Taking a pricing proposal to the executive team

Members of the Pricing work group build the executive deck slide by slide, from the decision up front to the stop rules.

Updated October 13, 2026

Put the decision on the first slide, show the evidence and the exposure account by account, and ask for a staged test with agreed stop rules rather than a full rollout.

Open with the decision. Elena Verna's first slide names the use case being charged for, the value metric, and the proposed price and package. Her evidence slide separates awareness of the paid offer, friction in buying it and the offer itself. Kyle Poyar would show a pricing-page usability test and buyer interviews before arguing the offer has to change.
Show every account's change. Kyle gives the migration its own slide: each account's current price, new plan, new price and delta, overlaid with customer health. A 100% increase for an account already at risk of churn calls for an exception or a different path.
Make the trade-off explicit. Dan Hockenmaier puts two prices side by side and asks whether the next dollar of margin does more in the company's hands or the customer's pocket, marking which estimates come from observed behavior. Japna Sethi brings a decision table by segment; at Productboard, the fear that a free plan would cost sales pipeline decided which experiments ran first.
Ask executives to approve a pilot. Kyle's final slide names the segment, the package, the holdout, the return date, a break-even threshold and a pipeline stop rule. Alvaro Morales adds a report that replays real usage under the new rates and limits rollout to cohorts whose bills pass.

Group chat with Kyle, Elena, Alvaro, Dan, Japna — the Pricing work group

Question:

How do you present a pricing strategy to executives?

Elena VernaLeads growth at Lovable. Former SVP Growth at SurveyMonkey

I’d put the decision on the first slide: which customer use case are we charging for, what value metric tracks that use case, and what price and package are we proposing? A value metric might be usage, a feature, or an outcome. Then show the effect on acquisition, retention, and revenue together. I’ve argued that revenue is the outcome of the growth and monetization system, and a forecast-only pricing case can miss damage to longer-term growth.

YouTube+1

For the evidence slide, separate three possible problems: customers’ awareness of the paid offer, friction in buying it, and the offer itself. I’ve seen pricing-page reach among relevant users below 20 to 25%, which makes awareness a useful first check before proposing a model change. Show the baseline for each step, the expected movement, and the experiment that would change your mind. For an actual monetization-model change, ask executives to agree on the hypothesis and decision group, then give the team room to run the test.

Spotify

Japna SethiDirector of Product at Atlassian. Former Head of Product-led Growth at Productboard

I’d make the executive ask explicit: approve a staged test for a specific segment and package boundary, with conversion, expansion, and sales-pipeline guardrails. The risk that could kill the proposal should determine the first test.

When we introduced a free plan at Productboard, pipeline cannibalization was a real concern. We sequenced experiments around that risk, including a pricing-page test that drove 3x engagement, and looked at how the free offering affected the sales motion.

amplitude I’d bring executives the same kind of decision table: expected upside by segment, what might shift out of paid or sales-led plans, the test we’ll run, and the metric that would make us pause or proceed. Pricing-page engagement is an early signal; the executive decision needs evidence on customer behavior and the business impact.

Kyle PoyarFounder of Growth Unhinged. Former Operating Partner at OpenView

The migration analysis deserves its own slide in the executive deck. For each account, show what it pays today, the plan it would move to, the new price, and the delta. Then overlay customer health. A 100% increase for an account already at risk of churn calls for an exception or a different migration path. I’ve recommended this analysis because it makes the revenue opportunity and the exposure visible before anyone approves a rollout.

YouTube

The decision slide should ask for three things: the proposed pricing and packaging, the migration rules for existing customers, and the test you’ll run before a full launch. I’d track new-customer conversion and expansion alongside churn risk. Pricing is an ongoing process of customer feedback and monitoring, so executives should approve a way to learn and adjust, too.

Spotify

Dan HockenmaierPartner at Reforge. Former Chief Strategy Officer at Faire

I’d add a slide that forces a choice about where the next dollar of margin goes. In my pricing essay, I contrasted two reasonable approaches. A higher price can pay for sales, marketing, and product work that wins customers. A lower price can bring in more users and make a marketplace more useful to everyone already there. The choice depends on whether the next dollar does more work in our hands or in the customer’s pocket.

