< Work|Calendly

Rebuilding Calendly's Permissions System

Enterprise Systems Design UX Architecture B2B

Calendly grew quickly, and over the years fast decisions added up to a rigid and limiting system. Users had all-or-nothing control, with none of the nuance different companies needed, and admins had no good way to manage event types from one place. For our largest customers, that rigidity was quietly costing us enterprise accounts.

As Principal Design Lead, I partnered with our Staff PM and Tech Lead to run a Product Inception. What began as a set of workshops became a five-stream program to rebuild permissions and user management from the ground up, so organizations could delegate, shape their own branding, and set privacy the way their policies required. Today, sales can pursue enterprise accounts that were simply out of reach before.

At a glance
Team
5 senior designers across 5 work streams, partnering with a core leadership team of a Staff PM, Architect and Tech Lead
Role
Principal Design Lead
Responsibilities
Product & Design Strategy, Information Architect, Inception Facilitator, Research
Industry
Enterprise Scheduling
Timeline
3 months strategy & inception
11 months execution
Platform
Web and Mobile

Context & Problem

No one set out to build an inconsistent system. Each team shipped its part of the product with care, but without a shared picture of how permissions and user management should not only fit together, but also how it should scale for the larger customers Calendly was attracting. Choices that made sense at one point in time began to work against each other as our customers grew larger and more complex. We didn't need another patch. We needed a cleaner, more flexible foundation for permissions, user management, and access to objects.

Planning

Product Inception

I designed a series of workshops, built on an inception framework, that brought stakeholders and customers together to work through the problem as one group. Around thirty people took part, including our CEO, CTO, and CPO alongside leaders from customer success, marketing, research, and data. I chose each activity so that everyone stayed oriented and had a real hand in the work as we mapped the product and the customers who depended on it.

Product inception workshop board
Research

Learning how enterprise accounts actually run

Our customer success teams and account managers knew these customers best, so we started with them. Through their eyes we traced how accounts used Calendly across sales, recruiting, and finance, and where it sat among the other tools in their day. Seen from an admin's point of view, recurring needs began to surface around privacy, security, sharing, and hands-on management.

Research

Five organizational archetypes

We synthesized what we learned from 60 customers into five archetypes, each describing a distinct way an organization is shaped and governed. They gave the whole team a shared language, and a way to test every idea against real structures instead of the most recent request.

Five organizational archetypes
Solution

A modular container system

Rather than one structure for everyone, we designed a system that grows with the organization. A small team can keep things simple. A large company can add layers, including an optional groups layer for separating departments or regions, until the product reflects how it actually operates.

Modular container system diagram
Solution

Workspaces as the home for objects

Objects were no longer strictly tied to a person. People could own objects, objects could live inside a workspace, and people could hold membership in that workspace. Many users already know this pattern from Google Drive, Asana, and Airtable, which gave us confidence it would feel familiar from the first day.

Workspace-based object management model
Solution

Personal and shared workspaces

Separating personal workspaces from shared ones gave administrators a clear line for managing access, while leaving each person a space of their own.

Personal workspaces vs. shared workspaces
Solution

A new Admin Management Center

All of this comes together in one place. Admins can now manage users, roles, teams, and groups, decide who sees which event types, assign role-based admin permissions, and keep departments separate from one another.

Admin Management Center, people table
Program

Results

Before After

No way to delegate management to department or group leads, everything routed through a single admin

Groups feature, with delegated group admins who can manage their own members, pull department-level reporting, and set up complex routing.

Brand and policy updates required an admin to manually log into individual accounts and change settings one by one

Managed Events, letting admins centrally control branding, visibility, and settings to allow flexible customization.

Users could only belong to one team, so a cross-functional initiative or campaign couldn't get its own team without breaking someone's primary org structure

Teams as a nested layer within Groups, letting a person belong to multiple teams at once.

All-or-nothing visibility, which became a non-starter for companies with strict client data privacy policies.

Configurable visibility, so organizations with strict privacy needs and organizations that wanted full transparency could both be supported by the same underlying system.

New System

Impact

This work unblocked the business in three concrete ways.

01 Unblocking Enterprise Sales

For the first time, sales could pursue clients with strict privacy requirements, such as financial institutions, that the old model couldn't support.

02 Supporting Complex Organizations

Large companies no longer had to bend themselves to fit the product. Global companies with regional structures, like Pinterest, and parent companies managing several subsidiaries, like Adobe, could be set up the way they actually work.

03 Aligning the Product Org

Teams that had been solving permissions problems on their own now share a single foundation to build on.

INSIGHTS AND PRINCIPLES

What Made This Work

Research at real scale

Sixty customers distilled into five archetypes gave us patterns we could trust, not anecdotes.

Partnership from the start

Our Staff PM and Tech Lead shaped the work with me throughout, rather than meeting it at handoff.

Guided autonomy

I led and mentored five senior designers across five streams, with enough shared structure to keep the work coherent and enough room for each stream to move at its own pace.

Built for the next five years

We designed for organizational structures we hadn't met yet, not only the backlog in front of us.