In 2021 Calendly was crossing the threshold from a product millions of individuals loved into a multi-tier SaaS company with a real go-to-market motion. I was a senior designer on the company's first dedicated Growth team, owning activation, conversion, and the design side of the pricing & packaging migration that came with it.
Approach
Three areas, one operating loop: research → ship → measure → iterate. Each surface I owned started with a question (why are users not upgrading, why are they downgrading, why aren't they activating) answered with research, then designed against the answer.
Senior Product Designer, Growth
2021
Calendly's first dedicated Growth team (design, PM, growth eng, research)
Onboarding · Paywalls · Upgrade flows · Self-serve checkout
Activation · Conversion · Pricing & Packaging migration
Multi-round usability research · A/B testing
Calendly's value lives in the second a user actually sends a scheduling link. The activation work I led targeted the gap between sign-up and first send, and the research showed the gap was wider than the team thought.
A new interstitial between "I just finished setup" and "I'm staring at my dashboard wondering what to do", purpose-built to push users into their first send, not into the back-end of the product. Tested with users mid-onboarding to make sure the prompt felt useful, not like a paywall.
An onboarding experiment that picked smarter defaults for new users based on their stated ICP (recruiter, sales, founder, freelancer) instead of the same blank "30-minute meeting" for everyone. Shipped with measurable activation lift in the experiment readout.
A new library of ready-made event-type templates, replacing the blank canvas that was killing first-send rates. Designed alongside the ICP work so that a user landing post-setup found something they could ship with one click. Now a core surface in Calendly onboarding.
The Failed Paywalls research started as a question every monetization team has: why are people hitting our paywall and not upgrading? I led the design side, translating the research into a redesigned paywall and upgrade flow.
Interviews with users who had hit a paywall and not converted. Three findings drove the redesign:
I. Most users who didn't upgrade didn't know other features came with the tier they were considering.
II. Some users couldn't find business value in Calendly before their free trial ended, particularly consultants and freelancers who downloaded out of curiosity.
III. Users who eventually did upgrade often didn't realize they were also unlocking related features. They were buying one thing and getting more.
Rebuilt the upgrade flow to surface related features inline, frame the change as "how their account will change", and show grouped capabilities by use case rather than feature laundry list. Tested at 6.6-7.0 out of 7 on ease-of-upgrade and ease-of-finding-the-right-plan across multiple usability rounds, a step-change up from the previous version.
A pass through the product to remove paywalls that were firing twice: once when a user clicked into a feature, once when they tried to use it, that the data and the research both showed were tanking conversion. Replaced redundant blocks with in-context hints and trial-warning patterns that gave users room to evaluate.
An in-checkout add-on flow: purchasing Salesforce, Workflows, or another add-on directly inside the upgrade modal without losing the integration setup context. 8 of 9 participants completed add-on purchases successfully in V2 testing. The pattern became the default add-on flow in Calendly.
Calendly's 2021 pricing & packaging change was a high-stakes moment. The kind of project where the design has to make the new packaging feel obviously better than the old one to existing customers, while still pulling new users into the right tier.
Designed the plan-recommendation surface that appears at the top of the pricing page, on paywalls, and in the upgrade modal, guiding users toward the right tier based on usage and ICP. The teams-vs-individuals toggle redesign tested cleanly: 4 of 10 participants switched views immediately on a teams task, with the others quickly correcting via the in-grid switch.
Owned the checkout flows for the migration: seat selection, plan switching, the billing modal, the integration where add-ons hit checkout. Every participant in V2 testing checked out with the correct plan, a bar that sounds low until you've watched users fail at upgrading their own software.
"Growth design at Calendly meant being the person in the room arguing for users who weren't. Research told me what they were doing. The design had to tell the company what to do about it."
The work outlasted the projects. The redesigned upgrade flow, the plan-recommendation surface, the templates library, and the in-checkout add-on pattern all became default Calendly experiences and ran for years after I left. Several of the activation experiments fed directly into the company's broader monetization strategy as it scaled.