Medium

Put two prices side by side. For each, show what you expect to happen to conversion, usage, contribution margin, and the ability to pay for customer acquisition or service. Mark the estimates drawn from observed behavior separately from assumptions.

For a marketplace commission increase, the failure case could be sellers leaving, reducing selection and ultimately buyer demand. I’d ask executives to approve a limited rollout and the conditions for stopping it, since a near-term revenue gain can hide a slower loss of marketplace activity.

Question:

Kyle, Elena would check awareness and buying friction before proposing a pricing-model change. How would you show executives that the offer itself needs to change, using an example from your public work? Please cite the public source.

Kyle PoyarFounder of Growth Unhinged. Former Operating Partner at OpenView

Elena’s diagnosis is where I’d start. I’d show executives a pricing-page usability test and buyer interviews first: can target buyers identify the right plan, understand the benefit, and complete the purchase? I’ve seen a clearer pricing page have roughly the same effect as changing price points in portfolio pricing projects.

Spotify

Then I’d show where the package limits adoption even after buyers understand it. In my interview about Algolia, I described how putting valuable new capabilities behind expensive enterprise tiers drove upgrades in the short term while bottom-up adoption weakened. Algolia moved to usage-based, pay-as-you-go access to its core capabilities; that changes what a developer can actually buy and try, which a clearer page alone cannot fix. I’d present that as the hypothesis, with new-customer activation and paid conversion by segment beside expansion revenue, and ask executives to approve a staged offer test.

Apple Podcasts

Question:

Alvaro, Kyle proposes an account-level migration analysis and a staged offer test. How would you verify that the proposed plans produce correct bills before executives approve a rollout? Please cite your public work.

Question:

Dan, Kyle's Algolia example shows a higher-tier package weakening bottom-up adoption. How would you show executives whether wider adoption is worth more than the near-term revenue from that package? Please cite your public work.

Dan HockenmaierPartner at Reforge. Former Chief Strategy Officer at Faire

Kyle’s Algolia case calls for a cohort model that follows new users past the first invoice. Compare the current higher-tier package with a broader-access offer: how many users activate, how many convert to paid, what they spend over time, and how much each path costs to acquire and serve. The executive decision hinges on whether extra adoption generates enough future contribution margin to outweigh the upgrades the current package captures now.

I’d be especially careful with the timing. In my pricing essay, I argued that a lower price can let users create value and bring in more users, while a higher price can fund sales, marketing, and product work. Price elasticity and network effects determine which path has more leverage.

Medium I’d ask for a staged test with a holdout, track adoption and paid conversion by cohort, and revisit the revenue comparison after those cohorts have had time to expand. The forecast should show the break-even assumption on conversion or expansion, so executives can see exactly what the broader offer has to achieve.

Question:

Elena, Dan would stop a marketplace price rollout if seller activity or buyer selection fell. How would you present those early signals to executives alongside a slower revenue outcome, and decide when to stop the test? Please cite public work.

Question:

Japna, Dan proposes a holdout and a cohort forecast for broader access. In your Productboard free-plan case, how would you show executives whether new adoption offsets lost sales-led pipeline before approving a wider rollout? Please cite public work.

Question:

Kyle, given Dan's cohort break-even test and Japna's sales-pipeline risk, what would you put on the final approval slide so executives know what they are approving and when the team must return for a decision? Please cite public work.

Kyle PoyarFounder of Growth Unhinged. Former Operating Partner at OpenView

My final approval slide would specify the eligible segment, the proposed package and price, the old offer or holdout, and the date the team returns with results. I’d put Dan’s break-even threshold for paid conversion and expansion next to Japna’s sales-led pipeline guardrail, with a stop rule if the new plan shifts qualified deals out of the pipeline faster than it creates paying customers. Those thresholds should be agreed before the pilot.

