Jen Wesolowsky
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Jen Wesolowsky
UX / UI Designer · Greater NYC Area

Turning dense data into interfaces people actually use.

I believe UX is more than screen deep. Great experiences come from understanding business goals, the technology underneath, and the people using a product every day, not just how it looks.

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Industries
B2B SaaS Field Service Management Travel & Hospitality Cruise Digital Media
Background since
2012 BFA, The College of New Jersey

About

I'm a product designer who got my start designing for one of the most complex content ecosystems around: travel, before moving into marketing tech and fintech. Since 2018 I've been a Senior Product Designer at WorkWave, where I own UX/UI and product design end-to-end across a multi-product B2B portfolio.

I work at the intersection of psychology, craft, and strategy: understanding why a user hesitates, where a workflow breaks down, and how a design system can scale past the first release. That's meant owning research, usability testing, and Figma-based design end-to-end on data-rich, mobile-first B2B and B2C flows, and tying that design work directly to adoption and revenue.

Outside of work

When I'm not designing, I'm usually outside running, mountain biking, or gravel riding through anything that gets me into nature, often chasing a good sunset to close out the day. At home I run a small barn with four rescue horses, Muffin, Mama, Megan, and Freddie, who keep me grounded, patient, and laughing. When I need to slow down, I crochet (most people close to me have ended up with a handmade hat or scarf from me by the holidays) and paint, though I'm still very much a beginner there.

$5M+
Product portfolio owned
1,500+
SMB–enterprise customers served
3x
Module adoption growth
$2M+
ARR added via 2 new builds + 1 redesign
$15M+
TAM expansion

Selected work

4 projects
WorkWave · Sales Center

Mapping how sales teams own territory

Led research and design for map-based territory management inside Sales Center, a platform used by canvassing and door-to-door sales teams. Interviewed sales managers, canvassing managers, and field reps to understand how territories get defined, assigned, and protected from overlap today, then translated those findings into a freeform "lasso" drawing tool tied directly into automatic lead-assignment rules.

Validated the prototype in a live customer review, where stakeholder feedback shaped follow-on requirements: deleting a lassoed area while retaining historical lead pins for reference, date-range based editing of knock statuses, and GPS "breadcrumb" tracking so managers can confirm reps actually walked an area.

Service blueprint for the territory management workflow, showing planning, assignment, field execution, and cancellation phases across customer, frontstage, and backstage layers
Service blueprint mapping the full territory lifecycle: Planning & Definition, Assignment & Sync, Field Execution, and Cancellation, across customer actions, frontstage employee actions, and backstage systems. Used to surface gaps still owned by engineering before scoping the lasso tool.

Designing the flow, end to end

9 steps
Manager's dashboard surfaces 45 pending leads and 38 unqualified, the volume that makes manual territory assignment unworkable.
STEP 01 Manager's dashboard surfaces 45 pending leads and 38 unqualified, the volume that makes manual territory assignment unworkable.
Starts a new assignment rule from scratch.
STEP 02 Starts a new assignment rule from scratch.
Adds a condition: rules can route leads by any lead attribute, including territory.
STEP 03 Adds a condition: rules can route leads by any lead attribute, including territory.
Opens the territory drawer and picks a color, so ownership stays visually distinct on the map.
STEP 04 Opens the territory drawer and picks a color, so ownership stays visually distinct on the map.
Lassoes the territory freehand, point by point, rather than picking from a fixed list of zip codes.
STEP 05 Lassoes the territory freehand, point by point, rather than picking from a fixed list of zip codes.
Finishes and saves the shape: the territory is now a real polygon tied to a name and color.
STEP 06 Finishes and saves the shape: the territory is now a real polygon tied to a name and color.
Ties the new territory directly to an assignment rule, so matching leads route to it automatically.
STEP 07 Ties the new territory directly to an assignment rule, so matching leads route to it automatically.
Rules stack in priority order, so managers can see exactly which territory wins when areas overlap.
STEP 08 Rules stack in priority order, so managers can see exactly which territory wins when areas overlap.
The result: color-coded ownership on the live map, filterable by pending leads, leads, and opportunities, viewable as the rep or the manager.
STEP 09 The result: color-coded ownership on the live map, filterable by pending leads, leads, and opportunities, viewable as the rep or the manager.
Map-based UXResearch-led designFigmaField service SaaS
WorkWave · ServiceExpress

