Open to senior design opportunities

Chetan Pagare

Sr. Staff UX Designer & Product Strategist

16+ years designing complex B2B2C products — AI automation workflows, self-service commerce, and enterprise field tools. Strategy, research, design systems, and delivery. End-to-end. Outcomes-driven.

[email protected]
0+
Years Experience
0+
Products shipped
0+
Teams led
0
Industries
$0.4M+
Measurable cost savings delivered
AI / ML B2B2C SaaS E-Commerce UX Design Systems InsurTech Self-Service Product Strategy Automation Workflows
Selected Work

Case Studies

Four projects spanning AI automation, self-service commerce, platform redesign, and enterprise design systems.

01Cowbell Cyber2024–2025
AI / MLWorkflow AutomationOCRException UX
AI-Powered Submission Automation

Redesigned an insurance underwriting platform — replacing 100% outsourced manual data entry with an intelligent OCR + LLM pipeline. 1,000+ daily submissions at 90% accuracy. Vendor eliminated Feb 2025.

View Case Study
$2.4M
Annual savings
0%
AI accuracy
0.2×
Faster quotes
$120K
Revenue · 6 months
0%
Conversion rate
0%
Transaction success
02Cowbell Cyber2024–2025
Self-Service UXE-CommerceSalesforceDesign System
Resiliency Self-Serve Platform

Transformed a broker-dependent purchase process into a self-service marketplace — enabling SMBs to discover, buy, and manage cyber security services independently for the first time.

View Case Study
03Cowbell Cyber2025–2026
UX ResearchSession AnalysisNav. ArchitectureCompetitive Bench.
PH Experience 2.0

Full-scale redesign of Cowbell's policyholder digital platform — transforming a passive document store into an active lifecycle management surface. Research-led with 3,394 FullStory sessions.

View Case Study
0.9%
Nav. efficiency
0/8
KPI criteria met
0%
Fewer dead-ends
0 DS
Unified source
0%
Annual savings
0
Stakeholder groups
04Hilti2017–2023
Design SystemsComponent LibrariesDS LeadershipEnterprise UX
Design System Lead

Built, maintained, and propagated the Hilti Design System across the company's product portfolio — a single source of components, patterns, and UX standards. 16% annual cost savings across 4 stakeholder groups.

View Case Study
About

Designing at the intersection of strategy & craft

I'm a Sr. Staff UX Designer and Product Strategist with 16+ years designing complex B2B2C products — currently at Cowbell Cyber, an InsurTech and Fintech SaaS company.

I work end-to-end: from initial discovery and research through to high-fidelity design, engineering collaboration, and post-launch measurement. I've built design systems, led product initiatives without a PM, and delivered measurable business outcomes across Fintech, InsurTech, and Enterprise software.

My work sits at the boundary of complexity and clarity — taking technically difficult, high-stakes products and making them feel obvious for the people who depend on them.

Sr. Staff UX Designer
Cowbell Cyber · InsurTech / Fintech SaaS
2022–now
Design System Lead · UX Lead
Hilti · Enterprise Field Tools
2017–2022
Sr. UX Designer
Schlumberger · Oil & Gas
2014–2017
Sr. UX/UI Designer
Cognizant · Multiple product lines
2009–2014
Expertise

What I do best

Product Strategy
End-to-end execution: roadmap ownership, success metrics, cross-functional pod leadership across engineering, data, and legal.
AI-Assisted Workflows
Confidence scoring, exception handling, and human-in-the-loop oversight that drives real-world adoption — not lab demos.
Design Systems
Figma component libraries, scalable token structures, governance frameworks, and DS adoption across distributed engineering teams.
User Research
Usability testing, FullStory session analysis, field studies, persona development, and behavioural analytics-driven iteration.
Self-Service & E-Commerce UX
Cart flows, transparent pricing, in-flow compliance, activation tracking, and multi-stakeholder purchase journeys for B2B2C contexts.
Cross-Functional Leadership
Alignment across Legal, Finance, AI/ML, and Engineering. Roadmap decisions, stakeholder communication, and collaboration at scale.
Let's Connect

Ready to build
something meaningful?

