Our deal stuck in legal for three months because nobody could justify the ROI.
The prospect loved the product. Sales had navigated the technical evaluation perfectly. We'd beaten two competitors. The champion was ready to sign.
Then procurement asked: "Show us the business case for this investment."
Sales didn't have one. We'd never built an ROI calculator. We'd never quantified the cost of the problem we solved. We had customer stories and feature comparisons, but no financial model showing why spending $100K with us made sense.
The deal died. Not because our product wasn't valuable—because nobody could defend the price.
That's when I learned the Business box in Pragmatic isn't optional. It's the difference between "prospects love our demos" and "prospects actually close."
The Business box—pricing, business cases, ROI models, and sales tools—is where positioning turns into numbers buyers can justify to procurement, finance, and executives.
Most PMMs skip this box. Pricing feels like a finance problem. Business cases feel like sales' job. ROI calculators feel too complex to build.
So you build great positioning (Focus), create compelling messaging, run successful campaigns—and watch deals stall in procurement because nobody can justify the spend.
If you can't quantify the value you create, you can't charge for it. And if sales can't defend your pricing, they'll discount until they can.
What the Business Box Actually Is
Pragmatic's Business box includes pricing strategy, business case development, ROI/TCO modeling, and revenue models.
Most PMMs think: "Finance owns pricing, sales owns business cases, I don't touch this."
Wrong. PMMs should own the business case framework that sales uses to close deals.
Here's why: You understand the value you create better than anyone. Product knows what the product does. Sales knows what prospects say they need. But PMMs know what market problems create urgency from the Market box, what differentiation buyers care about from the Focus box, and what proof points make buyers believe us from competitive positioning.
That's everything you need to build a business case.
I learned this when I finally asked sales: "Why are deals stalling in procurement?"
They said: "Prospects can't justify the ROI to their CFO."
I asked: "Do you have an ROI calculator?"
They said: "We have case studies."
Case studies aren't business cases. Case studies say "Company X got Y% improvement." Business cases say "If you're spending $500K on this problem today, we'll save you $300K annually, payback in 8 months, 3-year ROI of 275%."
One is a story. The other is a financial model procurement can defend.
The Pricing Mistake That Kills Deals
Most B2B SaaS companies price by looking at what competitors charge, pricing slightly below them if you're newer or slightly above if you're more enterprise, then hoping deals close.
This is competitor-based pricing. It works until a prospect asks: "Why does this cost $100K?"
Sales says: "Because competitors charge $120K."
Procurement says: "We're not buying from competitors. We're evaluating whether to buy at all. Show us why this is worth $100K."
Sales can't. Deal stalls.
The problem: Competitor-based pricing doesn't give buyers a framework to justify the purchase internally.
What works: Value-based pricing with a clear ROI model.
Value-based pricing says: "Here's the cost of the problem you're solving today. Here's how much we reduce that cost. Here's the payback period."
I helped a company shift from competitor-based to value-based pricing. Before the change, they priced at $50K/year based on competitors charging $60K. The sales narrative was "we're cheaper than Competitor X." Win rate was 35% and average discount was 22%.
After shifting to value-based pricing at $75K/year based on saving customers $250K annually, the sales narrative became "you're spending $500K/year on this problem, we reduce that to $250K, payback in 4 months." Win rate jumped to 52% and average discount dropped to 8%.
Same product. Higher price. Better win rate. Lower discounting.
Why it worked: Sales could defend the price with a financial model procurement could justify.
How to Build an ROI Model Buyers Can Actually Use
Most ROI calculators are garbage.
They ask prospects to input numbers they don't know like "How many hours per week do your employees spend on manual data entry?" and spit out aspirational results like "You'll save $500K per year!" that nobody believes.
The test: Can a prospect fill out your ROI calculator without help, and does the output match reality? If not, it's not a useful tool—it's wishful thinking in spreadsheet form.
Here's the ROI model structure that actually works. First, identify the cost categories you impact. Don't guess at value—ask customers what costs decreased after they bought your product.
