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Easy Apply
Lead the visual presence across digital platforms, creating cohesive designs, enhancing user experiences, and maintaining brand identity. Collaborate with teams to innovate and manage design systems while solving technical challenges.
Simply Business is a digital insurance brokerage that specializes in one thing: protecting the businesses our customers are working hard to build. We’re doing this by simplifying the insurance-buying process for all small businesses, blending together a combination of technology, data, and insurance knowledge. Our proprietary technology platform allows small business owners to easily search and compare quotes from over 20 top-rated insurance providers, customize their coverage, and purchase and access their policies - all online.
Founded in the UK in 2005, Simply Business is an insurtech pioneer with nearly 20 years of experience supporting small businesses. Simply Business is passionate about building an outstanding product for our customers - one that empowers their entrepreneurial spirits.
More importantly, we’re doing it all while taking care of our people. We’ve consistently been named a best place to work, including most recently ranking in Built In’s 2025 Best Companies to Work for in the US (Top 100), and Best Places to Work in Boston.
We want team members who have the drive to challenge boundaries. If you’re smart and passionate about delivering brilliant customer experiences, we’d love to hear from you.
As a Senior Digital Designer at Simply Business, you will be a driving force in defining and executing our visual presence across all digital platforms. This is a hands-on role for a highly skilled and ambitious individual who thrives in a fast-paced, evolving environment. You will be instrumental in designing compelling digital experiences, with a particular focus on our website's visual appeal, user journey, and brand consistency. Your expertise in WordPress, combined with your exceptional problem-solving abilities and capacity to navigate ambiguity, will be critical to our continued growth and succeed.
Digital Design Execution & Strategy:
- Translate marketing and business objectives into effective and engaging digital design solutions, ensuring brand consistency and adherence to guidelines.
- Collaborate closely with marketing and product to conceptualize, design, and deliver impactful digital experiences from concept to launch.
- Continuously seek opportunities to innovate and enhance our visual identity in line with our OKRs by staying informed about industry trends, new technologies, and digital design best practices.
Visual Storytelling & Brand Consistency:
- Champion the visual brand identity of Simply Business, ensuring all digital touchpoints are cohesive, impactful, and resonate with our target audience.
- Develop and maintain visual design systems and guidelines, ensuring consistency across various digital assets and platforms.
- Infuse creativity and a keen eye for aesthetics into all designs, enhancing user engagement and conversion.
Design System Ownership & Development:
- Help with the definition, creation, and maintenance of our comprehensive design system, including UI components, patterns, guidelines, and documentation.
- Collaborate with our marketing department to ensure that the design is on brand and meets the strategic needs to deliver on our OKRs
- Collaborate with internal UX designers, engineers, product managers, external agencies and freelancers to ensure the design system effectively addresses user needs and technical constraints.
- Evangelize the adoption and consistent application of the design system across the FoH of the website.
- Continuously audit and evolve the design system based on user feedback, performance data, and evolving design trends.
- Strong competence in WordPress for website development, proactively identifying and resolving build challenges arising from resource constraints or platform limitations through intelligent problem-solving.
WordPress Expertise & Templating:
- Confidently operate within the WordPress environment, demonstrating strong ability in both the creation of new custom templates and the expert editing of existing ones.
- Apply design principles directly within WordPress, ensuring designs are visually appealing, responsive, and optimized for performance.
- Collaborate with the team to ensure seamless implementation of designs and templates, proactively identifying and resolving technical challenges.
Problem-Solving & Adaptability:
- Exhibit exceptional problem-solving skills, particularly when encountering technical constraints or resource limitations during digital build processes.
- Proactively identify design challenges and propose practical solutions that balance creative vision with feasibility.
- Thrive in an environment of ambiguity, comfortable with evolving requirements and capable of pivoting quickly while maintaining high standards of quality.
Project Ownership & Collaboration:
- Efficiently manage multiple design projects simultaneously, prioritizing tasks and working effectively under tight deadlines.
- Present design concepts and rationale clearly and persuasively to stakeholders at all levels.
- Contribute to a collaborative team environment, providing constructive feedback when applicable.
Qualifications:
- Bachelor's degree in Graphic Design, Digital Media, Web Design, or a related field.
- 7+ years of progressive experience as a Digital Designer, with a strong portfolio showcasing a diverse range of digital projects (websites, landing pages, campaigns, etc.).
- Deep understanding of design principles, typography, color theory, and visual hierarchy.
- Demonstrable expert-level proficiency in WordPress or similar, including hands-on experience with theme/template creation, customization, and troubleshooting.
- Experience with animation, motion graphics, or video editing for digital platforms.
- Mastery of industry-standard design software (e.g., Adobe Creative Suite: Photoshop, Illustrator, InDesign, Figma, Wordpress, Aftereffects).
- Solid understanding of UX/UI principles, responsive design, and web accessibility standards.
- Proven ability to work effectively in a fast-paced, deadline-driven environment.
- Exceptional problem-solving skills, with a track record of creatively overcoming design and technical challenges.
- Strong communication and interpersonal skills, with the ability to articulate design concepts and collaborate effectively with cross-functional teams.
- A highly ambitious and proactive individual who embraces challenges and thrives in ambiguous situations.
- Excellent communication, collaboration, and presentation skills.
Preferred Qualifications:
- Experience contributing to and maintaining a mature design system.
- Familiarity with front-end development technologies (HTML, CSS, JavaScript) and their impact on design.
- Experience with A/B testing and data-driven design decisions.
- Experience in the financial services or insurance industry, particularly with small business audiences.
- Experience with motion design or micro-interactions.
Here are some of the great benefits and perks that come from being a Simply Business employee:
-Group plan for medical, dental, vision, and prescription drug coverage
-Short term disability, long term disability, and life insurance coverage
-Participation in the Company’s bonus program-Participation in 401(k) plan with a 5% employer match
-Commuter benefits to help cut down on parking and public transit costs
-25 days of vacation time plus 10 sick days and 10 company holidays
-A genuine investment in your learning and development-Regular team outings and volunteer opportunities
-An awesome office space
-A hybrid working model, giving our employees great choice and flexibility to work in a way that’s best for their particular job, their teams, and their lives.
Simply Business is an equal opportunity employer. We’re committed to welcoming and helping employees grow within an inclusive & diverse culture. And that commitment starts with our interview process.
Once you apply, your info will be reviewed by a team with a mix of levels and experiences. We pride ourselves on fostering a sense of community, which is only made stronger by each individual at SB, so you’ll have the opportunity to meet a variety of people throughout the process. Get excited!
Most of our first round interviews will take place over Zoom. In subsequent interviews, there may be an opportunity/expectation to meet team members in person.
If it looks like you could be a good fit for the role, we’ll ask you to interview on Zoom first regardless – you’ll need WiFi and a laptop, or a 4G-enabled smartphone. If you don’t have access to either of these, or you need support with your application, get in touch with us at [email protected].
Please email us with any questions or if you want to pause your application for a bit – we’ll be happy to keep you updated on future opportunities like the one above. Want more info on working at Simply Business? Check out our careers page: simplybusiness.com/careers/
Top Skills
Adobe Creative Suite
Aftereffects
CSS
Figma
HTML
Illustrator
Indesign
JavaScript
Photoshop
Wordpress
Simply Business Boston, Massachusetts, USA Office
We are located in downtown Boston, accessible to every line on the T and surrounded by a lot of history and a lot of great places to grab lunch.
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