The Staffing Leaders Guide to Sales Enablement

A roadmap for L&D leaders to enable their sales and recruiting teams to optimize productivity and performance and be recognized as a strategic partner impacting revenue growth


There are thousands of books written on sales strategies, sales tactics and sales management, but there are very few that focus on how to enable sales and recruiting teams to optimize productivity and performance.

This is not a guide for salespeople or sales managers or recruiters, but rather a guide for staffing industry leaders and specifically Learning and Development (L&D) Leaders, Sales Enablement Leaders, CHRO’s, Training Managers, and anyone responsible for improving employee performance.

The challenge for rapidly growing staffing firms is that learning and development including sales enablement and their leaders are perceived and often treated as a tactical, transactional support function rather than strategic business advisers responsible for revenue impacting outcomes.


In fairness, most training teams are so focused on supporting their people and servicing their customers and candidates that they don’t have the time to assess their program holistically, working hand in hand with executive leadership to solve real business problems.

At its core, training alone is ineffective 99% of the time.

You need the right conditions to sustain newly learned skills and imparted knowledge, and you need an engaged leadership team that leads from the front and consistently coaches to fully integrate the new skill, behavior or message into your culture making it part of “what you do, and how you do it.”

If you don’t have this, you’re wasting your time and money.

If you’re a leader in a staffing firm responsible for enabling your sales and recruiting teams to improve performance and effectiveness.

This ebook provides an overview of the discipline of sales enablement including best practices for creating and sustaining a best-in-class sales enablement discipline. Every recommendation in this ebook is backed by research and has been applied in the field with real salespeople, recruiters, managers and L&D professionals from within the staffing and recruiting industry.

The job of training, learning and development can be one of the most fulfilling and rewarding professions. You have the unique opportunity to be the single most important and valued partner to your sales and recruiting teams.


But you can’t get there if you don’t prioritize your build-out of each component of the sales enablement ecosystem.

This ebook provides the guidance you need to make the shift from tactical support function to strategic partner recognized for impacting sales and recruiter performance and revenue growth. 

You are the key driver in transforming the most important part of your organization, your recruiters and salespeople and their managers.

The Rise of Sales Enablement

Research shows that more salespeople than ever are struggling to make quota.

According to a study from CSO Insights, over the past five years the number of salespeople making quota has dropped by ten percentage points and the percentage of companies achieving their revenue goals has dropped by four percent.

For anyone trying to build a business, this decline in performance is incredibly frustrating.

You’ve likely invested in CRM and ATS solutions and other technologies designed to make your recruiters and salespeople more productive and effective. You’ve likely also invested in marketing collateral, training programs and worked on honing your hiring practices to attract, hire and retain top talent.

So why aren’t you seeing a return on your investment?

The answer is simple.

Today’s staffing and recruiting organizations are not keeping up with and adapting to the pace of change to effectively support and enable their sales and recruiting teams. There are two macro level and six micro level changes occurring that many organizations are struggling to keep pace with.


Macro-Level Changes

Disruptive Technologies

Selling and recruiting has, and will continue to become even more technology driven. Sellers and recruiters will be forced to engage buyers and candidates through technology.

We’re already seeing the impact of this disruption as desirable sales skills are shifting from soft skills (relationship, rapport building) to harder skills like data mining and business acumen skills.


War For Younger Talent

Workers are hitting retirement age at a faster pace in which they can be replaced with new recruits.

According to a McKinsey study, the labor market for the past 50 years has grown at 1.7% but predicts it will drop by 0.3% over the next 50 years. This translates into more competition for an even smaller pool of qualified talent.

To be successful, companies will need to make improvements in defining their ideal target candidate profile to make successful hires.

Sales enablement and L&D professionals will need to onboard these new recruits as quickly as possible and provide the services necessary to drive sales and recruiting professionals to higher and higher levels of productivity.


Micro-Level Changes

Multiple Buyers Make for Complex Sale

Research shows that the average buying team includes 6.4 buyers.

Research also shows that these teams are made up of buyers from a wider range of disciplines (cross-functional teams).

Sellers need to learn to sell to teams vs. individual buyers (it is rare to find a hiring manager today who makes a decision 100% on their own). Sellers will need to learn to sell to and manage a group of multiple buyers and identify each of their unique challenges and vision for success.

Increasing Formalized Buying Process

As more and more staffing firms are trying to move up-market and increase deal size and sell projects and/or SOW (statement of work) business, the buying team grows and the buying process tends to follow a more formalized process.

Sellers will need to develop the skills and knowledge training to effectively appeal to each of the unique buyer personas (on the buying team) and understand how corporate America makes buying decisions.

Additionally, Sellers must improve their business acumen skills.

ROI Driven Business Decisions

The percentage of customers requiring an ROI analysis has gone from a five year average of 40% to 61%.