Open to senior IC and leadership roles in product design — B2B SaaS, AI workflows, and platform-scale products.

India · US Visa valid 2029English · Marathi · HindiMBA · Dynatech · 2009–2011
© 2025 Chetan PagareSr. Staff UX Designer · Product Strategist
UX / Product Design · Case Study · 01

AI-Powered
Submission Automation

Redesigned an insurance underwriting platform — replacing 100% outsourced data entry with an intelligent OCR + LLM pipeline. 1,000+ daily submissions at 90% accuracy.

Sr. Staff Designer · Cowbell Cyber · Mar 2024 – Feb 2025
0+
Daily Submissions
Up from ~200
0%
AI Accuracy
vs 80–85% human
0.2×
Faster Quotes
8–12 hrs → <15 min
$0.4M
Annual Savings
Vendor eliminated
01 — Problem
A pipeline that couldn't scale
Every cyber insurance application arrived via email and required a human to download PDFs, ship to an outsourced vendor in India, wait 8–12 hours, fix errors, then route to underwriters. The $240K/year Patra contract was growing — not shrinking.
01
Broker emails PDF
02
Team forwards to vendor
Patra Corp, India
03
Manual transcription
8–12 hour turnaround
04
Error review
15–20% error rate
05
Route to underwriters
Often mislabeled → 3–5 day delays
06
Quote generated
$322K/year total cost
02 — The Product
Five surfaces, one pipeline
Each UI surface addresses a specific friction point. All tested with underwriters and ops leads before engineering handoff.
Submission Inbox
Real-time AI-classified queue with confidence scores.
Auto-classified
OCR Review
Side-by-side PDF viewer with AI-extracted fields.
90% accuracy
Exception Queue
Surfaces only low-confidence extractions.
67% less review
Audit Trail
Every AI decision tracked and queryable.
100% traceable
Analytics
Throughput, accuracy, and cost-per-submission.
Live metrics
03 — Process
11 months, end-to-end
No PM until month 6. I owned discovery, framing, prototyping, specs, and post-launch iteration.
Mar–Apr '24
Discovery
Shadowed underwriters for 3 weeks. Mapped 47 failure points. 40+ user interviews.
Process mapFailure taxonomy
Apr '24
Problem Framing
Defined confidence scoring UX requirements. Wrote opportunity brief for ML and leadership.
HMW statementsConfidence UX spec
May–Jun '24
Concept & Prototype
2 design sprints. 6 concepts tested with 12 underwriters. Key insight: users wanted to review, not retype.
6 prototypesUsability reports
Jul–Nov '24
Iterative Build
Weekly agile sprints. One surface per sprint. Close ML collaboration on confidence signal design.
5 surfacesWeekly demos
Dec–Feb '25
Launch & Measure
Phased rollout to 3 teams. Hit 90% accuracy in week 6. Vendor offboarded Feb 2025.
Accuracy dashboardsPatra offboarded
04 — Design Patterns
Four patterns that made AI trustworthy
Confidence display
Surface confidence, not raw data
A 3-tier system (Auto / Review / Manual) instead of raw OCR scores. Reduced cognitive load 60% in testing.
Exception-first
Only show what needs a human
90% of submissions route automatically. Reviewers only see fields below the confidence threshold.
Override design
Make corrections safe and fast
One-click override with reason tagging feeds directly into the ML retraining pipeline.
Auditability
Every decision is traceable
Audit is a first-class surface — embedded inline wherever decisions are made, not in a separate admin panel.
05 — Results
What we delivered
0%
Field extraction accuracy
Exceeds 85% manual baseline
0.2×
Faster time-to-quote
8–12 hrs → under 15 min
$2.4M
Projected annual savings
Vendor + headcount reallocated
0+
Daily submissions
Previous cap: ~200/day
0%
Less manual review
Exception queue design
0
Compliance incidents
Full audit trail
06 — Reflections
What I'd tell myself on day one
Design for trust before efficiency
Showing confidence signals — even imperfect ones — drove adoption faster than hiding AI decisions behind a clean UI.
Your UX spec is an ML spec
Every threshold I defined in the UI was a target the model had to hit. Day-one ML collaboration made the product feasible, not just desirable.
Exception design is business strategy
Setting the exception queue threshold required alignment across UX, actuarial, and legal. It's a risk decision, not just a UI decision.
Don't wait for the PM
Six PM-less months forced me into stakeholder alignment and roadmap ownership — territory that made me a sharper strategic designer.
AI-Powered Submission Automation · Cowbell Cyber · 2024–2025 · ← All Projects
UX / Product Design · Case Study · 02

