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How to Overcome the Common Challenges to Implementing Sales Enablement Strategies


sales enablement strategy challenges

In our previous article, we explored what Sales Enablement is, why it matters, and how to implement it. To recap, sales enablement is the process of providing the sales organisation with the information, content, tools, and training that help sellers sell more effectively and efficiently. It is also a way to create a better buying experience for your customers, and to build long-lasting and profitable relationships with them.


However, implementing sales enablement strategies is not a simple or straightforward task. It involves many challenges and obstacles that can hinder your sales enablement goals and outcomes. According to a report by CSO Insights, only 34.4% of sales enablement initiatives met or exceeded their expectations in 20201


Some of the common challenges to implementing sales enablement strategies are:

  • Lack of alignment and collaboration between sales and marketing teams

  • Lack of buy-in and support from senior leadership and sales managers

  • Lack of clear and consistent sales enablement vision, objectives, and metrics

  • Lack of adequate and relevant sales enablement content and tools

  • Lack of effective and scalable sales enablement training and coaching

  • Lack of data-driven and customer-centric sales enablement approach


These challenges can negatively affect your sales enablement performance and results, such as sales productivity, revenue, customer satisfaction, and retention. Therefore, it is essential to overcome these challenges and create a successful and sustainable sales enablement strategy. 


Here are some tips and best practices to help you overcome the common challenges to implementing sales enablement strategies.


Align and collaborate with your sales and marketing teams


One of the key challenges to implementing sales enablement strategies is the lack of alignment and collaboration between your sales and marketing teams. Sales and marketing teams often have different goals, priorities, and perspectives, which can lead to silos, conflicts, or miscommunication. This can result in inconsistent and ineffective sales enablement solutions, such as sales content, tools, and training, that do not meet the needs and expectations of your sellers and your customers.


To overcome this challenge, you need to align and collaborate with your sales and marketing teams, and ensure that they have a common vision, goal, and language, and that they work together to support the entire customer journey, from awareness to advocacy. You also need to ensure that your sales and marketing teams have access to the same information, content, tools, and training, and that they communicate and collaborate effectively.


To align and collaborate with your sales and marketing teams, you can do the following:


  • Establish a sales enablement team or function that oversees and coordinates the sales enablement activities and initiatives across the sales and marketing teams.

  • Define and document your sales enablement vision, objectives, and metrics, and communicate them clearly and consistently to both the sales and marketing teams.

  • Create and update a sales enablement playbook or framework that outlines the roles and responsibilities, processes and workflows, and best practices and guidelines for the sales and marketing teams.

  • Use a sales enablement platform, such as SalesPro, to store, organise, and distribute your sales enablement information, content, tools, and training, and to track and measure their usage and effectiveness.

  • Hold regular meetings and feedback sessions, and use tools like Slack, a cloud-based collaboration platform that helps you communicate and collaborate with your team.


Get buy-in and support from your senior leadership and sales managers


Another challenge to implementing sales enablement strategies is the lack of buy-in and support from your senior leadership and sales managers. Senior leadership and sales managers are the key stakeholders and influencers of your sales enablement strategy, and they can either enable or hinder your sales enablement efforts and outcomes. 


However, they may not understand or appreciate the value and benefits of sales enablement, or they may have competing or conflicting priorities or agendas, which can prevent them from supporting and investing in your sales enablement strategy.


To overcome this challenge, you need to get buy-in and support from your senior leadership and sales managers, and ensure that they are aware and aligned with your sales enablement vision, objectives, and metrics, and that they are committed and accountable for your sales enablement success and results. 


You also need to ensure that your senior leadership and sales managers are involved and engaged in your sales enablement activities and initiatives, and that they provide the necessary resources and guidance for your sales enablement strategy.


To get buy-in and support from your senior leadership and sales managers, you can do the following:


  • Identify and understand the needs, expectations, and pain points of your senior leadership and sales managers, and tailor your sales enablement pitch and proposal to address and solve them.

  • Demonstrate and quantify the value and impact of your sales enablement strategy, and show how it aligns with and supports the business goals and customer needs of your organisation.

  • Provide and share the data and evidence that support your sales enablement strategy, and show the current state, the desired state, and the gap and opportunity for improvement.

  • Solicit and incorporate the feedback and input of your senior leadership and sales managers, and address their concerns and objections.


Define and measure your sales enablement strategy vision, objectives, and metrics


A third challenge to implementing sales enablement strategies is the lack of clear and consistent sales enablement vision, objectives, and metrics. 


Sales enablement vision, objectives, and metrics are the foundation and direction of your sales enablement strategy, and they help you plan, execute, and evaluate your sales enablement activities and initiatives. However, they may not be well-defined, documented, or communicated, or they may not be SMART (specific, measurable, achievable, relevant, or time-bound), which can lead to confusion, ambiguity, or inconsistency in your sales enablement strategy.


To overcome this challenge, you need to define and measure your sales enablement vision, objectives, and metrics, and ensure that they are aligned with and support your business goals and customer needs, and that they are SMART. 

You also need to ensure that your sales enablement vision, objectives, and metrics are documented and communicated clearly and consistently to your sales enablement team and other stakeholders, and that they are tracked and measured regularly and accurately.


To define and measure your sales enablement vision, objectives, and metrics, you can do the following:


  • Review and analyse your business goals and customer needs, and identify the problems or opportunities that you want to address or explore with your sales enablement strategy.

  • Formulate and articulate your sales enablement vision, which is the overarching statement that describes the desired state and outcome of your sales enablement strategy.