Historically, the ability to discuss or demonstrate ROI of a solution has not been part of the “sales toolkit” for staffing industry professionals.

With most staffing firms shifting to sell managed team solutions, managed services, SOW business, and other forms of projects and “solutions,” sales and L&D Leaders will need to provide content and training services that support their salespeople and address this skill and knowledge gap.

Today’s Buyer Seeks Outcomes, Not Your Product/Service

Buyers are not so much interested in what your product or service is and does, as much as the outcome and business results it produces.

They want to know how your service will help them solve their challenges or achieve a business goal. This requires a very different selling approach that translates capabilities into business value.

Longer Sales Cycles

Sixty percent of sales cycles with new customers last over six months. That is up from 41%.

This is reflective of other trends such as larger buying teams and the increasing sophistication of solutions being sold. Salespeople and sales leaders will need to learn to adapt their approach to these longer sales cycles.

Buyer Experience

According to Forrester Research, only 19% corporate buyers believe that their time spent with salespeople is valuable and lives up to their expectations.

Buyers no longer need salespeople to tell them what services they provide-they can read your website for that. L&D leaders will need to design content and training services that position their salespeople as authoritative thought leaders in which salespeople can share fresh ideas, insights and perspectives unique to the buyer persona and phase of the buyer journey.

sales enablement

Staffing industry sales professionals who fail to make this transition will be left behind and in the “transactional commodity bucket.”

These changes have led to fewer and fewer salespeople making quota and the rise of sales enablement as a formal and strategic discipline. Most staffing and recruiting firms beyond “start up phase” have at least one full-time employee dedicated to training and talent development.

So what’s gone wrong?

In over 90% of the 300 staffing firms we’ve consulted, we found:

  • Training leader(s) do not have a seat at the executive table, and even those who do are not collaborating with their executive leadership team at a strategic level.
  • Staffing industry CEO’s and CFO’s indicate their training leaders struggle to quantifiably demonstrate how their training services deliver revenue impacting outcomes.
  • Staffing firms have not designed the right content, value messaging and training services to keep pace with these changes.
  • Manager enablement including frontline coaching is not non-existent.

The remainder of this guide and it’s goal is to provide you with a roadmap to build a best in class sales enablement discipline that is sustainable, repeatable and scalable and has a quantifiable impact on sales and recruiting performance and your revenue growth.

The goal is also to help you and measure the value training, learning and development brings to your organization to ensure your voice is heard at the executive table.


What You’re Trying To Enable and Scale Across Your Organization

For as long as the sales profession has been in existence there has been a belief that sales is an art and not a science.

Everyone believed (and many still do) that sales is all about the relationships and that great salespeople have “the gift of gab.” They’re “people people.”

Today however, modern sales and L&D leaders know that sales is just as much science as it is art.

We now have the tools we need to track sales activities and sales behaviors and link them to results.

We no longer need to rely on gut instinct and guess at what is working. This is great news for L&D leaders because you can target your training efforts much more effectively.

Through our work with hundreds of staffing firms and consulting with their sales and recruiting organizations, we’ve identified two levels of sales team success: Relationships, and Sales Process Maturity.

To help you understand what it is you’re trying to enable and scale across your organization let’s consider the strength of customer relationships capability maturity model and the sales process maturity adoption model.

As you read through them, think about your sales organization and which level your sales team falls into.

Strength of Customer Relationships Capability Maturity Model

Capability maturity models are often mistaken for a collection of best practices. The reality is they are designed to illustrate the phases an organization progresses through for continuous improvement in a particular discipline or function.

The intent is to help business leaders determine what practices and perceptions currently exist within their organization and provide a roadmap for the organization to pursue continuous improvement.

Maturity models can take industry “best practices” and convert them into “future state” or next steps.

By doing a quick evaluation of your organization’s capability and capturing “today’s behaviors” associated with each phase, you will gain an understanding of:

  1. What business capabilities are lacking
  2. What skills and knowledge are needed
  3. What training and coaching is needed
  4. What can be done next to improve the sophistication and effectiveness of the function or discipline

The strength of relationship maturity capability model depicted below highlights how sellers and their sales effectiveness evolves over time.

As you develop more and more of your sellers into “strong promoters” and “trusted advisors” you increase overall team quota attainment which accelerates the growth of your organization.



Sales Process Capability Maturity Adoption Model

The sales process capability maturity adoption model depicted below highlights how sales capabilities and sales effectiveness improves with increasing levels of sales process capability and adoption.

sales process capability maturity adoption model

The more mature and the greater the adoption of your sales process, the more you are able to scale sales effectiveness and accelerate your growth.

Now that we understand what it is that we are trying to scale and enable across our organization let’s discuss sales enablement and how it differs from sales training.


