Increasing website leads 50% for a $3B scheduling platform
Sole designer on enterprise web and design system
Web Design
Illustration
COMPANY
Calendly
ROLE
Senior Designer
type
Client at agency
Time/tenure
3-month launch & 2022–2023 retainer
Calendly
Overview
Calendly is a $3B scheduling platform trusted by over 10 million users and 100,000+ companies.
My agency was brought in to target enterprise buyers, overhaul slow workflows, and build the foundation to scale. I was the sole designer on the account, working on a 3-month initial launch and a year-long retainer.
Calendly
The Challenge
Calendly had 30,000+ daily visitors arriving at a website that wasn't doing its job. The design didn't communicate the product's sophistication, the messaging wasn't tailored to enterprise buyers, and slow collaboration among marketing, sales, and design was costing them speed to market.
The biggest miss was enterprise: Calendly was perceived as a solo-user tool. The website wasn't making the case for security, scalability, or admin controls, which is what gets sign off on six-figure contracts.
Calendly
The Solution
We rebuilt the enterprise page, introduced persona-specific solution pages, redesigned pricing, and integrated Clearbit and Marketo to route qualified leads directly to account executives.
Enterprise Page Solutions Pages Pricing Redesign Design System 100+ Illustrations Localization ×5 A/B Testing
The design system was built 0→1 . Localization was baked into the system from the start, with flexible components that handled up to 30% text expansion across five languages. Over the course of the engagement, I created 100+ illustrations, from abstracted product examples to human-centric visuals — including a stretch run of 40+ in a single night.
Calendly
Performance Results
Three months of focused execution turned out so well that we signed on for a year-long retainer to keep improving.
Increase in website leads
Driven by enterprise strategy
Faster time to market
Via design system and headless CMS
Illustrations shipped
Across website
The enterprise positioning shift changed how Calendly communicated to its highest-value audience segment. The design system and new headless CMS site meant marketing and design could ship independently.
Calendly
Final thoughts
30,000 daily visitors, enterprise buyers, live A/B tests — every decision had a data trail. The combination of system thinking, conversion strategy, and high-volume creative output over a full year shaped how I approach every project since.
Calendly
Credits
Kate Kassab
Daniel Slovinsky
Jennifer Garcia
Nic Mansfield
Senior Designer
Developer
Sr. Marketing Manager
Design Mentor
COMPANY
Calendly
ROLE
Senior Designer
TYPE
Client at agency
TIME/TENURE
3-month launch & 2022–2023 retainer
Maturing design at $10B crypto infrastructure startup
Increasing website leads 50% for a $3B scheduling platform
Sole designer on enterprise web and design system
Web Design
Illustration
Calendly
Overview
Calendly is a $3B scheduling platform trusted by over 10 million users and 100,000+ companies.
My agency was brought in to target enterprise buyers, overhaul slow workflows, and build the foundation to scale. I was the sole designer on the account, working on a 3-month initial launch and a year-long retainer.
Calendly
The Challenge
Calendly had 30,000+ daily visitors arriving at a website that wasn't doing its job. The design didn't communicate the product's sophistication, the messaging wasn't tailored to enterprise buyers, and slow collaboration among marketing, sales, and design was costing them speed to market.
The biggest miss was enterprise: Calendly was perceived as a solo-user tool. The website wasn't making the case for security, scalability, or admin controls, which is what gets sign off on six-figure contracts.
We rebuilt the enterprise page, introduced persona-specific solution pages, redesigned pricing, and integrated Clearbit and Marketo to route qualified leads directly to account executives.
Calendly
The Solution
Enterprise Page Solutions Pages Pricing Redesign Design System 100+ Illustrations Localization ×5 A/B Testing
The design system was built 0→1 . Localization was baked into the system from the start, with flexible components that handled up to 30% text expansion across five languages. Over the course of the engagement, I created 100+ illustrations, from abstracted product examples to human-centric visuals — including a stretch run of 40+ in a single night.
Calendly
Performance Results
Three months of focused execution turned out so well that we signed on for a year-long retainer to keep improving.
Increase in website leads
Driven by enterprise strategy
Faster time to market
Via design system and headless CMS
Illustrations shipped
Across website
The enterprise positioning shift changed how Calendly communicated to its highest-value audience segment. The design system and new headless CMS site meant marketing and design could ship independently.
Calendly
Final thoughts
30,000 daily visitors, enterprise buyers, live A/B tests — every decision had a data trail. The combination of system thinking, conversion strategy, and high-volume creative output over a full year shaped how I approach every project since.
Calendly
Kate Kassab
Daniel Slovinsky
Jennifer Garcia
Nic Mansfield
Senior Designer
Developer
Sr. Marketing Manager
Design Mentor
Increasing website leads 50% for a $3B scheduling platform
Sole designer on enterprise web and design system
Web Design
Illustration
Increasing website leads 50% for a $3B scheduling platform
Sole designer on enterprise web and design system
Web Design
Illustration
COMPANY
Calendly
ROLE
Senior Designer
TYPE
Client at agency
TIME/TENURE
3-month launch & 2022–2023 retainer
Calendly
Overview
Calendly is a $3B scheduling platform trusted by over 10 million users and 100,000+ companies.
My agency was brought in to target enterprise buyers, overhaul slow workflows, and build the foundation to scale. I was the sole designer on the account, working on a 3-month initial launch and a year-long retainer.
Calendly
The Challenge
Calendly had 30,000+ daily visitors arriving at a website that wasn't doing its job. The design didn't communicate the product's sophistication, the messaging wasn't tailored to enterprise buyers, and slow collaboration among marketing, sales, and design was costing them speed to market.
The biggest miss was enterprise: Calendly was perceived as a solo-user tool. The website wasn't making the case for security, scalability, or admin controls, which is what gets sign off on six-figure contracts.
Calendly
The Solution
We rebuilt the enterprise page, introduced persona-specific solution pages, redesigned pricing, and integrated Clearbit and Marketo to route qualified leads directly to account executives.
Enterprise Page Solutions Pages Pricing Redesign Design System 100+ Illustrations Localization ×5 A/B Testing
The design system was built 0→1 . Localization was baked into the system from the start, with flexible components that handled up to 30% text expansion across five languages. Over the course of the engagement, I created 100+ illustrations, from abstracted product examples to human-centric visuals — including a stretch run of 40+ in a single night.
Calendly
Performance Results
Three months of focused execution turned out so well that we signed on for a year-long retainer to keep improving.
Increase in website leads
Driven by enterprise strategy
Faster time to market
Via design system and headless CMS
Illustrations shipped
Across website
The enterprise positioning shift changed how Calendly communicated to its highest-value audience segment. The design system and new headless CMS site meant marketing and design could ship independently.
Calendly
Final thoughts
30,000 daily visitors, enterprise buyers, live A/B tests — every decision had a data trail. The combination of system thinking, conversion strategy, and high-volume creative output over a full year shaped how I approach every project since.
Calendly
Kate Kassab
Daniel Slovinsky
Jennifer Garcia
Nic Mansfield
Senior Designer
Developer
Sr. Marketing Manager
Design Mentor