For a sales-led offer, I’d name the handful of experienced reps running the pilot and have them log buyer objections, actual discounts, close rates, and deal size. I’ve recommended starting with reps who consistently hit quota because their calls help refine the proposal and talk track before the rest of sales adopts it. The approval is for that pilot and its migration exceptions; the team returns for a wider rollout decision once conversion, pipeline, and account-level price impact are in view.

YouTube

Question:

Alvaro, Kyle would pilot the new offer with sales reps and check actual discounts before a full rollout. For a usage-based price, which billing checks would you put beside that sales evidence in the executive approval request? Please cite public work.

Alvaro MoralesCo-founder and CEO of Orb. Former Engineering Manager at Asana

Beside Kyle’s sales pilot, I’d put a bill-difference report built from actual usage. Replay a representative period under the proposed usage rates, and compare each resulting bill with the current bill, contract terms, and the price the rep quoted. Group discrepancies by customer cohort so executives can see the exposure before approving wider rollout. I’ve described using connected usage and pricing data to backtest different revenue strategies against past usage patterns.

Apple Podcasts

I’d have engineering and finance check the cases most likely to produce a wrong bill: usage arriving late, corrected events, unusual contract terms, and the date a customer switches plans. For a billing migration, I’ve publicly described event backfills as a way to amend reported usage and revert a mistake. That gives the team a concrete recovery path to test before moving a cohort.

X The approval request should name the owner of each unresolved discrepancy and limit rollout to cohorts whose bills and customer-facing usage totals pass those checks.

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Frequently Asked Questions

How should a consultant or agency price its services?
By the shape of the work: a fixed fee for a defined deliverable, a retainer for ongoing access, prepaid units for variable requests. Add a performance fee only once the metric, baseline and client duties are agreed.
How does a young startup or community choose a business model?
Find the behavior that creates value and charge where it does the least damage to it. Test a small paid offer with real buyers, then check they keep paying after the first purchase.
Should a transaction fee be flat or a percentage?
Flat when the work and value per transaction are about the same, a percentage when value or risk grows with order size, and volume tiers when each extra transaction is worth less.
How many pricing tiers should a SaaS product have?
Most end up with three to five plans, and Good-Better-Best is the usual default. Choose the value metric first, then step each tier up with the customer's sophistication.
How do you break down a competitor's pricing?
List each plan's model, value metric and upgrade triggers, use the product yourself, then work out where the revenue sits and whether a high price pays for sales or is margin.
How should AI features and agents be priced?
Bill for a unit customers can verify, such as a resolved ticket, check it against the cost of heavy users, and let people finish a real task before they pay.
How do you move existing customers to a new pricing model?
Simulate each account's first bill, test the model on new buyers, then move existing customers in cohorts with notice, a fallback plan and a migration date that respects renewals.
How long should a free trial be?
Long enough for retained customers to reach the paid value. For a simple self-serve product, start with 14 days as a test, then compare 14 and 30 days on revenue and retention at the same cohort age.
What makes people pay at a paywall?
A wall that stops them partway through a job they care about, a limit on the unit they value, an offer that fits their usage, and copy and checkout that don't leak buyers.

All pricing questions →

Frequently Asked Questions

Taking a pricing proposal to the executive team

Pricing

Frequently Asked Questions

How should a consultant or agency price its services?

How does a young startup or community choose a business model?

Should a transaction fee be flat or a percentage?

How many pricing tiers should a SaaS product have?

How do you break down a competitor's pricing?

How should AI features and agents be priced?

How do you move existing customers to a new pricing model?

How long should a free trial be?

What makes people pay at a paywall?

Your ideas, super powered.

Taking a pricing proposal to the executive team

Pricing

Frequently Asked Questions

How should a consultant or agency price its services?

How does a young startup or community choose a business model?

Should a transaction fee be flat or a percentage?

How many pricing tiers should a SaaS product have?

How do you break down a competitor's pricing?

How should AI features and agents be priced?

How do you move existing customers to a new pricing model?

How long should a free trial be?

What makes people pay at a paywall?

Your ideas, super powered.