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Creative Director, Brand

Hi, we're Oscar. We're hiring a Creative Director to join our Brand team.

Oscar is the first health insurance company built around a full stack technology platform and a focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

 

About the role

The Creative Director, Brand is responsible for managing and inspiring a best-in-class internal creative team. This role will lead the development of creative across all channels, from sales enablement to major brand campaigns and identity development. They will be responsible for maintaining and advancing our brand attributes in service of our wider business goals. The Creative Director will partner with senior stakeholders across the organization to help shape meaningful work and represent the brand at large.  

You will report to the Head of Brand.

Work Location:

Oscar is a blended work culture where everyone, regardless of work type or location, feels connected to their teammates, our culture and our mission.

This is a hybrid position in our New York City office (in Hudson Square) and you will be expected to come into the office at least two days each week. #LI-Hybrid

Pay Transparency:

The base pay for this role in the states of California, Connecticut, New Jersey, New York, and Washington is: $174,400 - $228,900 per year. The base pay for this role in all other locations is: $156,960 - $206,010 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, annual performance bonuses, and company equity grants.

 

Responsibilities

  • Lead brand efforts across all workstreams including major initiatives like brand identity development and paid brand awareness campaigns 
  • Manage team of direct reports across copy, design and art direction to foster career growth and overall development while supporting day to day resourcing and function across the team 
  • Stay current on industry best practices and leverage new opportunities, while setting and upholding creative standards across the team 
  • Builds cross functional relationships across teams at Oscar to support brand goals 
  • Influence stakeholders by supporting development of key strategic insights and strong brief writing 
  • Act as a culture carrier by inspiring, encouraging and motivating individuals; helping them shape their creative talents and skills
  • Facilitate trainings and upskilling for knowledge management across the organization 
  • Compliance with all applicable laws and regulations
  • Other duties as assigned 

Qualifications

  • 10+  years of experience in creative direction or visual design, either agency or in-house. 
  • 8+ years of experience running end to end integrated marketing and advertising creative campaigns, could include digital, social, broadcast, radio, out of home and direct mail.
  • 5+ years of direct experience managing a team and proven success developing creatives and contributors across levels.
  • 5+ years of experience working with and presenting to C-suite stakeholders.

Bonus Points

  • Experience translating complex or regulated subject matters into emotionally resonant narratives (e.g. healthcare, finance, tech).
  • Strong portfolio showing range across campaign, identity and team development.
  • Deep understanding of audience segmentation and accessible design.
  • Expertise in Adobe Creative Suite, Figma, other design tools. 

 

This is an authentic Oscar Health job opportunity. Learn more about how you can safeguard yourself from recruitment fraud here

At Oscar, being an Equal Opportunity Employer means more than upholding discrimination-free hiring practices. It means that we cultivate an environment where people can be their most authentic selves and find both belonging and support. We're on a mission to change health care -- an experience made whole by our unique backgrounds and perspectives.

Pay Transparency:  Final offer amounts, within the base pay set forth above, are determined by factors including your relevant skills, education, and experience. Full-time employees are eligible for benefits including: medical, dental, and vision benefits, 11 paid holidays, paid sick time, paid parental leave, 401(k) plan participation, life and disability insurance, and paid wellness time and reimbursements.

Reasonable Accommodation: Oscar applicants are considered solely based on their qualifications, without regard to applicant’s disability or need for accommodation. Any Oscar applicant who requires reasonable accommodations during the application process should contact the Oscar Benefits Team (accommodations@hioscar.com) to make the need for an accommodation known.

Artificial Intelligence (AI) Guidelines: Please see our AI Guidelines for the acceptable use of artificial intelligence during the interview process at Oscar.

California Residents: For information about our collection, use, and disclosure of applicants’ personal information as well as applicants’ rights over their personal information, please see our Notice to Job Applicants.

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Average salary estimate

$201650 / YEARLY (est.)
min
max
$174400K
$228900K

If an employer mentions a salary or salary range on their job, we display it as an "Employer Estimate". If a job has no salary data, Rise displays an estimate if available.

What You Should Know About Creative Director, Brand, Oscar Health

Hi there! We’re Oscar, and we’re excited to announce that we’re looking for a Creative Director, Brand to join our dynamic team in New York City. Oscar isn’t just another health insurance company; we’re trailblazers who use technology to revolutionize how health insurance works, serving our members with care. In this vital role, you’ll lead a best-in-class internal creative team, inspiring them to bring our brand to life across numerous channels—from impactful sales materials to major brand campaigns. You’ll ensure that our brand message resonates and aligns with our business goals while supervising and nurturing a talented group of creatives. Your responsibilities will include partnering with senior stakeholders across the organization, developing strategically sound briefs, and keeping our creative standards razor-sharp. You’ll also foster an inclusive and collaborative culture, facilitating personal growth and upskilling within the team. Plus, you won’t be working solo—you’ll be deeply integrated with cross-functional teams to achieve our brand aspirations. At Oscar, we believe in a hybrid workplace that values connection, creativity, and inclusiveness, which means you’ll enjoy the flexibility of working both remotely and in our friendly Hudson Square office. If you’re eager to make a substantial impact in a forward-thinking company that’s genuinely committed to changing healthcare, we’d love to hear from you.

