Tactical insights for first-time founders to outsmart the burn, the churn & the breakdown.

Hey Founder,

You've been "working on pricing" for a while.

There’s a Notion doc, a competitor matrix, and three versions of a new tier structure. You’ve asked customers what they’d pay, moved features between plans, and promised yourself one more round of research.

Yet the pricing page hasn’t moved.

Or maybe it did, but the economics didn’t. You raised the list price, pulled the last ten deals, and found customers still paying what they always had.

The page changed. The bank account didn’t.

Pricing isn’t one decision. It’s three: what customers pay for, how much, and whether those economics survive long enough to become cash.

This issue is about finding which of the three is actually broken, so you stop fixing the layer that feels productive and fix the one that moves the margin.

Let’s dive in.

Pricing starts with the number on the page and ends with cash. In between, it moves through sales, negotiation, delivery, invoicing, and collection.

That’s why a company can spend months “working on pricing” while the economic break sits somewhere else.

I see this across SaaS companies, agencies, and service businesses. One has a usage problem, another a scope problem, and another thinks pricing is broken when the issue is discounting.

The break lands in one of three places:

I call them Structure, Level, and Permission.

Structure determines what revenue grows with.
Level determines how much contribution each customer creates.
Permission determines whether those economics become cash.

Structure and Level usually create something to work out: a better meter, revised tier, or clearer price.

Permission creates something to do: quote the number, decline the exception, bill the overage, or send the renewal notice. 

In 2019, Jon Yongfook, founder of Bannerbear, wrote about charging $9 a month for an early SaaS product. The price felt safe, but it could not support the business he wanted to build. He raised the entry price for new customers to $49 and watched the market response.

Rebuilding tiers or moving features around would not have fixed a price that was simply too low. That was a Level problem. 

Lovable offers a different lesson. As the product evolved, it adjusted how credits, complexity, and usage mapped to what customers received, and changed how customers could buy when the original subscription model stopped fitting behavior.

Users pushed back on unpredictable credits and a changing buying experience, so Lovable watched what happened and adjusted when the experience or economics did not hold.

In both cases, the fix started with identifying the layer that was actually broken. Fix the wrong one, and you can spend months improving something that was never the bottleneck.

Before you change anything, figure out which layer is holding you back. 

Don’t start with: “Should we raise prices?”

Start with: Where does the price stop making economic sense? In what you charge for, in the number itself, or in what survives after the deal is signed.

Structure problems show up in customer behavior, sales conversations, or billing.

In customer behavior.

Usage or work expands while revenue stays flat, and your highest-value customers are not your highest-paying ones.

That can happen when you charge per user but value comes from activity, when a recurring service grows from four deliverables to nine, or when a project fee has no clear point where extra work becomes an extra fee.

In sales.

Another clue is how hard the price is to explain. For early companies, simple beats optimal: a customer who understands the price in one sentence is easier to sell than one who needs a call to decode it.

In billing.

If customers can’t predict the bill, ask for caps or custom arrangements, or comparable customers pay very different amounts, the structure may not fit how they buy.

Ask: Does the basis of the charge move with customer value and the work or cost required to serve them?

If not, start with Structure. If usage and value have drifted apart, change the meter. If the price is hard to explain or predict, simplify it.

Structure asks what customers pay for. Level asks whether the number leaves enough behind.

Look at two things:
i) how easily you win and
ii) what remains after you serve the customer.

For win rate, focus on qualified, competitive new-logo opportunities. If you’re winning more than 40–50%, investigate whether you’re leaving money on the table. If you’re winning fewer than 20%, and verified loss reasons repeatedly say “too expensive,” investigate whether the market is rejecting the price.

Neither number is a verdict. A high win rate can reflect a strong product, while a low one can come from poor qualification, unclear positioning, weak sales execution, or genuinely high pricing. But both tell you where to look.

A 75% blended margin can still hide customers you would be more profitable without.

Customer contribution is what remains after winning, implementing, serving, supporting, and customizing an account. If two groups pay similar prices but one consumes far more work, one segment is subsidizing the other.

