B2B Deal Evaluation Factors

CFOs can veto most purchases, and they don't care about features. 88% of CFOs say they need detailed cost and ROI analysis before approving a tech purchase. We used Wynter to survey 50 CFOs from $50M+ B2B companies. We asked what they need to see before approving your next tech purchase. Want to get to "yes" faster? Focus on these: • Hard ROI, not soft benefits. As one CFO put it: "If an ROI involves replacing labor it is not a hard ROI unless I will truly cut the headcount or hire less people. If the headcount will be reassigned I think of that as soft benefits since my total expense does not change." • Risk is a dealbreaker for 44% - "Risk is a veto criteria," one CFO told us. Another said: "Risk is an overall governor and can kill a deal if not understood and mitigated." • Company size matters - Small company CFOs (200-500 employees) want immediate financial impact. Large ones (1000+) want what one called "cost information including the long-term vision of the cost profile." • Feature comparisons must link to outcomes - "I care about feature comparisons only to the extent that they are linked to outcomes and benefits." Most revealing response? "For me to make a decision, a buyer needs to provide clear, business-driven justification with a focus on: cost, risk, how does this tool solve a critical problem, alternatives." The takeaway? If the deal size is large enough to summon the CFO, your business case should be built from the CFO perspective, not the user perspective.

💡 In B2B marketing, the fundamental unit of purchase decision-making is the Buyer Group. In other words, getting the different members of the Buyer Group to agree on a specific vendor is what has to happen to close a deal. LinkedIn partnered with Bain & Company and NewtonX to research the main drivers of Buyer Group decision-making. We found that [1] being known across the Buyer Group of a target account and [2] being trusted by the marketplace were the most important dimensions when being bought. 🎯 81% of purchases were made of vendors that everyone or almost everyone in the Buyer Group knew on Day One. 🎯 Only 4% of final purchases that were made were of vendors/products that only the expert recommenders knew. 🎯 Buyer Group members will pay more for products that their colleagues already know (by a ratio of 3:1), because your colleagues knowing about a vendor makes it a less risky choice. 🎯 Buyer Groups will not fight for products that their colleagues don't know, even if they think that product is better (3:1) because persuading colleagues to take a risk is more difficult than sacrificing potential functionality/quality. 🎯 All other things (like price and product quality) being equal, Buyer Groups will pick a well-known product/vendor over ones that are less well-known (3:1), because less well-known vendors were harder for the group to agree on. 🎯 The further away you are from technical knowledge of the product in your Buyer Group role, the more you rely on brand factors to shape your decision-making. Legal, finance, HR and Procurement, for example, have huge influence here and are much more influenced by brand than product experts and users. We feel our findings open up a few new ways of thinking about how to be successful in B2B marketing and selling - and show the role played by brand in every live sales process. Brand is not just an investment in getting bought in the future. It is a form of decision-insurance and risk-mitigation that makes it one of the main reasons that products get bought right now. Jann Martin Schwarz Jamie Cleghorn Tom Stein Nick Primola Rob Gold Sascha E. Jackie Cutrone #B2BMarketing #BuyerGroupMarketing #B2Believe

In large deals, the real competition is rarely another product. It is inertia. The most effective large deals are often shaped early. When the business user begins exploring a problem, and the right conversations start happening at that stage, the deal gradually evolves into a sole-sourced decision rather than a late-stage RFP comparison. Because once a deal reaches a formal RFP stage, many vendors appear to be at the finish line. In reality, the direction of the deal was usually influenced much earlier. Many deals look healthy for months. The champion is engaged. The demos land well. The value is understood. And then, close to the finish line, the deal slows down… or quietly becomes “No Decision.” More often than not, the issue is not price or product. The deal simply never travelled far enough inside the organisation. Large buying decisions are rarely made by one person. They are shaped by a group. The business user evaluates usability. IT looks at integration. Security looks at risk. Finance looks at cost. Leadership looks at long-term impact. Each of them is solving a different problem. If the conversation is only happening with one or two people, the deal remains fragile. This is where relationship mapping becomes one of the most important disciplines in selling large deals. Not just knowing your champion, but understanding the ecosystem around the deal. Who influences whom? Who signs. Who can block progress quietly? Who needs confidence before the decision moves forward? Building that map takes time. It means asking better questions. • Who else will review this internally?  • Who will be responsible for implementation?  • Who owns the budget?  • Who needs to see this before we move ahead? As more people across the organisation understand the value, the deal becomes stronger. It stops being one person’s initiative and starts becoming a shared decision. And shared decisions move forward with far less resistance. The best sellers know that closing large deals is not just about presenting a solution well. It is about shaping the deal early and building alignment across people, priorities, and perspectives. #LargeDeals #Enterprises #SST