Rebuilt from the ground up: a zero-touch path from address to paid invoice

ServiceExpress is a guided, multi-step quoting flow built to replace high-friction chatbots at the exact moment a homeowner's interest peaks. I owned this end-to-end (research, usability testing, and design), running focus groups and moderated tests to validate each step before handing it to engineering.

At its center is a property-intelligence step that returns verified lot and structure measurements from aerial imagery instantly, removing the manual back-and-forth that usually stalls a quote. The flow carries a homeowner from service selection through measurement, customization, package selection, payment cadence, purchase, and a legally required terms acknowledgment, then collects the post-purchase logistics needed to schedule the first visit, with zero human touchpoints. Built against an internal target of under 1% measurement error; field results are still being measured.

Service blueprint for the ServiceExpress quote-to-purchase flow, showing AI measurement, conversion and checkout, and post-sale field readiness phases with supporting technology and open questions
Service blueprint mapping the full rebuild across four phases: SwiftForm & AI Measurement, Conversion & Checkout, and Post-Sale & Field Readiness, including the supporting tech stack (MeasureAI, Stripe, Pendo, CRM sync) and a logged risk register for known edge cases like API latency and timezone handling.

The flow, start to finish

10 steps
Captures contact details and desired services in one short step, no separate lead form before the quote begins.
STEP 01 Captures contact details and desired services in one short step, no separate lead form before the quote begins.
Pulls verified lot and structure measurements from aerial imagery and public records instantly: the property-intelligence step that replaces a manual site visit.
STEP 02 Pulls verified lot and structure measurements from aerial imagery and public records instantly: the property-intelligence step that replaces a manual site visit.
Tailors the service to the property: grass type, irrigation zones, and other inputs that drive an accurate price.
STEP 03 Tailors the service to the property: grass type, irrigation zones, and other inputs that drive an accurate price.
Lets the homeowner choose a payment cadence before pricing even appears, so the decision doesn't stall checkout later.
STEP 04 Lets the homeowner choose a payment cadence before pricing even appears, so the decision doesn't stall checkout later.
Presents tiered packages with a clear
STEP 05 Presents tiered packages with a clear "best value" default and itemized inclusions, reducing under-quoting risk without office oversight.
Itemized purchase summary: price, discount, tax, and total, before any commitment.
STEP 06 Itemized purchase summary: price, discount, tax, and total, before any commitment.
Required terms acknowledgment at the point of sale, satisfying operational compliance without adding a separate step.
STEP 07 Required terms acknowledgment at the point of sale, satisfying operational compliance without adding a separate step.
Immediately after purchase, the flow pivots to scheduling logistics, starting with gate access, so the first visit doesn't get blocked at the door.
STEP 08 Immediately after purchase, the flow pivots to scheduling logistics, starting with gate access, so the first visit doesn't get blocked at the door.
Captures and verifies an arrival-notification phone number, so the homeowner knows exactly when the crew is on the way.
STEP 09 Captures and verifies an arrival-notification phone number, so the homeowner knows exactly when the crew is on the way.
Confirmation: preferences saved, first visit ready to schedule, zero human handoff required.
STEP 10 Confirmation: preferences saved, first visit ready to schedule, zero human handoff required.
Lead captureProperty intelligenceCompliance UXMobile-first0→1 flow
WorkWave · Unified Calendar

Turning three fragmented schedules into one source of truth

The Unified Calendar aggregates CRM tasks and external Google/Outlook calendars (via Nylas) into a single, color-coded view inside Sales Center, eliminating the multi-system context switching that was costing field reps active selling time.

