At Corgi, we're building an AI-native insurance carrier. We underwrite and issue policies while selling direct to the customer, which lets us price risk better and move faster than anyone in the market. We've raised over $108M and we're launching a trucking insurance carrier from zero.
The $40B+ trucking insurance market is still being underwritten by people with paper files and 1990s rating engines. We're going to fix that, and we need a designer and writer who can get our product, our marketing site, and our customer-facing to the next level.
This is a hybrid creative role. Half product designer, half marketer, all owner. You'll ship the UI for the workflows our producers and customers actually use, you'll write the blog and the policy explainers, and you'll build the collateral our AEs hand to embedded partners when they walk into a pitch.
You'll be the design and marketing function for this line of business in its first year. That means you don't get to specialize. It also means you get to ship more in one quarter at Corgi than you would in two years anywhere else.
You'll work directly with the two executives leading this division:
Brianna Lynch began her career at EY before leading FP&A and Corporate Development at HarbourVest Partners. She then joined Affiliated Managers Group, an $880 billion asset manager based in MA, where she worked across M&A and Investor Relations acquiring and advising private equity, hedge fund, and venture capital firms. After traveling through Europe and advising startups, she joined Corgi in 2025 as Head of Finance and leading M&A efforts with Drew.
Drew Bregman previously founded a behavioral assessment company that helps the NSA and U.S. military identify talent. Before that, he co-founded Corgi's M&A team, as well as the sales division at Corgi's subsidiary Beagle (40% MoM growth), and earlier built transportation management software as an engineer at a large freight brokerage. He cares a lot about design and will be in Figma reviewing work with you.
- Audit every customer-facing and producer-facing surface we have, web pages, dashboards, emails, PDFs, and tell us what's good, what's broken, and what we should kill
- Establish a clean visual system for the trucking line: typography, color, components, document templates, deck templates
- Ship the first iteration of the partner pitch collateral the AE team will use to close embedded partnerships (deck, one-pager, integration brief)
- Stand up the blog and publish the first 3 to 5 posts, with a content calendar through quarter end
- Redesign one high-traffic flow in our producer portal end to end
- Run the content engine. Weekly blog posts shipped, social cadence operating, partner-facing materials updated as we close new platforms
- Lead the design of new product surfaces as we launch them, including the embedded quote experience our platform partners will integrate
- Build the customer education library: policy explainers, COI walkthroughs, claims process material, all written in plain English and designed to actually be read
- Own the brand expression across the entire trucking line, including how we sound in writing and how we look in product
- Product design. Ship UI in Figma for our producer portal, embedded quote flows, and internal tools. Real shipped work, not mockups that sit in a board.
- Marketing site and landing pages. Design and write the pages that convert: home, partners, product, pricing, blog, and the partner-specific landing pages we'll spin up as we close embedded deals.
- Blog and SEO content. Own the editorial calendar. Write posts that rank for the queries our customers actually search, and that build credibility with the trucking industry. Edit and ship outside contributors as we scale the program.
- Sales and partnership collateral. Build the decks, one-pagers, integration briefs, and case studies the AE team needs to close partnerships and direct fleet business.
- Customer education. Translate dense insurance and trucking material (policy forms, endorsements, FMCSA filings, claims processes) into customer-facing content that actually helps.
- Brand consistency. Make sure everything we ship feels like one company.
- 2 to 5 years in design, marketing, or a hybrid role at a high-growth startup
- Strong Figma portfolio with shipped software UI work, not just brand or print
- Excellent writer. We'll ask for two writing samples and we'll read them carefully
- You understand how a blog actually drives pipeline (SEO, distribution, conversion), not just how to publish posts
- You can take a dense, technical topic and make it land for a non-expert reader without dumbing it down
- High agency, high ownership, low drama
- Prior experience at an insurtech, fintech, logistics, or B2B SaaS company
- Have written or designed for a regulated industry (insurance, healthcare, financial services)
- Comfortable with light front-end work (HTML, CSS, basic component edits in our codebase)
- Have built a content program from zero, with documented traffic or pipeline growth
- Familiarity with trucking, freight, or commercial insurance
- $70,000 to $120,000 base, determined by experience and portfolio strength
- Equity
- Health, dental, vision
- In-office in Boston, 5 to 6 days a week
- Screening call (30 min)
- Portfolio and writing sample review (async)
- Paid work trial: design one shipped surface plus write one blog post on a brief we provide (paid $1,000 flat)
- Onsite with the team, including a working session on the work trial deliverable
- Offer call within 48 hours