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How to Leverage Sales Effectiveness to Win More Deals

By Tom Pisello | November 27, 2018

BB-1-750x581 What do World Series Champs and Content-Driven Sales Reps Have in Common?

I was catching up with Peter Ostrow on his way to a Red Sox World Series home game last month. As a lifelong Boston fan, attending this game with his brother was a dream come true. Fortunately for us, Peter, a Practice Director for SiriusDecisions, still took time out from his World Series excitement to take our call and bring us up to speed on his latest research on Sales Enablement. Maybe it was having the World Series top of mind, but certain similarities and KPIs stood out to me, no matter what type of field.

Although a good defense is often touted as the key to victory for championship teams, the World Series is often won or lost not on pitching, but on hitting. You need runs to win, and the best hitting team is most often the winner.

In fact, statistics show that the team with the better season-long on-base plus slugging (OPS, a key performance benchmark calculated as the sum of a player’s on-base percentage and slugging average) has won each of the last five World Series and eight of the last 11. The good news for Peter and the Boston fans going into the Series was that no other team had a better batting average and OPS than the Red Sox. So it was no wonder that the Red Sox took the Series, dramatically outscoring the LA Dodgers.

According to Peter, when it comes to sales enablement, winning or losing could be similarly predicted. It’s not about the defense, staving off the competition, but about the offense: the ability for a seller to leverage sales content in the “moment of truth”.

BB-2-750x581 And most organizations recognize how the right offense and content fueled engagements can drive success, with the majority, 62% of B2B marketing organizations, now having a centralized content team to produce content, according to SiriusDecisions research. This in addition to content generated from product teams and sales groups, almost as if each group is being paid by the pound for producing content.

So there’s no shortage of sales content, however:

So how do you excel at sales content to get the winning customer engagement advantage? According to Peter, getting your sales content right can help you round the bases and win:

FirstBase-750x582 First base: Facilitate buyer decision making
It is important for sellers to help buyers with their evaluations, providing key content to help facilitate buyer decision making throughout the buyer’s journey:

  1. Educationhelping buyers understand their challenges better, helping to prioritize issues and present the “art of the possible”.
  2. Solution – guiding buyers to the right solution, explaining key features and quantifying the benefits and financial justification business case.
  3. Selection – providing pricing and proposals, competitive insights and total cost of ownership comparisons, to help the buyer make the final decision.

Providing buyer’s journey content can help inspire and accelerate the prospect from “do nothing” to “Yes”.

SecondBase-750x582 Second base: Deliver content in context
Content is needed throughout the cycle, to make each seller more capable, confident and credible throughout the prospect engagement.

The best sales enablement teams categorize and assure they have the right content classified and grouped into it’s intended purpose as follows:

  1. Empowerment content – helping sales be ready for client engagements, with educational content, providing them with the education and knowledge needed to better communicate and quantify differentiating value and sell more effectively. For internal consumption, this type of content delivers the “What to Know”.
  2. Activation content – helping provide the messaging, insights, data, analytics and storytelling to share with prospects. This type of content is designed for external consumption, and is the “What to show”

Both empowerment and activation content can be best further sub-divided into the context of when it will be used:

  1. Pre-engagement – content used to entice the prospect to engage, or to prepare and ready the seller for the engagement.
  2. During engagement – content used to help fuel the prospect conversations and reviews.
  3. Post engagement – resources and content used to follow up with the prospect after the conversation and engagement, to gain internal consensus and approvals.

ThirdBaser1-750x582 Third base: Serve the right content at the right time
Sales reps often have trouble finding the content they need when they need it. It’s hard to mount an offense and hit successfully when your sellers are wasting much time searching, reaching out to marketing and others for what they need, or recreating content they can’t find.

The ability to search and have the results be relevant is important, serving up just the right pieces of content to move the deal forward – not too much to overwhelm the seller or prospect or too little to empower and activate.

Mobile is essential, so that when on the road and meeting with customers, can get to the content when needed most, without having to struggle with download delays or connection challenges.

And when the seller finds the right content, they need to be able to easily customize and personalize the content, smartly, intelligently and as automated as possible for each unique engagement and conversation.

Going beyond, Peter indicates that the best enablement creates the ability for content to “find” sellers – trigger based on the sellers’ activity, the context of the selling situation, and buyer interaction.

And the best practices don’t stop there. When content is delivered to buyers it is essential to automate this sharing and provide tracking of how prospects interact with the content. Which content do they engage with, how long did they engage, and most important in today’s decision by buying committee environment, who did they forward the content to?

Reaching third base successfully, helping reps find the right content, can help provide a key advantage, with:

HeadingHomer2-750x582 Heading home: Optimized outcomes
According to Peter and SiriusDecisions, a meager 33% of the content assets are tracked back to the outcome. This means that although they may be tracking the basics, 2 out of 3 organizations don’t tie content usage and consumption back to outcomes – like how the content can help accelerate sales cycles, improve win rates or increase deal size.

Without this visibility, it’s impossible to track and understand how seller consumption of learning assets or buyer engagement with selling assets is making a real impact.

If you are able to make this connection, you can achieve three key improvements to hit the ball out of the park:

The Bottom-Line
Good hitting has been proven as a key indicator of generating a World Series win. A good offense, via sales content management, is similarly vital to winning the sales game.

According to Peter and SiriusDecisions, enhanced content-driven sales effectiveness can deliver significant tangible outcomes and competitive advantage:

  1. Increased rep efficiency – less time wasted searching for content, customizing wantonly and recreating content
  2. Improve marketing productivity – content that is developed is used, less investment in wrong types and pieces of content
  3. Improved selling effectiveness – Accelerate win rates, deal velocity, deal size, renewal rates and customer lifetime value (up and cross-sell).

To learn more about content-driven sales effectiveness, join our upcoming webinar featuring SiriusDecisons’ Peter Ostrow and Mediafly’s Isabelle Papoulias.

Tom “The ROI Guy” Pisello is an entrepreneur, speaker, and author of the book Evolved Selling™: Optimizing Sales Enablement in the Age of Frugalnomics. He joined the Mediafly team in 2018 through the acquisition of the company he founded and led, Alinean Inc. In his role as Mediafly’s Chief Evangelist, Tom is responsible for developing new practices for sellers and marketers to communicate and quantify business value to increasingly frugal buyers. He also leads Mediafly’s Advisory Services group in helping companies evolve their selling practices from transactional to value-led. Outside of the office, he is the proud father of two daughters.

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