The core design challenge was balancing dense, multi-source data against a touch-friendly interface built for reps working from a tablet in the field, plus a creation flow that keeps each event's source system explicit so ownership and sync direction stay unambiguous.

Service blueprint for the Unified Calendar feature, showing Nylas OAuth, calendar aggregation, and event editing phases with supporting technology and a logged risk register
Service blueprint mapping the Nylas OAuth connection, calendar aggregation across Sales Center, and event editing, plus a logged risk register covering API performance targets, rate limiting, sync conflicts, and manager-visibility open questions still being scoped.

The flow, start to finish

5 steps
Entry point: the Sales Center dashboard, where reps already track leads and opportunities. The calendar lives one click away, not in a separate app.
STEP 01 Entry point: the Sales Center dashboard, where reps already track leads and opportunities. The calendar lives one click away, not in a separate app.
Month view aggregates three sources into one color-coded calendar: Sales Center activity reminders, CRM next-action and expected-close dates, and read-only PestPac dispatch appointments.
STEP 02 Month view aggregates multiple sources into one color-coded calendar: Sales Center activity reminders and CRM next-action and expected-close dates.
Creating a new event keeps the source system explicit (Sales Center vs. PestPac vs. external), so ownership and sync direction stay unambiguous.
STEP 03 Creating a new event keeps the source system explicit (Sales Center vs. external), so ownership and sync direction stay unambiguous.
A filled-out event: title, description, date, time, and reminder, created without ever switching apps.
STEP 04 A filled-out event: title, description, date, time, and reminder, created without ever switching apps.
Back in the unified view immediately after creation: no refresh, no app switch, no lost context.
STEP 05 Back in the unified view immediately after creation: no refresh, no app switch, no lost context.
Data aggregationTablet-firstCalendar UXSystems thinkingFigma
Earlier work

Before this, I built UX foundations across travel, martech, and fintech

TripAdvisor Media Group
2012 – 2018 · Ewing, NJ

Launching Cruises, a 0→1 product

Led UX design for Cruises, a completely new product built to support TripAdvisor's evolving competitive position in travel booking. Designed the mobile menu redesign that simplified navigation across a sprawling content surface, and built interactive prototypes to validate flows before development.

0→1 product designResponsive UIPrototyping

Experience

2018 – Present

Senior Product Designer

WorkWave
  • Own UX/UI and product design end-to-end across a $5M+ product portfolio spanning CRM, Custom Forms, and Sales Agent, serving 1,500+ SMB-to-enterprise customers in pest control and lawn/green markets
  • Defined a 3-year cross-product design vision that grew module adoption 3x and helped exceed annual budget targets by 10–20% year over year
  • Delivered two 0→1 product builds and one major redesign, adding $2M+ in portfolio ARR and expanding TAM to $15M+
  • Sales Center: led research and design for map-based territory management, including a freeform "lasso" drawing tool tied into automatic lead-assignment rules
  • ServiceExpress: owned research, usability testing, and design for a ground-up rebuild of the lead-to-purchase flow, replacing a chatbot with a property-intelligence-driven, self-serve checkout
  • Unified Calendar: designed a tablet-first, multi-source calendar aggregating CRM and Nylas-connected external calendars into one view for field reps
2012 – 2018

UX Designer

TripAdvisor Media Group · Ewing, NJ
  • Designed Cruises, a new product supporting TripAdvisor's strategic position in travel
  • Led UX for new Meta experiences and display advertising surfaces
  • Redesigned the mobile menu for a smoother, more direct user flow
  • Built interactive prototypes and animations to enable rapid testing and iteration
  • Created responsive interfaces adapted across multiple screen sizes

Tools & craft

Tools
FigmaSketchJiraConfluenceTrelloZeroheightClaude Code
Strengths
Design systems0→1 productResponsive UI

Let's talk about your dashboards.

Open to Senior UX Designer roles focused on data-rich, B2B products. Reach out directly. I'll respond fast.

Email me