Resiliency Self-Serve
Platform

Transformed a broker-dependent purchase process into a self-service marketplace — enabling SMBs to discover, buy, and manage cyber security services independently for the first time.

Sr. Staff Designer (Director-Level IC) · Cowbell Cyber · Aug 2024 – May 2025
$0K
Revenue · 6 months
Growing 15% MoM
0%
Broker dependency reduced
Self-serve adoption
0%
Transaction success
vs. 87% projected
0.2×
Faster activation
2.8d vs. 9 broker-assisted
01 — Context
From insurance provider to cyber resilience platform
By 2024, cyber insurance alone wasn't enough. SMBs needed proactive tools — MDR, Pen Testing, Identity Protection — but Cowbell's portal had zero e-commerce capability. Every purchase required a broker, taking 2–3 weeks. 8,000 eligible policyholders. Zero self-service revenue.
01
SMB identifies a need
No self-service option
02
Contacts broker
2–3 week delays common
03
Broker quotes manually
No transparency
04
Legal & contracts
DocuSign loops, AR involved
05
Activation begins
No tracking or visibility
06
Invoice sent manually
0% self-service recovery
02 — The Challenge
Four layers of complexity, all interdependent
UX Complexity
Users needed to understand inherently technical security products without expertise. Cart-based multi-service buying conflicted with an existing broker-trust model.
Technical Architecture
Real-time bidirectional Salesforce sync, PCI-DSS compliant payments, and third-party partner provisioning — all behind a simple, trustworthy UI.
Legal & Compliance
Digital ToS with audit trails, GDPR/CCPA-compliant data handling, and revenue recognition split across two business units.
Stakeholder Alignment
Five teams — Product, Engineering, Salesforce, Legal, Finance — with competing priorities and different sprint cadences.
03 — Process
Zero to marketplace, in 9 months
Aug–Oct '24
Discovery
Analyzed 12 B2B SaaS platforms. 23 interviews with IT Managers, CISOs, CFOs — 94% prioritized pricing transparency. Built 3 core personas.
Competitive analysis23 interviews3 personas
Nov–Dec '24
Design & Testing
Expanded portal IA from 3 → 7 sections. 127 wireframes across 6 journeys. 47-component e-commerce design system. Task completion 83% → 96% across 3 test rounds.
127 wireframes47 components3 test rounds
Jan–May '25
Build & Launch
Agile 2-week sprints. Salesforce admin interface design. QA across 23 scenarios, 47 edge cases, 5 device types. Zero critical bugs at launch.
Salesforce integrationWCAG 2.1 AA
04 — Key Decisions
Five bets that defined the platform
Decision 01
Full shopping cart, not single-purchase flow
61% of SMBs needed 2–3 services simultaneously. A cart model enabled bundle discovery and reduced multi-service friction.
Outcome
↑ 38% avg
order value
Decision 02
Full pricing transparency — no "Contact Sales"
94% of research participants named pricing transparency their #1 purchase factor. Visible-pricing platforms converted 2.3× better.
Outcome
31% conversion
vs. 22% avg
Decision 03
Digital ToS in-flow, not a separate signing tool
Rather than routing users to DocuSign, we designed an in-checkout expandable ToS preview with scroll-to-enable and automated signed PDF generation.
Outcome
1.2% drop-off
at ToS step
Decision 04
5-stage activation pipeline with proactive notifications
Post-purchase anxiety was the biggest usability issue. A transparent activation tracker eliminated the "in the dark" feeling after payment.
Outcome
CSAT 6.7→8.9
−52% tickets
Decision 05
Separate Invoice section for finance workflows
CFOs and Controllers need a centralized transaction view disconnected from service discovery. Separation enabled self-service recovery of failed payments.
Outcome
98% payment
success rate
05 — Results
What we delivered
$0K
Revenue · first 6 months
Growing 15% month-over-month
0%
Browse-to-purchase conversion
vs. 22% B2B SaaS industry avg
0%
Cart abandonment rate
vs. 67% e-commerce industry avg
2.8d
Avg service activation
vs. 9 days broker-assisted
−18h
Ops workload saved / week
Via Salesforce automation design
0
Critical post-launch bugs
23 scenarios, 47 edge cases
06 — Learnings
What worked · what was hard
Early alignment saved 6 weeks
Monthly strategy sessions with Legal, Finance, and Partner Management prevented last-minute compliance surprises.
Design system paid for itself immediately
4 weeks upfront to build 47 e-commerce components reduced design time for subsequent features by 60%.
Salesforce sync was harder than scoped
Bidirectional real-time sync required 3 additional weeks for edge-case error handling. State diagrams created upfront became the only reliable reference during debugging.
Payment edge cases require stress testing
Initial designs didn't account for expired cards, fraud holds, or partial payment failures. Sandbox testing across all failure modes was essential to reaching 98% success.
CRS Self-Serve Platform · Cowbell Cyber · 2024–2025 · ← All Projects
UX / Product Design · Case Study · 03

