Sales Enablement Guide

Developing a Sales Enablement Strategy

Explore our step-by-step breakdown of establishing, implementing, and scaling your sales enablement strategy. We've outlined the 5 key components of comprehensive sales enablement and how to set up your strategy for long-term success.
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Whether you’re building a strategy from the ground up or refining a system that’s already in place, it can be daunting. Follow these step-by-step guidelines to implement and develop a foolproof sales enablement strategy.

Start with the 5 key ingredients for success:

Step 1: Establish clear structure for your sales enablement strategy

Establish a formalized structure of your sales enablement strategy as early on as possible. Without an established strategy in place, your sales enablement plans can (and probably will) unravel quickly. Because of the ambiguity that is associated with the function of sales enablement, it’s imperative that your C-Suite and all teams your strategy will touch are cross-functionally aligned with what the main goals and expected outcomes of the strategy are. Typically, this will come in the form of a charter.

Step 2: Create a sales enablement charter

Transparently outline the sales enablement charter of your organization early and often. Because the expectations of an enablement strategy vary across companies, it’s important to formally align at the very start of your planning process. Ensuring that your enablement person or program has a complementary vision of a sales enablement is the only way to set a strong foundation for success. 

Are you looking for a point person for your learning and development efforts? Refinement of your onboarding processes? Someone to centralize cross-company communication? All of this sounds great, and it can all be included in your charter, but the important part is that it’s there, clearly documented and laid out, setting the groundwork for a scalable strategy that’ll stick. 

A formalized sales enablement charter is more likely to gain executive support and engage cross-functional collaborators in these efforts. Aligning with your exec team throughout the process is key. The author of  the charter should first sit down with executives to define what they’re looking for in this sales enablement strategy. Don’t be intimidated by creating a charter. It doesn’t need to be a step-by-step guide of your enablement processes; after all, things will change along the way. The charter should act as a blueprint, outlining the mission, key stakeholders, and expected results of your sales enablement process.

CSO Insights 2019 annual sales enablement study found that organizations that had a formalized enablement charter saw win rates 8.7 percentage points higher than the study’s average. The results are there, and they’re important. So what goes into a viable formal charter? Key aspects to outline in your charter include: vision, mission, goals, strategy, tactics, and outcomes. 

Step 3: Prepare and consult a customer-centric sales enablement strategy 

When you’re setting that foundation and building out a sales enablement strategy, or refining what's already in place, you should approach the development through the lens of the Customer Journey. This should be at the center of both your sales enablement strategy and your formalized sales process, the two should be analogous in structure and goals.

Creating a Customer-Centric Sales Enablement Strategy

Sales enablement strategies should arm reps with the information they need to have impactful conversations with customers — where they are.

That’s where the importance of the buyer’s journey comes in. A key component of a comprehensive sales enablement plan is a fully mapped-out customer path. That way, you can provide your reps with the knowledge that they need to curate their messaging specifically for where prospects are within their customer journey. This should uncover potential gaps in your current messaging and sales enablement strategy. A strong sales enablement plan supports teams from buyer’s initial awareness all the way through adoption. 

One CSO Insights study found that 42% of organizations that do align their sales enablement services to the customers paths achieve an 8.1% better win rate. That means that not taking the time to check in and ensure that your current strategy is well aligned is costing you too much. 

Step 4: Make sure your sales enablement strategy is aligned

Evaluate how aligned your Sales Enablement strategy is with your customer’s journey by asking yourself these questions: 

  • Have you collaborated with sales, marketing, CX, product teams and your existing customers to map out your buyer’s journey?  
  • Is that journey the primary design point for your current SE strategy?
  • Do you have specified content for reps to utilize at each stage?
  • Does your current sales enablement tech stack empower reps to have curated conversations that move prospects through that journey?

Step 5: Understand how sales enablement strategy impacts the customer

Customers have an increasing amount of control over the buying process. They’re doing the bulk of their research independently before any initial interaction with your reps. It’s important that your reps are able to pinpoint where your prospects are within their buyer’s journey and curate their messaging accordingly. 67% of B2B decision makers say they prefer not to interact with a salesperson as their primary source of research (Forrester). Consider not only where your prospect is in the buyer’s journey, but when they want to talk: 

- 19% of buyers want to connect with a salesperson during the awareness stage of their buying process, when they're first learning about the product.
- 60% want to connect with sales during the consideration stage, after they've researched the options and come up with a short list.
- 20% want to talk during the decision stage, once they're decided which product to buy. 

