Vertafore is a leading provider of administrative software and services to insurance agencies. AMS360 was their top seller for small to medium sized companies.
I was brought onboard by a former manager from Microsoft to help transition AMS360 into a true SaaS product as well as to establish the UX team and practice for the company.
Not only was the product being transitioned but the overall development organization was moving from a classic waterfall approach to SCRUM.
Role:
Sr. UX Designer
Placing UX in the context of the team and the new agile process was both communication, stakeholder alignment and design.

AMS360 had its start with MS DOS and had evolved organically over more than 15+ years by the time I joined the team in 2010.
The design had grown organically as features had been added. Design decisions were based on customer asks.
The technology and UI was an awkward combination of web/browser and local Windows executables, tied to newer SaaS orientated web services.
There was a high degree of business logic build into the UI, making changes complicated.
AMS360 is a management system for midsized insurance agencies, allowing the agents to sell and manage insurance policies for both business and private customers.
Besides insurance the system handles financials.
We planned for a gradual transition on both the product technology and design side.
Shown below is the design as it was when I initiated the redesign, an example of an initial wireframe.
The first gradual change in the build byt introducing a side pane navigation, and then the jump to the final design.
The existing navigation blended global and contextual tasks, overwhelming users by presenting everything at once.
User research revealed two trends pulling in opposite direction:

The tasks were organized into a hierarchy of global to context specific actions and separating out navigating to views.

Note the switch in upper right corner (Switch to Classic). We maintained the ability to switch between old and new experience over the 6 releases I was involved in.
Next goal was to address more of the business critical forms, that at this point was still .exes in Windows.

The wider product team at Vertafore was one of the most committed I have ever worked with. While we all lived the many changes, the openness and willingness to see change through was inspiring as it was challenging.
As a lead designer, my main learnings were:
Bring focus the design practice through activities that build momentum for end user and customer focus
Enable agile/lean UX. Quick turn around of clear deliverables
Provide UX vision and mission for team, discuss with customers and stakeholders
Be visible, collaborate, embrace ideas from the wider team
Embed in wider team process and tools