The Most important question for your Head of Sales

Sales Leader

The Most important question for your Head of Sales

Sales Leader

As one of the oldest professions in the history of human civilization, much has been written about Sales; that Sales is an Art-form, there are master practitioners and then there are the rest. There are consultants & coaches galore who can help you & your sales teams get better by implementing Value selling, Solution selling or a myriad of other selling approaches. Most of these approaches target Sales Managers & Individual Salespeople themselves.

What has not been covered in as much detail is the life of the Head of Sales & the challenges they tackle regularly. The Head of Sales has a variety of titles across industries ranging from VP – Sales all the way to Chief Operating Officer, but you know who you are – usually these are the folks with the deepest battle scars, scary good sales stories and a chest adorned with medallions. They’ve saved many fiscal quarters, delivered nail-biting finishes that kept the Street happy and blown away customer expectations.

Sales Complexity

If you bear responsibility for all-up Sales for your organization then you must be already familiar with the pressures of month-end, quarter-end, fiscal year-end whilst simultaneously balancing:

  • Product Mix: so each Product team meets their business objectives nee P&L
  • Setting & Delivering Sales Quota: for yourself & your entire team to have a financially rewarding year
  • Managing Sales capacity: to meet current business needs & secure the future
  • Driving closure on key deals: negotiating on the key deals for this fiscal period
  • And much much more

At its simplest, heading Sales is like juggling 10 grenades at once. Oh, and it only gets harder each year with new products, changing business models & revised targets each year.

The Most Important Question

If what is described above seems familiar, then here is the most important question that you need to answer.

“Could your Sales team do more?”

As the Head of Sales, you might think this is a given! After all, every team must find efficiency & improve productivity year over year and that is a fundamental premise on which we build our business. On the other hand, some of you might have mastered the art of prioritization so you know which products you won’t prioritize this upcoming quarter. Regardless your entire sales team may not concur with your prioritization.

However, your salespeople would disagree if you asked them the same question. After all, they have so much going on at any point in time. They are thinking about all the things that you are concerned about and more!

There is another school of thought that lazy salespeople are the best because they’ll find the shortest, smartest way to deliver results. If that works on your team, well congratulations, you may save the quarter or even the year, but this approach, unfortunately, doesn’t scale well for the most organization.

These short-cuts, sales hacks eventually compromise the long-term benefits of mindful sales execution. No great sales organization ever was built on hacks, they are built on the back of great products, great sales teams, precision planning and maniacal execution.

The Most Important Answer

Before we delve in, two welcomes are in order:

Firstly, welcome to the world of sales force productivity; often confused with the CRM-fixes-it-all worldview.

Secondly, welcome to the cliched “there is no perfect answer”!

This strategic dissonance between sales leaders & field sellers is not unique, nearly every organization, large or small, new or established, experiences this discord.

At Vymo, our belief is that there are 2 fundamental reasons for this discord:

1. Field Agents lack tools that might help them increase productivity

For instance, over a 1-year period, 80% of sales people average less than 1 customer meeting per day! If that could be improved by 20%, what would be the revenue upside? Worse still, the typical field seller has no idea what they are averaging!

2. Sales Leaders lack visibility to the activities of the field sellers

Similarly, Sales leaders have a view, from CRM systems on opportunities, deal value & forecast win date. However, they have no scientific way to know forecast accuracy in advance! This is where great Sales leaders employ precision questioning & sales coaching.

One way to affirm forecast accuracy is by correlating sales activities on the opportunity, which unfortunately are not recorded in the CRM.

For instance, if your sales team averages 8 meetings & 20 calls on a $100K opportunity and you have a $120K deal forecasted for, say, the current month and the sales team has only made 2 customer calls, you can be reasonably sure that this deal is either an outlier or at-risk. As a Sales leader you would rather focus on such outliers.


This “do-more” question is huge & omnipresent in sales, spanning industries & geographies. And with the rapid pace of change in business and technology, it is imperative to “do more”. In closing I have a few questions for you:

  • How are you dealing with this “do more” challenge?
  • How are you empowering your sales team to “do more”?

What do you think? We would love to hear your views, comments on this post.


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