Frequently Asked Questions (FAQs) for Creative Director, Brand Role at Oscar Health
What are the main responsibilities of the Creative Director, Brand at Oscar?

The Creative Director, Brand at Oscar will lead brand efforts across every workstream, including developing major brand identity initiatives and managing brand awareness campaigns. They will supervise a talented creative team, promote career growth, and ensure that our brand’s voice and visual style align with our business goals. Collaboration with senior stakeholders is key, enabling the director to craft significant insights and strong creative briefs that resonate with our audience.

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What qualifications are required for the Creative Director, Brand position at Oscar?

Candidates for the Creative Director, Brand position at Oscar should have a minimum of 10 years of experience in creative direction or visual design. Additionally, they need at least 8 years of experience managing integrated marketing campaigns and 5 years directly managing a creative team. Experience with C-suite stakeholders and a strong portfolio showcasing a range of creative work are also vital for consideration.

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What benefits does Oscar offer for the Creative Director, Brand role?

Oscar provides a comprehensive benefits package for the Creative Director, Brand role, including competitive salaries, unlimited vacation, annual performance bonuses, and company equity grants. Employees enjoy health benefits, paid holidays, parental leave, and contributions to a 401(k) plan, making Oscar a great place to grow both personally and professionally.

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How does the Creative Director, Brand position at Oscar fit into the company's mission?

The Creative Director, Brand plays a pivotal role in advancing Oscar's mission to transform healthcare by crafting compelling narratives about health insurance that resonate emotionally with our members. By upholding and promoting the brand's identity, this role ensures that our messaging is consistent, engaging, and perfectly aligned with our goal of creating a supportive environment for our members.

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What is the work culture like at Oscar for the Creative Director, Brand role?

Oscar fosters an inclusive and collaborative work culture, allowing for a blend of in-office and remote work. We encourage creativity, innovation, and the sharing of diverse perspectives, ensuring that all team members feel connected and valued. As a Creative Director, you'll not only influence the creative direction but also act as a culture carrier, inspiring your team to reach their fullest potential.

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Common Interview Questions for Creative Director, Brand
What is your experience with managing creative teams in a corporate environment?

When answering this question, highlight specific experiences you’ve had in leading creative teams, focusing on how you supported their growth and development. Discuss key projects you’ve overseen, challenges you’ve faced, and how you fostered a collaborative environment that promoted innovative ideas.

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How do you approach integrating brand strategy across various channels?

Employ a structured approach when discussing your strategies. You could mention how you develop a cohesive narrative that’s adaptable across different platforms while ensuring that each piece of content reinforces the overarching brand message. Provide examples of past campaigns that illustrate your effectiveness.

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Can you give an example of a successful campaign you directed from concept to execution?

In your response, choose a campaign that had a tangible impact, detailing your thought process from initial idea generation to execution. Include your role in guiding the team, the obstacles you overcame, and how the campaign met or exceeded your goals, thus showcasing your leadership and creative acumen.

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What tools and software are you most proficient in for creative design?

Be specific about the software and design tools you use, such as Adobe Creative Suite, Figma, or any other relevant platforms. Discuss your level of expertise with these tools and provide examples of how they enhanced your team’s output and collaboration on creative projects.

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How do you stay updated with the latest design trends and technologies?

Share your methods for staying current, whether through industry publications, conferences, networking with peers, or continuous learning opportunities. Mention how you apply these insights to keep your creative team's work fresh and innovative, enhancing the brand's competitive edge.

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Describe a time when you had to present a creative concept to C-suite stakeholders. What was your approach?

Emphasize the importance of tailoring your presentation for the audience. Discuss how you prepared, focused on key insights to capture their interest, and used storytelling techniques to convey the concept effectively. Highlight any positive outcomes product of your ability to engage higher management.

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What strategies do you use to ensure your team creates accessible and inclusive design?

Discuss the significance of inclusivity in design and how you implement these practices in your projects. Share specific instances where you incorporated feedback from diverse user segments and any adaptations your team made to ensure that the final product is accessible to all populations.

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How do you measure the success of a branding campaign?

Outline the metrics you consider essential for measuring success—these might include brand awareness, engagement rates, lead generation, and customer feedback. Provide examples of campaigns you analyzed in terms of these metrics and how that data informed future branding strategies.

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What are the key elements of a strong creative brief?

Focus on the essential components of an effective creative brief: clear objectives, understanding the target audience, messaging, desired tone, and deliverables. Share strategies for collaborating with stakeholders to gather the necessary insights that inform a robust creative brief.

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What do you think is the most challenging aspect of being a Creative Director?

Discuss the balance between nurturing creativity and meeting business objectives. Acknowledge the challenges in aligning creative visions with corporate goals while motivating team members to maintain high standards. Illustrate your approach to overcoming such challenges through effective communication and leadership.

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Oscar Health is an American health insurance company headquartered in New York City. Through telemedicine, healthcare-focused technology interfaces, and clear claims pricing systems, the company focuses on the health insurance market.

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Full-time, hybrid
DATE POSTED
April 15, 2025

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