Senior Art Director

San Francisco, CA /
Growth /
Our Mission
We’re here to create a safer, happier and more mindful future for all with the help of data science, engineering, design, and mobile technology. We're starting by reinventing insurance, by rethinking the technologies that enable it, but our true goal is to build a platform that rewards people for driving well—creating safer roads with fewer accidents in the process.

Backed by impressive funding, we're poised to re-engineer a trillion-dollar category, and that’s just the beginning. We’re using rich customer insights, advanced technology and data science to build our cloud-native InsurTech solution, and other things we haven’t even dreamt up yet. We're out to change behavior and promote mindful living at a societal level. But the key to us being successful in our mission isn’t just about nailing the technology—it’s about hiring talented people who can help us make a quantifiable impact in the world. We’re growing our world-class team.

And that’s where you come in.

The Role
The HiRoad brand design team is responsible for the definition and evolution of the HiRoad brand, ensuring impeccable development and implementation of best-in-class brand expressions across multiple media formats and marketing channels. We are a cross-functional, collaborative and empathetic team dedicated to creating innovative, compelling narratives, platforms and campaigns that drive our business and brand forward.
We are looking for an experienced and well rounded Senior Art Director to help lead creative initiatives, be an instrumental part of a growing team, lead external creative partners and mentor in-house talent to produce award-winning work. You'll work across our content, brand, communications, creative and growth teams to evolve and grow the brand and product’s look, feel and personality for our inbound channels. You’ll partner with brand marketing, production, design and experience experts to deliver bold new solutions and life-enhancing innovations that allow us to stay ahead of the curve and find fresh paths forward for the HiRoad Brand.

About You
You have a passion for art direction and understand the importance of big ideas. You are an expert in your craft and are highly skilled in working with a team of visual artists, designers and copywriters. You are a highly strategic thinker with a proven track record for planning and leading efforts to execute across multiple media formats. You love identifying new opportunities to connect with customers through high-quality content that meets their unique needs at any given time.

Key Qualities

    • You create strategically. You have the ability to think big while operating at the finest level of detail. You have in-depth knowledge of all steps required in the creative process, including effectively and efficiently staffing projects, providing communication and direction, and giving timely and helpful guidance to improve creative solutions.
    • You lead by example. You can inspire others to exceed expectations through the work while actively seeking out ways to mentor younger creatives in their development. You know how to guide teams, agencies and production partners and you’re not afraid to roll up your sleeves to do the work.  
    • You are a builder of brands. You strive to continually evolve and grow the brand/product’s look, feel and personality. From establishing brand guidelines to defining the art direction for integrated campaigns, you strive to continually evolve our visual brand, including typography, color palette, imagery and overall tone and voice.
    • You are a master at your craft. Your design skills are outstanding, and you have the ability to guide, evaluate, and elevate design execution in ways that continually raise the bar in everything we do.
    • You’re customer obsessed. You maintain a deep and empathetic understanding of the customer, while advocating for customer-centric thinking and experiences. As a champion of our customers, you’re relentless in the pursuit to strategize, create and publish great content that connects and delivers exactly what the customer wants and needs.
    • You're a fantastic communicator. Both within your team, and without, you have to be able to give voice to your vision, and present your ideas effectively and objectively. Teams must be able to understand it and use it for their work. In addition, your delivery has to be as inspiring as your idea.
    • You're a team player who values culture. You’re a great listener, open to feedback and able to bring the brand vision to life. You’re low ego and don’t fall in love with your own ideas, and instead have a strong desire to push them. You involve your cross-functional team members throughout the process to assure your work delivers results and impacts the success of our content program, while celebrating wins and taking on challenges in a way that sparks a positive flow of energy.
    • You’re an entrepreneur. You’re a confident self-starter that has a passion for team building, process, and most importantly culture. In other words, you don’t just experience the culture, you help make it. You recognize that great company cultures come from the teams you’re a part of and nurture as a positive force—which is how healthy and successful companies grow.


    • Work closely with creative leadership in managing and inspiring the creative team as well as being accountable for creative deliverables.
    • Identify and champion areas and opportunities for growth within the creative team.
    • Help develop and inform creative briefs that provide strategic insights, and data driven results to inspire creative concepts and ideas.
    • Conceptualize new campaign ideas and social tactics based on established voice and tone. Develop creative proposals, mockups and decks to kickstart new campaigns.
    • Present ideas and concepts to stakeholders, collaborate and iterate based on feedback from cross-functional partners.
    • Provide art direction, guidance and oversight to internal and external creative teams as well as production partners.
    • Seek out opportunities to expand creative partnerships with vendors, artists, influencers and content creators that can help us shape and evolve our brand in new and innovative ways.
    • Lead the execution of creative solutions across a wide array of mediums including illustration, animation, video, and photography to drive innovative, interesting and useful content.
    • Maintain consistency and alignment to the HiRoad brand through ongoing definition and maintenance of our design style guide.
    • Track published content performance against goals, optimize where needed and regularly report results to the growth team. 
    • Test and iterate different types of content (written, voice, video, etc) across channels.

Requirements and Qualifications

    • 6-8 years of art direction and design experience, with at least 1-2 years of experience leading internal and external teams and projects.
    • A link to an online portfolio showcasing relevant work.
    • Experience managing creative development with proven mentoring, supervisory and team-building skills.
    • Experience guiding teams, agencies and production partners and experience rolling up their sleeves to do the work when necessary.
    • Ability to self-direct, multi-task, manage and prioritize work assignments.
    • Strong communications skills and an ability to present work intelligently and concisely in internal reviews and in stakeholder meetings. 
    • A deep understanding of the creative development process, have excellent art direction skills, and consistently deliver excellent design with a working knowledge of what goes into successful marketing campaigns and brand development.
    • Experience across multiple forms of creative expression and production: traditional, digital, social, experiential and product.
    • Experience using data and technology to come up with innovative brand experiences.
    • Comfortable working in a fast-paced start-up environment with multi-discipline teams.
    • Experience using data and technology to come up with innovative brand experiences.
    • Experience working remotely with teams in other locations and time zones.

Bonus Points

    • Experience working in growing start­up environments.
    • Experience working with teams in the insurtech and fintech industries.

Additional Details

    • Salary: We pay top-of-market salaries for most positions, factoring in experience, talent and location.  We do not offer equity.
    • Benefits: Medical, dental, vision, 401(k), wellness reimbursement, four weeks of PTO, six weeks of parental leave (12 weeks for parents who give birth), and great work-life balance.  
    • Location: May work from anywhere in the US, but will need to be actively available during the core business hours of 9:00AM - 5:00PM, PST, since a majority of time will be spent collaborating with team members in this time zone. Preferred SF Bay Area resident.
    • Some travel required once the San Francisco office re-opens. Frequency TBD
    • Candidates based in the SF Bay Area will be able to commute to the SF office, post-COVID, for in-person collaboration purposes and other gatherings. Frequency TBD.

What we need

    • A resume and a link to an online portfolio showcasing relevant work. If applicable, passwords should be included in portfolio submission.
BlueOwl, LLC is an equal opportunity workplace. We are committed to equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or Veteran status.  Pursuant to the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records.

If you are a San Francisco resident, please read the City and County of San Francisco's Fair Chance Ordinance notice.