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Best Practices for Sales Enablement

What are the steps to building a successful Sales Enablement strategy? If this is your first time, read this and level up from day one

Why is it so hard to find best practices on sales enablement? 

Even though sales enablement is such an important function within most emerging, high growth companies the profession itself is still in relative infancy. Despite mentions of sales enablement in Oracle sales training materials from the late eighties - the term began to pop up and more before the dotcom bubble burst in the late nineties/early two thousands. 

In the last five years this growth has exploded, with now over 10,000 people worldwide listing sales enablement in some part of their job description - a 3x increase over this period. 

As a result, thought leadership is still relatively immature as industry leadership has developed. Currently the landscape can be broken down into the following categories:

  1. Early movers - bloggers, independent consultants and retiring practitioners who were able to recognise the trend in sales enablement or remained in the field due to happenstance
  2. Analyst firms - Gartner, SiriusDecisions, Forrester and TOPO are all examples of analysts who have covered the sales enablement space 
  3. Vendor research - software vendors in the enablement space release inhouse research collected from surveys or partner with analyst firms to co-produce reports 
  4. Practitioner lead - when sales enablement professionals contribute their own thoughts via publications, podcasts and social media 
  5. Industry events and associations - the largest of which is the Sales Enablement Society 

 

Limitations of current thought leadership in sales enablement 

Given the maturity of the sales enablement industry there are inherent limitations to each of the authorities listed above.

Early movers have provided a good sounding board for changes in the profession however most lack the innovative best practices which truly come from the front lines. 

Analyst firms have produced a minimal amount of research targeting the entire industry, with trends in enterprise sales enablement best practice dominating the majority of publications. Modern buyers are also challenging the independence of analyst relations - with a number of large vendors having visible paid relationships with these companies. 

Vendor research has lead the charge in evangelising sales enablement best practices however it is hard for buyers to avoid skewed research which is used to generate demand for particular product features. 

Practitioners are becoming increasingly vocal however it is still hard to activate trailblazers due to confidentiality agreements and the lack of a united industry platform to advance sales enablement thought leadership. 

Industry events are on the rise - however sponsorship and revenue motivators can affect the quality of content and attendees generally are in the junior to middle management level; with a shortage of options for C-level/VP level execs with interest in improving sales enablement best practice

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How to build a successful Sales Enablement Plan? 

Define Your Sales Enablement Goals and Metrics 

The first step in creating a sales enablement plan is to have organizational adoption around what needs to be achieved and how it should be measured. 

For most firms goals include: 

  • Reducing sales cycle length 
  • Increase ACV (Annual Contract Value)
  • Reduce ramp time (how long it takes a sales rep to reach their target quota)
  • Improving breadth of training possibilities 
  • Improving deal conversion
  • Increase total sales 

For most sales enablement roles - goals like those listed above should be adopted as part of the job description and KPIs. Goals may also be more specific in nature and pertain to more specific business objectives:

  • Increase salesforce retention
  • Boost deal win rate against a particular competitor 
  • Ensure all deals are executed with respect to a particular method or strategy 

Once the goals have been determined it is necessary within a modern sales organization to match a measurable metric to each goal to ensure progress is being made. A goal can also have two metrics - one is a leading indicator to indicate if your sales organization is trending towards the performance standard you have defined and a lagging indicator to demonstrate if it actually has been achieved. See below for examples:

  • Reduce sales cycle length
    • Leading indicators: Time between 1st call to proposal, proposal to contract
    • Lagging indicator: Total sales cycle time from 1st conversation to closed won
  • Increase ACV
    • Leading indicators: Opportunity size (estimated), proposal amount
    • Lagging indicators: Closed won deal total
  • Improving training possibilities
    • Leading indicators: Number of courses created, time spent in each module
    • Lagging indicator: Number of certified sales reps 

 

Generate Organizational Buy-in to Your Sales Enablement Goals

It is all well and good to define your sales enablement goals and metrics - however in order for a sales enablement plan to be successful it requires buy-in across the entire organization to see that these results are achieved. 

For example, you may need product to release key fixes to allow you to overcome key challengers in competitor deal cycles or require sales leadership to be personally involved in the generation of new training assets. 

You may find that your goals may also require a shift after receiving the executive input so this is something to be prepared for. 

 

Adopt a Sales Methodology Across the Organization 

In order to have uniformity across the sales org, it is extremely important to advocate and standardize a single sales methodology for the next 12-24 months. 

Organizations in the United States typically choose between methods like BANT, MEDDIC or the Challenger Sales method. 

You may wish to create your own, if so it needs to cover the following areas:

  • Qualification Criteria for New Customers
  • Process from First Content to Closed Deal
  • Exit/Entry Criteria from Each Stage
  • Alignment to your CRM of Choice
  • How to report deal progress to executives 

 

Sales Training & Onboarding Best Practices 

During the emergence of sales enablement as a profession - the limitations of the role were initially siloed only to facilitate training and onboarding of new hires. Although the job mandate is now much broader - training & onboarding remains a fundamental part of any sales enablement plan. 

Here are some tips for you to see stronger results:

  • Shift from single-event to continuous learning opportunities 

Most firms host a singular sales kick off event and an initial two week training intensive. Complement this activities with ongoing training broken into quarterly initiatives.