What is Sales Enablement and How Does It Differ From“Sales Training?”

Training, and sales and recruiter training in particular, is geared for onboarding new hires, company retreats and sales kickoff events.

By design, the purpose of training is to impart knowledge on behalf of the learner. It is foundational for helping the employee do their job.

Training including new hire onboarding typically has a “start date” and an “end date.” For these reasons (and others), training alone won’t move the revenue needle.

Examples of sales and recruiter training include:

  • Shadow training
  • Employee reads a training manual
  • Employee watches a training video
  • Employee attends a training webinar or workshop

Sales enablement is a strategic, collaborative discipline designed to increase predictable sales results by providing consistent, scalable enablement services that allow recruiters, salespeople and their managers to add value in every customer and candidate interaction.

Staff Training - Green Office Folder on Background of Working Table with Stationery and Laptop. Staff Training Business Concept on Blurred Background. Staff Training Toned Image. 3D.

To be effective, sales enablement must be treated as a strategic revenue generating discipline that is set apart from other functions such as finance, marketing or operations. Sales enablement is not a one-off initiative, ancillary task or project with a start date and end date.

Training is one service that makes up sales enablement. Sales enablement services as whole includes:

Content Services

  • Customer/Candidate Facing Content
  • Internal Facing Content (Playbooks, Scripts, Templates, Rebuttal Books, etc.)

Training Services

  • Knowledge Training
  • Methodology Training
  • Skills Training

Coaching Services

  • Coaching Skills
  • What to Coach
  • When to Coach
  • How to Coach

To a large degree, sales enablement services can and should be authored and consumed through integrated enablement technologies. Technology enables your enablement services to be repeatable and scalable and they ensure continuity.

Before we discuss enablement services and supporting technology we first must recognize and understand the importance of collaboration and the role that L&D and enablement leaders play in orchestrating cross-functional team collaboration.


Orchestrating Formalized Collaboration

Everyone agrees on the need to collaborate but rarely do teams stop to apply and structure a formal process for collaboration. Instead the focus is on short term goals such as producing a piece of collateral or selecting a sales or recruiting tool.

Enablement is a collaborative effort and your primary role is to orchestrate the efforts of others to create consistent and effective enablement services that align with the buyer and candidate journey.

orchestrating formalized collaboration for sales enablement

Cross functional collaboration is seldom easy, but setting up a model for collaboration with clearly defined roles and responsibilities drives productivity and makes enablement scalable and repeatable.

Enablement and L&D professionals must:

  1. Be highly skilled at getting things done through other people and departments (it has been said “everything is selling”)
  2. Set up a collaboration model with clear responsibilities to drive enablement productivity and scalability

Organizations with a more formal approach to collaboration are as much as 21% better at achieving quota than organizations with no or ad hoc collaboration efforts.


The RACI Collaboration Model

The RACI model is the simplest, most effective means for defining and documenting project roles and responsibilities.

Knowing exactly who is responsible, who is accountable, who needs to be consulted, and who must be kept informed at every step will significantly improve your collaboration and likelihood for project success.

This model defines participation across four roles:


The people responsible for doing the work. They must complete the task or objective or make the decision. Several people can be jointly responsible.


The person or stakeholder who is the “owner” of the work.

He or she must sign off or approve when the task, objective or decision is complete. This person must make sure that responsibilities are assigned in the matrix for all related activities.

Success requires that there is only one person accountable, which means that “the buck stops there.”


People or stakeholders who need to give input before the work can be done and signed-off on. These people are “in the loop” and active participants.


These roles should be pre-defined for each type of enablement service (for example, a content service such as designing a playbook) because the role an individual plays may be different for each service.

By pre-defining these roles by sales enablement service type, the cross functional team can avoid the time spent negotiating responsibilities each time a new service is created.


Designing Training Content From the Customer, Candidate’s Perspective

The first thing a prospective customer or candidate notices about your organization is how well your recruiters and salespeople understand them including their role, their job function, their industry and what it is they want to achieve.


In today’s hyper-informed world, customers and candidates wish to engage sales and recruiting professionals differently than they have in the past.

They no longer want nor do they need to be informed about your products or services or be on the receiving end of a pitch. They can read all about that stuff on your website and your social media.

This makes for a challenging sales and recruiting environment. But, just because candidates and buyers are more informed and have access to more data doesn’t mean they necessarily have more wisdom or confidence in the decisions they must make.

What they don’t have access to are the ideas, insights and perspectives of your recruiters and salespeople.

Today’s top performers demonstrate value by sharing perspectives and insights by combining deep knowledge of their customers and candidates and their desired goals with their experience and insights gained from working with similar customers and candidates.

For these reasons, the customer and the candidate must be the focal point for sales enablement and they must be reflected in every enablement service you provide.

