The Windward Risk Managers’ Story

Navigating Complexity in Independent Insurance

Windward Risk Managers provides comprehensive underwriting, claims handling, policy support, and general customer service. At the heart of their agent experience is Mariella Gonzalez, Director of Agency Support, leads a 10-person team supporting 5,500+ agents. As the team scaled, so did the challenges around onboarding, policy changes, and workflow usage governance within Duck Creek, a platform essential to policy creation and processing for its agents’ network.

The Challenge

A System Under Strain: Agent Confusion Caused Downstream Impact

Agents faced workflow inefficiencies when using Duck Creek, like identifying forms in the quoting process or accessing proper guidelines for handling claims and policy issues. Toggling back and forth between Duck Creek and the agent portal was time-consuming and disruptive.

Without embedded training, agents had to consult subject matter experts and external knowledge repositories for help, leading to policy delays and frequent calls to Windward’s support center. This caused a high call volume of L0/L1 calls into the customer service team, often leading to needless agent frustration.

“We didn’t have visibility into who was getting stuck where,” said Mariella. “There was no data to work from—and the training materials weren’t embedded into our Duck Creek workflows.”

The Solution

Enabling Agents in the Flow of Work at Key Friction Points

Windward implemented Whatfix to create embedded Flows, Self Help content, and pop-ups directly in Duck Creek. This enabled its agents to have embedded workflow support within the application at the moment of need, targeting key friction points that previously resulted in additional calls to the customer service team.

High-engagement content, like a “Processing a Mortgage Change” Flow, received nearly 800 plays. The “New Windward Risk Managers” Pop-Up (a change management campaign to support its company rebrand) was shown over 100,000 times in just seven weeks, helping agents stay aligned with corporate messaging and deflecting customer confusion. Embedded PDF guides, in-app beacons, and Smart Tips further boosted visibility into the Duck Creek’s features and frequent updates, driving user adoption across its agents and maximizing its Duck Creek ROI.

The Results

Frictionless Workflows Unlocked Agent Efficiency and Reduced Burden on Support

Post-implementation, the Self Help search success rate jumped from 61% in Q1’24 to 87% in Q1’25, indicating that agents found the information they needed independently. Its contact center saw fewer basic queries, allowing teams to shift their focus to higher-value tasks.

With Whatfix, Windward created a self-reliant agent network to navigate policy workflows and drive sales without bottlenecks confidently.

“Providing our agents the tools they need when and where they need them helps agents complete the sale faster and more efficiently,” said Mariella.