Did you know there's a shadow committee evaluating every B2B deal you're trying to close—and you've never even spoken to them?! Research (https://lnkd.in/g_nsV2cH) from the B2B Institute, NewtonX, and Bain & Company reveals a fascinating blind spot: "Hidden Buyers" wield nearly equal decision-making power as your primary sales contacts (49% vs. 51%)—but they operate with completely different priorities. These key influencers may be from procurement, finance, or legal. Here's the cognitive disconnect that may be costing you deals: ➡️ Your primary buyer thinks like an engineer: Does this solve our problem? Can we implement it? What's the ROI? ➡️ Hidden Buyers think like guardians: Can we trust this company? What's their reputation? Are they legitimate players in our industry? This creates what I call the "feature-trust gap." While you're perfecting your product demo, procurement is Googling your company's credibility. While you're calculating ROI, legal is assessing your long-term viability. That means, if you're relying on product features and innovation alone to make the sale, you might lose out.  In B2B, emotional decision-making might be more critical than in B2C, not less. Consider the psychology: ✔️ Higher financial stakes amplify the need for confidence ✔️ Professional reputations are on the line—no one wants to champion a vendor that fails ✔️ Complex buying processes create more friction points where trust can erode This validates a principle I've long advocated: **great brands avoid selling products.** They don’t promote features and tout technologies without linking them to emotional values. They cultivate deep trust that travels through organizational hierarchies, reaching stakeholders you'll never meet but who hold veto power over your success. The strategic implication isn't to abandon product excellence—it's to recognize that brand strength and technical superiority must work in concert. Your Hidden Buyers aren't evaluating your latest feature release; they're evaluating whether betting their career on your company is a smart move. Question for reflection: When did you last audit your brand through the lens of someone who's never met you but whose opinion could sink your deal? P.S. For those interested in learning how to build this kind of emotionally-grounded brand power, I dive deep into these principles in "What Great Brands Do" (https://lnkd.in/bp22ccV)— still relevant after all these years.