PH Experience
2.0

Redesigning Cowbell's policyholder portal from a passive document store into an active lifecycle management platform — grounded in session data, usability research, and three measurable KPIs.

Sr. Staff Designer (Director-Level IC) · Cowbell Cyber · 2025–2026
0.9%
Nav. efficiency gain
vs. baseline audit
0%
Fewer dead-ends
Session recording analysis
0/30
Usability tasks
R1→R3 improvement
0/8
KPI criteria met
Across 3 dimensions
01 — Problem
The platform was invisible to the people it served
Policyholders had a portal — but session recordings showed the majority never returned after their first login. The platform held critical data: policy documents, renewal timelines, coverage limits. But it surfaced none of it proactively.
3,394
Sessions with zero meaningful interaction
+70%
Bounce rate on policy detail pages
More time on navigation than on content
+7,816
Support contacts for self-serviceable tasks
02 — Evidence
From session recordings to actionable evidence
Before proposing solutions, I built an evidence base from FullStory session recordings, click heatmaps, and support ticket taxonomy. The data revealed five compounding failure patterns.
Outdated Renewal Awareness
Policyholders missed renewal windows because the portal displayed dates without context, priority, or notification.
Dead-End Page Flows
Users landing on policy detail pages had no clear next action — 70%+ exited rather than engaging with coverage data.
Worst-Click Destination Bias
Click maps showed 3× more traffic to support links than to core portal features — users were routing around the product.
Confidence Gap
No visual representation of coverage adequacy or risk posture. Users couldn't answer "am I protected?" from the portal alone.
Strategy Vacuum
No design precedent, no component library, and no analytics infrastructure existed before this project began.
Compliance Exposure
Policy document access was buried 4+ clicks deep. For audit or claims scenarios, this created meaningful risk exposure.
0%
of active policyholders never used the dashboard — the portal's primary surface. A design product isn't a design product if it forces users to work around it.
03 — Process
Research-first, outcome-anchored
Phase 01
Session Analysis & Baseline Audit
3,394 FullStory sessions reviewed. Click heatmaps, dead-end flows, and support ticket taxonomy mapped into a failure inventory.
FullStory auditHeatmap analysis
Phase 02
Competitive Landscape & Flow Analysis
Benchmarked 10 fintech and insurtech portals. Identified navigation architecture patterns that reduce time-to-information for non-expert users.
10 platformsIA benchmarking
Phase 03
Navigation Architecture & Dashboard Concepts
Three dashboard concepts tested with 12 policyholders. The "Lifecycle" model — surfacing time-sensitive actions — won on task completion and confidence scores.
3 concepts12 participants
Phase 04
Stakeholder Review & Engineering Feasibility
Aligned on scope with PM, Engineering, and Legal. Defined data contracts for real-time policy status, renewal countdown, and compliance indicators.
Data contractsScope alignment
Phase 05
KPI Definition & Success Criteria
Three KPI dimensions finalized — Reliability, Usability, Revenue — each with baseline measurement and tracking method defined before production build began.
3 KPI dimensionsMeasurement plan
04 — Design
Before & After: The Dashboard Redesign
Two screenshots — same product, 14 months apart. The original portal surfaced no proactive context and offered no lifecycle visibility. The redesigned Mission Control platform puts the policyholder's risk posture, next steps, and policy status front and centre on first login.
