How Pricing and Packaging Should Evolve From MVP to Growth
- Stephanie Roulic
- 2 days ago
- 4 min read
At Startup Boston Week, Michael Goldenberg (VP Sales and Customer Success, SquareWorks) delivered a practical session on one of the most misunderstood parts of building a startup: pricing.
Founders often obsess over product, hiring, fundraising, and go-to-market strategy. Pricing gets pushed to the bottom of the list. But according to Goldenberg, that’s a mistake.
“Pricing shouldn’t be an afterthought,” he told the room. “It should be part of your overall strategy.”
Drawing from years of experience helping early-stage venture-backed software companies grow from zero revenue to eight figures, Goldenberg broke down how founders should think about monetization from MVP to scale.
Start With Market Value, Not Your Costs
One of the clearest takeaways from the session: don’t build pricing based on your internal costs.
Yes, startups eventually need healthy margins. But early on, pricing should be anchored in what customers believe the solution is worth.
Goldenberg urged founders to ask:
What pain are you solving?
How urgent is the problem?
What alternatives already exist?
What does the market expect to pay?
“The first thing you need to understand is what the market will bear,” he explained.
That means getting outside the building and speaking directly with potential customers, partners, and people who understand your target market.
Not Every Market Supports Premium Pricing
Goldenberg noted that pricing power depends heavily on market context. If you’re entering a crowded, commoditized market, aggressive pricing may be necessary to compete.
If you’re creating a new category or solving a problem customers don’t yet have a clean solution for, you may have room to charge a premium.
In other words: pricing isn’t one-size-fits-all.
Choose a Pricing Model That Matches Behavior
He walked through several common SaaS pricing models and where they work best.
Per-User / Seat-Based Pricing
This model works when usage scales naturally as teams grow. But buyers will often question who actually needs a paid seat.
Expect pushback like:
Can only admins have licenses?
Can multiple people share one seat?
Do occasional users need full access?
Founders using seat-based pricing should think carefully about admin, power-user, and light-user tiers.
Usage-Based Pricing
Usage pricing sounds attractive in theory: customers pay more as they use more, but Goldenberg warned that it only works well when usage naturally increases without requiring behavior change.
Examples like infrastructure or compute products often fit. But products that require teams to adopt new workflows may struggle.
If customers have no commitment, they may simply underuse the product.
Tiered Subscriptions
The classic “good, better, best” pricing page remains popular for a reason, but bundling can create friction when buyers only want two features from a mid-tier package.
Goldenberg recommended allowing strategic add-ons so customers don’t feel forced into overpaying.
Custom Enterprise Pricing
For more complex or high-value sales, customized packaging can outperform public pricing tiers. Rather than forcing every buyer into a standard package, enterprise deals can be structured around:
Company size
Scope of rollout
Support requirements
ROI potential
Customers Buy Outcomes, Not Features
Goldenberg simplified the value into three categories. Customers buy products that help them:
Make money
Save money
Reduce risk
That framing matters when pricing.
Revenue-driving products are often easiest to justify. If a solution can help close five extra deals, the ROI math is clear.
Efficiency tools can be harder. Saving time only matters if that time gets converted into business value, such as:
Avoiding a new hire
Reallocating team capacity
Increasing output
If you don’t help buyers connect efficiency gains to dollars, they’ll say they don’t have a budget.
Investors Care About More Than Revenue
Goldenberg also shared how investors evaluate monetization quality.
CAC Payback
How long does it take to earn back the cost of acquiring a customer?
A sub-12-month payback period is often viewed favorably.
Lifetime Value to CAC Ratio
If customers churn quickly, lifetime value drops and acquisition becomes less attractive.
Net Revenue Retention (NRR)
Goldenberg called this one of the most important metrics. NRR measures whether customers stay and expand over time. Strong retention suggests real product value.
Investors would often rather see slower new growth with excellent retention than flashy new sales followed by churn.
Don’t Overprice Too Early
One of the strongest founder lessons from the session was this:
It can be easier to land a customer at a reasonable price and expand later than to demand maximum pricing upfront and lose the deal entirely.
Once a product becomes embedded and proves value, renewals and upsells become far easier. “If they start with you, it becomes your deal to lose,” Goldenberg said.
Should Pricing Be On Your Website?
His answer: it depends.
Put Pricing Publicly If:
The product is simple
Low-cost
Self-serve
Transactional
Keep Pricing Off If:
The product is complex
ROI needs explanation
Packaging is customized
Different customers need different scopes
In those cases, publishing a number too early may scare qualified buyers away before a sales conversation happens.
Final Advice for Founders
Goldenberg closed with a reminder that pricing is never static: you’ll adjust, you’ll learn and you’ll get it wrong sometimes.
But great monetization systems share a few traits:
Grounded in customer value
Simple enough to understand
Flexible enough to evolve
Supported by strong retention metrics
Designed for long-term expansion
Pricing isn’t just about revenue. It shapes perception, sales velocity, retention, fundraising, and how efficiently a company scales.
For early-stage founders, that makes pricing one of the most strategic decisions on the table.