𝗧𝗼𝘁𝗮𝗹 𝗖𝗼𝘀𝘁 𝗼𝗳 𝗔𝗰𝗾𝘂𝗶𝘀𝗶𝘁𝗶𝗼𝗻 (𝗧𝗖𝗔) – 𝗧𝗵𝗲𝗿𝗲'𝘀 𝗠𝗼𝗿𝗲 𝘁𝗼 𝗖𝗼𝘀𝘁 𝘁𝗵𝗮𝗻 𝗣𝗿𝗶𝗰𝗲! The single largest driver of demand is “Cost,” which brings "latent demand" in-market in the form of "active demand." The total amount of potential demand in the market is determined by where cost is on the Price Elasticity curve. As the cost goes down, demand goes up...and vice versa. For B2B SaaS, that Price Elasticity value is generally around -0.25 to -0.5, meaning that: 👉 Price increases by 10% 👉 Subscriptions decrease by 2.5% to 5% Markets are generally VERY sensitive to price. The 4Ps still matter, even in B2B markets! In fact, market demand is SIGNIFICANTLY more sensitive to Price than Promotion (all that marketing you're doing). 👉 A 10% excess Share-of-Voice only leads to 0.5% to 1% market share growth per year. --- 𝗡𝗢𝗧 “𝗣𝗿𝗶𝗰𝗲” 𝗯𝘂𝘁 𝗖𝗼𝘀𝘁! Buyers don't feel the Price you sell for – they feel what it 𝗖𝗼𝘀𝘁𝘀 them to buy. Your product’s Pricing often represents only a small fraction of the buyer’s “𝗧𝗼𝘁𝗮𝗹 𝗖𝗼𝘀𝘁 𝗼𝗳 𝗔𝗰𝗾𝘂𝗶𝘀𝗶𝘁𝗶𝗼𝗻," which includes – 1️⃣ Product Price (what you charge) 2️⃣ Buying Costs 3️⃣ Risk Costs "Buying Costs" can be significantly greater than the product's price and break out into: 1️⃣ Cost of the Buying Process itself (𝘥𝘰𝘻𝘦𝘯𝘴 𝘰𝘧 𝘱𝘦𝘰𝘱𝘭𝘦 𝘸𝘰𝘳𝘬𝘪𝘯𝘨 𝘰𝘷𝘦𝘳 𝘮𝘰𝘯𝘵𝘩𝘴) 2️⃣ Deployment & Data Migration Costs (𝘯𝘰𝘵 𝘦𝘷𝘦𝘯 𝘚𝘢𝘢𝘚 𝘥𝘦𝘱𝘭𝘰𝘺𝘴 𝘪𝘵𝘴𝘦𝘭𝘧) 3️⃣ Integration Costs into Existing Systems & Processes 4️⃣ Training & Social Acceptance Costs for the Staff using the product --- Finally, there's the considerable 𝗥𝗶𝘀𝗸 𝗖𝗼𝘀𝘁. This isn't something ethereal; it has a measurable real-dollar value. 🔸 No one in B2B buys on "Value"; they buy on "Risk-Adjusted Value" 𝗪𝗶𝗻 𝗯𝘆 𝗢𝗽𝘁𝗶𝗺𝗶𝘇𝗶𝗻𝗴 𝗧𝗖𝗔, 𝗻𝗼𝘁 𝗣𝗿𝗶𝗰𝗲 𝗼𝗿 𝗠𝗮𝗿𝗸𝗲𝘁𝗶𝗻𝗴! Why are large companies (like Microsoft, Salesforce, Oracle, Adobe, etc.) able to consistently win the majority of deals while selling clearly lower-value products at premium prices? Sophisticated companies understand these non-price related costs and have special ways to lower those costs for buyers. 👉 𝗕𝗿𝗮𝗻𝗱 𝗧𝗿𝘂𝘀𝘁 – by devoting long-term resources to Brand Marketing, large companies dramatically reduce the "Risk Premium" for a buyer compared to buying from an unknown supplier. 👉 𝗩𝗲𝗻𝗱𝗼𝗿 𝗢𝗳𝗳𝗶𝗰𝗲𝘀 – Large players deploy special-purpose onsite teams dedicated to ensuring deployment, integration, and data migration issues are handled for the buyer or with close help. Most large players like Microsoft or Oracle have permanently staffed onsite teams at all or most of the Fortune 500 companies. This allows companies like Microsoft to significantly reduce BOTH the "cost of buying" and the "risk cost" associated with going with Microsoft. And this allows them to not worry about innovation or technical excellence while selling at premium pricing.

Most B2B companies skip straight to "Why us?" And then wonder why complex deals stall. After years of working with our Megadeals methodology and integrating insights from Jonas Lind's Decidable research, here's what I've learned: In high-complexity deals (complexity 5 & 6), buyers don't choose the best option. They eliminate what they can't defend. That distinction changes everything about how you should build messaging. There are three behavioural gates every risk-bearing stakeholder must pass through before a deal can close: 𝗥𝗲𝗰𝗼𝗴𝗻𝗶𝘁𝗶𝗼𝗻 — The buyer sees themselves in your description of the problem. Not awareness. Mental framing. 𝗥𝗲𝗹𝗲𝘃𝗮𝗻𝗰𝗲 — The buyer connects your approach to their specific role's accountability. Not a generic value prop. 𝗦𝗮𝗳𝗲𝘁𝘆 — Every risk-bearing role can defend the decision under scrutiny. This is where most deals die. The equation is multiplicative: Recognition × Relevance × Safety = Decision Movement If any one gate scores zero, the deal cannot close. No matter how strong the other two are. Here's the uncomfortable truth: most messaging strategies only address Gate 1 (maybe). They build awareness and assume the rest takes care of itself. It doesn't. The practical shift: → Layers 1–3 (Change Drivers, Pains, Short-term Coping) open Gate 1 (Recognition) → Layers 4–6 (Category, Subcategory, Dimensions) open Gate 2 (Relevance) → Layer 7 + Deal-Closing Messaging opens Gate 3 (Safety) And here's the part most teams miss: 80–90% of seller time is spent in deal-closing — but with content built for Gate 1 and 2 only. The result? Rainmakers close. Everyone else churns pipeline. The fix isn't hiring more Rainmakers. It's building a Messaging Architecture that does what Rainmakers do instinctively — systematised and scaled across every stakeholder in every deal using a deal orchestratrion support system (like Njord) What's the gate that blocks most of your deals? In my experience, it's almost always Gate 3 — Safety. Curious if others see the same pattern?

