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How to Win Big Sales Opportunities with Big Plays

How to Win Big Sales Opportunities with Big Plays

blog author
Written by Mike Schultz
President, RAIN Group

Too many sellers have similar problems:

  • Bloated pipelines filled with dead wood
  • Lack of clarity on what opportunities to focus on
  • No plan to win their biggest, most important opportunities
  • Losing too often to the competition

In our article, How to Fill Your Sales Pipeline, we shared how to make your pipeline real and manageable. But how can you identify which sales opportunities are worth pursuing? And once you do, how can you go above and beyond to outsell the competition and win your biggest deals?

Sellers often treat their pipeline opportunities the same. They define need, qualify, propose, present, and wait for a win or loss. Maybe a few require more focus, but not always the right ones. If you don’t know where to invest your time and energy, your performance will suffer.

In this article, we provide a framework for managing your opportunities and share when and how to use Big Plays to win your most important sales.

Without a rigorous, consistent, and thoughtful approach to deciding which opportunities to pursue, you're likely to:

  • See lower overall average win rates
  • Open yourself up to discounting and price pushback
  • Spend tremendous amounts of time and effort with little or no return
  • Pursue most sales opportunities with an average focus whether they're deserving of your attention or not
  • Get frustrated and demotivated with your lack of success in selling

Some opportunities need more focus, enough that you should make Big Plays to win them. Others should get less focus, even to the point where you actively try to minimize your time on them. Knowing which opportunities are worth your investment requires forethought and a framework for analysis.

If your pipeline is full enough, you need to make choices on where to spend your time so you can yield the most wins. If your pipeline isn't full enough, you need to make the same choices to maximize your prospecting time.

For each opportunity, the key is to define your pursuit intensity.

Pursuit Intensity: The Secret to Driving Sales Opportunities

The framework we teach in our programs on winning sales opportunities is the CARE framework. CARE is a mnemonic device, but also reminds you to be careful, thoughtful, and disciplined as you choose how to pursue your sales opportunities.

When you take a structured approach to assessing pursuit intensity, you gain time to focus on the best sales opportunities and win more of them.

Competitive Position

Evaluate yourself for this sales opportunity against the following 5-point scale in relation to your competitive position.

  1. Pole: (As in pole position—the best starting position—in a car race.) You have a superior relationship with the buying team, and the following criteria apply to you:
    1. You’ve been involved in the buying process early
    2. You may have shaped the buying process
    3. Your solution fits the buying decision criteria
    4. You’ve proven that results are achievable with clients of a similar industry and size
  2. Challenger: You have a good connection with some of the buying team, have been involved in the buying process early, fit most of the decision criteria, and have proven results are achievable.
  3. Upstart: You have a connection with some of the buying team and have advantages that can make you an attractive option to the buyer.
  4. Pack: You have a surface-level relationship with the buyer, have been looped into the process along with other competitors, have a somewhat good understanding of the decision criteria, and have had a limited discussion on your ability to deliver desired results.
  5. Late: You have no prior relationship with the buyer, have been looped into the buying process late, are unsure about the competition and decision criteria, and haven't had an opportunity to demonstrate that desired results are achievable or that you deserve stronger consideration.

Depending on where you are in the sales process and future interactions you have with the buyer, your competitive position may change. As you uncover more information, you should reconsider your pursuit intensity and adjust your plans accordingly.

As you evaluate the competition, ask yourself:

  • Are you aware of all the competitors involved in the sale?
  • Are you aware of the current advantages you have over other competitors?
  • Have you demonstrated the advantages of your solution to relevant stakeholders?
  • How do you usually stack up against your competitors?
  • Does the buyer prefer working with one of your competitors?
  • Have you substantiated your advantage over the competition?


Attractiveness is often the most important category when analyzing pursuit intensity. Assign a 1-5 score within each of the criteria for this category and add them up for an overall attractiveness score.

Decision Timing

  • Has the buyer indicated a time frame for making a decision? Is it favorable?
  • How many people are involved in making the decision? Will multiple stakeholders slow down the process?
  • Is the buyer waiting for a budget cycle?
  • Is there anything that might delay the decision-making process?
  • Does the buyer have a history of 'having a time frame' but then pushing it off?

