Charles Wu
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03

Enterprise org consolidation

Enterprise customers had teams scattered across dozens of stray accounts, and consolidating them was slow, manual work. I designed an internal tool that turned it into a guided flow — saving CSMs hours every week and keeping customers on board.

75% Reduction in CSM task time
TeamDesign lead · cross-functional team of 5
When2023
01

The challenge

M&A and organic sprawl meant enterprise customers ended up running Calendly across a half-dozen disconnected orgs — one per acquired team, one per department that signed up on its own. Consolidating them by hand took a Customer Success Manager ten-plus hours per account, with the admin stuck waiting and no visibility into what was happening to their team’s data.

None of it scaled: dozens of these requests a year, each eating weeks of coordination, each with a window of dual access that was really a compliance gap wearing a to-do list.

02

Process

I mapped the full journey across three people who never saw each other's side of it — the CSM, the enterprise admin, and the person being migrated. The service blueprint showed exactly where automation could remove a manual step without taking control away from the admin.

A service blueprint outlining the users, actions, and interactions in the consolidation process
The blueprint: three roles, one migration, and the handoffs between them.

The result was three connected surfaces, each built for the person using it.

Internal tool that allows a CSM to begin a migration process
CSM: prepares the migration once the admin has signed off.
Admin dashboard where an admin can review and process member migrations
Admin: reviews what’s pending and decides when it happens.
An email informing a user of migration status with instructions
End user: a plain email that explains what to do next.
Nothing gets lost in the move — export and import carry scheduling data across the seam.
03

Results

  • 10+ hours reduced to 1–2 hours per migration
  • 99% completion rate, zero data-loss incidents
  • 88% admin CSAT

“These changes will greatly speed up my workflow... and simplify communication with my customers.”

— Customer Success Manager
04

Reflections

What worked

CSMs were in the room throughout. Their frontline read on what actually breaks kept the design honest instead of theoretical.

Opportunities

I'd write the service blueprint first next time — it surfaced cross-app dependencies I only found midway through, after some of the technical direction was already locked.