Hey everyone,
This week I’m hosting 1:1 pricing strategy sessions with over a dozen early-stage SaaS founders at Boulder Startup Week. Most are building in AI (or adjacent to it), with others working on network-based or vertical SaaS tools. Pricing maturity varies widely, some have usage-based models tied to company metrics, others are pre-launch with no structure yet.
The challenge I’m working through is: how to deliver meaningful value in just 30 minutes. I want to help them validate pricing direction, clarify value metrics, and spot early growth signals, but I also don’t want to rush or overwhelm.
So I’m turning to the group:
For those of you who’ve done short-format consulting or founder sessions, what’s worked well for you in a tight window like this? Frameworks outlined by Ulrik (pricing customer, survey) and James Wilton (aligning pricing metrics) are my starting points
- How do you structure the conversation?
- What do you focus on when pricing is still fuzzy or evolving?
- Any simple tools or leave-behinds you’ve used that resonate?
Appreciate any insights or frameworks you’d be willing to share. Just trying to make these sessions as impactful and actionable as possible.
Thanks in advance!
James
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Hi James,
I do some light pro bono consulting with early-stage startups and recently participated in a roundtable with a dozen founders, many at a similar stage to what you’re describing.
What’s worked well for me is to start by asking “What’s top of mind for you?” That quickly surfaces whether they’re trying to validate a direction, untangle a model, or just get started. I tailor the conversation from there. Sometimes it’s stress-testing a value metric, other times it’s helping them define a basic structure they can build on.
I usually anchor on a few fundamentals which all of us know but may not be top of mind for a founder.
Who’s the customer? (Segment clarity is often missing)
What’s the core value metric?
How does usage or value scale with the customer’s success?
To your point, I try not to overreach in 30 minutes. The goal is to give them something clear and actionable (which could be something to think about more), such as a reframe, a diagnostic question, or a quick suggestion for what to test next. It’s a good outcome if they leave with a sharper lens on their business and one concrete step forward.
Happy to dive deeper or share tools if helpful. Good luck with the sessions.
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Hi Andrew,
Thanks so much for this thoughtful response , it was incredibly grounding before my week of 1:1 pricing sessions. Your point about anchoring on customer, value metric, and how value scales was especially helpful in structuring the conversations. I ended up referencing that exact flow more than once.
I met with 14 founders across B2B SaaS, consumer tools, and AI platforms. One theme that came up repeatedly, which I imagine you’ve seen too, is that many early founders think of segmentation at a high level (B2C, B2SMB, B2Enterprise), believing their product can stretch across all of them. In practice, maybe 1–2 of the companies I spoke with could credibly do that. It opened up good conversations about focus, packaging, and value communication.
One follow-up I’d love your take on:
I’m thinking about how to extend this work beyond the free advisory format. One idea is offering structured customer validation as a service, running segmentation interviews or lightweight surveys (e.g., Van Westendorp, MaxDiff, feature bundles) to help founders validate value metrics and price points. Have you seen anyone do this well, or do you have thoughts on how to position something like that?
Thanks again for your guidance, really appreciate it. If you’re open to a quick call, that would be great.
Best,
James