away from them. If you know that your closing percentage is going to take a dip and sales cycles are going to extend, you have to prepare by building a larger pipeline, and do so earlier.

It's critical to have your team increase their outbound prospecting efforts and marketing campaigns needed to fill your pipeline the month or two beforehand. This is easier said than done, but it is possible to give your team a shot to be successful during these slower periods if you prepare for and get out ahead of them. 

For our team at SnackNation — and for most sales teams — there are two important dates that affect how and when deals close. The first is the decision date — that's when your prospect needs to decide whether or not to make their purchase. The second is when the prospect actually needs access to your product. This second date is key as it often determines the decision (or closing) date. If you ask the right questions and identify where you are genuinely solving a problem for your prospect, the urgency for your product will be there. 

Since most companies are planning for the new year, many are working on projects or campaigns that need to hit the ground running at the start of Q1. Focus on the deals in your pipeline that need to go live at the beginning of the year, and you can solve their problem and yours by closing them in Q4. 


Some responses were edited for clarity and length. Images via participating companies.

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