Ongoing Strategic Advisory
1:1 Pricing Coaching
A pricing strategist in your corner.
You run the experiments. We make sure you're running the right ones. For strong teams that want ongoing strategic guidance without a full engagement.
Any Stage
Monthly
$3K USD/month
Who This Is For
You have a capable team. Maybe you've already been through a pricing overhaul. Maybe you're making pricing decisions regularly and want a strategic sounding board before you commit. You don't need someone to do the work. You need someone who's seen this pattern 400 times and can spot the trap you're about to walk into.
This is the right fit if:
You want to build pricing capability inside your team — so you’re not dependent on outside consultants forever.
You’re actively running experiments — and you want expert eyes on the design and the results before you act on them.
You need honest feedback — not validation. When your instinct is wrong, you want someone who’ll say so.
What You Get
Experiment Design & Review
We help you structure pricing tests that actually answer the question you’re trying to answer. Define success criteria before you run. Read the results without second-guessing. Stop designing experiments that confirm what you already believe.
Continuous Improvement Cycles
Your product changes. Your customers change. Your competitors change. We help you iterate on packaging, entitlements, and price points so your pricing stays aligned with the value you’re delivering — not the value you were delivering eighteen months ago.
Team Capability Building
Over time, your team develops the instinct to spot pricing opportunities and the framework to act on them. The goal is for your team to think about pricing the way they think about product: strategically, continuously, with data.
How It Works
Two sessions per month. Semi-monthly cadence.
Real-time troubleshooting between sessions when something comes up.
Access to our frameworks, tools, and thinking.
Think of it as having a pricing strategist on retainer — without the overhead of a full engagement. The kind of call where you can say “we're about to do this, talk me out of it” and get an honest answer in fifteen minutes.
Investment
$3K USD per month
Paid monthly in advance.
Frequently Asked Questions
+What does 1:1 pricing coaching cover?
Coaching sessions cover whatever pricing challenge is most pressing — pricing model design, packaging decisions, price increase planning, competitive positioning, pricing page optimization, sales enablement, or experiment design. Each month includes 2 sessions with Bill Wilson plus async support between sessions.
+How is coaching different from the Strategy Review?
The Strategy Review is a one-time diagnostic — a 60-minute deep dive with a recorded teardown. Coaching is an ongoing relationship at $3K/month where you have a pricing advisor available for the decisions that come up month after month: new feature pricing, competitive responses, expansion into new segments, price increases.
+Can I cancel coaching at any time?
Yes — coaching is month-to-month with no long-term commitment. Most clients stay for 6-12 months as they work through pricing changes and see the results, but you can pause or stop whenever you need to.
+Who is coaching best suited for?
Coaching works best for founders, CEOs, or heads of product who are making pricing decisions regularly and want an experienced advisor to pressure-test their thinking. It's especially valuable during periods of change: new product launches, market expansion, fundraising, or preparing for a pricing overhaul.
Not sure coaching is the right starting point?
Start here
Strategy Review
A single 60-minute session with pre-research and a pricing page teardown. $1,500. The fastest way to get expert eyes on your pricing.
$5–50M ARR · 16–20 weeks
PACE System™
Our full-service engagement where we run the entire process. From $120K.
$1–4M ARR · 8–12 weeks
FastTrack™
Your team builds the model with our guidance. From $55K.
Pricing Insights
Explore our latest thinking on the pricing challenges this service solves.
Why Your SaaS Packaging Is Built Backwards (And How to Fix It)
Feature-first packaging is the reason so many SaaS companies hit a ceiling on willingness to pay. There's a different starting point: designing packages from the outside in, beginning with what your customers are actually trying to accomplish.
Who's in Charge of Pricing? The Roles You Need to Make Pricing a Strategic Part of Your Business
It’s a good question, so I thought I’d share a few of the roles you need to make pricing a strategic part of your business.
Unlocking the Potential of Annual Plans: A Data-Driven Guide to Boosting SaaS Customer Retention
Explore the benefits of annual plans, the key metrics to consider, and even provide you with a handy calculator.
Ready to talk pricing?
Book a call and let's figure out whether coaching fits where you are.
30 minutes · With Bill, not a sales team · 400+ SaaS companies advised