Map out these stages and the coinciding content to give consistency to your process. The first step is to create a customer-centric strategy. From there, arm your reps with up-to-date information. 70% of companies rated their ability to close new deals as the top aspect of selling that needs major improvement or process redesign. Build out an enablement tech stack that equips your reps with the knowledge that they need to move customers through that journey seamlessly. Once this process is well defined and deeply ingrained, your sales team should recognize the buyer’s journey as second nature and have the tools to interact effectively at each and every step of the way. 

Step 6: Know what content should be in your sales playbook

Once you’ve fleshed out and aligned your sales enablement strategy with the customer journey, you can focus on building out a Sales Playbook. This playbook should serve as an integral part of your strategy, the centerpiece of your documentation process, and an instant access point of the most relevant assets and information for your reps to relay to prospects. 

  • Competitive battle cards
  • Objection handling
  • Best practices
  • Ideal customer profile
  • Industry specific messaging
  • Sales documentation process
  • Email/call/demo scripts
  • Product and feature information 
  • Pricing breakdowns
  • Security FAQs

Step 7: Define sales enablement for all roles 

When it comes down to it, sales enablement is bigger than just sales. Every year, sales enablement as a function is reaching beyond and across team lines. The term “revenue enablement” is one that you might be seeing coming up more often. It asserts that your strategy should support every single person who has any customer-facing touch points. And why shouldn’t it? Each and every individual that interacts with your customers, at any point in their journey, has the ability to impact their customer experience. If you’re going to invest in enabling your sales reps, why not apply those same tactics to enable as many cross-functional teams as possible?  

To do this, you’ll need enablement to be well-defined early on, often, and across teams. Specify what successful enablement looks like for you and your team, and ensure that key stakeholders are involved in that conversation. Enablement is often thought of as a way to bridge the all-too-common gap between Sales and Marketing. The obvious function of enablement in this regard is to streamline the process that moves marketing’s valuable content and collateral over to sales to utilize those assets and close more deals. These two teams are essential and should be the primary touchpoint of your initial enablement design plan. Of course, enablement should foster stronger communication between these two teams, while simultaneously looking beyond the imagined restrictions of enabling these two teams alone. 

As the reach of enablement continues to grow, we can expect to see enablement expanding its impact even further. In fact, this is something you should be focused on. Research has shown that this is becoming a company wide-effort, increasingly looping in their C-Suite and L&D teams on the endeavor. If you’re arming your sales team with the information that they need to effectively communicate with prospects, why wouldn’t you put the same emphasis on supplying support teams with that knowledge as well? Empowering all customer facing teams with the knowledge that they need to have consistent messaging across the board will enhance your buyer’s experience and lend itself to new or expanded business. 

Psst! Enabling Support teams is nothing to scoff at. Did you know that 70% of revenue is derived from existing customers? A deal doesn’t fully close once the ticket is filled out. Keeping reps and support empowered and on the same page is too valuable to overlook. All customer-facing teams should be armed with updated product information, feature breakdowns, and customer stories that they need to create and foster authentic and durable relationships with buyers.       

By holistically mapping out what the expectations are for each team in terms of enablement, you’ll better position yourself to track the measurable outputs of your sales enablement strategy. Not to mention that you’ll be getting more people involved and invested in your efforts. Internal advocates for your sales enablement strategy will strengthen your process as a whole. 

Step 8: Empower Valuable Conversations

Consistently enabling all customer-facing teams to have meaningful conversations with customers and prospects is an integral part of a strong sales enablement strategy. Here at Guru, we believe conversation is key. According to a Salesforce study, 92% of all customer interactions happen over the phone. The trends show us that we’re going back to the basics: strong one-on-one relationship building. 

Customers expect personalized conversations now more than ever. They’re looking for consistency across sales and support teams. And even though the bulk of selling happens over the phone, 85% of prospects and customers still report being dissatisfied with their on-the-phone experience. The technology is bountiful, but it means nothing without utilizing its potential. For the last few years, the industry has focused on automation technologies; now is the time to leverage the analytics that those technologies have provided us with to tailor and personalize messaging. 

