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The statistics about number of stakeholders involved in a purchase are misleading they fail to account for the decision-making role, department, degree of authority, or influence of each of these stakeholders. Are they four user buyers and one VP? Or, are they four VPs across different departments and someone from IT? These aren't likely scenarios, but you get my point. To be fair, Brent Adamson and Matt Dixon allude to this in The Challenger Customer when citing a quote from an IT vendor: “For us it’s not 5.4 people, but 5.4 committees of people!” Still, it would be interesting to analyze the typical power and role structure in a software purchase. Using a weighted average, where each stakeholder type is assigned a value based on their management level, would likely be more revealing and useful. For example, assigning higher values to VPs than to individual contributors could provide a clearer picture. My guess is that applying this approach would show that software buying complexity has increased by an order of magnitude—not only are there more stakeholders involved, but more of them are now at the executive level with the CFO chief among them. This change in the size and makeup of the buying group has made mapping, navigating, and driving consensus more challenging than ever. So, in 2024, navigating 8.2 committees might be closer to the new reality.

Win rates and deal size increase the more buyers are involved in the sales process. Let's call that buy-side multi-threading. Equally important is sell-side multi-threading. Otherwise known as team selling. Gong Labs just released research that shows that team selling has a tremendous impact on win rates. Involving just one more persona - sales engineer/sales manager/CSM - in the deal DOUBLES win rates. GONG TEAM WIN RATE ANALYSIS  ::  No team selling = 15%   ::  One persona = 30%  ::  Two personas = 43%  ::  Three+ personas = 50% Doing and expertly coordinating both can have a compounding effect. The best metaphor I can come up with is thinking of the AE as a wedding planner They plan and coordinate who sits next to whom and when.

Brent Adamson and Matt Dixon, whether they intended to or not, ignited the buyer enablement movement. I'm rereading The Challenger Customer from a different perspective. We recently introduced a buyer engagement platform, and I'm curious to see if a reread will inspire ideas on how technology can help sellers apply the insights from Brent's and Matt's sequel to The Challenger Sale. They use a compelling analogy to illustrate how complex the B2B buying environment has become beyond just having to manage a markedly higher number of stakeholders. 'Business is increasingly running itself like a dysfunctional legislative body.’ They go on to say, ‘The buying process suggests that in most B2B commercial environments, purchasing looks a lot like a bickering Congress or Parliament on a bad day.’ I hope not, but I get their point. The comparison is pertinent. Within buyer organizations, there are many often hidden agendas, political structures that don’t appear on org charts, power brokers, and internal ‘lobbyists’ we must be aware of to strategize how to drive buying group engagement, consensus, and preference. How can we successfully navigate this complexity? Multi-threading is crucial, but building direct relationships with multiple stakeholders can be challenging. The key is to humanize each stakeholder, even if we don’t have direct access. Consider: What’s top of mind for them? What project or initiative are they working on that they must nail? What is <stakeholder name> thinking about after they log off? Why is this so important to them? What’s the upside/downside? What’s their “emotional win”? What does a “fantastic” outcome look like for both them and the group? This approach helped us recently land a six-figure deal. It informed our business case narrative, every conversation, every communication. Instead of thinking of a buying committee as a ‘dysfunctional legislative body,’ think of them as a group of colleagues who genuinely care about doing a great job and making meaningful contributions. By learning about and being sensitive to their individual and collective worries and aspirations, you'll be better equipped to drive consensus and align your solution with the greater good. That’s buyer enablement. #buyerenablement #revenueenablement #salesenablement

For over five decades, sales methodology experts have insisted that pain is the singular driver of buyer action. This thinking is rooted in loss aversion theory, which suggests people are more motivated to avoid losses than to pursue gains. However, this perspective is outdated and inadequate for addressing today's increasingly high-stakes, complex, multi-stakeholder, and scrutinized purchasing processes. In my experience working on very high-value deals, tapping into aspirations as the primary driver is far more effective than focusing on pain. Aspiration is defined as a "strong desire to achieve something high or great." A board-level priority represents exactly that—an ambition that the entire organization rallies around and discusses at every executive meeting. So, anything you do to show that your solution can: Increase the odds of reaching that aspiration Accelerate its achievement Help them exceed it will get you much farther than focusing on pain. Once you understand the aspiration, the focus shifts to homing in on the fear of failure. The negative consequences, and therefore the fear of not achieving them, can be severe. My thesis is that focusing on aspirations taps into emotions—hope and fear—that are far more powerful than pain. Corporate aspirations reflect a public declaration that the company can and must exceed the status quo. There’s already consensus around these aspirations, making them non-negotiable goals the whole organization is aligned on. So, my advice is: Ride the aspiration wave instead of making pain waves.

The Shift Sales Enablement Leaders Need to Make: From Content Management to Change Management Sales Enablement typical relies on Product Marketing to deliver rep-facing content: playbooks, product info, sales collateral, case studies, etc. While content may be king, real value doesn’t come from creating and managing content—it comes from managing change. This is where Sales Enablement needs to shine. Your need to collaborate with product marketing to translate terabytes of content into sound bites, sellers can use in conversations. Step 1: Translate marketing messaging into sales speak . Step 2: Double down on change management by: Driving adoption: Ensuring salespeople not only access but actively use the training and resources provided. Reinforcing skills: Continuous coaching and support help reps master and retain new skills long-term. Fostering accountability: Implementing systems that track progress and hold reps accountable for adopting new processes and tools. When enablement leaders focus on change management, in partnership with product marketing, they drive long-term, sustainable growth.