Ever have 3.5x pipeline coverage and still miss by 20%? Well, here's a potential solution for ya. To be clear, this stuff happens often, and it tends to be a surprise to some leaders. Mainly because lots of folks still think that pipeline VOLUME is the same as pipeline HEALTH. If you're looking at your pipeline and don't really have a clue about what's in it AND you're comfortable with a bit of math, here's a different way to gauge your pipeline health. You can call it something like the "30-Point Quality Score." I'm not a marketing whiz, so feel free to come up with something more creative if you want. Anyway, here's how it works...instead of tracking gross dollar coverage, score each opportunity across six dimensions (0-5 points each, 30 points max): 1. Stage velocity (0-5 pts): - 0 pts = Sitting 3x longer than average cycle. - 3 pts = At average cycle length. - 5 pts = Moving faster than average. 2. Multithreading (0-5 pts): - 0 pts = Single contact. - 3 pts = 2-3 contacts. - 5 pts = 4+ contacts across buying committee. 3. Source quality (0-5 pts): - 0 pts = Cold inbound form fill. - 3 pts = Marketing qualified lead. - 5 pts = Rep-generated with champion. 4. Budget confirmation (0-5 pts): - 0 pts = "We think we have budget." - 3 pts = "Budget approved, waiting on timing." - 5 pts = "Budget allocated with PO number." 5. Intent signals (0-5 pts): - 0 pts = Passive engagement. - 3 pts = Responding to outreach. - 5 pts = Multiple stakeholders actively engaged. 6. Next step commitment (0-5 pts): - 0 pts = Vague "let's reconnect." - 3 pts = Calendar invite scheduled. - 5 pts = MAP with named owners. So your total quality-weighted pipeline = Sum of (deal size x quality score/30). For example: - Deal A: $100K × (25/30) = $83K quality-weighted. - Deal B: $100K × (12/30) = $40K quality-weighted. Now you can start tracking quality-weighted coverage instead of just gross coverage. I mean, you can keep celebrating 500 opportunities at $50M total value if you want. But it might be more effective to start tracking 150 opportunities with validated champions, defined next steps, and budget confirmation. I'd personally recommend the latter, mainly because your board doesn't care how many deals you forecast. They care how many you close. Math doesn't lie. Even when your pipeline does.

The # 1 reason buyers choose a vendor? It’s not ROI. Not the product. Nope, not even price. It’s defensibility. LinkedIn’s new global study of 750 senior B2B buyers - Buyability: The Future of B2B Marketing Success - found that the top drivers of decisions are: “Can I justify this?” “Can I defend it if it fails?” Mimi Turner, LinkedIn’s head of marketplace innovation, puts it simply: “Defensibility is more important than utility.” I mean, this isn’t new. The “no one gets fired for buying IBM” energy still rules. But B2B companies keep making it worse: - Hiding pricing - Extravagant claims with no proof - One-off case studies framed as the norm - Copy that needs a buzzword translator The study outlines 5 emotional drivers of “buyability”: 1. Confidence it’ll work 2. Ease of the decision 3. Internal alignment 4. Managing the downsides  5. Defending the choice if it fails That last one topping the list. So what makes a risky choice safe? Peer validation. Recommendations from “people like me” were 3x more influential than price or performance. So if your landing page is missing: - Credible proof - Named logos from similar ICPs - Clear, reusable copy for internal convos Then, no amount of CTA tests and layout changes will change anything. Your focus should be on helping the buyer justify the purchase AND cover their ass if things go south. 

