If I had a dollar every time I heard this…

Over the past year, I’ve had countless conversations with founders, CROs, and revenue leaders who are wrestling with one big challenge:

“How do we price this right — and how do we keep it right as we scale?”

Gone are the days when pricing was a slide in your pitch deck or a guess based on what your competitors charge. Today, pricing is a living, breathing component of your go-to-market strategy. And if you treat it like a one-off decision, it will come back to bite you.

Here’s what I’m hearing — and what I’ve learned firsthand in the trenches.

🔁 Pricing isn’t one decision. It’s a system.

Startups often default to the “set it and forget it” mentality. But the truth is:

Pricing evolves across stages (pre-revenue, $1M ARR, $10M ARR, and beyond)
It reflects your business model (SaaS, managed service, product-led, or enterprise sales)
It impacts your CAC, ACV, margins, expansion rate, and churn

You need a strategy that can move with you, not hold you back.

💡 Founders are asking smarter questions now

In 2020, I used to hear:

> “What should we charge?”

Now I hear:

- “How do I support both self-serve and enterprise pricing?”

- “How can I build pricing that encourages expansion?”

- “What’s the right model to align with partners and resellers?”

- “How do we structure our quoting process and enforce discounts at scale?”

- “Should we introduce a platform fee or per-module pricing?”

- “Can our CPQ system support usage-based licensing?”

That’s a massive mindset shift. Pricing is now strategy, not just finance.

🔍 What great pricing strategies have in common

✅ 1. Simplicity wins

If your sales team or your partners can’t explain it in one sentence — it’s too complex.

Simplicity = Speed = Scale.

✅ 2. Value-based, not fear-based

Don’t underprice to close deals or win logos. Price based on value delivered and what it costs you to support the customer.

✅ 3. Tie pricing to your GTM motion

Land-and-expand? Usage-based? Seat-based? Make sure pricing aligns with how you sell and grow accounts.

✅ 4. Use quoting tools + approval workflows

A modern CPQ (Configure Price Quote) tool is not a “nice-to-have.” It enables discount governance and deal velocity.

✅ 5. Review pricing quarterly

Stay ahead — not reactive. Market shifts. Buyer behavior changes. Costs evolve.

✅ 6. Introduce “good enough” guardrails early

Even at $100K ARR, enforce discount ceilings, approval flows, and naming conventions.

💼 Enterprise License Agreements (ELAs)

ELAs can be a tactical weapon to: - Lock in multi-year deals - Reduce churn risk - Create predictability - Upsell with built-in flexibility

🔄 Your pricing model = GTM multiplier

Enables reps to pitch more confidently
Gives CS a roadmap for expansion
Aligns with marketing’s messaging
Creates a smooth customer journey

🎯 Final thought: Treat pricing like a product

Build it.

Test it.

Refactor it.

Make it measurable.

Empower your team to sell it.

And evolve it as you scale.

if you need help with creating your pricing strategy…. just reach out

#Startups #PricingStrategy #GTM #CROPlaybook #QuotingTools #EnterpriseSales #B2BSaaS #CPQ #RevenueOps #ProductLedGrowth

📦 “We need to rethink our pricing”