Unfortunately, very few staffing firms do this.

Instead, they create content and provide training services where the focal point is their product; the candidate, or their service offerings and other features and benefits such as the depth and breadth of their candidate database, or their recruiting screening and interviewing methodology.

Training and content services created from this design point encourage sellers and recruiters to go into “broadcast pitch mode.” Think Most Placeable Candidate.

While there is a time and place for the Most Placeable Candidate approach, today’s informed buyer expects their time with a salesperson to be valuable. They expect to learn something.

This is just one reason why many salespeople and recruiters struggle to fill the top of their funnel and achieve quota attainment

Content Services

Salespeople add value and move up the relationship spectrum by sharing fresh ideas and valuable insights during each customer interaction.

But not every interaction is verbal.

Offering the right piece of content at the right time is what keeps the value flowing, and maintains forward momentum, even if the salesperson isn’t sitting across the table from the prospect.


To be successful at helping customers move forward, salespeople need customer facing enablement content for each phase of the buyer’s journey. 

Awareness Stage

During this stage the buyer realizes they have a problem to solve or a goal to achieve.

Messaging and enablement content for buyers in this stage focuses on helping the customer understand their issues or their desired goals at a deeper level. The messaging and content during this stage is purely educational in nature.

Consideration Stage

During this stage and based on research conducted during the awareness stage, the buyer defines the scope of their problem and/or the goal they’re trying to achieve and begins to consider their options for resolving the issue.

Messaging and enablement content for this stage focuses on educating the client on your solution and how it helps customers solve the problem and/or achieve the desired goal/outcome.

Enablement content includes eBooks, explainer videos, and customer case studies.

Commitment Stage

During this stage the buyer must decide if they are committed to making the change and investing the time and resources to solve the problem and/or achieve the goal. They’re weighing the pros and cons of whether or not moving forward with a solution is worth the investment.

Enablement content for this stage focuses on ROI tools that help the customer quantify the ROI of your solution, and customer case studies.

Decision Stage

During this stage the buyer must make a final decision and pick a solution, vendor or candidate. Messaging and enablement content during stage includes customer testimonial videos and customer references, product trials, pilots, and proposals.

What sales professionals want and need is content that can be used for their specific selling situations, such as content that addresses a specific issue or industry need.

Therefore, content services must be a collaborative effort. Whenever salespeople have to create their own content from scratch you know something is wrong with the overall enablement approach.

At most, salespeople should only have to tailor and customize content that has already been provided. If salespeople can’t find the right content, aren’t satisfied with its quality or don’t know how to use the tools, then fixing these problems is the responsibility of the enablement team.


Training Services

To effectively enable sales and recruiting, your training must address three requirements:

Knowledge Training

Product training or services training fall under this category. Industry and market training as well as business acumen, buyer personas, buyer journey, sales process and sales tools training all fall under knowledge training.

Methodology Training

Methodology training helps sales professionals understand what to do, what to say, and when to say it and why. Methodology training connects the buyer’s journey to the sales process and the candidate journey to the recruitment process.

Skills Training

Skills training covers those capabilities that are needed to execute the methodology along the buyer’s journey. This can include questioning skills, objection handling, interviewing skills, rate negotiation, active listening, and others.

Of the more than 300+ staffing firms we’ve engaged, 95% of training services are focused on knowledge training. Company history, industry and market training and recruiting process including ATS training are most common.

Very, very few staffing and recruiting firms have a formal sales or recruiting methodology and therefore don’t provide methodology training or skills training.

Training Delivery and Consumption Models

Twenty years ago we started to see the rise of learning management systems (LMS) including Moodle, the first open-source LMS platform.

sales training delivery and consumption models

Having an LMS platform was revolutionary at the time because it enabled L&D leaders to author, publish and deliver training content online.

They could also track and measure which learners completed which training modules and when. Online quizzes could also be administered to test learner retention and comprehension.

Not only was it good for L&D leaders but learners loved the blended learning approach in which they consumed training online via an internet connection and through live, instructor-led training workshops.

Over the past few years however, forward-thinking L&D leaders and practitioners have learned that traditional LMS platforms don’t enable them to make a quantifiable (financial) impact on the business.

The reason is LMS platforms were never designed to track, measure and improve learner competency and improve sales/recruiter skill execution. Instead, they were designed simply to impart knowledge.

Those same forward thinking L&D leaders and practitioners also discovered that learning management systems don’t provide continuous, ongoing reinforcement.

The forgetting curve, first introduced in the 1800’s and corroborated through additional research, shows the decline of memory retention over time when there is no attempt to retain it.

Research shows that humans tend to halve their memory of newly learned knowledge in a matter of days unless they consciously review the learned material.

People forget 50% of the information they just learned within one hour. Within 24 hours they have forgotten an average of 70% of new information. Reinforcement training services help learners retain more information longer.