I interview 10-15 customers and ask: "What changed financially after you implemented our product?" The answers reveal real cost categories. Sometimes they eliminated two contractor positions, which is labor cost reduction. Sometimes they reduced Salesforce storage costs by 40%, which is tool cost reduction. Sometimes they closed deals 30% faster, which is revenue acceleration. Sometimes they cut customer churn from 8% to 4%, which is retention improvement.
For each category, I document what cost decreased specifically, how much it decreased in percentage or dollar amount, how long it took to realize that value, and how often this happens across customers.
This gives you the foundation for a credible ROI model.
Then build the simplest input model possible. Your ROI calculator should require 3-5 inputs maximum. If it requires more, prospects won't complete it.
For a sales enablement product, the inputs might be number of sales reps, average rep salary (defaulting to $80K), and hours per week spent searching for sales content (defaulting to 5).
That's it. From those three inputs, you can calculate the annual cost of content search inefficiency using the formula: number of reps times average salary times hours per week divided by 40, times 52 weeks. For example, 50 reps at $80K spending 5 hours per week equals $260K per year in wasted time.
The annual savings from your product assuming 70% reduction becomes $260K times 70%, which is $182K per year. The payback period is your price divided by annual savings, so $75K divided by $182K equals 4.9 months. The 3-year ROI calculation is 3-year savings minus 3-year cost, divided by 3-year cost, which is $546K minus $225K, divided by $225K, equals 143% ROI.
The key: Use defaults based on industry benchmarks for everything except the 2-3 inputs prospects definitely know, like number of reps. This makes the calculator usable without extensive research.
Next, add conservative assumptions so procurement believes it. The biggest mistake in ROI models is being too optimistic.
You claim 90% improvement when reality is 40%. You assume 100% adoption when reality is 60%. You ignore implementation costs, training time, and ramp period.
Procurement knows you're inflating numbers. They discount your ROI by 50-70% automatically.
What works: Build conservative assumptions into your model and show them clearly. For that sales enablement ROI calculator, I'd assume time savings of 70% reduction, not 100%, because reps still need to customize content. I'd assume adoption rate of 80% of reps, not 100%, because some won't use it. I'd include a ramp period of 90 days to full value, not immediate impact. And I'd include implementation cost for training time and setup.
Why this works: When procurement reviews your ROI model and sees conservative assumptions, they don't discount it as much. Your 100% ROI with conservative assumptions is more credible than your competitor's 300% ROI with optimistic assumptions.
Finally, provide multiple ROI scenarios. Don't just show one number—show a range based on different inputs.
The low scenario uses conservative inputs with minimal impact, like 3 hours saved per week with 60% adoption. The medium scenario uses typical inputs based on customer averages, like 5 hours saved with 80% adoption. The high scenario uses aggressive inputs from your best customers, like 8 hours saved with 95% adoption.
This lets prospects self-select which scenario matches their context. The conservative scenario builds credibility, the high scenario shows upside potential, and the medium scenario is what they'll present to procurement.
The Business Case Template Sales Actually Uses
ROI calculators are great for initial justification. But when a deal gets to procurement or CFO review, you need a formal business case document.
The structure that works starts with an executive summary on half a page. State the problem directly: "You're currently spending $500K annually on this problem through your current approach." Explain the solution: "Our platform reduces this cost to $200K annually by this specific mechanism." Show the investment required: "$75K annual subscription plus $25K implementation equals $100K year 1." Then deliver the return: "Payback in 6 months. 3-year NPV of $650K. 3-year ROI of 217%."
Then a current state analysis on one page quantifying the cost of the problem today. Break it down into labor costs calculated as hours times hourly rate times frequency, tool costs for existing solutions being replaced, opportunity costs from revenue lost or deals delayed or customers churned, and risk costs from compliance penalties or security incidents.
Use their numbers, not yours. If they say they have 50 reps spending 5 hours per week, use those numbers. Don't inflate them.
The proposed solution section on half a page explains exactly what changes. What manual work gets automated, what tools get replaced, what workflows get faster, and what risks get mitigated. Be specific. Not "improves efficiency"—"reduces content search time from 5 hours to 1.5 hours per rep per week."
The financial analysis on one page lays out Year 1 costs including subscription at $75K, implementation at $25K, and training at $10K for internal time, totaling $110K. Year 1 benefits include labor savings of $182K from reduced content search time plus tool savings of $30K from eliminated existing solution, totaling $212K. Year 1 net benefit is $102K.