"Peeling the onion" discovery is a bunch of baloney. "Peeling the onion" is the prescribed recipe for discovery offered by an online training "masterclass" on the topic. “Peeling the onion" typically refers to the process of uncovering layers of complexity or deeper truths about a situation or issue. It suggests that, just like an onion has many layers, some subjects require careful exploration to reveal underlying factors or motivations. The concept relies on the equivalent of the “5 Whys” technique, designed to drill down to the true cause and cost of the problem. In theory, this sounds reasonable. If you walk into a discovery call cold, this is certainly better than nothing. But here's the problem with this so-called "best practice." There’s no mention of pre-call preparation. No emphasis on conducting research to uncover likely board-level priorities. No guidance on forming pain and value hypotheses rooted in that research. No requirement to become an expert on your buyer persona's desired outcomes, OKRs, their jobs-to-be-done, and the challenges they face. No focus on understanding industry trends, regulations, or shifts that are putting pressure on the buyer’s business. And no consideration of identifying the characteristics of their ideal customer profile. To excel at discovery, you don't need to peel the onion. You need to show up with a bushel of pre-peeled onions that your buyer actually cares about. White onions. Red onions. Shallots. These are the vertical/persona/use case issue categories salient to your buyer. Great discovery is a combination of meticulous call preparation, targeted vertical/persona/use case-specific insights, and thoughtful questions that expose the need for your differentiated value. This approach lets you lead with an informed perspective and opens the door to more meaningful conversations—ones that align with your buyer’s priorities, drive real impact, and initiate and accelerate deal momentum.

Here’s how I drive buyer engagement for high-value opportunities from the get-go. Before a discovery call, I create a buyer-branded microsite using WinRoom, starting with the Executive Summary page template. I leverage our account research GPT to gather insights—CEO quotes, performance trends, recent press releases, SWOT analysis—to formulate pain and value hypotheses tied to a strategic priority, using McKinsey’s SCR (Situation-Complication-Resolution) framework. I relabel "Complication" as "Challenge" and "Resolution" as "Required Capabilities" for a buyer-centric focus. The “Situation” and “Challenge” sections synthesize the pain hypothesis. The “Required Capabilities” synthesizes the value hypothesis. To personalize further, I add a buyer-specific screenshot (e.g., their homepage, CEO Letter to Investors or a recent press release) and a CXO quote to headline the “Show Me You Know Me” section. This discipline allows me to open the call with insights aligned with board-level priorities. It reminds me of my days at Gartner when I had the most insightful research at my fingertips for opening calls. Next, I craft the agenda and add discussion questions for each topic in WinRoom. This becomes my call plan. I’m ready. I walk into the call excited to help the buyer make a meaningful impact on something that truly matters to the C-suite, confident that we can make it happen. During the call, I use targeted, vertical market use-case-specific statements and questions to explore and expose current state gaps and risks, and position our differentiated value as the ideal solution. Post-call, I review the recording and summary and add the 'Current State Limitations' template to the buyer WinRoom. The template precisely and concisely describes typical gaps, risks, and required capabilities for the vertical's key use cases. This enables sellers to help the buyer define the problem statement more thoroughly and effectively than they could on their own, while ensuring it aligns with the seller’s differentiated value. I edit the template based on our conversation and quickly share it with the buyer through their WinRoom, which now also contains the agenda and discussion questions for our next call. I invite the buyer to add comments or edits to the summary. Now we’re aligned, sitting on the same side of the table. The lesson: Buyer enablement starts way before the initial call. NOTE: The template wording is crafted with input from top reps, product marketing SMEs, and, ideally, actual customer and prospect conversations. No need to reinvent the wheel every single time. No need to learn how to write copy like David Ogilvy or Don Draper. And, better alignment with marketing positioning and messaging. Years ago, I coined the phrase “Prepare to win!” It’s a mantra that guides this entire process and ensures success. P.S. WinRoom evolves, with follow-on pages added at key engagement points.

Introducing Playboox WinRoom WinRoom equips sellers with the ability to create shared buyer-branded microsites to collaboratively build business cases, mutual action plans, and financial impact analysis that drive buyer engagement based on your differentiated value. With WinRoom, you can hyper-personalize every aspect of the revenue cycle—from initial engagement to deal management, onboarding, and renewal. Our team of revenue enablement experts works with you to develop business case, mutual action plan, and ROI calculator templates tailored to your verticals, personas, use cases, and messaging, which makes it easy for sellers to rapidly build and personalize the buyer WinRoom aligned with your messaging. WinRoom offers a unique set of capabilities, including buyer engagement analytics, an ROI calculator, an asset library, video screen recording, AI writing assistance, and testimonial templates. The Task Dashboard and due date notifications help sellers stay on top of MAP task deadlines. Our integration of WinRoom, Playmaker, and Ebsta AI-enhanced revenue intelligence brings the first and only solution that facilitates guided forecast and pipeline management, deal execution, call management, and buyer enablement within Salesforce. The Playboox Revenue Execution platform gives you everything you need to drive flawless execution across your revenue team and cycle. Shout out to our friends at Ebsta for this collaboration.