I’ve coached 20 sellers who’ve closed $10M+ deals with public companies. EVERY SINGLE ONE of those deals started with the company's 10-k. Here's how to analyze your first 10-k: BACKGROUND: A 10-k is the annual filing every public company listed on US stock exchanges must file. It's a gold mine for sellers. When analyzing, here are the 7 areas I focus on: 1. Business Section: Is where the company describes its own business. This will tell you WHAT the company actually does, not just what you hear on the street. You may get a very different understanding of what drives revenue for the company after reading. 2. Risks Factors The risk factor section highlights risks to the current and future ability of the company to deliver business results. The first 4-5 risks are typically the most important to review. If it’s mentioned in the 10-K, the risk is big enough that it has C-suite attention on it, which means it likely has funding available to mitigate it. If your solution can help, you have a running start. 3. Legal Proceedings Are essentially a risk that materialized into litigation that has a high likelihood of resulting in financial and/or operational losses. Examples: Volkswagen’s emissions scandal, BP's oil spill, etc. Even if the judgment has been finalized, the company will be taking measures to ensure the issue never arises again. This is again an opportunity for relevant suppliers to come forward with creative solutions to the problem. 4. Management Discussion & Analysis (MD&A) This is a PRIORITY section for sellers. The business section mentioned in #1 details WHAT the business is. The MD&A section elaborates on HOW they do what they do. This section often has detail that is more usable and relevant because it discusses issues the business is dealing with right now as well as the impact of those issues in practical terms highlighting recent use cases. 5. Financial Statements: 10-K’s typically show high level financial results for the trailing three years. Top and bottom line revenue, gross margin, cash flow. Look at each of those over the past three years and note the trends. That will give you plenty to talk about with executives to find out what is driving them. This is executive-speak. They love this kind of conversation. They hate talking about products. 6. Company presentations and earnings calls The investor relations website offers you more gold with access to earnings calls as well as other documents like investor day presentations, which sometimes get to an even more granular level of detail on specific initiatives underway within the account. 7. Competitive analysis Search the 10-K with keywords like “competitive” and “advantage" to find mention of competitive pressure particularly in the business section, MD&A as well as earnings calls transcripts. Then research THEIR 10-K’s as well to find out their competitive standing vs. your customer and their approach to the business. What would you add?

📊 We analyzed 119 Entrepreneurship Through Acquisition deals in Jul-Dec 2025 and passed on 114. When an investor passes, it's probably for one of these reasons: 1️⃣ Searcher Risk (~17% of deals fell into this bucket) - Searcher doesn't seem capable of leading the team post-close (blue collar team, ivory tower searcher, for example) - Searcher lacks sufficient work experience or life experience for the business - Searcher lacks skills/competencies in areas crucial to the business (b2b sales, for example) - Searcher comes across as cocky, uninformed, or resistant to feedback - Searcher lacks the financial profile to secure an SBA loan - Etc. 2️⃣ Business Risk (~19% of deals fell into this bucket) - Customer concentration: losing the top 1-2 clients would cause a default on the debt - High CapEx needs: growth is very capital intensive, true cashflow multiple is often quite high (EBITDA is not a good metric for businesses like this) - Not resilient in a downturn: dependent on new construction, or expanding consumer spending, etc. - Seller key-person risk can't be overcome - Business performance has been unpredictable and inconsistent - Etc. 3️⃣ Deal Terms (~32% of deals fell into this bucket) - Business seems overvalued (or, at least, less attractive than other opportunities we're seeing) - Lack of downside protection in the deal structure: small or no seller note, for example 4️⃣ Investor Terms (~9% of deals fell into this bucket) - Searcher offering investor terms lower than market norms 5️⃣ Deal Size (~19% of deals fell into this bucket) - Deal is too large or too small to be the right fit for our fund Anything I missed?