Resilience Cyber Insurance

Industry: Cybersecurity | Duration: 6 Months

Resilience Cyber Insurance is a risk visibility and underwriting platform developed to bridge the gap between cybersecurity operations and financial risk planning. Designed in collaboration with cross-functional teams at Resilience, the platform helps CISOs, CFOs, brokers, and risk managers understand, communicate, and act on cyber risk—supporting more informed decisions and improved insurability. Replacing fragmented workflows and unclear reporting structures, it brings technical, financial, and insurance data into one unified, human-centered interface.

User journey mapping and the design process focused on understanding real stakeholder behaviors: how security teams monitor exposures, how brokers assess risk profiles, how CFOs track cyber ROI, and how risk managers align technical posture with insurance coverage. Each touchpoint—from onboarding and risk scanning to policy renewal and reporting—was redesigned to increase clarity, transparency, and collaboration.

Project objectives:

  • Modernize the cyber insurance experience through a unified, data-driven platform

  • Reduce friction in underwriting and renewal workflows for both internal and external users

  • Help organizations quantify cyber risk and align it with business and financial priorities

  • Bridge the communication gap between cybersecurity teams and executive stakeholders

  • Enable brokers to provide clear, evidence-based risk profiles and improve client relationships

  • Create a shared language around risk posture that is actionable across roles (CISOs, CFOs, Risk Managers)

  • Increase transparency into how cyber insurance works, including policy levers and coverage logic

  • Support proactive decision-making through real-time alerts, actionable dashboards, and strategic insights

Feature prioritization emphasized visibility, actionability, and strategic communication. Key features included real-time dashboards for control effectiveness, alerts for insurability gaps, simulated attack scenarios, ability to drilld down into systems and understand what type of breach it is and risk and CFO-ready tools to contextualize cyber risk in financial language. We also designed broker-accessible summaries to streamline renewals and build client trust.

Feature prioritization emphasized visibility, actionability, and strategic communication across user roles. Key features included:

  • Real-time dashboards to monitor control effectiveness and overall risk posture

  • Alerts for insurability gaps, control drift, and non-compliance risks

  • Simulated attack scenarios to help organizations visualize potential breaches and impacts

  • Drill-down capabilities to investigate specific systems, breach types, and associated risks

  • CFO-ready reporting tools to translate technical risk into financial exposure and ROI terms

  • Broker-accessible risk summaries to streamline renewals, improve client advisory, and build trust

The platform integrates multiple real-time data sources, including threat intelligence (CVEs, attack surface scans), security tooling (SIEM, endpoint protection), insurance data (coverage limits, claims history), risk frameworks (NIST, MITRE ATT&CK), and financial modeling (cost estimation, downtime risk scoring). By consolidating all this data into a single intuitive experience, Resilience enables organizations to reduce cognitive load, align cross-functional teams, and take confident, informed action—turning cyber insurance from a reactive process into a proactive strategy.

Team Composition

Role: Lead Product Designer

Led end-to-end product design efforts for a complex, cross-functional cybersecurity insurance platform focused on risk visibility, executive reporting, and client empowerment. I was responsible for shaping the holistic user experience across key journeys—from onboarding and risk assessment to policy management and renewal.

  • Directed UX strategy, wireframes, and interactive prototypes across user personas including CISOs, CFOs, IT analysts, and insurance brokers

  • Conducted stakeholder interviews, user research, and facilitated synthesis workshops to surface insights and drive strategic alignment

  • Designed actionable cyber action plans, restructured critical notification systems, and led the overhaul of platform IA and reporting tools

  • Created presentation decks and documentation to support product vision, internal education, and stakeholder buy-in

  • Collaborated closely with engineering, marketing, and data science teams to ensure the platform was not only functional but educational, trustworthy, and human-centered

Core Design Team:

  • Fernando Díaz – Product Design Partner

  • Jamie Fong – UX Researcher

  • Suzie Wilson – Delivery Lead

Stakeholders & Collaborators:

  • Travis Wong, Carlos Hernandez, Tim Riley – Product Team

  • Brian Bochner – Marketing

  • Ann Irvine – Chief Data Analytics Officer

Overview

The Problem:
Risk and security teams across insured organizations were navigating complex cyber threats using siloed tools, fragmented workflows, and unclear insurance policies. From initial assessment to post-incident reporting, each stage of the journey required switching between disconnected systems—reducing clarity, slowing decision-making, and eroding trust in both the platform and the insurance process.

Challenges:

  • Lack of real-time alerts made it difficult for users to respond proactively to emerging threats—leading to delayed actions and increased risk exposure.

  • Fragmented workflows between IT, underwriting, and executive teams created silos, duplicated work, and slowed down critical decision-making.

  • Disconnected data and unclear reporting made it hard to tie specific security events to financial loss or risk exposure, limiting the organization’s ability to prioritize investments or communicate ROI.

Supporting Data:

  • User interviews with 14 participants—including CISOs, CFOs, Security Analysts, and Underwriters—revealed frustration around lack of transparency, inconsistent workflows, and poor communication across departments.

  • Journey mapping and service blueprinting exercises exposed gaps in how security data was surfaced and shared—particularly in translating technical metrics into executive insights.

  • Internal stakeholder interviews (e.g., Chief Risk Officer, Regional SVP) underscored the need for the platform to act not just as a technical tool, but as an educational and relational bridge—supporting trust with brokers, clients, and executive teams alike.

