STAMFORD, Conn., November 8, 2022

Key Issues Facing Chief Sales Officers Heading into 2023

Q&A with Craig Riley

Two years of constant and compounding disruption in the sales environment have left many chief sales officers (CSOs) with a burned out workforce and revenue target pressures. 2023 will serve as a tipping point for sales where the decisions CSOs make in response to challenges such as scarce talent and shifting buying dynamics will separate the winners from the losers in the years to come. 

We sat down with Craig Riley, Chief of Research in the Gartner Sales practice, to discuss the leadership vision for CSOs in 2023, and how those at the helm of the sales organization can create teams that thrive in today’s uncertain and digital-first world. 

Members of the media who would like to speak with Craig regarding this topic can contact to schedule an interview.

Q: What are the top trends affecting chief sales officers as we head into 2023?

A: There are three core trends impacting CSOs and their larger sales organizations heading into next year: 

  1. Digital commerce overtakes seller-led purchasesMost buyers prefer using digital commerce channels to make a purchase. A Gartner survey of 725 B2B buyers from December 2021 found 72% of B2B buyers recently completed a significant transaction via a digital channel, compared to 28% who used a rep-led channel.  
  2. Constant and compounding disruptions threaten revenue growth — Increasing inflation, tightening labor markets, and unreliable supply chains, otherwise known as the “triple squeeze,” are affecting buying behaviors and disrupting selling dynamics. 
  3. Hiring and retaining sales talent is harder than ever — Sales organizations are experiencing higher than target seller attrition, rising wages and an increase in the time it takes to fill a B2B seller role.    

These realities are interconnected and unfortunately create a pervasively uncertain environment that pose significant planning challenges for CSOs at the start of 2023. Uncertainty isn’t only difficult for sales leaders to cope with - it also hurts buyers’ confidence and their purchase experiences, which has a ripple effect on sellers’ deal quality and their ability to accurately forecast if, and when, a deal will close. CSOs who put plans in place to minimize the presence of these challenges create a huge growth opportunity for their larger sales organization.  

Q: Attracting and retaining top sales talent has always been difficult, but why is it particularly hard in today’s environment, and how should CSOs navigate the talent market to build a high-performing sales team?

A: A recent Gartner survey of over 900 B2B sellers revealed that 89% report feeling burned out.

They are unclear on their future within the business and believe their leadership is disconnected from the reality in which sellers operate. 

Between seller exhaustion, the Great Resignation, and the rising cost of living, hiring cycles are slower, retention more difficult, and new sales talent more expensive. This contributes to an environment where growing sales headcount is difficult and expensive. For example, a CSO with an attrition rate of 27% would likely require 37% new-to-role sellers to achieve even a modest net 10% increase in sales headcount. This environment leaves CSOs open to risks such as extended open territories and reduced workforce productivity.

CSOs can 1) improve retention by reducing seller “drag,” or demotivation at work, by diagnosing its sources, providing clear career growth opportunities, and empowering sellers and 2) create a more relevant and attractive sales role by redefining the traditional seller role in a way that integrates them into digital channels and automates low-value seller activities. Taking these actions will enable a high-performing sales team, one which ensures the proper structure is in place, to meet business goals. 

Q: How can CSOs acquire new customers and grow existing business in today’s increasingly disruptive and digital-first customer environment?

A: In addition to addressing talent management challenges of expanding the sales talent pool, sales leaders must prioritize two main efforts: implementing a unified customer engagement strategy and creating an adaptive sales organization.

Presently, digital and seller engagements alone fail to deliver the commercial outcomes CSOs want. Both fail for similar reasons: alone neither helps customers learn how to make high-quality and low-regret purchases. By building better customer engagements across both digital and human channels, CSOs can create more effective customer learning paths, or deepen customers’ understanding of how to accomplish their goals. Customers who experience self-reflective learning paths have a 147% greater likelihood to buy more than they originally expected.

Creating an adaptive sales organization requires CSOs to get off their back foot and be proactive, rather than reactive, in understanding how uncertainty is changing customer needs. This means leveraging a technology-augmented approach to deliver valuable customer engagements in variable environments and create a more buyer-centric operating model.

As one example, most sales organizations succeed in customer journey mapping but fall short at giving their sellers data on customer information journeys, their emotions and interpersonal dynamics. Technology such as customer sentiment tracking or conversational intelligence are critical to giving sellers what they need to fundamentally understand the underlying issues and decision making path of a customer.

Learn more in "Leadership Vision for 2023: Chief Sales Officer" and the virtual showcase, “Gartner Chief Sales Officer Leadership Vision for 2023.” Additional information is available in the Recession Playbook for Sales Leaders.  

If you are a member of the media who would like to speak further on these topics with Craig, please contact Members of the media can reference this material in their articles with proper attribution to Gartner.

About Gartner

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