Redesigning the migration platform — from the ground up

SKYKICK

SkyKick's migration platform was a critical utility for IT partners — trusted for its technical depth and data integrity. Years of incremental fixes had left it complex, expensive to support, and difficult to evolve. I led a ground-up redesign that dropped support tickets by 47%, grew migration projects by 53%, and unblocked scale with partners like GoDaddy.

RedesignStrategy
Timeframe2020–2023
Team3 PMs, 9 Engineers, +1 Designer (Q3 2021), +1 Researcher (2023)
Redesigning the migration platform — from the ground up
The Flights dashboard — the central control surface of the redesigned experience.

Problem

The product had outgrown its original architecture. Built on a backend never designed for the scale it had reached, years of incremental fixes had left the product fragmented and hard to evolve. Support escalations ran at 15–20%. Feature velocity had slowed. The experience didn't reflect how partners actually worked. IT providers manage migrations alongside active customer relationships — yet the product enforced a rigid, linear wizard. Once a migration began, many settings locked — and there was no going back.
Before state showing disconnected planner wizard and monitor
The legacy product: two disconnected experiences, no way back.

Approach

We reframed migration as orchestration, not a wizard. Rather than refine the existing wizard, I re-examined the migration model itself. Support data and partner interviews pointed to a structural problem: the product was built around system sequencing, not partner workflow. IT partners don't run one migration at a time. They manage dozens — across different customers, timelines, and configurations — simultaneously. A linear wizard forced them to work against their own process. Working with product leadership, I defined three principles to guide the redesign: transparency, configurability, and predictability.
Early wireframe exploration showing non-linear layout concepts
Quick wireframes kept exploration fast and assumption-light.

Solution

One unified experience, built around how partners actually work. The redesign replaced two disconnected tools with a single, flexible experience. Active migrations could now be adjusted, observed, and refined — without restarting.

1

Faster path to initiation

Partners begin with just the essential inputs, gather discovery data from the source server, and refine configuration as they go — rather than completing every step before starting.

Source server discovery tool
The source server tool let partners gather configuration data before committing to setup decisions.
2

Migration Flights

Mailboxes could be segmented into prioritized batches, allowing staged rollouts — executives first, broader teams later. I named the feature Flights. It became intuitive in early testing and a marketing pillar.

Flights dashboard in draft state showing warning patterns
Draft state: warning patterns surface issues before a migration goes live.
3

Live plan reconfiguration

Mailbox settings could be modified after a migration was active. The no-going-back constraint was gone — and with it, the support dependency it had created.

Mailbox management view
Partners can move mailboxes between flights and apply unique configurations to each batch.

Outcomes

Less friction, more migrations. Partners responded well — long-requested features improved the quality of their service delivery. For SkyKick, the redesign extended the life of its flagship product and primary user acquisition engine.

"Flights, the customization, is most valuable to us. That's going to be absolutely monumental in the control that we have on all migrations moving forward."

— IT technician
47%
Reduction in support tickets
53%
Increase in migration projects
24%
Increase in migration seats