Previous Design · v6.1 Static Document Store
Previous PH Dashboard design
Dashboard buried below marketing banner — zero policy context on load
Cowbell Factors chart requires expert knowledge to interpret
No renewal timeline, no compliance status, no next-step prompts
Support and eRiskHub surface equally to core policy actions
PH Experience 2.0 Active Lifecycle Platform
PH Experience 2.0 redesigned dashboard
Personalised welcome + active policy summary visible on first screen
Policy period progress bar — renewal awareness without clicking
Quick Actions surface the 5 highest-value tasks based on user state
Intelligence Modules: risk score, recommended actions, and documents unified
Passive document store
Active lifecycle dashboard
Generic CRS promotional banner
Personalised policy card with live data
Static risk chart (expert-only)
Cowbell Factor score + recommended actions
No prioritised next steps
5 Quick Actions ranked by urgency
Previous Design
Static policy document store
No renewal or expiry visibility
Coverage data buried 4+ clicks deep
Zero proactive notifications
No risk posture or compliance status
Users exit to broker for basic answers
Updated Design
Active lifecycle management platform
Renewal countdown with 60/30/7-day triggers
Coverage summary visible on first screen
Proactive in-portal action prompts
Live compliance status with remediation paths
Self-serve answers to 80% of common questions
05 — KPIs
Three KPIs grounded in research
Reliability
Session return rate
+0%
Target: +25% · Exceeded
Policyholders returning within 30 days of first login — the primary proxy for perceived platform value.
Usability
Task completion rate
0/30
Tasks completed unaided · R3 testing
From 9/30 at baseline to 17/30 post-launch across three rounds of testing.
Revenue
Renewal capture rate
0/8
KPI criteria met · 87.5% achievement
In-portal renewal actions initiated without broker intervention — tying design directly to revenue retention.
06 — Impact
What the project moved forward
0.9%
Navigation efficiency gain
Time-to-task vs. baseline
0%
Fewer dead-end sessions
Post-launch vs. pre-launch
7/8
KPI criteria met at launch
Across all 3 dimensions
0%
Dashboard adoption (was 0%)
Active users engaging dashboard
0%
Support tickets for self-serve tasks
Ops workload reduction
0
Critical post-launch defects
All device types tested
07 — Learnings
What this project taught me
Define KPIs before wireframes
Setting measurable success criteria upfront changed every conversation — from "does this look good?" to "does this move the metric?"
Session data is a design brief
3,394 FullStory sessions gave us more honest requirements than any stakeholder interview. Users showed us where they were confused — we didn't have to ask.
Proactive surfaces beat reactive ones
The biggest usability gains came from surfacing time-sensitive information before users went looking for it. Anticipation beats navigation.
No component library is a constraint, not an excuse
Building the design system in parallel added 3 weeks — but ensured consistency across a team that had none, and reduced design debt before it accumulated.
PH Experience 2.0 · Cowbell Cyber · 2025–2026 · ← All Projects
Design Systems · UX Leadership · Role Study · 04

Hilti
Design System

Building, maintaining, and propagating the Design System across Hilti's product portfolio — a single source of components, patterns, and UX standards unifying digital experiences into the Hilti ecosystem.

