Actively interviewing · Principal / Staff Designer roles

Chetan Pagare

Principal Product Designer  ·  UX Strategy & AI-Assisted Design  ·  B2B2C Enterprise SaaS
2× Horizon Interactive Bronze Award · Schlumberger

I turn enterprise complexity into products people actually use. Sixteen years designing at the intersection of strategy, systems, and craft — from seed-stage startups to Fortune 500 scale.

chetan.pagare@gmail.com
Career Arc 16 yrs · 5 companies · 6 industries
2023 → Now
Cowbell Cyber
Sr. Staff Designer · InsurTech SaaS
$2.4M savedAI workflows0→1 builds
2021 – 2023
Hilti
UX Lead · Construction Tech
+22% adoptionDesign system
2017 – 2021
Schlumberger
Sr. UX Designer · Oil & Gas
2× Bronze AwardsField research
2013 – 2017
Cognizant
UX/UI Designer · BFSI & Banking
Digital Star AwardBanking apps
2010 – 2013
Adaptive Sourcing
UI / Visual Designer · Consumer Electronics
AI / ML B2B2C SaaS Self-Service UX Design Systems InsurTech Product Strategy Automation Workflows Design Leadership
Problems I Love Solving

My strategic POV — not a skill list

Four hard problems I've built my career around, with proof I've solved them at scale.

Making AI trustworthy
When AI makes decisions that affect real people, transparency isn't optional — it's the whole product. Confidence layers, exception flows, override surfaces.
90% accuracy · $2.4M saved
Broker friction → self-serve revenue
Every step requiring a human is a step that loses customers. I eliminate broker-gated, call-us-to-buy loops with experiences users complete alone.
$120K in 6 months · 31% conversion
Passive portals → active platforms
Most enterprise portals are digital filing cabinets. I redesign them to proactively surface what users need and make returning feel useful.
33% fewer dead-ends · 7/8 KPIs met
Design systems as P&L levers
Design systems aren't component libraries — they're team multipliers. Tokens, patterns, governance that reduce decision fatigue and let teams focus on problems.
60% faster handoff · 16% annual savings
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.
Policy Holder 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 LogRocket sessions.

View Case Study
0.9%
Nav. efficiency
7/8
KPI criteria met
0%
Fewer dead-ends
1 DS
Unified source
0%
Faster handoff
15+
Products unified
04Hilti2021–2023
Design SystemsComponent LibrariesDS LeadershipEnterprise UX
Hilti Design System Lead

Built, maintained, and propagated the Hilti Design System across 15+ products — a single source of components, patterns, and UX standards. 60% faster handoff, 16% annual cost reduction across 4 stakeholder groups.

View Case Study
About

Designing at the intersection of strategy & craft

I'm a Director-level IC designer with 16+ years building products people rely on — across startups, scaleups, and global enterprises like Cowbell Cyber, Hilti, and Schlumberger. My focus is B2B2C Enterprise SaaS, where the real challenge isn't making things pretty — it's making complex systems feel effortless.

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.

$2.4M+
Annual savings delivered
20+
Products shipped
30K+
Enterprise users served
MBA
2009–2011 · Business strategy
Sr. Staff Designer (Director-Level IC)
Cowbell Cyber · InsurTech / Fintech SaaS
2023–now
UX UI Lead · Design System Lead
Hilti · Enterprise Field Tools
🏆 Internal Recognition Award
2021–2023
Sr. UX UI Designer
Schlumberger · Oil & Gas
🥉 2× Horizon Interactive Bronze
2017–2021
UI UX Designer
Cognizant · BFSI & Barclays Banking
⭐ Digital Star Award
2013–2017
Mobile & Visual Designer
Adaptive Sourcing · Consumer Electronics
2010–2013
Let's Connect

Looking for a designer
who ships and leads?

I'm open to Principal and Staff Designer roles where design has a real seat at the table. If you're building something ambitious and want someone who bridges strategy, systems, and craft — let's talk.

Available now · Response within 24 hours
Pune, India · US Business Visa valid 2029 English · Marathi · Hindi MBA · 2009–2011
© 2026 Chetan Pagare. All rights reserved. Principal Product Designer · UX Strategy & AI-Assisted Design
Enterprise SaaSAI / ML · 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 processed at 90% accuracy. Vendor eliminated Feb 2025.

