What Crossbeam taught Harker Roslin about b2b SaaS pricing & packaging

Harker Roslin says a B2B SaaS company's pricing roadmap is its product roadmap. Rigid billing tools create technical debt that slows product changes by a quarter or more. Most tools aren't built for annual recurring revenue, forcing fragmented catalogs and cumbersome price changes at renewal.
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the pricing roadmap is the product roadmap. And if pricing and packaging and monetization is the A, you know, it's your P1, it is the most important thing at the company, everyone is laser-focused on it. What really sort of like a stranglehold on it though, is if you have delivered a pricing and packaging infrastructure that is so rigid that major changes take entire quarters or quarter plus to deliver against because you're having to rip out existing or hack around existing structures.
What is rigid infrastructure around money?
Some of it has to do with the tooling that you choose. Who's your payment processor? Did you roll your own? Are you using another company? What are their constraints exist around their product? Are you using a tool for revenue reconciliation so that all of your revenue reporting can occur in one system? Your enterprise deals are happening in Salesforce or HubSpot. Order forms are being filled out the same way that enterprise work has always happened, but your self-service tier happening in, you know, Stripe or whoever is doing, you know, your payment processing, what's creating the invoices? So usually there's going to be some other tool. And if your pricing and packaging is not aligned with what that tool can do, it's gonna hurt. Now you're fighting with a tool that's not designed to do the things that you're trying to do with your pricing and packaging.
You should.
So one of the answers there is choose a more flexible tool and think about what are the different pricing scenarios that you're vetting and could this tool do all of them? Could it do all of them well?
What, what is, what's an example of where like you've run into a tool that was too rigid for the job you needed to do?
For sure. If I'm a B2B SaaS company, my world revolves around ARR. Most tools are not designed to understand this. You are hacking around a tool that is not designed to do that thing, and anytime you're doing that, you're creating technical debt, probably a lot of it. And additionally, you are fighting the friction that like the tools that you're using on your own codebase don't want these things to happen together. And so the hack tends to be really inflexible. So if you wanna change the price of monthly subscriptions at renewal, it's a whole nother product catalog. You know, like it's just, it's not designed to do that.
I feel like I'm hearing you describe, we select billing tools and we try to get our billing tools to manage product catalogs and subscriptions, but we also have software tools that we use in our code to manage what people have access to. Yes. And often there's a disconnect between those billing tools and those, for lack of a better term, feature management tools.
The thing that I found myself desperate for doing this work was the ability to move people from one version of pricing and packaging to another and to be able to track who's in each bucket. The product catalog, it should be in my mind, everything you sell at all the prices that you sell it at. So whether you have a Pro, a Pro Plus, and then an Enterprise plan, or you have far more offerings than that. And then the ability to say, okay, here's the plan, here's what you get, and have those entitlements and those gates and those meters be able to be enforced in your application, ideally in an API call that is performant.
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