With more and more employees working virtually or remote and without the capability to track and measure training effectiveness and learner competency or the ability to reinforce the material, L&D leaders had struggled to elevate their role and their department within their organization because they didn’t have the functionality and supporting data to quantify their value.

But that was then.

Today we have sales readiness software which is outcome-oriented and identifies the capabilities your recruiters and reps need to win more deals and develop those capabilities. It provides tools that equip your employees with the right knowledge and helps them develop their selling skills so they can use that knowledge in real life scenarios.

For example, with sales readiness software staffing firms can certify their reps and recruiters are “conversation ready” with video and AI powered skills certification and coaching.

Learners can participate in video role play practice in which they’re tasked with executing real world customer/candidate conversations demonstrating they can apply the skills, methodology and knowledge they learned.


AI Powered Coaching automates and speeds up the feedback loop with model pitch comparison, keywords analysis, transcription in multiple languages, submission length, speech pace and filler word usage including speech articulation.

Quantitative and qualitative feedback pinpoints skill and knowledge gaps and helps reinforce and drive adoption of what has been taught ensuring skills mastery and training ROI.

All of this helps sales and recruiting managers and subject matter experts build a regular coaching cadence, and gives them the analytics they need to monitor how their employees are improving.

Finally, you can track and measure learner competency, deliver automated training reinforcement and iterate for continuous improvement.

Under the new, mobile training model, learners consume training content via their mobile app (or internet connection).

Training is delivered via short animated micro-learning videos that typically last 2-3 minutes per lesson. The training video(s) introduce the skill, behavior, knowledge or methodology as the central idea for the learning module.

Courses are followed up with quizzes to test for learner retention and comprehension. Quizzes are followed up with video enabled certification exercises that give recruiters and salespeople the opportunity to practice executing the skills, knowledge and methodology taught in the training.


Learners spend all of their time in workshops engaged in individual and group exercises ensuring they can apply what they’ve learned in the field.

Coaching Services

Sales and recruiting managers must be included in sales enablement because they are responsible for ensuring go-to-customer and go-to-candidate strategies are carried out effectively. They need to be enabled with the skills, knowledge and tools for their people to be successful.

sales enablement coaching services

For example, sales enablement can provide a sales tool for a sales rep but if the rep’s manager is not also versed on how the tool is designed to be used in the field then they cannot coach to drive reinforcement and adoption of the tool.

This puts your enablement investment at risk.

Your coaching services should include:

What & How to Coach

This includes a repeatable coaching framework of best practices, tools and job aids to set expectations for how coaching works, the topics that will be discussed and the tools that will be used.

Coaching Skills

Examples of coaching skills include leading with questions, empathy, active listening, and positioning among others.

Coaching Tools

An example of a simple coaching tool would be a coaching call plan that helps managers plan for their coaching conversations.

The plan would include what the manager says to open the conversation, questions they will ask to get their subordinate to self diagnose the obstacle holding back their performance and questions they will ask to empower the employee to take self-responsibility for improving performance.

Coaching services also include the creation and delivery of content, tools and training for your managers to reinforce your sales training and recruiter training.

For example, if your sales team completes methodology training for objection handling, you would create tools such as exercises, role play scenarios or questions the managers ask of their subordinates to reinforce and drive adoption of your objection handling methodology.

This is how you protect your training investment.

Effective coaching covers key areas including lead generation and conversion, opportunity management, skills and behaviors (training reinforcement), and account/territory management.


Evolving Your Coaching Maturity

In all likelihood, there is room for improvement in how your managers coach and the consistency in which they coach. Consider the following coaching capability maturity adoption model and take stock of where your managers currently reside on the model.

Haphazard Coaching

Coaching occurs on a haphazard and random basis including how, when and whether to coach at all. All coaching is left up to the front line sales and recruiting manager(s).

Ad Hoc Coaching

Some guidance has been provided on how to coach and when to coach but the guidance has not been consistent nor is it reinforced.

Managers provide coaching inconsistently and are not held accountable to coaching teams members. When coaching does take place it tends to be “scrutiny based” and focuses on past performance rather “empowerment based” and focused on future behavior.

Formal Coaching

There is a formal coaching methodology that is supported with training services and content services.

Front line managers are held accountable to coaching team members and following the prescribed coaching methodology. Reinforcement training and coaching is provided to reinforce and drive adoption of the coaching methodology.


Coaching Services Target Audience

Directors and VP’s

Your management hierarchy from the top down must be enabled to, and consistently “coach the coaches.” VP’s must consistently coach their Directors and Directors must consistently coach their managers ensuring continuity and improving overall coaching effectiveness.

Frontline Sales & Recruiting Managers

They are responsible for ensuring go-to-customer and go-to candidate strategies are carried out effectively. They need to be enabled with the skills, knowledge and tools for their people to be successful.