Resilience Cyber Insurance faced challenges with fragmented communication, evolving client security needs, and a steep learning curve across stakeholders. Bridging IT, underwriting, and executive teams required clearer metrics, cohesive education, and more integrated systems to communicate risk in a way that felt empowering, actionable, and human.

User Research & Stakeholder Alignment

In initial research, we conducted in-depth interviews with 14 stakeholders, including CISOs, CFOs, security analysts, and underwriters. We mapped their current workflows, identified pain points around siloed tools, lack of real-time alerts, and the inability to connect technical threats to business impact. We also documented the confusion caused by opaque policy terms and unclear ROI on cyber investments. We interviewed 14 participants across a diverse range of roles, including:

  • External customers: Security analysts, Directors of Cybersecurity, IT leads, CISOs, and Information Security Officers

  • Internal stakeholders: Chief Underwriting Officer, Regional SVP, Chief Risk Officer, and Chief Claims Officer

Through these interviews, we uncovered critical insights about risk assessment workflows, decision-making bottlenecks, and the mismatch between data presentation and user mental models. These findings directly informed our journey mapping, information architecture, and product strategy, ensuring that both user empathy and organizational context shaped every design decision.

To create the most meaningful impact, we prioritized the needs of the CFO and CISO personas—ensuring that the redesigned product supported executive-level decision-making, clear reporting dashboards, and scalable governance workflows, while still addressing the operational requirements of technical users.

Challenges from user perspective:

  • “I don’t get real-time alerts, so I often find out about issues too late to act meaningfully.”

  • “Our teams work in silos—there’s no clear workflow connecting security, finance, and risk.”

  • “I can’t tie a specific breach to its financial impact, which makes reporting up to leadership feel vague and reactive.”

  • “It’s hard to understand how our cyber insurance actually works. The language, scoring, and process feel opaque and disconnected from our day-to-day needs.”

  • “I need clearer, more human-centered tools that educate—not just overwhelm me with data.”

Pain Point Analysis: Auditing the Existing Platform

We conducted a comprehensive audit of the existing Resilience Cyber Insurance platform, combing through each screen, workflow, and feature interaction with a fine-tooth comb. Our goal was to uncover usability issues, structural inefficiencies, and missed opportunities that were impacting user engagement, comprehension, and trust.

Key Findings:

  • Low Motivation in Cyber Action Plan
    Users lacked clarity and incentive to act. Critical tasks were presented without context, urgency, or visible reward. The plan failed to:

    • Highlight connections to real-world risk scenarios

    • Show how actions could improve insurance coverage or policy terms

    • Quantify the impact of taking (or not taking) specific steps

  • Critical Notifications Buried
    High-severity alerts were hidden below the fold on the landing page. These time-sensitive risks, if unaddressed, could lead to major incidents—but were visually and behaviorally deprioritized.

  • Notifications & Filtering Overhaul Needed
    The side filter panel appeared disconnected and created wasted space. If filtering is limited, this function should be relocated to the main section. If expanded, it needs a full interaction redesign. Additionally, users need a smoother way to:

    • Update self-reported information

    • Receive contextual reminders

    • See reward mechanisms (e.g. improved coverage) for keeping data current

  • Inconsistent Interactions
    Asset and exposure modules lacked expected UI behaviors such as hover states, leading to confusion and reduced confidence in the system’s polish and reliability.

  • Insurance Renewal Workflow
    The renewal experience was fragmented and under-leveraged. We identified an opportunity to streamline the insurance renewal process by integrating platform engagement data, auto-surfacing policy-improving behaviors, and redefining key risk categories—not just combining existing ones, but crafting new, more actionable categories.

Real-time dashboards

Feature prioritization emphasized visibility, actionability, and strategic communication across user roles. Key features included:

  • Real-time dashboards to monitor control effectiveness and overall risk posture

  • Alerts for insurability gaps, control drift, and non-compliance risks

  • Simulated attack scenarios to help organizations visualize potential breaches and impacts

  • Drill-down capabilities to investigate specific systems, breach types, and associated risks

  • CFO-ready reporting tools to translate technical risk into financial exposure and ROI terms

  • Broker-accessible risk summaries to streamline renewals, improve client advisory, and build trust

We also redesigned the renewals process to surface relevant signals—such as risk posture improvements, unresolved vulnerabilities, and user engagement—so that brokers and clients could enter renewal conversations with greater clarity and leverage. This transformed renewals from a reactive transaction into a strategic, data-informed dialogue.

To support this transformation, we created a centralized Education Hub where users could access cybersecurity frameworks, policy definitions, risk terminology, and product guidance. By reducing ambiguity and aligning technical and financial understanding, the hub empowered users to make more confident, informed decisions across departments and roles.

Project Summary

The final solution was met with overwhelmingly positive feedback from pilots, dispatchers, and stakeholders. By integrating real-time data into a clean, intuitive interface, FPO significantly reduced cockpit workload, improved situational awareness, and restored trust in digital tools. Pilots especially appreciated the clarity of the vertical flight plan view and the ease of accessing route-critical information without toggling between systems.

In flight simulations and live demonstrations, users praised the system’s responsiveness, thoughtful design, and alignment with actual cockpit needs.

“This is the first digital tool that actually thinks like a pilot.” – SME Pilot

To support rollout and cross-team visibility, we developed a short product video that walked stakeholders through the pilot journey, showcased key interactions, and demonstrated how FPO supports real-time decision-making. The video was featured in an internal product showcase and helped align engineering, design, and operations teams around a shared vision for modernizing flight workflows.