6 Considerations for an Enterprise Sales Enablement Pilot

 In All Things Productivity, Blog

As the sales cycle at B2B companies continues to become more complex and product/solution information is more abundant, sales leaders are realizing how educated and opinionated prospects are by the time they get to talk to them and because of this know they need to teach prospects something new in their 1:1 encounters or else risk frustrating a potential customer. CEB talks about 57% – which describes how far along in the purchase process a typical B2B customer is before they engage directly with any supplier. This is critical because, during that time, customers learn about products and decide on what product features they think they need for their business.

At the same time, marketers at B2B companies have implemented a myriad of systems over the last decade to tracks what prospects are doing in that first 57%—from Web Analytics to Marketing Automation to Social Monitoring—allowing them to have greater insights into prospects than ever before.

With a plethora of data and an ever increasing rate of content production, sales innovators are going beyond the normal prescriptive sales process and creating a new vision for Sales Enablement focused on proactively driving client outcomes using data. At Docurated, we’ve worked with hundreds of enterprises on their journey to a new state of Sales Enablement and have seen what works and what doesn’t in terms of launching “pilots”.

1. Define the Core Business Driver for Sales Enablement

Because Sales Enablement is such a “hot” concept, it has also become an overloaded term. Sales Enablement can be applied to meeting generation, education, closing, expansion—anything that happens within the sales funnel. However, in a pilot, you need to think deeply about the specific goals for your business. The table below articulates example pilot goals for different types of businesses/teams.

Unique Aspect of Business Current Situation Sales Enablement Pilot Sales Enablement Outcome
Complex Sales Long and unpredictable new rep ramp time Focused on new rep onboarding Less rep turnover and higher percentage reaching quota
Bell curve High % of B performers Give B reps insight into what A reps do B reps start achieving same results as A reps
Competitive category Difficult selling cycle with high closed-lost rate Sales Enablement focused on product/service differentiators Earlier action on competitive risks to reduce closed-lost rates
Millions of SKUs Low customer satisfaction due to poorly educated sales reps Sales Enablement focused on upskilling sales reps Better sales education leads to higher customer satisfaction


2. Define the Starting Point

We’ve found some patterns in logical starting points for Sales Enablement teams. The most progressive Sales Enablement teams start with a pilot, versus taking the RFP approach. We fully support the Pilot first mentality and encourage everyone we talk with to invest their resources there.

We hear from our customers and see from our own experience that the RFP process is time and resource-consuming and outcomes are often undesirable. The more onerous the RFP process, the more likely it is that nothing will be done and the status quo remains, and often times there is failure to differentiate among mature products or identify innovators.

Successful pilots involve one or a few product lines or teams and create proof points to continue scaling.

Starting Point Pros Cons
Mature product/service line
  • Likely large source of revenue for the company, so impact would be big
  • Likely high profile clients and some of your company’s top performing “influential” sales reps.
  • Sometimes can be hard to get top performers to buy into trying something new
Mature product/service in transition
  • Likely attention from the entire commercial team and a desire to try something new
  • If in a dying market then a risk of throwing good money after bad
  • If moving from one go-to-market to another potentially a significant degree of change management
New product/service
  • Can “tell the right story at the right time” from the beginning
  • Limiting by product line makes it harder to tell impact of potential gains across all product lines
Recently acquired produce/service
  • Likely standalone team, so easier to roll out and drive adoption
  • Need to rationalize just one team participating in the pilot

We also see customers looking to run a pilot against a segmented customer tier. The matrix below can be used as a guideline to pick the right sales enablement approach based on a tiering of customers by size and product/service complexity.

  • Tailored: Personalized message focused on most pressing business needs to a wide range of customer stakeholders in order to build that consensus. Reps who really tailor with every interaction typically have a small set of ‘named’ accounts, anywhere ranging from a single digit count to the mid-twenties.
  • Prescriptive: Accurately predicting each sales scenario and providing pre-canned supporting content for each persona and situation. Especially good for new or inexperienced reps and highlight regulated industries.
  • Hybrid: A mix of tailored and prescriptive. Prescriptive used earlier in the funnel and as a deal progresses messaging becomes more tailored.
  • Automated: Fully-automated and personalized Sales Enablement marrying content with CRM, Marketing Automation and other tools.

3. Define What Data Your Team Needs

Data is at once the greatest opportunity and greatest challenge for most large companies. Businesses are awash in data but often struggle to leverage it. For the Sales Enablement pilot, you need to define a practical and achievable list of the right data to marry together that can surface the most accurate recommendations to your team:

    • CRM: Customer Name, Industry, Opportunity size, Opportunity Stage, Contact title, Contact role, Competitors, Legal Terms, Contract Length, Product/Service, Options, Tier, Primary Contact Role, Technographics, firmographics, intent, engagement, microblog
    • Email: Sender, Recipient, Body, Date, Attachment Types, Attachments
      Local storage: Directories, File types, file interaction length of time, opens, copies, changes, prints
    • Sharepoint: Historic activity, microblog posts, opens, cuts, prints, names, roles, relationships

Cloud storage: usage, views, freshness, author, shares, downloads, replies, forwards, searches, historic activity

  • Intranet: teams, permissions, searches, content types
  • Marketing Automation: Leads, domains, lead score, site activity, inferred location, first-page visit, last page visit, downloads

In our experience, CRM and Email data is a must and organizations pick 2-3 other content stores for the pilot.

4. Define IT Involvement

Connecting to all your structured and unstructured content is an IT project – no matter what anyone tells you. You need to make sure all the underlying permissions are set correctly so that no data is leaked or no non-compliant information is sent to prospects. Bring IT into the project early and partner with them on the repositories you are going to connect the Sales Enablement platform to.

5. Define Success Criteria

By definition, a pilot is just a starting point. As such, make sure to clarify what you don’t plan to accomplish in the pilot. Set expectations upfront of achievable metrics that can be used to measure the success of the pilot. At Docurated, we try to distinguish Lagging Indicators—the financial outcomes of Sales Enablement like new business, upsells, and renewals — from Leading Indicators. Leading Indicators can include:

  • A score measuring sales rep adoption volume (e.g., Daily Active Users)
  • A score measuring how well reps use your product or service
  • A customer satisfaction metric like C-SAT or Net Promoter Score
  • The conversion rate of first meeting to a second meeting
  • The conversion rate of meeting to pipeline
  • Pipeline velocity
  • The change in marketing content usage
  • The change in time reps spend prepping for meeting
  • The change in ad-hoc requests to marketing
  • The number of “at risk” accounts that were moved back to pipeline

Consider aggregating these into a “scorecard” for the overall health of the Sales Enablement pilot.

6. Define the Roadmap

At large companies you may end up with multiple, overlapping, and confusing Sales Enablement initiatives across many product lines and departments. Consider a Sales Enablement Steering Committee or Center of Excellence to bring these initiatives together to ensure internal efficiency and a smooth external client experience. For more information on scaling Sales Enablement at your company please read The Rocket Fuel For Sales Leaders Who Need to Scale.


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