Some organizations have mentoring programs and/or peer to peer coaching in which case these people can benefit from coaching services.


Sales Enablement Technology

Thousands of forward-thinking organizations around the globe are seeing success from investing in sales enablement software. Sales reps are having more meaningful and productive conversations, AI certifies whether or not reps are staying on message, analytics guide them through lead nurturing and follow-up.

Unposed group of creative business people in an open concept office brainstorming their next project.

Yet those benefits don’t even scratch the surface!

With sales enablement software rapidly gaining traction - so too has confusion around the related technology.

Part of the challenge is many of the industry analysts such as CSO Insights, Forrester, Gartner, Aberdeen, etc., use different terminology to describe the many different sales enablement tools and software that exist on the market today.

Additionally, many of today’s sales enablement software products offer multiple functionality which also creates confusion.

When you take all of that into consideration along with the number of sales enablement technology providers, it’s no surprise things get a little murky! The sales enablement software market was valued $1.1 billion in 2019, and is projected to grow to $2.6 billion by 2024.

So no, it’s not just a passing fad or marketing jargon. Sales enablement software delivers legit business value.


What is Sales Enablement Technology?

Generally speaking, sales enablement software is designed to enable customer facing professionals and their managers to add value at each touch point of the buyer journey with the goal of achieving repeatable and scalable sales results. It’s purpose is to improve sales productivity and sales effectiveness, all of which adds value to your organization.

There are a wide spectrum of tools, ranging in features and functionality.

Some are “enterprise” solutions encompassing all sales enablement functionality into a single software platform while others are more “point solutions” focused on solving a specific challenge.

startup business, software developer working on computer at modern office

What is best about most sales enablement tools is you really do NOT have to be a big company to take advantage of, or afford them. Technology continues to get cheaper making it more affordable for even the smallest of start-ups.

At a high-level, there are different types of sales enablement software to support salespeople in a variety of different ways. Forrester Research highlights three types of sales enablement software that are “rapidly becoming foundational to the 21st century sales tech stack.”

Sales Content Management Software

Software to help companies organize, find and promote the right sales assets.

Think about how much time salespeople waste searching for content? Sales Content Management software solves this problem.

Examples include Highspot and Seismic, both of which integrate with our sales readiness platform.

Sales Readiness Software

Software designed to equip recruiters, sellers and managers with the content, training, coaching and analytics they and their managers need to optimize each and every buyer interaction and improve effectiveness.

Our sales readiness platform is one example and is hosted by MindTickle, whom Gartner has recognized as a market leader in their product category.

Sales Engagement Software

This type of software focuses on managing, measuring, and optimizing how sellers interact with your buyers. These include platforms like SalesLoft and herefish by Bullhorn.

What is most important is that you understand which type of sales enablement software solves which of your challenges for your sales and delivery organizations.


Your Enablement Charter

Your enablement charter functions as your business plan and is your guide for turning a random sales enablement effort into a formal, scalable and strategic enablement discipline that has a quantifiable impact on the business. Your charter also helps keep your discipline on track.

It is your charter that you use to sell to your CEO and CFO to get them to buy in internally.


Steps to Developing Your Charter

  1. Meet with executive leaders and seek to understand the goals of the organization including market share, expansion, vision, etc.
  2. Meet with other department leaders to find out what they are doing and what they think they could do with the right programs and processes in place.
  3. Find a champion to support you and your efforts, ideally your sales or recruiting leader.
  4. Take stock of all random enablement initiatives.
  5. Align with and understand the business strategy. Understanding the goals of the business will tell you what is important to the organization. To gartner support and funding for your enablement function, it is essential that your end goal be in support of these objectives.
  6. Align with and understand the sales strategy. Your sales strategy tells you how the organization expects to achieve its sales goals and your enablement strategy must be aligned to support it. Your goal is to determine how sales enablement can effectively support the execution of the sales strategy.
  7. Align with and understand the delivery (recruiting) strategy. Your delivery strategy tells you how the delivery organization expects to achieve its revenue goals and deliver on what sales sells. Your enablement strategy must be aligned to support it. Your goal is to determine how enablement can effectively support the execution of the recruiting strategy.


Enablement Governance Advisory Board

Setting up an enablement governance model is designed to help you engage executive sponsors, stay connected to the organization’s strategies and objectives and solve strategic issues. It also provides the mechanism in which you report on the progress of your initiatives.

With an effective governance model, enablement rises from a tactical function to a strategic discipline. Without it, enablement will always be fighting for support and the resources it needs.

The good news is, you will have already laid the foundation for enablement governance when you engaged your senior executives in the review and approval of your enablement charter.

