Thimble is quick-thinking insurance for fast-moving businesses. We work hard to make it easy for 140+ professions like handymen, landscapers, DJs, artisans, and mall Santas (yes really) to get the insurance they need to take on every opportunity.
It’s the first business insurance provider that puts customers in control: small businesses of any size can get a policy by the job, month, or year from Thimble in minutes and modify, pause, or cancel anytime.
Thimble is simple, scalable, and flexible, which is why we made MONEY Magazine’s 2021 “Best Insurance for Small Businesses” AND we’re Fast Company’s #1 “Small and Mighty” Company. We’re also rated 4.8 out of 5 stars on Trustpilot and the App Store and have sold over 200,000 policies to more than 65,000 small businesses.
Founded by veteran entrepreneurs Jay Bregman and Eugene Hertz, Thimble is growing the $250 billion business insurance market by making it more accessible: 75% of Thimble customers are first-time business insurance buyers. For that reason and so many more, Thimble has raised over $45 million in backing from IAC (NASDAQ: IAC) and other top venture capital firms.
For more information, visit thimble.com.
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.
Treat every person, and their ideas, with respect. Cherish diversity.
About the Role
Thimble is looking for a Vice President of UX/Design who is a proven leader and has a history of scaling startups to new and greater heights. The ideal candidate will lead and grow a multi-disciplinary team, be a design evangelist, lead with vision, and be a creative problem solver. We are looking for someone who has a passion for consumer-led design, works well with technology, and will be as comfortable both in leading and developing a team as well as rolling up their sleeves to deliver best-in-class products and experiences.
Thimble will continue to grow by expanding both our insurance product offerings and our customer base, and the VP of UX and Design will be tasked with maintaining our design principles of simplicity and the speed to purchase despite more complexity in our product offerings.
- Inspire and build a team of Product, UX, and Visual Designers, as well as UX Researchers and Data Analysts
- Partner with Product, Marketing, Business Development, Insurance and Leadership to help define our short and long term product roadmap
- Present new initiatives and proposals, as well as analysis to our leadership team on a recurring basis
- Define a Design Vision Strategy and communicate across the organization
- Create team metrics based on company-wide strategic KPIs
- Drive decisions by leveraging data, research, Customer Success feedback, and analytics to improve the experience
- Own design for all platforms, including Desktop, Mobile Web, and Apps. Expand the design vision to channels other than D2C, such as broker and partner tools
- 10+ years experience designing consumer-facing desktop and mobile applications
- 5+ years hiring, managing and building design organizations
- A history of scaling an early stage startup to the next level
- A passion to lead and mentor a team of designers, researchers, and analysts
- Demonstrated experience in developing strategy, aligning a roadmap to outcomes and the company mission
- A proven track record of solving complex design problems with elegant design solutions
- Comfort with rapid iteration, experimentation, and prototyping at various levels of fidelity
- Excellent verbal, written and visual presentation skills
- Able to work in a fast-paced environment where priorities often get reordered
- What You’ll Do in 30 days:
- Learn about business insurance and the products we provide
- Dive into our current user experience and other channel products that we offer
- Meet with other department leads and the cofounders to better understand Thimble’s mission and how the teams work together
- Work with the current team to understand everybody’s roles and the team processes
- Work with the Product Team to understand their processes, and how Thimble’s strategic KPIs impact the roadmap
- Understand current data availability and capabilities
- What You’ll Do in 60 days:
- Review the current structure of the team and access the hiring needs and team structure 1 year out
- Get involved in roadmap meetings and project priority setting
- Analyze 3rd-Party tools needed to enhance team performance
- Take a deep dive into major on deck projects
- Begin the process of creating a design vision.
- What You’ll Do in 90 days:
- Present and socialize the Design Vision to Leadership
- After a thorough review of the Thimble experience and design, present a Thimble 2.0 redesign that involves both experience and design enhancements
- Have complete ownership of all processes, budgets, and systems at this point as well as having ultimate ownership of the look and feel of the experience
-Comprehensive health, vision, and dental coverage
-23 days paid vacation, 10 company-wide holidays, 1 VTO (Volunteer Time Off), and unlimited sick time
-Parental Leave: 100% paid 12 weeks and 2 weeks gradual return
-Ability to work remotely
-Company computer hardware of your choice
-Remote office/Work from home reimbursement
-Monthly co-working space and/or child care reimbursement
-Monthly wellness reimbursement & ClassPass monthly credit
-Other health & wellness perks including One Medical, Teladoc, Talkspace, Kindbody, and Health Advocate
-Early Fridays (no meetings after 3:00 pm EST) or Summer Fridays (out of office at 3:00 pm EST)
-Weekly happy hours, trivia, and fun!
-Generous stock options