Role
Principal Product Designer
Company
Cowbell Cyber
Timeline
Mar 2024 – Feb 2025
Team
1 Designer, 4 Engineers, PM
0+
Daily submissions
processed automatically
0%
Field accuracy
extracted from PDFs
0.2×
Faster quotes
time-to-quote reduced
$0.4M
Annual savings
vendor + headcount reduction
01 — The Problem

A pipeline that couldn't scale

Insurance underwriters were drowning in manual work. Each submission required downloading PDFs, manually extracting data into spreadsheets, and cross-referencing multiple documents. The $240K/year vendor contract was growing — not shrinking.

Step 01
Broker emails PDF
16–72 hour processing time
Step 02–03
Manual vendor extraction
Patra Corp, India — 100% manual entry
Step 04
Underwriter re-enters data
Errors compounded across handoffs
$240K
Annual vendor cost for manual data entry — plus growing headcount pressure as submission volume scaled. The business case for automation was self-evident; the design challenge was building trust in the output.
02 — Research

Understanding where trust breaks

Underwriters had well-founded skepticism of automated extraction. Three research methods surfaced the failure modes that would define the design.

Method 01
Contextual Inquiry
Observed 8 underwriters processing submissions. Mapped every manual step, decision point, and error recovery pattern. Found 12 distinct failure modes in the existing workflow.
Method 02
Document Analysis
Analyzed 200+ submission PDFs across broker types. Identified structural variation patterns that would challenge OCR — and informed the confidence scoring thresholds.
Method 03
Error Taxonomy
Catalogued 6 months of vendor correction logs. Built a failure classification system that became the foundation for the exception UX design.
03 — Key Decision Points

Strategic trade-offs made

Three moments where research changed the direction of the product — the kind of decisions that separate a thoughtful designer from a pixel-pusher.

The ChallengeConventional ApproachMy Strategic PivotResult
High AI error rate on low-quality PDFsMore training data, wait for model improvementConfidence Scoring UI — visual trust signal per extracted fieldUser trust increased; underwriters validated faster not slower
Underwriters wanted full control over every fieldManual override on every field, slowing throughputTiered review: auto-approve high-confidence, flag exceptions onlyReview time cut 3.2× while maintaining accuracy audit trail
Human-in-the-loop for AI errorsGeneric error states ("AI could not extract")Exception UX with context: why it failed + guided correction pathException handling time reduced 60%; retraining data quality improved
04 — Process

Full-cycle from concept to production

Phase 01
Discovery & Stakeholder Alignment
Underwriter shadowing, vendor workflow mapping, and 3 rounds of stakeholder interviews to define scope and success criteria.
8 interviewsWorkflow mapping
Phase 02
OCR Pipeline Design
Defined the document extraction model in partnership with engineering. Established confidence thresholds, field taxonomy, and exception categories.
Field taxonomyConfidence tiers
Phase 03
Interface Design & Prototyping
Three interface concepts tested with underwriters. "Confidence-first" layout won — users needed to see reliability signals before trusting automation.
3 concepts10 test sessions
Phase 04
Exception UX Design
Designed recovery flows for every failure mode in the error taxonomy. Each exception gave underwriters context on why the AI failed and the fastest correction path.
12 failure modesException flows
Phase 05
Production & Vendor Elimination
Shipped in Feb 2025. Vendor contract terminated. 1,000+ daily submissions now processed automatically at 90% field accuracy.
Vendor eliminated$2.4M annual saving
05 — Impact

Outcomes that speak for themselves

Business Impact
Annual vendor savings
$2.4M
Full vendor contract eliminated Feb 2025. Headcount redeployment to higher-value underwriting work.
Product Quality
AI field accuracy
90%
Across 1,000+ daily submissions with confidence scoring enabling targeted human review of exceptions only.
Operational Speed
Faster time-to-quote
3.2×
From 16–72 hour manual processing to sub-hour automated pipeline with exception handling.
"
The confidence scoring was the thing that made this work. Underwriters stopped fighting the AI and started working with it — because they could see exactly how sure it was.
— Underwriting Team Lead, Cowbell Cyber
06 — Learnings