Now you need to keep them engaged and one of the best ways to do it is with an enablement advisory board. Your enablement advisory board serves a different purpose than the RACI collaboration model previously discussed.

Businesswoman doing conference presentation in meeting room

In contrast, your enablement advisory board is strategic in nature and focused on results rather than the micro-details of how you achieve them.

Establish a clear purpose:

In meetings, members of your advisory board can learn more about what enablement is doing and how it is impacting the business. Visibility into enablement will allow the advisory board members to provide input on strategic direction, ensuring enablement stays aligned to the company objectives and strategies.

The primary responsibilities of the enablement advisory board should be:

  • Defining and evolving the long term sales enablement strategy, ensuring that it is derived from the business strategy and supporting the sales strategy.
  • Making strategic decisions that require broad senior executive involvement.
  • Solving conflicts that are too complex to be resolved by referencing the charter and collaboration model.

The members of your advisory board are high level executives focused on making high level decisions.

Don’t invite tactical team members or discuss tactical details in these meetings. Focus on sharing results and metrics that demonstrate your progress and the quantifiable impact it is having on the business.

Measuring Results

How you define success and the metrics you use to measure success needs to be aligned with the maturity of your enablement discipline.

measuring sales enablement results
Success should be measured in milestones that show the progress of your initial efforts from where you started, not what you want to achieve.

Learning and Development teams often use the Kirkpatrick-Phillips model which covers the five levels of data collection.

Level 1: Reaction and Planned Action

Usually a survey is issued immediately following a training event. This determines if learners and their managers were prepared for their participation in training, and collects their reaction to the learning experience and their immediate plans for how they will apply the training.

Level 2: Learning and Confidence

Evaluates what degree of learning took place, often administered through a quiz. It answers the questions: do learners and managers recall the information accurately? Are they confident in their understanding?

Level 3: Application and Implementation

This is collected a set period after a training milestone (for example, 30 days post training). Here data is collected that evaluates whether or not the new behaviors and knowledge have transferred back to the job and are being demonstrated by the learners and their managers in their day-today activities.

Level 4: Business Impact

This connects behavior change, skill use, methodology use, product knowledge and other learning outcomes to leading indicators such as conversion rates, pipeline volume, and new meetings. It answers the question: Are attendees who demonstrate they have learned the material are actually doing better?

Return on Investment

This is generally reserved for the highest visibility projects. The team qualifies the full ROI of a learning investment including tangible and monetized benefits in comparison to burdened costs.

Leading Indicators

Placements. Revenue. New Bookings. No matter how your organization measures sales results these metrics all share a common trait; they measure the past. The problem with measuring results or the past is it is too late to do anything about them.

Way too many sales and recruiting organizations are focused on past performance.

This focus may work for senior level executives, but it is not the right approach for sales and recruiting managers, especially those on the frontline, who are expected to impact and improve results.

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Measuring results is certainly not the right approach for enablement and L&D leaders who are developing services designed to build capabilities that impact performance down the road.

Conversion rates are a good example of a leading indicator that can help predict future performance. Additional examples of leading indicators to consider:

  1. Number of connects (conversations) required to convert to meeting/interview
  2. Ratio of first contact to follow-up meetings
  3. Ratio of first meetings to new qualified opportunities or job orders
  4. Ratio of leads converted to qualified leads
  5. Email response rate
  6. Open rate for content shared with prospects and customers
  7. Conversion rates between phases of the buyer’s journey
  8. Seller competencies as assessed by sales leaders

To avoid paralysis by analysis, limit your metrics to a handful and be specific about what you are measuring and why.


Getting Started

Consider the following questions to identify the relevance and effectiveness of your content services.

  1. How effective are our current content services? How are we measuring this?
  2. From which audiences do we gather feedback and how can we improve our feedback process from all audiences?
  3. Are we designing content from the perspective of the customer and the candidate or, are we creating content that is inward looking and services-centric (talking about our services)?
  4. Who or which departments create content in our organization and how is that content organized and managed?
  5. To what degree are our people using our content and how is adoption being measured?
  6. How effective is cross-collaboration between our departments for effective content creation ensuring it meets the needs of the target audience(s)?

To get started, you first need to identify your current state.

You can’t define a clear path for moving forward without first having a clear and candid understanding of where things stand today.

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Be objective in your assessment as there is no right or wrong current state. Your current state is your current state.

Besides, the best way to learn often comes from learning what doesn’t or hasn’t worked in the past. Consider the following questions as you assess the current state of your sales enablement function.

Formalized Collaboration

Consider the following questions to identify the effectiveness of your cross functional collaboration.

  1. Does our L&D and enablement team have the resources and support they need to effectively engage in cross functional collaboration?
  2. How formal are our enablement collaboration efforts?
  3. How effectively do we define roles and responsibilities?
  4. With which teams do we collaborate with best and why? Which are our weakest and why?
  5. What are the obstacles to effective collaboration for each functional/departmental area? How can we overcome them?