  • Define and document your sales enablement objectives, which are the specific and measurable goals that you want to achieve with your sales enablement strategy, and that support your sales enablement vision.

  • Select and define your sales enablement metrics, which are the measures that help you evaluate the progress and impact of your sales enablement objectives, and that are SMART.

  • Use a sales enablement platform, such as SalesPro, to store, organise, and track your sales enablement vision, objectives, and metrics, and to generate and view reports and dashboards that show your sales enablement performance and results.


Create and deliver adequate and relevant sales enablement content and tools


A fourth challenge to implementing sales enablement strategies is the lack of adequate and relevant sales enablement content and tools. 


Sales enablement content and tools are the resources that help your sellers sell more effectively and efficiently, and that help your customers buy more easily and confidently. However, they may not be sufficient, up-to-date, or accessible, or they may not be relevant, engaging, or personalised, which can result in low sales productivity, poor customer experience, and lost sales opportunities.


To overcome this challenge, you need to create and deliver adequate and relevant sales enablement content and tools, and ensure that they are sufficient, up-to-date, and accessible, and that they are relevant, engaging, and personalised for your sellers and your customers. You also need to ensure that your sales enablement content and tools are aligned with and support your sales process and customer journey, and that they are created and delivered in a timely and efficient manner.


To create and deliver adequate and relevant sales enablement content and tools, you can do the following:


  • Conduct a content and tool audit and gap analysis, and identify the types, formats, and topics of content and tools that your sellers and your customers need and want, and that your sales enablement team lacks or needs to improve.

  • Create and update your content and tool strategy and plan, and define the goals, audience, message, and tone of your content and tools, as well as the channels, formats, and frequency of your content and tool distribution.

  • Use a content management system, to help create and manage your content marketing campaigns.

  • Use tools like Canva, a graphic design platform that helps you create and design your content, such as infographics, flyers, or videos.

  • Use tools like Grammarly, a writing assistant that helps you check and improve your content, such as spelling, grammar, or clarity.

  • Use a sales enablement platform, such as SalesPro, to store, organise, and distribute your sales enablement content and tools, and to track and measure their usage and effectiveness.


Provide effective and scalable sales enablement training and coaching


A fifth challenge to implementing sales enablement strategies is the lack of effective and scalable sales enablement training and coaching. 


Sales enablement training and coaching are the methods that help your sellers improve their knowledge, skills, and behaviours, and that help them apply the sales enablement information, content, tools, and training to their sales situations. However, they may not be effective, engaging, or personalised, or they may not be scalable, flexible, or accessible, which can result in low sales performance, retention, and satisfaction.


To overcome this challenge, you need to provide effective and scalable sales enablement training and coaching, and ensure that they are effective, engaging, and personalised for your sellers, and that they are scalable, flexible, and accessible for your sales enablement team. You also need to ensure that your sales enablement training and coaching are aligned with and support your sales enablement objectives and metrics, and that they are provided and delivered in a timely and efficient manner.


To provide effective and scalable sales enablement training and coaching, you can do the following:


  • Conduct a training and coaching needs and gap analysis, and identify the topics, areas, and methods of training and coaching that your sellers need and want, and that your sales enablement team lacks or needs to improve.

  • Create and update your training and coaching strategy and plan, and define the goals, audience, content, and format of your training and coaching, as well as the frequency, duration, and evaluation of your training and coaching.

  • Provide various learning formats and methods, such as online courses, workshops, mentoring, coaching, or shadowing, and tailor them to the needs, preferences, and styles of each seller.

  • Use a sales enablement platform, such as SalesPro, to store, organise, and distribute your sales enablement training and coaching, and to track and measure their usage and effectiveness.

  • Use tools like Gong to record, transcribe, and analyse your sales calls and provide tips and techniques to improve your sales skills.


Use a data-driven and customer-centric sales enablement strategy


A sixth and final challenge to implementing sales enablement strategies is the lack of a data-driven and customer-centric sales enablement approach. 


A data-driven and customer-centric sales enablement approach is the practice of using data and insights to guide and inform your sales enablement decisions and actions, and to focus on the needs and expectations of your customers. However, you may not have access to or use the right data and insights, or you may not have a clear understanding or empathy for your customers, which can result in low sales effectiveness, efficiency, and experience.


To overcome this challenge, you need to ensure that you have access to and use the right data and insights to support your sales enablement strategy, and that you have a clear understanding and empathy for your customers and their customer journey. You also need to ensure that you use data and insights to test and validate your sales enablement ideas and approaches, and to personalise and optimise your sales enablement solutions for your customers.


To use a data-driven and customer-centric sales enablement approach, you can do the following:


  • Use various sources of data, such as customer feedback, sales reports, web analytics, CRM systems, and sales enablement platforms, to collect and analyse data and insights about your sales performance and results, and your customers’ needs and expectations.

  • Use a CRM platform that helps you manage your customer relationships and interactions.

  • Apply insight to your Google Analytics to track and measure your online customer journey, website traffic and conversions.

  • Use tools like SalesPro to track and measure your sales enablement performance and results.

  • Use frameworks and methods, such as experimentation, testing, or prototyping, to test and validate your sales enablement ideas and approaches, and to measure their impact and value.

  • Use tools and techniques, such as segmentation, personalisation, or automation, to personalise and optimise your sales enablement solutions for your customers, and to deliver a consistent and personalised buying experience.


Implementing sales enablement strategies is a challenging but rewarding task, that can help you improve your sales performance and results. By overcoming these common challenges to implementing sales enablement strategies you can create a successful and sustainable sales enablement strategy.


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