The fix may be a higher price, but it could also be paid implementation, a minimum commitment, tighter scope, a different segment, or a different charging model.

Ask: Does this price leave enough contribution for us to win, serve, and retain this customer well?

Permission is the gap between what you could charge and what you actually collect.

Sometimes the leak is hesitation. You know the numbers are defensible, but keep waiting for a cleaner moment: next quarter, next renewal, after the feature ships, after the next big customer signs.

Other times, it’s an operating habit. Sales gives away concessions. Delivery absorbs work the contract does not cover. Legacy pricing has no review date. Finance extends payment terms. Customers use more than they pay for, and nobody invoices the overage.

Each choice feels small. Together, they change the economics of the company.

The number on your pricing page is an intention. It still has to survive sales, procurement, discount requests, delivery, invoicing, and collection.

You can raise list price by 20% and capture none of it if sales discounts it away, implementation stays free, scope stays loose, and customers stay untouched.

You can also leave list price unchanged and improve contribution by removing free work, tightening scope, billing for usage, or changing payment terms.

So don’t ask, “Did we raise prices?”

Ask: How much of the economics we approved reached contribution and cash? 

Pull ten comparable new-logo deals from one segment or sales motion. Don’t mix enterprise with self-serve or renewals with new logos.

For each deal, record:

Then find where the economics change: before the proposal, during negotiation, delivery, invoicing, or collection. The first recurring gap is the one to fix. 

2. Name the Broken Layer

Once you see the gap, name it correctly:

Don’t redesign pricing to solve collections, tell sales to “hold the line” when the meter is broken, or raise the headline price when the leak is free implementation, loose scope, or unbilled overages.

Choose one new-logo cohort or renewal segment and set the rules before the first conversation:

For example, test paid implementation with the next ten enterprise opportunities while holding subscription price steady. Require executive approval for waivers, then measure win rate, discounting, whether onboarding becomes funded, and how quickly the first invoice is paid.

Compare win rate, realized vs. listed price, sales-cycle length, direct cost to serve, customer contribution, and cash collected/time to collection. 

A founder asked me:

Before deciding whether to raise, measure the traction you already have.

At this stage, traction is evidence that people outside your company want this enough to use it, pay for it, and come back.

Look at how many customers have paid, how many are active now, how many have renewed, expanded, or referred someone, and whether you know why the last few customers bought.

If you’re pre-revenue, look for commitment in another form: are people returning on their own, completing the valuable action, or committing real time, data, access, or money to a pilot?

A waitlist is not traction. A large market is not traction. Your competitor’s round is not traction.

Then ask: Is this a market where speed actually decides the outcome?

If there’s a real window to win distribution, secure partnerships, hire scarce talent, or establish the category, and you know what capital would buy, start fundraising conversations.

If you still can’t explain who buys, why they buy, and what brings them back, focus on minimum viable traction first.

You can still talk to a few investors, but use those conversations to learn. Ask: “If we raised in the next 6–12 months, what evidence would you need to see to believe capital would accelerate the business?”

A competitor with more money can move faster. But speed matters only once you know where you’re going. 

Send it my way, just hit reply.

Save these for later: 

Before you go…

You can’t control every SAFE term or predict where your next round will land. But you can decide how much of your company you’re willing to sell, understand what you’ve already committed, and enter the next negotiation knowing your limits.

Know the math before the market knows your price.

That’s your real moat.

See you next Thursday,

— Mariya

Hit reply and let me know. I read every single one (for real).

1. Early stage? Start with one of my practical finance guides.

2. Stuck on something specific? Book a 1:1 and we’ll work through it together.

3. Past $2M ARR? Work with me and the team at FounderFirst to run your CFO function.

Hey, I’m Mariya, a startup CFO and founder of FounderFirst. After 10 years working alongside founders at early and growth-stage startups, I know how tough it is to make the right calls when resources are tight and the stakes are high. I started this newsletter to share the practical playbook I wish every founder had from day one, packed with lessons I’ve learned (and mistakes I’ve made) helping teams scale.

Mariya Valeva

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