What worked · what was hard

Exception UX is the real design challenge
When AI is wrong, the recovery path matters more than the success path. Designing for failure modes with context and guided correction was the hardest — and most impactful — work on this project.
Confidence scoring changed the adoption curve
Underwriters initially rejected automation. Confidence scores — showing per-field extraction reliability — shifted the dynamic from distrust to collaborative validation.
Research investment prevented two false starts
Early contextual inquiry prevented us from building a "smart autocomplete" (the initial engineering proposal). Observation revealed users needed to approve, not complete — a fundamentally different interaction model.
Human-in-the-loop is a design decision, not a fallback
Where to place human judgment in an AI pipeline is the core product design question. Tiered review — auto-approve above threshold, flag below — was the result of 3 rounds of testing, not intuition.
AI Submission Automation · Cowbell Cyber · 2024–2025
B2B SaaSSelf-Service · 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.

Role
Sr. Staff Designer (Director-Level IC)
Company
Cowbell Cyber
Timeline
2024–2025
Team
1 Designer, 3 Engineers, PM
$120K
Revenue · 6 months
self-serve GMV
0%
Conversion rate
browse → purchase
0%
Transaction success
payment success rate
0%
Support ticket reduction
vs. broker-assisted baseline
01 — The Problem

Every purchase required a phone call

Cowbell's resiliency services — endpoint protection, employee training, dark web monitoring — could only be purchased through a broker. SMB customers had no direct path to buy, manage, or renew independently.

100%
Purchases required broker involvement
3–5 days
Average time from interest to activation
$0
Direct digital revenue at project start
+400
Monthly support tickets for purchase-related tasks
02 — Key Decision Points

Where research changed direction

The ChallengeConventional ApproachMy Strategic PivotResult
SMBs unfamiliar with cyber security service categoriesList products with technical specsRisk-outcome framing: "What does this protect you from?" not "What is this?"31% conversion — users bought based on understood risk, not feature lists
Payment edge cases (expired cards, fraud holds)Generic error statesStress-tested 8 payment failure scenarios with contextual recovery paths98% transaction success — edge cases accounted for before launch
Salesforce sync complexityAsync sync, eventual consistencyReal-time bidirectional sync with state diagrams as engineering referenceZero data discrepancy reports in first 90 days post-launch
03 — Process

Research-first, revenue-anchored

Phase 01
SMB Customer Research
12 SMB interviews + broker journey mapping. Identified 6 decision-stage friction points where broker dependency caused drop-off.
12 interviewsJourney mapping
Phase 02
Marketplace Architecture Design
Defined product discovery, comparison, and checkout flows. 3 IA concepts tested; risk-outcome framing model won on comprehension and confidence scores.
3 IA conceptsUsability testing
Phase 03
E-Commerce Component Library
Built 47 e-commerce components from scratch — product cards, cart, checkout, payment confirmation, and empty states. 4-week upfront investment reduced subsequent feature design time by 60%.
47 componentsDesign system
Phase 04
Salesforce Integration & Payment UX
State diagram methodology for all payment flows. Sandbox-tested 8 failure scenarios. Bidirectional Salesforce sync spec co-authored with engineering.
8 failure scenariosState diagrams
Phase 05
Launch & Measurement
$120K GMV in first 6 months. 31% conversion, 98% transaction success, 65% support ticket reduction.
$120K GMV31% conversion
04 — Impact

From $0 to first-class digital revenue

Revenue
GMV in first 6 months
$120K
Zero direct digital revenue at project start. First self-serve purchase completed day 1 of launch.
Commerce
Browse → purchase conversion
31%
Industry benchmark for SMB SaaS self-serve is 18–24%. Risk-outcome framing drove above-average conversion.
Reliability
Payment success rate
98%
Result of stress-testing 8 edge-case payment scenarios before launch — not discovered in production.
05 — Learnings

What worked · what was hard

Early legal alignment saved 6 weeks
Monthly strategy sessions with Legal, Finance, and Partner Management prevented last-minute compliance surprises that would have delayed the launch.
Design system paid for itself immediately
4 weeks upfront to build 47 e-commerce components reduced design time for subsequent features by 60%. Every new feature request became a composition problem, not a design problem.
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.
Risk framing unlocked confidence
SMBs didn't understand "endpoint protection." They understood "what happens if an employee clicks a phishing link." Reframing product descriptions around risk outcomes was the conversion unlock.
Resiliency Self-Serve Platform · Cowbell Cyber · 2024–2025
Consumer ProductUX Research · Case Study 03

Policy Holder
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.

