What are the Key Challenges IT Sales Leaders are Facing in 2019?

In this ever-developing market we are constantly facing new challenges in our sales teams. Changes in technology, public interest, politics and new research means even when sales are going well there will always be a sticking point we need to give more attention to as Sales Leaders.

At our latest World Class IT Sales Leaders event we asked delegates what their biggest challenges are right now. After collating this feedback we’ve summarised below the trends we identified in what we heard.

Social Media

With social media taking over all forms of communication sales leaders are asking themselves how they can embrace this technology and build it into their activity.  The key questions are:

  • How to market through social media?
  • How to utilise social media channels to grow your pipelines?
  • The best ways to use social media outside of LinkedIn

Supporting this there were also challenges around new ways of providing added value support to your stakeholders:

  • How do provide added value content in innovative ways?
  • How to go about building a video content strategy?
  • How to provide added value without selling a service?


In an increasingly competitive environment staffing environment it’s coming more and more difficult to secure the top talent over your competition.  If your competition are able to get that five star candidate before you do it can put you at a huge disadvantage.  Sales leaders are asking not only how to win the talent but how to build out the team and nurture current talent:

  • How do you build out a successful sales team?
  • What skills should you look for when hiring sales people?
  • How do you attract the top talent over your competition?


There are many more general issues that Sales Leaders identified as being at the front of their minds now.  These are addressed as follows:

  • What issues are slowing down buyer momentum and how do we get around them?
  • The best ways to overcome the procurement barrier
  • How to sell effectively to multiple stakeholders?
  • How to budget for and measure the ROI in DG & marketing activity?
  • Support with the shift from a start up to a scale up business
  • How to address the skills gaps within a multi-generational team?
  • Understanding the psychology of the sales process, taking into account new research and how to influence emotional responses

Mental Health

Mental health continues to be a topic that sales leaders are highly concerned with.  Recent media attention on this topic has heightened the importance for leadership teams to be seen to be taking action to improve their team’s mental health.  Alongside this, recent research has identified the impact that poor mental health can have on a sales team’s performance.  Key challenges were summarised as:

  • How do you manage stress within your sales team?
  • What can sales leaders do to lead by example with practicing psychological safety in the workplace?

We are looking to run a series of breakfast events in the coming months that will address each of these topics.  We’re looking at bringing in relevant industry experts to provide further information, training and support for sales leaders.  If you would like to register your interest in our upcoming events email Paul@enterprisesp.co.uk