UX Writer


About Us
Thimble is a leading insurtech platform for small business customers and agents. Thimble allows customers to quickly get insurance coverage by the job, month or year using its award-winning app, website, or over the phone.

Founded by serial entrepreneurs Jay Bregman and Eugene Hertz, Thimble works with a variety of carriers to bring the best insurance solutions to small businesses, brokers and agents. Since it was founded, Thimble has delivered more than 170,000 policies to small businesses across the United States.

Thimble was acquired by Arch Insurance, a unit of Arch Capital Group Ltd. (Nasdaq: ACGL), a publicly listed Bermuda exempted company with approximately $15.6 billion in capital at Dec. 31, 2022. Arch, which is part of the S&P 500 Index, provides insurance, reinsurance and mortgage insurance on a worldwide basis through its wholly owned subsidiaries.

Thimble's innovative culture and technical expertise are an incredible addition to Arch Capital’s portfolio of offerings. The acquisition expands Arch’s suite of digital solutions for small business customers and brokers. Thimble will remain a separate subsidiary, working closely with the Arch Group team. 

For more information, visit thimble.com.

Our Values
Our unique culture is built around our six core values:

Think Wild, Act Tame
Be relentlessly creative. Question everything. Get to know the rules so well, you can use them in new ways. Be the industry’s compliant radicals.

Green Means GO
Act. Move forward. Learn. You can only make a decision based on the best information you have – so make it.

Own Every Detail
Be ruthlessly precise. Disciplined. Sweat the small stuff.

Simplify, Simplify, Simplify
Get to the point. Make it crystal clear. Cut everything else. It’s our job to make insurance easy – however hard that is for us.

Every Moment Counts
Show up early and ready. Deliver on time or before. Make the most of your time, so others can make the most of theirs.

Stay Human
Treat every person, and their ideas, with respect. Cherish diversity.

About the Role 
Thimble is seeking a User Experience (UX) Writer to pair language with best-in-class design and further our mission of making business insurance simple for 300+ professions. You’ll work directly with the User Experience, Product, Broker, Customer Service, and Insurance teams to create user-focused solutions across mobile, desktop, and the Thimble app with a brand voice that’sinformative, friendly, quick, and honest. 
This role will play a crucial role in creating innovative features and interactions on a team honored by Fast Company’s 2021 Innovation by Design Awards for Best UX Design. You’llreport to our Lead UX Designer, have limitless opportunities to engage with product design and research, taking your writing to the next level as you empower our diverse customer base to build businesses around their passions. 


    • Write engaging copy for Thimble's Product teams 
    • Work collaboratively with other members of the design team and with other multi-disciplinary team members (including marketing, engineering, and compliance) to build a user-centered platform that is human and intuitive regardless of a customer’s familiarity with business insurance 
    • Offer a content-first perspective throughout the product development process, and influence strategic decisions to improve the overall customer experience and ensure consistency throughout the customer journey 
    • Drive consensus in a fast-paced, agile environment, and advocate for solutions that balance the needs of our customers with our business goals and underwriting requirements 
    • Maintain documentation of product copy in our Source-of-Truth files 
    • Advocate and support UX research projects, e.g. writing and editing customer surveys and packaging user insights 
    • Collaborate with our Support Team to keep Help Desk content up to date for a many-faceted user base 
    • Help Thimble’s users feel empowered to buy exactly the right insurance for their business and be reassured that our coverage is there for them when they need it 


    • 2+ years in a UX writing or technical writing role such as information architect, content strategist, or similar. Bonus if you've written for a design system. If you have other writing or UX experience that you think translates to this role well, we'd love to see it in your resume/portfolio/writing samples!
    • A systems thinker who loves to build elegant solutions for complex problems 
    • Experience working on digital products. This role sits within the user experience design organization, so a foundational knowledge of what goes into product design is key 
    • A customer advocate with UX research skills that considers the user’s needs at every step of their journey 
    • Figma experience is a plus 
    • Interest in small businesses and business writing is a plus  
    • Interest in learning UX design a plus 

What Success Looks Like

    • Thimble delivers beautiful, functional products to our customers on time 
    • Every customer understands what they’re buying and why 
    • Every customer gets insured with ease and leaves feeling confident 
    • Thimble’s fun, educational brand voice stays consistent as we scale 

What You’ll Do in 30 Days

    • Have a foundational understanding of Thimble’s product offerings 
    • Become familiar with Thimble’s brand voice and house style 
    • Onboard to the Product and UX teams’ workflows (with hands-on support from our current content strategist) 
    • Begin delivering copy for new products + experiments 
    • Familiarize yourself with our Figma workflow 

What You’ll Do in 60 Days

    • Learn the Compliance team process and how to reconcile regulatory changes 
    • Onboard to writing for UX Research projects 
    • Collaborate with Thimble’s Support Team to create user Help Desk content 
    • Begin to take sole ownership of content work 
    • Identify opportunities for content-first initiatives and content-led UX improvements 

What You’ll Do in 90 Days

    • Start taking all new UX copy requests 
    • Take new flows through the Compliance process independently 
    • Begin personalizing our product copy to make the experience dynamic and relevant to small business owners in over 140 professions 
    • Implement our process for user testing of product copy 
Thimbler Benefits & Perks
-Fully remote company
-Thimble Fridays! (out of office at 12:00pm local time)
-Comprehensive health, vision, and dental coverage
-PTO: 20 days vacation, 8 floating days, 10 company-wide holidays, 1 VTO (Volunteer Time Off), and unlimited sick time
-Parental Leave: 100% paid 12 weeks + 2 weeks gradual return
-Company computer hardware of your choice
-Work from home setup reimbursement
-Monthly co-working space and/or child care reimbursement
-Monthly ClassPass credit
-Quarterly wellness reimbursement
-Other health & wellness perks including: One Medical, Teladoc, Talkspace, Kindbody, and Health Advocate
-Virtual events, happy hours, trivia, and fun!
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