How to Find Winnable Deals: The Intelligent Enterprise Seller's Playbook

Anand Shah

The Intelligent Enterprise Seller’s Playbook, a framework inspired by the folks at Emergence, can help sales teams instantly recognize winnable deals and spot new opportunities to fill pipeline. The key is real-time data — not just getting a hold of it once, but using it in the right way to derive, and then act on, insights you won’t find anywhere else.

Closing large, complex enterprise deals takes skill, insight, and timing. That’s why my most recent post introduced you to the Intelligent Enterprise Seller’s Playbook, a framework inspired by the folks at Emergence, that can help sales teams instantly recognize winnable deals and spot new opportunities to fill pipeline. The key is real-time data — not just getting a hold of it once, but using it in the right way to derive, and then act on, insights you won’t find anywhere else.

In this post, I’ll expand more on the meaning behind this graph, providing greater detail about what the data in each quadrant signifies about a customer, so you know how, when, or even if you should make a play. I’ll also talk through action steps for deals found in each quadrant so you can hit the ground running. 

What is the Intelligent Enterprise Seller’s Playbook?

The intelligent enterprise sales playbook is a graph that maps business health and engagement score to identify winnable deals |

Let’s quickly review what this graph plots. 

  • The Y-axis is essentially an engagement score that shows a company’s activity around or demonstrated need for your solution. You might also think of this as their “probability to close” score. Most CRM solutions deliver some sort of number in this regard. 
  • The X-axis is a bit more tricky. If you’re a Databook user, you’ll know this as the Databook Score, which indicates propensity to buy based on a proprietary algorithm. The Databook Score takes into account a company’s business health overall, along with other variables that can impact their ability to close a deal (such as timing, investor sentiment, financial health, management intent, your targeted keywords and use cases, etc.). If you’re not a Databook user, you can come up with a reasonable approximation of the number by researching publicly available financial, analyst, and investor reports. (Of course, this could take a while and won’t be as accurate if not done in real-time, so we recommend going the Databook route.)
  • The size of the bubble plotted correlates to deal and/or company size, and the color coding is entirely up to you. At Databook, we often color code to distinguish existing customers from prospects. You might also code companies by industry, deal status, or quadrant.

While anyone can source and apply publicly available data (along with substantial elbow grease) to create this graph, for now we’ll assume you have implemented the Databook application and have easy access to the data you need. With just a few clicks, you’ve plotted your numbers into quadrants like the chart demonstrates.

Now what?

From Plot Points to Sales Plays: What Each Quadrant Tells Us

Let’s break down the Seller’s Playbook square by square, looking at why companies land in a specific quadrant, what insights you can derive about their placement, and which steps will most benefit your sales strategy moving forward.

Top Right: The Sweet Spot

What does it mean?

Companies positioned in the upper right quadrant represent your highest potential committed deals. They have both the propensity to buy and the business health necessary to close the deal on time and on track. Furthermore, data decisively shows that your solutions are well aligned to these companies’ Board priorities and financial pain points. Management has likely discussed your use cases and has significant incentive to purchase soon.

What’s the right play?

      • DO: Start here, and spend time to convert these must-win deals. The ball is in your court. Ensure the sales decks and conversations clearly align to board priorities, as well as the financial and operational pain points your solution addresses.
      • DO: Check the sum total value of these deals. Are they enough to meet quota? 
      • DON’T: Take your foot off the gas. If the deals in this quadrant don’t deliver enough revenue, you have all the more reason to close these winners faster and pull in additional deals from other quadrants.

Top Left: Check Your Timing

What does it mean?

These are your current quarter committed deals that are most likely to push to next quarter or “close lost.” Why? Because the data shows they aren’t feeling the financial pain and urgency needed to move forward fast. It’s likely not the right time for any kind of large expansion deal (>$150K). 

What’s the right play?

      • DO: Inspect these deals closely. What’s missing? Did the timing slip up?
      • DON’T: Assume you should focus elsewhere. The Y-axis graph placement indicates higher engagement and probability of closing, so these deals are worth your time. 
      • DO: Engage with an SVP+ Economic Buyer. It may be the CFO, and your goal is to confirm that there’s a compelling event to instigate urgency for the business, while determining if budget exists to close this quarter. (Look for another upcoming post that will outline exactly how to do this.)

Bottom Right: Pipeline Potential

What does it mean?

Companies landing here are often overlooked because they’re not immediately winnable deals. But make no mistake: Opportunity abounds here. In fact, I like to think of this as your magic pipeline quadrant. Companies here represent high-potential target opportunities and accounts. Data confirms that there are C-level investments at these companies focused on your solutions. Moreover, these companies are experiencing financial pain and urgency. In other words, companies here are ideal for landing within a 3-6 month timeline—if you do your homework and engage before the competition.

What’s the right play?

      • DON’T: Wait. Time is truly of the essence if you want to convert these opportunities on schedule. Remember that urgency is temporary.
      • DO: Immediately kick off outbound sales motions (such as inside sales, ABM, field sales, QBRs with customer success at existing accounts,etc.). The X-axis placement shows these are high propensity-to-buy accounts. They just need outreach, nurture, and engagement.

Bottom Left: Re-Evaluate

What does it mean?

The companies found in this quadrant have the lowest probability of becoming “best-case” deals. Why? Because the data indicates they are experiencing significant headwinds and/or they have limited financial pain and urgency to close. Furthermore, they’re not deeply engaged with your solution or use cases. It’s highly possible they’re not in the market for your solution right now.

What’s the right play?

      • DON’T: Assume this is the full story. Check your CRM hygiene and make sure the data is accurate. Sometimes mistakes happen.
      • DO: Apply pressure. Get the company’s account team to make a decision fast. They need to either commit or push out, so you can focus your efforts elsewhere on more winnable deals.

Data-Driven Insights Will Always Improve Your Selling

If there’s one takeaway from my explanation of this graph, it’s that data is incredibly powerful when you know what to look for and how to use it. My sales team uses it to assess our customers and prospects. And we also use it at a leadership level, because it offers high-level visibility into sales team efficiency. With a quick glance at this chart, I can see where deals are landing, which in turn tells me where sellers need to be focusing more attention or if they might be able to use their time more productively. 

Now that I’ve walked you through a greater explanation of the Seller’s Playbook, you have a better idea of how to apply this tactical exercise for your own needs. Now, keep boosting your skills by going back to the basics of business--check out my video series here

About the Author
  • Anand Shah

    Anand Shah is CEO and Co-founder of Databook. Anand brings to Databook more than 15 years of experience as an expert in consulting Fortune 500 CXOs on how companies drive top-line growth for the enterprise. Before founding Databook, Anand was an Engagement Partner at Accenture Strategy, leading their engagement with the World Economic Forum on Digital Transformation, and a global lead for Accenture’s Strategic Insights group. Anand holds a dual-MBA from Columbia Business School and London Business School, a Master’s Degree in Finance from the University of Reading, and a Bachelor’s Degree in Computer Science from Imperial College London.

You might also like...


Navigating the CFO’s Mindset: What Every Seller Should Know

Here are some of the key principles sellers should note when engaging financial decision-makers in large enterprises.

Read more: Navigating the CFO’s Mindset: What Every Seller Should Know


4 Strategies for Building a Champion in a Remote World

Building a champion in a remote-first world presents unique challenges. These four tactical strategies can give you an edge.

Read more: 4 Strategies for Building a Champion in a Remote World


C-Suite Engagement Guide

Getting to the c-suite isn’t easy—but it’s not impossible either. Here’s everything you need to know about how to engage the c-suite the right way.

Read more: C-Suite Engagement Guide