7 Critical Sales Leadership Challenges

Steven Rosen - Star Results Blog

7 critical sales leadership challenges 

Let’s face it; sales leadership has become increasingly more difficult. Next year’s sales objective is going up, and your budget is being reduced. You face challenges of doing more with less, increased competition, pricing pressures, staff turnover, and increased customer expectations. I have spoken to some sales executives trying to understand their most difficult challenges.

I’ve compiled a list of the most critical challenges sales leadership is facing and some advice on how we can overcome these challenges. Feel free to share your top challenge and what you are doing about it.



  1. Needs Alignment – Customer relations and maintaining client satisfaction lie at the heart of nearly every facet of sales. Customer buying behaviors are constantly changing, and the only way to stay successful is to adapt your sales operations to match them. Please speak to your customers regularly and implement their insights into your team’s sales processes to ensure that your customer’s needs align with how your team is selling your company’s product or service.
  1. Data Overload – With the advent of big data, customers have unprecedented information at their disposal. When your customer has access to in-depth information about your product, your company, and your competitors with the click of a button, it can be tough to differentiate your company and its brand. As an executive, it’s your responsibility to tailor your team’s sales processes to reflect an increasingly knowledgeable consumer and stand out from the competition.
  1. Lack of Coordination with MarketingA truly successful company has sales teams synchronized with the people responsible for advertising its product. Speak regularly with your fellow executives in marketing and ensure that your company’s sales processes align with its marketing operations.
  1. Ineffective Sales CoachesDespite the proven efficacy of well-executed sales coaching, it’s likely that many of your sales managers will be insufficiently trained in how to conduct it properly. As an executive, it’s your responsibility to ensure that your sales managers are coaching their reps effectively. Coach them yourself and invest the necessary time and resources in finding a coaching program that’s right for your team.
  1. Adapting to Changing Technology – According to Matt Heinz, President of Heinz Marketing, “technology adoption among sales professionals has been well behind” other fields. Take the necessary time to find and implement innovative new technologies that could help your company grow. CRM platforms, pipeline analytics, and candidate assessment tools can exponentially increase the productivity of your managers and reps.
  1. Sales Rep Retention – While retaining reps is more in line with the responsibilities of a sales manager, ultimately, sales teams with high rep turnover tend to perform poorly, and overall sales performance is a jurisdiction that lies squarely with you, the sales executive. Create incentive structures and a company culture that will motivate your managers and your reps to stay with the company. Their increased productivity will make up for whatever time and resources you need to spend to earn their loyalty.
  1. Inconsistent Sales Processes – Excessive product diversity can often lead to sales process inconsistency and hamper the efficacy of your department. Implement a comprehensive sales enablement strategy to maximize your team’s output.

Sales leaders are faced with a plethora of challenges that they are expected to deal with regularly. While these challenges may seem daunting, sales executives with a clear vision can undoubtedly overcome them. You are the sales leader, and you ultimately have to ensure that your team is operating effectively. Become aware of these common challenges facing sales leadership and meet them directly, and your opportunities for success will be endless.

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Steven Rosen 2022

Hi, I’m Steven Rosen, and I’ve been coaching sales executives for over 20 years!


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Steven Rosen - Executive Sales Coach


Steven A. Rosen

Steven helps companies transform sales managers into great sales leaders. His focused coaching helps clients achieve greater personal and professional success. Steven is the author of 52 Sales Management Tips - The Sales Manager’s Success Guide.

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