Note: A longer time frame isn't always a bad thing. When driving demand and shaping a buyer's agenda for action in big ways, it might take longer to make a decision.


  • Is the potential for revenue with this buyer desirable?
  • Is your profit margin favorable?
  • Is there a favorable recurring revenue stream?

Growth Potential

  • Is the buyer in a profitable industry for you?
  • Do you have other offerings that may interest the buyer in the future?
  • Has the buyer's company been growing?
  • Does the buyer have the financial capacity to keep buying from you?
  • Is there a potential to expand into different departments, geographies, or buying centers?

Attractiveness of Logo

  • Will winning this company draw other companies to you?
  • Does the buyer have an attractive and recognizable brand?
  • Is the buyer in an industry where you want to build more depth?

Relationship Strength

To evaluate the strength of your relationship with buyers, you should ask yourself:

  • Does the buyer see you as a partner?
  • How does the buyer view the value you deliver?
  • If you were to end the relationship, how would the buyer perceive that loss?
  • If someone else proposed to the buyer that they should replace you, how would the buyer view that?
  • To what extent are you required to participate in a buyer's competitive bidding process?
  • How likely are your buyers—specifically the people with whom you have direct relationships—to replace you on their own?
  • Does the buyer recommend you to others?

Click here for more detail on how to evaluate your buyer relationship strength. >>

Effort to Win

To evaluate the amount of effort it’ll take to win the sale, you need to answer the questions in each of the following categories.

Time Investment

  • How much time do you anticipate investing in this opportunity?
  • How easy is it to work with the buyer?
  • Will you be looped into the implementation phase, which may take away from your core selling activities?

Financial Investment

  • Are you pursuing a Big Play that's costing you money to win the sale?
  • Are you giving away samples, trials, etc. beyond what you usually do?

Resource Strain

  • How many resources do you need to loop into the process to help win?
  • Do you have access to necessary resources?

Political Clout

  • Do you know the Domino or other internal decision makers who may make your life easier to win the sale?
  • Do you have a long-standing relationship with the buyer and organization?
  • Do you have any prior bad experiences that may cause buyers to perceive you negatively?

Click here to learn more about Decision Roles. >>.

Cultural Fit

  • Do your work styles, missions, beliefs, and values align?

The Value of a Big Play to Win Big Opportunities

You’ve determined your pursuit intensity. You may even have a few leads that look promising. So how do you win your biggest sales opportunities?

Sellers who win big sales go over-and-above the competition to win them. When the potential impact for you is huge, you want to do everything possible to get the win. Anything less and you essentially serve up the win to your competition.

When you need to win and win big, you need a Big Play.

A Big Play can be thought of as a "partner investment." This is because bold strategies tend to be perceived by the buyer as an investment in a long-term relationship.

Examples include:

  • Flying a buyer and their team to a customer site to allow them to experience what it's like to work with you and see your offering in action
  • Offering a money-back guarantee for a pilot project to prove to the buyer your solution will work
  • Creating an executive retreat where you bring together company leaders to brainstorm ways they can capitalize on new trends in their industry
  • Making some or all of your fees contingent on achieving success milestones for the buyer
  • Partnering with a buyer in a new way to co-create value
  • Creating a surprise-and-delight moment in the sales process that makes the buyer say, "Wow, that must have taken a lot of effort. Nobody else did that for us."

Big Plays can be practically anything that surprises and delights, pushes the relationship strength meter high, or drives the buyer to choose you.

A smart Big Play can be worth the investment, whether that investment is in money, time, staff, development, or otherwise.

When to Use a Big Play

It's time to make a Big Play when you want to either create a major sales opportunity or win one. However, you can only use them so often. They take real investment. If they don't, they're not Big Plays.

You need to make a case for why a Big Play is a good idea for a particular opportunity. Consider the following 7 criteria when deciding whether to make your move:

  1. Effort: How much effort will it take to execute the Big Play?
  2. Cost: How much investment will the Big Play require?
  3. Acceptance probability: Big ideas don't matter if the buyer won't play along. If you're thinking of inviting them to, say, an all-expenses paid conference in another state, you should be fairly positive the invitation will be received warmly.
  4. Timing: How long will it take to execute the Big Play?
  5. Payoff amount: What’s the possible payoff in terms of revenue, margin, loyalty, or ROI?
  6. Payoff likelihood: What are the chances that the Big Play will generate the desired result?
  7. Opportunity cost: What are the chances that other Big Plays at this or another account are more attractive than this one?