The Customer Relationship Spectrum

Consider the following questions to identify where your sales organization resides on the customer relationship spectrum.

  1. Holistically, where does your sales organization reside today on the customer relationship spectrum? What evidence do you have to support your conclusions?
  2. Where would you realistically like to be and why?

Sales Process Maturity Adoption Levels

Consider the following questions to identify where your sales organization resides on the sales process maturity adoption model.

  1. Holistically, where does your sales organization reside today on the sales process maturity adoption model? What evidence do you have to support your conclusions?
  2. What would your ideal position be and why?

Content Services

Consider the following questions to identify the relevance and effectiveness of your content services.

  1. How effective are our current content services? How are we measuring this?
  2. From which audiences do we gather feedback and how can we improve our feedback process from all audiences?
  3. Are we designing content from the perspective of the customer and the candidate or, are we creating content that is inward looking and services-centric (talking about our services)?
  4. Who or which departments create content in our organization and how is that content organized and managed?
  5. To what degree are our people using our content and how is adoption being measured?
  6. How effective is cross-collaboration between our departments for effective content creation ensuring it meets the needs of the target audience(s)?

Training Services

Consider the following questions to identify the relevance and effectiveness of your training services.

  1. What do our current training services focus on today? Knowledge training? Methodology training? Skills training?
  2. In which categories do we need to develop additional training services?
  3. How do we need to evolve our training services to leverage new technologies and meet the changing needs of our workforce?
  4. How can we more effectively engage sales and recruiting with training services without taking them out of the field?
  5. How can we foster more peer-to-peer learning?
  6. How can we more effectively engage managers so they reinforce training?

Coaching Services

Consider the following questions to identify the relevance and effectiveness of your coaching services.

  1. Where on the coaching maturity model does your organization reside?
  2. To what degree do your managers understand what to coach and how to coach?
  3. How effective are your managers at each type of coaching?
  4. How consistently are your managers coaching team members? In each category?
  5. What level of support and resources are dedicated to supporting your managers?
  6. What additional training and content services are needed to effectively enable your managers?

Assessing The Relevance and Effectiveness of Your Enablement Services

Consider the following questions to assess the relevance and effectiveness of your existing enablement services.

  1. How well do our enablement services help our salespeople be relevant, valuable and differentiating with every customer and prospect interaction?
  2. How well do our enablement services align to the buyer’s journey?
  3. Are we providing more services for one phase of the buyer’s journey than others? If so, why?

Integrated Sales Enablement Technology

Consider the following questions to identify and understand how well your existing sales enablement technology supports your business strategy, sales strategy and the needs of your sales and recruiting organizations.

  1. What is our enablement technology strategy? Do we invest in enablement technologies for short term, silver-bullet solutions or to support the big picture, long term sales strategy?
  2. How well does our sales enablement technology support our sales enablement strategy?
  3. What technologies are missing? What functional areas need to be supported and/or automated with technology?
  4. What weaknesses in our CRM and/or ATS need to be addressed before it can serve as a stable foundation for enablement?
  5. Which technologies does enablement own in our organization?
  6. Is our enablement technology strategy in line with our enablement maturity or are we trying to do too much or too little?

Enablement Charter

Consider the following questions to identify the effectiveness and visibility of your enablement charter.

  1. How effectively have we made the business case for sales enablement?
  2. What gaps do we need to address in our enablement charter?
  3. Who are the key executives from which we still need buy-in?
  4. Who are the important influencers in our “sale?” (your internal sales to your leaders)
  5. What additional research must be completed before we can create an effective charter?

Enablement Governance and Advisory Board

Consider the following questions to identify how enablement governance and an enablement advisory board might help you.

  1. What questions might an enablement advisory board help us answer?
  2. Which leaders should be recruited for our advisory board and why?
  3. How often should we meet?
  4. How can we ensure our enablement efforts have the cross functional support we need?

Measuring Results

Questions to consider for tracking and measuring your impact on the business.

  1. How do we define success? How do we measure it?
  2. Are the metrics we use relevant and appropriate to our enablement maturity model?
  3. How can we more effectively measure our progress?
  4. What metrics should we be tracking and measuring today that we’re not?
  5. Have we properly set expectations with executive stakeholders?

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Next Steps

To learn more about Menemsha Group’s sales and recruiter enablement solution including how we leverage innovative technology and modern learning methods to make winning behaviors repeatable and deliver predictable revenue growth, download our eBook, Menemsha Group’s Sales & Recruiter Enablement Roadmap for Scalable Growth. In the eBook you will discover the tools, technologies, techniques, methodologies, content and processes we employ to help staffing and recruiting firms attain scalable, repeatable success.

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