Jen Wesolowsky
This portfolio is private
Product Designer · Greater NYC Area

Jennifer is a Senior Product Designer who turns dense, data rich B2B products into tools people actually want to use.

Partnering with Product and Engineering to make complex software feel inevitable.

About

Jen Wesolowsky

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

You'll usually find me outside running, cycling, or riding one of my horses. At home, I care for four rescue horses (Muffin, Mama, Megan, and Freddie), who keep life interesting. I also enjoy crocheting gifts for friends and family.

$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

3 projects
Tailoring the service to the property: grass type and irrigation zones
Product Design0→1Compliance UX

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

WorkWave · ServiceExpress
Sales Center lead detail screen
Product DesignPlatform RedesignB2B SaaS

Sales Center

WorkWave · CRM Redesign
Lead detail panel open beside the territory map showing a lead's photo, quick actions, and knock status
Product DesignField SalesMap UX

Door to Door Sales

WorkWave · From route to revenue

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
  • Form Packets: rebuilt the document signing experience to meet legal e-signature compliance, bundling multi-form jobs into a single link with DocuSign-grade controls
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.