Big Plays should be employed when pursuit intensity is high and the value of winning the sale is significant. If the opportunity meets these criteria, then a Big Play may be just what you need to put yourself and your company over the top to win the deal.

4 Examples of Big Plays

Not every Big Play is created equal. While every kind of Big Play requires some sort of investment, the type and level of that investment vary.

The first step in creating a Big Play is to define the goal you're trying to achieve. It could be that you need to:

  1. Strengthen your relationship with the key buyers
  2. Create new relationships to win the sale or grow the account
  3. Maximize the buyers' perception of the value of moving forward or choosing you
  4. Displace or win against a strong competitor

All four of these challenges can be overcome with the right Big Play. Here are examples of Big Plays that address these 4 areas.

1. Strengthening Relationships

One seller we know of invited their buyers to an off-site 1-day all-expenses-paid executive retreat. They invited leaders from their existing accounts that they knew their prospective buyers would like to connect with, and brought in a noted industry speaker.

They positioned the retreat as an exclusive gathering for senior leaders to exchange ideas, share insights, collaborate on issues, and find inspiration among an elite group of industry leaders. And they hosted golf.

This is big, even for a Big Play, but this client had accounts in the tens, and sometimes hundreds, of millions of dollars.

2. Creating New Relationships

One seller regularly offered to perform research for high-pursuit-intensity opportunities by using their company's unique capabilities and resources in the specific area the prospect focused in.

The cost to them? Committing several important team members to the research effort. The research regularly allowed them to establish connections with new contacts at the company and create groundswells for taking action.

3. Increasing Value Perception

To maximize the perception of value in the eyes of the buyer, we've seen sellers:

  • Facilitate value discovery sessions with their buyers to co-create value and brainstorm ideas.
  • Bring buyers to their client sites for meetings and tours to show off their capabilities in action and the positive effects of working with them
  • Create something custom for the buyer. For example, we know of one company that was selling ERP software to retail chains. As a part of their sales process, they visited store sites, interviewed key stakeholders, and did an analysis of what they learned. The seller presented this analysis along with a roadmap for improving the company's processes. No other company did this, and they were awarded the business.

4. Competitive Positioning

You can also use Big Plays with existing accounts to protect them from competitors and grow them. For example, say you're vulnerable in a certain area that leaves the door open for a competitor to establish themselves with an existing account. You may be able to prevent a competitor's entry by inviting the account to become a beta tester for your development of a new product or service the buyer would find valuable.

Not only will you give them the beta test for free, you'll also collaborate with them on making it just right for their environment.

The client gets to influence the design of the product or service, gain features or functionality they otherwise wouldn’t, and save on costs. At the same time, you collaborate deeply with your client, strengthen your relationship with the account, and preempt competitors.

Mixing and Matching Big Plays

A Big Play can also be designed to address multiple challenges. In one sale that we know of, several of the decision makers behind a purchase had a preference for a competitor. The seller worked with an internal champion to identify another senior executive at the company who was only loosely involved in the purchase decision but would be influential should she express a preference.

The seller had to create a new relationship and position himself favorably against the preferred competitor. To do so, he created an experience around his offerings and worked tirelessly to arrange schedules and build a case for why this other senior executive should attend. After weeks of effort, he was able to do so.

At the end of the session, the executive said to the core buying team, "This was great. I look forward to seeing it get underway and working with these folks."

What had been a 9-month sales process quickly turned to contracting. Two weeks later, the seller won the opportunity.

The possibilities for Big Plays are endless. These examples are meant to get the juices flowing. The idea is that when the stakes are high, a Big Play can be just what you need to stack the deck in your favor to help you win the deal.

Drive and Win Sales Opportunities

When you systematically assess your sales opportunities by identifying your pursuit intensity using the CARE framework, you’ll know which opportunities are worth pursuing and which ones are worth pulling out the stops for a Big Play.

Last Updated June 6, 2023

Topics: Sales Opportunity Management