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UI Designer


Get to know Highwing.

Commercial insurance has trouble using its data, limiting its ability to compete effectively and grow profitably. Highwing helps insurance move faster and go further. Insurance is built from millions of individualized data points about customers, claims, costs, and more. Without these data points, calculating and transferring risk at scale wouldn't be possible. The problem is that data is highly fragmented. Rather than businesses being buoyed by this data, they are drowning in it because there are no easy, reliable connections between systems. Highwing is the first open data platform for Insurance brokers and carriers. Think of us as the digital nervous system for Insurance. We connect data both inside and outside our platform in order to bring efficiency to the procurement of insurance.

What’s it like to work at Highwing?

Our Crew. Our team is composed of experienced designers, engineers and entrepreneurs. We believe software development is a team sport, and the best products are built by teams with diverse backgrounds who are empowered with a high degree of autonomy. We strive for rapid iteration and continuous improvement in both our products themselves and our approaches to building them. We work at a sustainable pace and know from experience that building a lasting product organization is a marathon, not a sprint.


As a UI Designer at Highwing, you will work closely with the Senior Product Designer to build out UI from user flows and wireframes. You will help build and manage the UI library (Atomic Design). You are passionate about processes and efficiencies, never becoming too attached to a single solution. Working in the fast-paced startup world, you can quickly iterate and get designs in the hands of users for feedback (not letting perfectionism hold us back).  You enjoy the satisfaction that comes with a gorgeous, pixel-perfect design — especially one that’s as functional as it is beautiful. You love feedback and discovery in all aspects of your work, constantly seeking out new ideas, insights, and techniques to improve its quality and usability. You recognize that product development is a team sport, and enjoy working closely with a team to turn concepts into reality. 

We will measure success in this role by product adoption, client useability, and organization and design of UI library.  Being a UI Designer at Highwing means you are a team player.  You should be proud of the functionality and usability of the product as a result of your designs.  As a team member, you are a user-centric thinker. You work from a place of empathy. You value collaboration, transparency and growth.  You will report to the Director of Product.


  • You’ll be assisting the Senior Product Designer in producing high-quality UX and UI design solutions throughout the product lifecycle - ranging from prototypes, wireframes, and flows to the visual design of individual components, layouts, and entire application flows - and testing them with users and stakeholders to validate they meet real needs
  • You’ll steward the practice of design across Highwing, ensuring a beautiful, consistent, and reusable design system is implemented across products and properties
  • You’ll work closely with engineering teams to bring designs to life, iterating as needed to respond to implementation concerns
  • Alongside our product managers, you’ll advocate on behalf of our users and engage regularly across all internal teams including sales, marketing, product, success, and engineering
  • You’ll give and solicit feedback effectively and frequently, helping shape our organization and team dynamics


  • In order to apply, applicants must have a portfolio displaying understanding of design principles and their UI skillset and user-centric design principles
  • 3+ years’ UI/UX design experience working in a fast-paced start-up environment 
  • Prior UI/UX design experience building enterprise (business) applications is a plus
  • Proficient in Sketch and familiar with Adobe Suite (mainly illustrator)
  • Start up mentality/experience
  • Strong understanding of design system management
  • Excellent written and verbal communication skills with a strong attention to detail
  • The drive to learn and grow as a designer
  • Creative and analytic mindset


$70,000 - 85,000; DOE

At this time, we can only consider United States-based applicants with authorization to work in the United States on a permanent, full-time basis; unfortunately, we cannot provide visa sponsorship or remote employment outside of the United States.

Our Core Values

Collaboration. We are playing a team sport. Building a successful enterprise is a team effort. But it is important to distinguish a team dynamic from a family dynamic. Teams thrive on unwavering support, respect and openness – but not unconditional acceptance. Talented jerks have no place on a great team. We consistently challenge each other to improve every day – not only with respect, but with uncommon positivity.

Autonomy. This is not a little kid’s soccer team. We believe extreme autonomy is valuable in not only maintaining happy, productive people, but also in building impactful, innovative products. So we don’t all swarm to the ball. We hire intelligent, diligent, passionate people who are capable of operating in large, sometimes ambiguous problem spaces with a great deal of freedom and decision-making authority. In exchange, we expect everyone to dig in, learn deeply about the space and take initiative every day.

Improvement. “Kaizen” is part of our everyday vocabulary. Our technology, our industry and our clients are always in a constant state of flux. We must regularly evolve with them, or we will quickly fall behind. That’s why we are dedicated to practicing “Kaizen,” the Japanese concept of continuous improvement. This means we are, above all, a learning culture. We approach every problem with a beginner’s mind. We look to improve every part of what we do, every day – from our product to our process and beyond. We always strive to give and receive feedback, even when it is difficult. And we allocate time specifically for learning and reflection, so we can avoid our failures and replicate our successes.

Transparency. Having stake in the business is about more than just equity. We believe the best way to give people stake in the business is to give them full visibility into it. That’s why we share everything transparently, from ongoing client meetings and project statuses to project financials. This allows everyone to see the work they’re doing and understand how that work ladders up, connects and impacts the business. This complete context enables better collaboration, more autonomy and faster improvement.

Empowerment. We believe in leading from behind. We believe great managers should act as resources, not gatekeepers. We keep organizational hierarchy minimal, and use it only as a way to help people achieve their maximum potential. This semi “flat” culture allows anyone in the organization to not only bring radical ideas to the table, but also to pursue them fully, without bureaucratic barriers in the way.

Kindness. Challenge directly, care personally. Kindness doesn’t simply mean being nice. And doesn’t mean avoiding constructive conflict. Kindness to us means challenging ideas with positive intent. It means being intentional, honest and generous with the way we treat one another, our partners, our clients and the world. We are hell bent on building an uncommonly positive and forthright culture, because we believe this form of kindness has the power to transform our work, our business and our industry.

Highwing Benefits Overview

Comprehensive insurance: We provide comprehensive employee and family health insurance and ancillary benefits (life insurance, disability, and more).

Learning & development stipend: We believe in continuous improvement (see above) - this includes you as a person and as a professional. That’s why we provide an annual learning and development stipend that you can use however you see fit to further develop as a professional in your area of expertise or the insurance industry as a whole. Attend conferences, read books, take online learning courses, and more!

Time-off to recharge: We have a generous paid time off policy - take what you need when you need it. And when we say time-off - we really mean time-off - don’t check your emails, don’t reply to Slack - relax and recharge.

Remote work: We’ve created an environment that supports remote work. While we love collaborating with everyone in the office at the same time (and the impromptu happy hours and lunch chats that ensue) - we understand that you may sometimes be more productive at home or in a different environment. We’ve built our team meetings and processes to support you to work your best wherever you see fit whenever you see fit.

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