Activity
Mon
Wed
Fri
Sun
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
What is this?
Less
More

Memberships

PricingSaaS

870 members • Free

4 contributions to PricingSaaS
Pricing Plumbing
Kickstarting the week with a question for the pricing pros: As pricing and packaging become more dynamic, the tech stack is playing an increasingly central role. What’s the biggest technical bottleneck your team faces when trying to experiment or innovate on pricing?
1 like • 19d
One of the biggest challenges I experienced was trustworthy, point‑in‑time cohorting and orchestration - in a multi‑month repackaging + price increase, almost every incident traced back to not being able to reliably identify, freeze, and track who should be touched at each step (eligibility → notification → migration → etc). A few example issues that we encountered: - We couldn’t programmatically surface which accounts had early‑day “handshake” promises (evergreen pricing/grandfathering). Out of caution, we excluded broad swaths of customers—even though only a small % actually had exceptions. - We didn't have a reliable, standardized way to ensure that all customers getting repriced had been notified on time with respect to each country's regulations. - Customers initially selected for repricing needed late-stage exemptions (e.g. had started renewal discussions with sales team, their usage patterns had changed, etc). We lacked a clean way to “unwind” those selections—even after notifications were sent. - Selection → execution drift: by the time the actual migrations came, account states had changed. Without point‑in‑time snapshots, cohorts silently mutated and the wrong customers were touched.
1 like • 17d
@Rob Litterst Outside billing platform, but it's tricky, since these migrations rely on input from multiple systems that aren't usually hooked together. You need usage/adoption data, structured contracts (if you have them), billing data (current plan, etc), customer demographics attributes, etc, and you need to make changes to the billing platform, internal customer database, create notifications/messages, and more. So if I had a magic wand, we would've had all of the necessary data at our fingertips without error-prone sql queries in a thin orchestration system that sat outside of/on top of existing billing, crm, internal, etc. systems.
Office hours is a win.
Just got off the Office Hours call, and found it hugely valuable. We're a small analytics startup, and I was definitely a little worried our questions were going to be too bespoke, but Ulrik has a great way of getting to the meat of the question and leveling it out so that it's relevant broadly. Lots of different business sizes and types, and I learned something from listening to everyone's Q&A. Big fan, and huge thank you to @Rob Litterst and @Ulrik Lehrskov-Schmidt for being so generous with your time!
2 likes • Nov 6
Agreed! I really enjoyed the insight from Ulrik as well as the perspectives and knowledge from others on the call - super helpful, ty ty!
Office Hours
Howdy pricing people! We're starting a new event series called Office Hours, where members can learn from experienced pricing experts. We'll be kicking things off with pricing legend Ulrik Lehrskov-Schmidt on Thursday, November 6th from 12:30pm - 1:30pm EST. Most of you know him, but if you don't, Ulrik is the one of the top pricing advisors in the world and has helped 200+ B2B SaaS companies evolve their pricing and packaging strategy. This is a first-come-first-served AMA format, and all questions are welcome! Once we get through submitted questions and follow ups, we'll open the floor to live Q&A. Drop your questions in the comments and add the event to your calendar at the link below: https://www.skool.com/pricingsaas/calendar?calDate=1763825305&eid=b2d04ef238754259a965e015465ff2d3 See you there 🫡 Rob
0 likes • Nov 6
@Rob Litterst Thanks!
Hello! Ex-Stripe now building in pricing - excited to connect
Hey folks, just learned about this community and am excited to dig in! For a bit more context, I spent 7 years at Stripe working on internal and customer-facing monetization, billing, repricing, and accounting projects+products - it was a front-row seat to two failure modes I kept seeing: 1) a systems-fit gap—teams have a pricing model in mind but must contort it to what CRM/Billing/ERP can run 2) and a confidence gap—they know they should repackage/reprice, but lack conviction on the optimal design and its impact on churn, conversion, reputation, etc. (I'm guessing these aren't anything new to anyone here!) After leaving that post earlier in the year, I've started a new company to focus _somewhere_ in the pricing/billing problem space, but still figuring out if/where I can add value. In any case, I keep time each week for office hours on pricing/packaging/billing - I love chatting through thorny questions across either systems‑fit and/or confidence gaps to swap patterns and pressure‑test options. If you've got something that fits the bill (pun intended?), feel free to grab a slot here (not pitching anything - just looking to help and learn 🙂) Excited to be here! -Chris
0 likes • Oct 31
😀
1-4 of 4
Chris Conley
2
9points to level up
@chris-conley-4349
Ex-Stripe building something new in pricing+billing

Active 6d ago
Joined Oct 30, 2025
Powered by