  • Embrace certification and recertification 

Examinations are a strong way for sales reps, management and the enablement team to see if training & best practices are being adopted in the organization. Furthermore, even if reps achieve certain levels of certification key materials need to be continually revised and updated - so be sure to create recertification courses or to include important components of previous modules in new training courses 

  • Encourage peer based learning 

One of the most important pivots in the last ten years has been the inclusion of high performing sales reps in creating and administering training programs. Not only does this spread “tribal knowledge” it also ensures your onboarding program includes the most-up-to-date information as strategies are shared directly from reps on the front lines. With these developments, the best sales enablement practitioners are often top reps who share a passion for helping others more than themselves.

  • Provide 1-1 mentorship opportunities 

Each new sales candidate going through the onboarding program should be paired with a mentor, who ideally has 1-2 years of experience in the organization. Mentors and mentees should meet once per week and sales enablement should administer the logistics and satisfaction reporting on these sessions for the entire sales org. 

Top performing companies also include a mentoring session every 10 weeks with a senior executive - which can be a great way for newer reps to feel like they have access to top stakeholders in the company 

  • Break up learning modules & make them independent

The thorn in the side of any sales enablement program manager is a bulky sales GTM plan or playbook riddled with interdependent training modules. 

In simpler terms, reps who have not taken previous certifications or trainings may not be able to understand or benefit from further training without completing given prerequisites.

This can create bottlenecks and the invent you need to update aspects of your training - the entire catalogue of training materials can be affected at once. 

Instead try to design training on specific topics which can be taken stand-alone, ideally across a handful of sessions.

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Sales Enablement Technology Best Practices 

The golden rule for sales enablement technology/tech stack is only to buy tools once you have 

  1. Defined your sales enablement goals
  2. Assigned reportable metrics to these goals
  3. Received feedback and buy-in from management 
  4. Defined your core sales methodology and standards 

 

Once you have completed the above here are some important products to consider:

CRM - Salesforce, Hubspot, Pipedrive and Freshsales are the most common CRM choices. From an enablement perspective - deal process should be defined with clear CRM stages, automation should be used to allow reps and managers to triage deals appropriately and data hygiene must be healthy to facilitate data driven decision making 

Virtual Meetings - Zoom or Google Meets to host virtual conversations 

Call Recording - Meeting intelligence can give insight into how customer interactions can be improved at scale. Popular tools for this are Chorus and Gong

E-learning & Certification - Do you have a tool to host all training that is developed, can measure viewership and provide basic examination/certification processes for your team?

Sales Content Management - having a system to track, manage and allow reps to edit sales collateral from their chosen CRM

Outbound Prospecting/Call Making - Hubspot CRM, Outreach and Salesloft are all industry leaders in allowing sales teams to prospect and call at scale. These can also be referred to as “sales engagement” tools 

Reference Generation and Management Tool - to generate, organize and deploy customer quotes 

Proposal/Quotation Tools - do we have a mechanism to create, track and edit offers dynamically with customers 

E-signature - can deals be signed or routed to the signing party effectively 

 

Best Practices for Sales Content Strategy

A sales enablement plan should define the scope for the enablement team to provide just-in-time content to the entire organization. Before any content is created the following should be evaluated:

  • Has sales been surveyed to determine which content is/isn’t working and what new content is needed
  • Has marketing and sales been consulted on what assets are being used? Objectively how effective are they?
  • Have closed won and closed lost customers been surveyed or called to ask what could have assisted them better in the buying process 

Once this has been conducted, sales content strategy needs to be segmented around internal assets and external assets development.

Internal assets refer to things like a detailed competitor matrix, battle cards, scripts and objection handling guides - used by reps to help them improve when speaking to customers 

External assets refer to things we send to customers in order to help them reach a buying decision - case studies, meeting summaries, sales decks, proposals and contracts. These are generally managed inside a CRM via a sales content management system like GetAccept

When putting together external assets remember the following rules:

  1. Limit slide length to 5 slides, maximum 7
  2. Include social proof from customers in the same industry, role, location
  3. When presenting an offer, keep the contract separate to the offer terms.
  4. Try to use quote, phrases from the prospect as much possible versus your own language 
  5. Encourage reps to personalize with research, fact findings and prospect company colours/logo. If you are sending static PDFs or word docs they are not worth sending 

 

Best Practices for Customer References

In the past, the generation and provision of customer references has been the sole function of marketing. Increasingly, high performing teams are assigning sales enablement with this key organizational responsibility.

Sales are closest to the customer, sometimes communicating more than several times per week; so generating these references can be less arduous than when sourced through traditional marketing channels. 

For reps of all abilities - citing customer stories can be a way to appear more knowledgeable about the industry and can be particularly helpful for building trust via expertise. 

Furthermore, when deals go dark - customer stories can be shared as a form of passive nurture exercise. 

One way in which customer references can be generated on mass, in high quality are through sales enablement managing a review generation program.

Long form reviews are more scalable than case studies and hold more relevance with buyers who value that they share both positives and negatives versus conventional marketing which is vendor biased. 

Sales enablement teams can work with sales operations to port these reviews into a chosen CRM and allow reps to select and share this content at will. In addition, stronger reviews can surface candidates for additional reference activities like longer form content, webinars or customer calls.

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