Design System Lead (DSL) · Hilti · 2017–2023 · 14+ Years Experience
SketchMarvelConfluenceJira
1 DS
Unified source of truth
Across all product teams
0%
Annual cost savings
Via shared component reuse
0
Stakeholder groups served
Design · Dev · Product · SME
🏆
Most Recognised Award
Internal recognition
01 — Component Library
One library, every surface
A centralised Sketch and Marvel component library maintained as the single source of truth for all product teams across buttons, forms, navigation, data tables, modals, and tokens.
Buttons
PrimarySecondary
GhostDisabled
Typography
H1 · Page Title
H2 · Section Heading
Body text — Regular 13px / 1.7 lh
Colour Tokens
hilti-red
navy-900
surface-100
Navigation
Dashboard
My Products
Services
Settings
Forms & Inputs
Text input
Dropdown select
Checkbox / Radio
Date picker
Cards & Tiles
Product card
Summary tile
Action card
Metric card
Data Tables
Sortable columns
Row selection
Pagination
Empty states
Modals & Alerts
Confirmation modal
Alert banner
Toast notification
Inline validation
02 — Ownership
Two areas, one mandate
Ownership Area 01
DS Artefacts & Libraries
Design tool library in Sketch and Marvel — components and screen template symbols
UX/UI standards & guideline documentation covering styling and behaviour
Maintenance and decommissioning lifecycle governance
Ownership Area 02
DS Processes
Component creation, definition, alignment, and approval workflow
Terminology standardisation across all contributing teams
Managed on Confluence & Marvel · work tracked in Jira
03 — Stakeholders
Four groups, one system
🎨
Designers
Feature Leads (FL)
UX Product Leads
UX Designers
💻
Developers
Web UI developers
Mobile developers
Quality Assurance
📦
Products
Product Owners
Delivery Heads
Product Managers
🔬
SMEs
Other DSLs
Branding
Researchers
04 — Responsibilities
Seven responsibilities, one role
Define & evolve the DSContinuously evolve the Design System and its processes in close collaboration with key stakeholders.
Handle component requestsReview and process requests for new UI components, patterns, and approved deviations from DS standards.
Maintain & communicate guidelinesCreate, publish, and timely communicate comprehensible DS guidelines and updates to all teams.
Manage design tool libraryOwn and maintain the shared Sketch/Marvel library used by designers across the entire product portfolio.
Educate & onboardEducate designers and product teams on DS role, usage, purpose, and processes — including new joiner onboarding.
User research for DS improvementsMitigate DS issues and identify improvements by conducting user research directly with internal stakeholders.
Ensure complianceReview UX/UI designs and implementations across all feature teams for conformance with DS guidelines.
"
A design system is only as strong as its adoption. Building the system is step one — building the culture around it is what makes it last.
— Chetan Pagare, Design System Lead · Hilti
05 — Day to Day
What the role looks like in practice
01
Educate key stakeholders and product teams on the DS Lead role, its value, and how to engage with the system effectively.
02
Establish and maintain a professional network across designers, developers, PMs, and branding — the DS's social infrastructure.
03
Proactively communicate DS updates to all relevant stakeholders so teams stay aligned, compliant, and unblocked.
04
Continuously improve the DS — optimise processes, documentation, communication patterns, and the design tool library.
05
Review UX/UI design work across feature teams to safeguard consistency with DS standards and interaction patterns.
06
Gather regular feedback from contributors and stakeholders, then onboard new joiners on DS usage, purpose, and governance.
Hilti Design System · Design System Lead · 2017–2023 · ← All Projects