Project chapter
Four years of unchanged pricing was costing us deals and retention. I led a cross-functional effort to redesign our packaging model from the ground up and delivered 30% conversion lift within six months.
Our pricing hadn't changed in over four years. We had two plans, and that binary choice was failing us. Small businesses (our core ICP) churned fastest. Prospects in the sales pipeline dropped off. Our entry plan lacked value; our full plan felt out of reach.
Our small business segment showed the worst retention of any cohort. The entry plan wasn't delivering enough value to make renewal feel obvious.
Two plans forced a binary choice. Prospects who wanted more than Launch but couldn't justify Elevate had nowhere to go, so they left.
Reps didn't have the right packaging to have value-led conversations. Discounting was filling the gap where clear tiering should have been.
I assembled a cross-functional team spanning product, engineering, data science, sales, and design. We needed to look at the full picture, from LTV trends and feature adoption patterns to lost-deal analysis and competitor teardowns.
Deep dive into LTV, MRR, NRR, and conversion timelines across cohorts. Feature usage patterns by segment. Competitor pricing that appeared in lost deals. Interviews with churned customers.
Strong cohort patterns pointed to a clear hypothesis: a lower-cost entry model with a middle tier would capture the segment we were losing. We aligned around a good/better/best structure and built the value proposition around outcomes at each tier.
Feature inventory, upgrade path design, cohort risk modelling, and message architecture. Key challenge: handling existing customers without triggering downgrades. Solved with early stakeholder alignment and no surprises at launch.
First 1–2 months involved real-time iteration based on activation data, trial conversion (day 7, 14, 30), and direct feedback from sales and support on discount requests and plan change patterns.
We replaced the two-plan model with three tiers, each designed to serve a specific stage of the customer journey. The key unlock: putting genuinely valuable features in the entry tier early, so customers experienced ROI before they were asked to grow.

No room for growth. Customers had to make a big leap or leave.
Natural progression. Customers grow through plans as their needs grow.
“Sarah's innovative approach to our pricing model transformed not just our conversion rates but how our entire team thinks about value proposition and customer segmentation.”
We made bets on usage limits and refined them in real time based on activation data. Waiting for certainty would have cost us months.
Lost-deal data from sales was our richest signal. The “nos” told us more about pricing gaps than any quantitative analysis could.
Stakeholder alignment built throughout, not just at the end, meant zero surprises at launch and a team that could speak to the changes confidently.