According to a Chorus report, reps are talking through 61% of discovery calls and are asked on average between 7-8 questions. This same report found that top managers invest over 12 hours in call reviews. In fact, a 3x increase in call reviews doubled meeting quota attainment, so cultivating those genuine conversations is key in our current selling climate. 

Sales enablement professionals should prioritize jumping onto sales calls to scope out exactly what kinds of questions their reps are facing everyday. This builds a level of empathy and understanding into your problem solving strategies. So, how do you ensure that your cross-functional teams are communicating the same message, clearly and consistently? 

Here's a quick list of the must-haves in your conversational toolkit. 

Live chat: Has your organization implemented a live chat tool? It's not for everyone! But consider this, live chat can drive 3x – 5x more conversions.

Tools to consider:

  • Intercom
  • Drift 
Conversational intelligence: Gives you the ability to capture positive feedback and create best practice guides to include in conversations.

Tools to consider:

  • Chorus
  • Gong
Real-time knowledge management: Centralize the internal knowledge that your reps need at their disposal to execute valuable real-time conversations. Make your company’s intelligence so readily available that referencing it becomes instinctual. 

Tools to consider:

  • Guru
  • Confluence

There is tons of tech software that empowers valuable conversations. Conversational intelligence capabilities will help your reps cut through the noise and focus on what's really important: driving valuable conversations that will close deals. 

Interested in how real-time knowledge management can drive better conversations?

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Step 9: Build out an intentional tech stack

It’s now assumed that enablement strategies are rooted in technologies, but in reality, they’re only a single piece of the pie, and it’s easy to assume they’ll solve all your enablement problems. Bear in mind that, “For any technology implementation to work, the first step must be behavioral. Only then can tools to enhance efficiency be considered.” (Mark Savinson, Forbes

Programs are plentiful, but there’s no magic catch-all software solution out there. It’s important to implement an intentional tech stack that actually empowers your teams. These tools should keep your teams within their workflows. Use tech that can produce insights native to your workflow. 

78% of sellers indicate that their current tech stack does not address their selling challenges. By those numbers, it’s safe to assume that there’s room for improvement. Enablement technologies reach beyond traditional sales asset management (SAM) tools. While SAM tools are critical, content is not the only thing that helps reps do their jobs. 

Here’s a comprehensive look at the tools and software to include in your sales enablement tech stack:

Sales engagement:

What is sales engagement software? 

  • Combine your sales prospect data and your marketing outreach by adding email prospecting solutions. Integrating with your CRM foundation, these offerings give you high-level insights. Which messaging is resonating? What do ideal contact cadences look like? Capture all of that information while reducing manual contact logging. 

When should you invest in sales engagement software? 

  • Once you’ve discovered your product market fit, you have to be able to scale your prospecting efforts, and doing the actual outreach messaging on a case-by-case basis is a poor use of a sales rep’s time. These solutions allow you to automate many of those efforts while also giving your team visibility into how your messaging resonates. 

Conversational intelligence:

What is it? 

  • Also known as sales coaching software, these solutions integrate into your meeting platform in order to automatically record, transcribe, and analyze your sales calls. Automatically identify next steps, common objections, and how often you use filler words in order to become a more effective seller.

When should you invest in conversational intelligence software?

  • Once you’ve expanded to the point that you’re no longer able to sit in and contribute input into every meeting, you still need to get insights on how your reps are performing. Recording and coaching technology gives you the ability to listen to calls retrospectively, address potential messaging or delivery shortcomings, and assess the performance and technique of individuals as well as your team’s overall approach. This will help you identify what’s not working and scale what is, effectively giving you the power to train and replicate the practices of your strongest reps. 

Sales asset management:

What is a SAM?

  • External marketing assets: they’re numerous, varied, and constantly being updated. A sales asset management system allows you to find the best assets for your prospects, ensure that they’re up-to-date, and track their impact and usability throughout the process. 

When do I invest in sales management software? 

  • As your company’s addressable market grows, your sales and marketing orgs will expand and realign. This is when you need an understanding of which marketing efforts are driving revenue and which aren’t. An effective SAM solution will give you these insights by showing how specific assets and collateral influence opportunities and deal closures.  