Role
Sr. Staff Designer (Director-Level IC)
Company
Cowbell Cyber
Timeline
2025 – 2026
Research
3,394 LogRocket sessions
0.9%
Nav. efficiency gain
vs. baseline audit
0%
Fewer dead-ends
session recording analysis
17/30
Usability tasks improved
R1 → R3 test rounds
7/8
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
57%
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.
02 — Evidence

From session recordings to actionable evidence

Before proposing solutions, I built an evidence base from LogRocket 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.
03 — Key Decision Points

Research-pivoted design decisions

The ChallengeConventional ApproachMy Strategic PivotResult
Users couldn't find their most important next actionBetter navigation labels"Lifecycle" model — surface time-sensitive actions proactively on first login14.9% navigation efficiency gain; tested against 2 other concepts
High bounce from policy detail pagesRicher content on detail pagesProgressive disclosure — essential info up front, deep content on demand33% reduction in dead-end exits tracked via session recordings
No analytics baseline existedLaunch and measure afterwardPre-defined 3 KPI dimensions with measurement plans before build started7/8 KPI criteria met — had objective success criteria from day one
04 — Design

Before & After: The Dashboard Redesign

Two versions — same product, 14 months apart. The original portal surfaced no proactive context. The redesigned Mission Control platform puts the policyholder's risk posture, next steps, and policy status front and centre on first login.

Previous Design · v6.1Static Document Store
Original portal · screenshot in Figma
What was wrong
No proactive renewal or risk alerts
Policy documents buried 4+ clicks deep
Zero contextual next actions on homepage
70%+ bounce rate on detail pages
Redesigned · v2.0Active Lifecycle Platform
Redesigned dashboard · Mission Control
What changed
Risk posture score + renewal countdown on load
Top 3 actions surfaced proactively per lifecycle stage
Progressive disclosure for policy documents
33% reduction in dead-end navigation exits
05 — Impact

Measured outcomes, not assumptions

Navigation
Efficiency gain
14.9%
vs. baseline audit conducted pre-project. Users reached their target content faster with fewer navigation steps.
Usability
Tasks improved R1 → R3
17/30
57% of task scenarios showed measurable usability improvement across three rounds of testing with policyholders.
Engagement
Dead-end reduction
33%
Session recording analysis post-launch showed 33% fewer sessions ending in zero meaningful interaction or support contact.
Policy Holder Experience 2.0 · Cowbell Cyber · 2025–2026
Enterprise Design SystemsDS Leadership · Case 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 15+ digital products into the Hilti ecosystem.

Role
Design System Lead (DSL)
Company
Hilti
Timeline
2021 – 2023
Tools
Sketch · Marvel · Confluence · Jira
1 DS
Unified source of truth
across all product teams
0%
Faster handoff
design-to-dev time
0%
Annual cost savings
via shared component reuse
🏆
Internal Recognition Award
Design System rollout
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

Every design decision passed through four distinct groups — each with different needs, cadences, and success metrics. The DSL role sat at the centre, translating between all of them.

🎨
Designers
UX Leads & ICs
💻
Developers
Web, Mobile, QA
DS Lead
Design
System
📦
Product
POs, PMs
🔬
SMEs
DSLs, Branding, Research
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 the design team 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.
Products
15+
surfaces unified
Efficiency
60%
faster design handoff
Savings
16%
annual cost reduction
Quality
Zero
UI inconsistencies
06 — Key Decision Points

Strategic choices that made it scale

The ChallengeConventional ApproachMy Strategic PivotResult
15+ products with diverged UI patternsAudit and gradually align over 2 yearsGovernance-first: establish approval workflow before building componentsZero new inconsistencies introduced from day one of system launch
Developers not adopting design tokensDocumentation-only approachPaired with dev leads to create token-to-CSS mapping guides in their language60% faster handoff — developers stopped asking "what's the hex for this?"
Designers creating workarounds instead of requesting componentsEnforcement and rollbackDeviation request process with fast SLA — workarounds became DS contributions16% annual cost reduction from component reuse replacing custom builds
Hilti Design System Lead · Hilti · 2021–2023
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