Founders running pricing by instinct
You know your product value, but you are tired of guessing if the price is right.
Pricing, Margins & Revenue Quality
Pricing decisions shape who you serve, how much support you can afford, and how durable your margins are. This playbook gives founders a practical way to diagnose pricing issues and make changes without chaos.
Executive summary
- Pricing is a strategy decision, not a math exercise. It shapes who buys, how much support they need, and how healthy margins stay over time.
- You can raise prices when demand is strong, discounts are common, or margins are shrinking for reasons other than direct costs.
- Most margin declines are caused by mix shift, discount creep, or rising delivery effort, not a single visible expense line.
- Revenue quality improves when you protect price fences, reduce one-off deals, and track cash, churn, and cost-to-serve together.
- A 90-day pricing cycle beats a once-a-year scramble: diagnose, test, roll out, and reinforce in clear phases.
Quick checklist
- Do we know our true gross margin by product, service, and customer segment?
- Are discounts tied to rules or negotiated ad hoc by sales or founders?
- Do we have a price change story we can tell in one paragraph?
- Is margin shrink driven by cost increases, delivery effort, or mix shift?
- Can we show cash impact (AR days, refunds, churn) alongside headline revenue?
Who this guide is for
Finance and RevOps leads
You can see margin pressure but need a way to explain it and fix it.
Teams seeing margin drift
Revenue is up, but gross margin and cash are trending the wrong direction.
What you will get from this playbook
A simple decision model for when to raise prices and how to test it.
A margin diagnosis framework that separates cost, mix, and process issues.
Concrete pricing mechanics that protect margin without killing growth.
What this playbook is not
- A one-size-fits-all price calculator or SaaS pricing textbook.
- A pricing strategy for enterprise procurement cycles and heavy legal negotiation.
- A promise that price changes are painless. They require change management.
In practice: this is best for teams between 10 and 300 employees that sell products, services, or a hybrid of both.
Pricing is a positioning decision
Quick take
Your price sends a signal about who you serve and how much support you can afford to deliver.
Define the three layers of pricing
List price: the number on the website or proposal.
Realized price: list price minus discounts, credits, concessions, and free work.
Economic price: realized price minus the true cost-to-serve (support, onboarding, customization).
- If list price is high but realized price is low, you have a discounting problem.
- If realized price is healthy but economic price is low, you have a delivery or scope problem.
Quick take
Margins are not just math. They reflect delivery effort, discounts, and customer fit.
Margin is a behavior signal
Rising revenue with shrinking margin usually means you are winning the wrong deals or underestimating delivery effort.
Stable margin but declining win rate usually means you are pricing above perceived value or targeting the wrong buyers.
How to tell if your prices are too low
Quick take
If sales closes fast and churn is high, you are underpricing or attracting the wrong buyers.
- Win rates are strong but average deal size is flat or declining.
- Sales uses discounts early to get deals over the line.
- Customers buy quickly but demand heavy support afterward.
- You rarely lose on price, yet margins are still shrinking.
Founder gut checks
- Would we still win half our deals if we raised price 10% tomorrow?
- Are we giving the same deal terms to wildly different customer sizes?
- Do we have one customer segment that seems easy and profitable compared to the rest?
Quick take
Discounts that feel mandatory are a signal the list price is misaligned with value or packaging.
If you are underpricing, where does it show up first?
Support and delivery teams feel the pain first. They see the cost-to-serve climb before finance does.
Sales knows when a deal is too cheap, but incentives reward closing, not profitability.
Further reading: How to tell if your prices are too low (without guessing)
Should you raise prices?
Quick take
Raise prices when demand is stable, discounting is common, or you are adding measurable value.
A simple decision filter
- Demand pull: pipeline is healthy and sales cycles are not stretching.
- Customer value: the outcomes you deliver are clear and measurable.
- Operational control: delivery effort is predictable and repeatable.
Quick take
Do not raise prices to cover internal chaos. Fix delivery or cost issues first.
How to raise prices without chaos
Start with new customers first. Existing customers need a separate narrative and timeline.
Document your value story: what is new, what is better, what costs more, and why it is fair.
Run a structured test with one segment or tier before rolling it out everywhere.
- Set discount guardrails in writing. Remove ad hoc exceptions.
- Train sales and success on the story and objection handling.