Knowledge management:

What is knowledge base management software

  • You need a place to house your company’s internal knowledge, and that’s what a knowledge management system is there to do. This is our sweet spot. An essential part of a successful enablement strategy is empowering cross-communication internally. Capture and surface everything from hard knowledge, like charts, marketing assets, benefits explanations, and policy info, to soft or tacit knowledge, like learned best practices and process how-to’s. An effective knowledge management system will keep teams within their current workflows and provide the knowledge they need to confidently do their jobs where they already are. 

When should you invest in knowledge management software? 

  • As you scale your product and team, it’s imperative that you start documenting internal knowledge (such as sales playbooks, products FAQs, and competitive analysis). As you grow, there will be a bigger and bigger need for your reps to have verified real-time knowledge on hand. Not only do you set individual reps up for long term success, but you ensure a standard level of knowledge across the organization, which creates coordination and consistency.

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Sales readiness:

What is sales readiness software? 

  • Also known as learning management systems (LMS), sales readiness software enables leaders to get new team members up to speed on everything they need to know about the company’s product, processes, and priorities. Allow people to learn at their own pace with a lesson repository, and make sure everyone is always compliant with required certifications. 

When should you invest in a sales readiness software?

  • Once your company grows to the point that a formal review process is needed, it’s safe to assume you need to standardize your onboarding process. By ensuring that every rep starts off with the same level of knowledge, you can track policy compliance while also creating an environment where reps can be assessed fairly.

Step 10: Measure the outputs of your sales enablement strategy

Sales enablement professionals know that the proof is in the pudding. Without it, you won’t see much investment by your exec team. You’ve probably gathered by now that there are a multitude of tactics, strategies, and tools that contribute to an enablement solution. Regardless of the size of your enablement effort, be it a complete overhaul or small shifts, be sure to make measuring the outputs of your efforts a top priority. 

So, how do you do it? Measuring the ROI on enablement can be difficult. Often, it comes in the form of tracking ramp time and sales cycles. But as we’ve seen, these efforts have a further reach across a company; to evaluate that, you’ll have to track a  dynamic and comprehensive set of metrics to demonstrate the effectiveness of your strategy. Measuring and aligning on indicators of success is the only way to validate and program and ensure continued scaling of the strategy you’ve built moving forward. 

Our best practices for measuring sales enablement success:

Monitor adoption

  • This is your first step. Track the adoption of the tools and processes that you’ve implemented by every person that your strategy should be touching. 
  • Utilize a simple survey application to gain perspective on this as early as possible. 
  • Establish what your benchmark is for healthy adoption of your tools. After you’ve laid the groundwork to track adoption, you can turn your attention to analyzing key metrics. 

Identify sales enablement metrics and KPIs to continuously analyze

  • Analyzing what knowledge empowered reps to close deals. 
  • Pinpoint what information is lending itself to the most closed deals. If you can identify and create data around this, you’ll be positioned to optimize your knowledge creation efforts. 
  • With better insights into what specific content and knowledge is resonating with your prospects, you can better inform your marketing and sales teams and hone in on creating relevant material. 

Evaluate impact on revenue goals

At the end of the day, sales enablement is a revenue-driver. Track how your strategy impacts your company’s revenue goals at large. 

Analyze sales cycles

The speed of your sales cycles is a key indicator of the success of your strategy. The little things add up and slow down sales cycles. Here are a few tricks to ensure that your enablement plan is ramping up your sales velocity:

  • Integrate your enablement solution into workflows. Make sure that knowledge and assets are readily available with the apps that reps already are. This will help them stay within their workflows and close deals faster. 
  • Make sure content is verified. By keeping information that reps relay to prospects up-to-date, they can feel assured in their responses and avoid the “I’ll get back to you on that” step of the sales process. 

Establish what you consider to be high quality activity for a rep (or a customer support or whatever team member your strategy supports) 

Examples of trackable high quality activities:

  • Time to second deal 
  • Deal velocity
  • Number of calls held per closed-won opportunity 
  • Messaging consistency 
  • Track who is consistently using a particular asset that is proven to be most successful for a particular ICP. 

Track employee ramp time 

  • Grouping teams into cohorts by start date
  • Measuring their success holistically against other cohorts to see whether your enablement plan is moving the needle or not. 

Dig in on how to measure the success of your enablement strategy with our 5 key metrics to track your sales enablement success

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