Experience
HRIS, payroll, and workforce management platform for agriculture
Head of Design
May 2023 – Jul 2025
Designed HR tools including payroll, timekeeping, and workforce logistics, incorporating AI features like bulk document sorting and data extraction, and paper timesheet ingestion.
Led product and design strategy during a phase of exponential growth, from early revenue to tens of millions in ARR.
Supported 30× customer growth during my tenure while upholding a high bar for product quality and user experience.
Scaled the design team from one to four, fostering a collaborative team culture through weekly critiques and biweekly sessions across product and brand.
Founding Product Designer
Mar 2021 – May 2023
Designed the Seso platform from 0 to 1 as a solo designer, creating the design system and foundational user experience that accelerated the path to product-market fit.
Home care platform for aging adults, two-sided marketplace for families and caregivers
Lead Product Designer
Aug 2016 – Mar 2021
Lead designer for internal tools that drove business operations efficiency from Series B through Series D.
Optimized scheduling and logistics, leading to a +3% improvement in gross margin.
Reservation software for tour and activity operators
Designer
Aug 2015 – Aug 2016
Contributed across brand, product, and marketing in a two-person team; the work remained foundational to the product after Booking.com’s acquisition.
2×4 Consulting
Product, web, and brand design consultancy
Owner
2015 – 2021
Designed e-commerce experiences and site architecture for startups in retail and delivery. Developed brand identities and visual designs for a range of clients.
MBI
Post-secondary school in Chicago
Web Designer & Developer
2013 – 2016
Built and maintained web pages, forms, emails, and CMS features supporting major fundraising campaigns that generated $1M+ in donations annually.
435 Digital
Digital agency under the Chicago Tribune
Web Designer
2012 – 2013
Created websites for local businesses.
A new music discovery platform
Side Project
Current
Designed and built a full-stack app for discovering and cataloging music, using Remix and a Supabase backend. Created as a personal project to deepen my development skills and explore modern web frameworks.
© 2025 Caleb Durenberger. All rights reserved.