- Update pricing sheets and proposals on a specific date, not gradually.
Why margins shrink even when revenue grows
Quick take
Mix shift and discount creep usually hurt margins more than direct cost changes.
- Mix shift: more customers or deals move into low-margin tiers.
- Discount creep: discounts grow in size or become standard rather than exception-based.
- Cost-to-serve drift: onboarding, support, or implementation hours increase.
- Scope expansion: teams promise extra services to close deals without pricing for it.
- Refunds and credits rise, creating revenue that looks healthy but does not stay.
The margin bridge in plain language
Start with last quarter margin. Add or subtract the impact of mix, price changes, costs, and discounting. The gaps show you where to act.
If you cannot explain the bridge in 5 minutes, you do not have pricing control.
Quick take
If delivery effort grows faster than revenue, margins will quietly collapse.
Further reading: Why margins shrink even when revenue grows
Diagnose margin and pricing issues quickly
Quick take
Separate price, volume, and cost before you debate solutions.
Three diagnostic cuts to run this month
- Price-volume-mix: did margin change because price changed, volume changed, or the mix changed?
- Segment margin: compare your top 10 customers to the rest. Look for cost-to-serve gaps.
- Discount map: average discount by rep, segment, or product tier.
Quick take
Most teams lack a clean view of cost-to-serve by segment. Fix that first.
What to collect if data is messy
Pull 20 deals by segment. Calculate realized price and estimated delivery hours for each.
Even a small sample will show you if one tier is dragging margin down.
Use levers after you know the cause
Price changes fix demand issues. Packaging fixes value mismatch. Scope control fixes cost-to-serve. Pick the lever that matches the cause.
| Lever | Best when | Watchouts |
|---|---|---|
| List price increase | Demand is steady and discounting is already common. | Legacy customers push back if value story is weak. |
| Packaging shift | You have multiple buyer personas with different needs. | Too many tiers create confusion and discount pressure. |
| Minimums and floors | Small deals consume outsized delivery time. | Needs a clear rationale for smaller customers. |
| Usage or consumption pricing | Value scales with volume and you can measure it cleanly. | Customers feel punished if usage is unclear. |
| Service scope tightening | Margins are eroding from custom work. | Sales must stop promising custom exceptions. |
Pricing mechanics that protect margin
Quick take
Good-better-best packaging reduces discounting by giving buyers a logical ladder.
Packaging that founders can explain
Most founders overcomplicate packaging. Keep three tiers, each with a clear outcome and buyer profile.
Use the middle tier as the default. Make the low tier intentionally limited so upgrades feel obvious.
Quick take
Price fences work when they are based on real usage or value differences.
Pricing fences that feel fair
- Volume or usage caps that reflect real cost drivers.
- Service level differences (response time, onboarding depth).
- Access to premium features or reporting depth.
Stop custom scope from leaking margin
If every deal includes a custom add-on, it should be a paid package, not a favor.
Put service scope in the proposal and align delivery teams to enforce it.
Revenue quality: the hidden driver of margin
Quick take
Revenue quality is about durability, cash, and predictability, not just top-line growth.
Metrics to track together
- Gross margin and contribution margin by segment.
- Churn and expansion (net revenue retention if applicable).
- AR days and cash conversion speed.
- Refunds, credits, and write-offs as a percent of revenue.
Quick take
A business with slower growth but strong cash and low churn is healthier than the inverse.
Red flags founders miss
Fast growth fueled by discounting often hides a weak value story.
Rising revenue with slow cash collection is a risk, not a win.
If customers churn after onboarding, pricing may be too low for the success effort required.
Further reading: Profitability reality check, Revenue leaks in growing businesses
A 90-day pricing and margin reset plan
Quick take
Short cycles beat big launches. Diagnose, test, then scale.
Days 1-30: Diagnose and align
- Map realized price, discounts, and margin by segment.
- Identify two price levers to test (e.g., minimums + packaging).
- Create a value narrative and update enablement materials.
Days 31-60: Test and learn
- Pilot changes with a narrow segment or new customers only.
- Track win rate, cycle time, margin, and support load.
- Collect qualitative feedback from sales and success teams.
Days 61-90: Roll out and reinforce
- Roll out the change with a clear effective date.
- Audit discounting weekly for the first month.
- Update comp or incentives if margin is a priority.