The 3-year projection shows total costs of $250K for subscription plus annual support, total benefits of $720K in cumulative savings, net benefit of $470K, and ROI of 188%.
Finally, a risk assessment on half a page addresses implementation risks and business risks. For implementation, adoption risk is mitigated by 30-day onboarding program and change management support. Integration risk is handled through pre-built connectors for your existing stack. Timeline risk is managed with 90-day implementation with phased rollout.
For business risks, vendor risk is addressed by our backing from specific investors, our ARR, and customer count. Product risk is handled by our 95% customer retention and 4.8/5 G2 rating.
Addressing risks proactively makes the business case more credible, not less.
Common Business Box Mistakes
I've watched PMMs make the same mistakes with the Business box repeatedly.
Pricing based on cost, not value is one. You calculate your costs for engineering, infrastructure, and support, then add a margin. The problem: Cost-plus pricing disconnects price from value. If you create $500K of value for $10K in costs, why would you charge $30K? The fix: Price based on value created. If you save customers $300K, charging $100K is defensible because of the 3:1 value-to-price ratio.
Building ROI models with aspirational numbers is another. Your ROI calculator claims customers will save 8 hours per day, achieve 200% productivity gains, and see results in week 1. The problem: Nobody believes aspirational ROI. Procurement assumes you're inflating by 70%. The fix: Use conservative assumptions based on median customer outcomes, not your best customer. Build credibility through conservative projections.
Having no pricing for different segments happens when you have one price for startups and enterprises, SMB and mid-market. The problem: Startups can't afford enterprise pricing and enterprises won't pay startup pricing because they assume you're not enterprise-ready. The fix: Build pricing tiers based on segment willingness-to-pay and value created. Startups get basic tiers, enterprises get advanced tiers with different features and support.
When sales can't defend pricing, you've set pricing but never armed sales with the business case tools to defend it. The problem: When prospects push back on price, sales defaults to discounting because they can't articulate value. The fix: Build ROI calculators, business case templates, and pricing justification talking points. Train sales on how to defend pricing with value, not discounts.
Why Pricing Conversations Fail
The uncomfortable truth: Most pricing conversations fail because PMMs position products on features, not value.
You tell prospects: "We have X features, Y integrations, and Z capabilities." Prospects think: "Cool, but why should I pay $100K for that?" Sales doesn't have an answer, so they discount to $70K. Then $50K. Then they ask PMM: "Can we create a basic tier for $30K?"
The problem isn't your pricing. It's that you never quantified the value.
If you can't answer "What does this save or make for the customer?" with a specific dollar amount, you can't defend your pricing.
I've watched companies struggle with pricing for years because they couldn't articulate value. They'd position on features like "we're faster," not outcomes like "we save you 200 engineering hours per month, worth $50K annually."
What changed: We stopped selling features and started selling outcomes.
Instead of "Our platform has automated workflows," we said: "Finance teams spend 40 hours per quarter reconciling data across systems. We automate 80% of that work, saving 32 hours per quarter—128 hours per year. At $100/hour burdened cost, that's $12,800 in annual labor savings."
Now sales could justify a $15K annual price with a clear ROI. Win rate went from 35% to 48%. Discounting went from 25% to 12%.
Same product. Same price. Different value narrative.
The Business Box Is Where Deals Close
You can have perfect positioning (Focus box), compelling messaging, and strong competitive differentiation. But if you can't help prospects justify the investment internally, deals stall.
The Business box turns marketing narratives into financial models that procurement, finance, and executives can defend.
Most PMMs avoid this work because it feels too numbers-heavy, too sales-focused, too far from traditional marketing.
But the companies that win don't just market better—they make it easier for buyers to say yes by giving them the financial justification to defend the purchase.
What works: Build an ROI calculator based on real customer data. Create a business case template sales can customize for each deal. Train sales on how to have value-based pricing conversations.
Then track what happens: Do deals move faster through procurement? Do win rates improve? Does discounting decrease?
If the answer is yes, you've done the Business box right.
If deals still stall on pricing, you haven't quantified value—you've just described features with numbers attached.
Go fix that. Your win rate depends on it.