Hi, we're Oscar. We're hiring a Senior Event Operations Manager to join our Marketing team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless 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:

This role sits within the Event Marketing Center of Excellence and is principally accountable for supporting internal stakeholders in the organization and delivery of assigned event programs as well as the creation of enablement materials for self-service event delivery. This role works independently to provide project and program management services to cross-organizational marketing partners and agency vendors.

You will report into the Associate Director of Corporate Events.

Work Location: This position is based in our New York City office, requiring a hybrid work schedule with 3 days of in-office work per week. Thursdays are a required in-office day for team meetings and events, while your other two office days are flexible to suit your schedule. #LI-Hybrid

Pay Transparency: The base pay for this role is: $135,792 - $178,227 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, and annual performance bonuses.

Responsibilities:

• Serve as a project manager for assigned event programs, ensuring timely and effective delivery, by tracking deliverables, managing stakeholders and communications, and providing event operational expertise throughout the process
• Coordinate with internal stakeholders and external agencies in support of event delivery, managing functional areas including but not limited to: venues, hotels, contractors, audio/visual and production, food and beverage, temporary staffing, health and safety, accessibility, environmental design and transportation
• Create scalable mechanisms and playbooks that enable stakeholders to successfully self-service the organization and execution of events in a matrixed organization, including through the development and delivery of written and visual training materials
• Assist in developing budgets, prepare regular reporting, and oversee measurement of assigned programs
• Act as strategic advisor to internal stakeholders, providing advice and support in all areas of event delivery
• Compliance with all applicable laws and regulations
• Other duties as assigned

Requirements:

• 8+ years of experience planning and executing event marketing programs
• Bachelor’s degree in a related field (event management, hospitality, technical theatre, marketing, communications, business, or similar).

Bonus points:

• Strong expertise in managing the delivery of multiple event operations functional areas (e.g., sourcing, space planning, venue management, vendor management, food and beverage, budgeting, risk management and compliance, accessibility, health and safety, atmospheric design, etc.)
• Experience planning events across a wide variety of formats (e.g., hospitality programs, ancillary events, tradeshows, and corporate meetings)
• Extensive experience in project management, demonstrating the ability to multi-task, quickly shift priorities, and proactively resolve challenges while operating with minimal supervision 
• Experience delivering events in-house at a brand or corporation
• Certified Meeting Professional (CMP) designation 
• Experience with field marketing and the design and operationalization of field or regionally-aligned marketing and event programs
• Team player with strong interpersonal and communication skills; ability to work with various groups across the organization and adept at stakeholder management
• Knowledge of various marketing and workplace productivity technologies and experience leveraging artificial intelligence to optimize the design and delivery of work product

Hi, we're Oscar. We're hiring an Intern to join our Internal Communications Team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless 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 Internal Communications Intern will support the Communications team in creating a connected, informed, and inspired employee experience. This role is perfect for a storyteller who is passionate about company culture and wants to learn how to bridge the gap between business strategy and employee engagement.

During this internship, you will help execute key communications channels, assist with large-scale internal events, and develop content that captures Oscar's unique voice for our team. You'll work on real-life projects that impact our team members and help make our mission to change healthcare feel tangible for every employee.

You will report into the Senior Manager, Internal Communications.

Work Location: This position is based in our New York City office, requiring a hybrid work schedule with 3 days of in-office work per week. Thursdays are a required in-office day for team meetings and events, while your other two office days are flexible to suit your schedule. #LI-Hybrid

Pay Transparency: The hourly pay for this role is: $27- $35 an hour. You are also eligible for employee benefits.. You are also eligible for employee benefits.

Responsibilities:

• Draft and edit compelling content for internal channels, including email newsletters, Slack announcements, intranet articles, and executive talking points.
• Assist in the planning and technical execution of company-wide forums, such as All Hands meetings, leadership Q&As, and office-specific culture events.
• Support the day-to-day management of internal platforms, ensuring information is organized, timely, and easy for employees to find.
• Assist in the production of digital assets and internal videos to make communications more engaging.
• Help monitor communication metrics and gather employee feedback to identify opportunities for continuous improvement in how we reach our teams.
• Partner with cross-functional stakeholders to communicate culture-building initiatives and business updates.
• Own and complete one high-impact summer project (e.g., refreshing an onboarding guide or launching a new Slack series) to be presented at the end of the internship.
• Perform other duties as assigned to support the Communications team.

Responsibilities

• Currently enrolled in an undergraduate or graduate program, preferably focusing on Communications, English, Public Relations, Journalism, or a related field.
• Superior writing and interpersonal skills—you know how to be professional but human.
• Foundational understanding of digital communication tools (e.g., Google Workspace, Slack).

Bonus points:

• No genius without grit. You have a relentless, can-do attitude and aren't afraid to try, fail, and iterate.
• Experience with content creation (writing, editing, design) for newsletters, blogs, or social media. Experience with basic design (Canva/Adobe) or video editing is a plus!
• Experience working in a fast-paced or high-growth environment.

Hi, we're Oscar. We're hiring a Brand Operations Manager to join our Brand team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless 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:

As a Brand Operations Manager, you will build a thriving creative culture through daily operations. You will manage projects at all stages—from conception to completion. You will lead cross-discipline teams, improve pipeline of work, engage partners, manage external talent, and create opportunities for cohesion within the team. You will create clarity from ambiguity and think two steps ahead to enable creative teams to deliver flawless creative work. 

You will report into the Head of Brand.

Work Location:

This position is based in our New York City office, requiring a hybrid work schedule with 3 days of in-office work per week. Thursdays are a required in-office day for team meetings and events, while your other two office days are flexible to suit your schedule. #LI-Hybrid

Pay Transparency:

The base pay for this role is: $111,780.00 - $146,711.25 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses.

Responsibilities:

• Manage project plans and timelines, including scoping, kickoffs, schedules, milestones, risk, budget, team member communications and delivery.
• Prepare debriefs at the end of each project cycle—identify and recommend improvements to internal processes including how to better measure the impact.
• Facilitate relationships between teams, finding resources, raising concerns to appropriate owners early, and resolving open issues that prevent progress.
• Lead daily team operations to manage schedules and maintain the pipeline of projects.
• Identify, vet and onboard efficiency tools for collaboration.
• Primary owner of assigned brand team project budgets and partner with brand and marketing communications leadership on managing yearly production budgets.
• Compliance with all applicable laws and regulations.
• Other duties as assigned.

Requirements:

• 4+ years in similar role within recognized companies.
• 4+ years experience working on integrated marketing and advertising campaigns including digital, social, broadcast, radio, OOH, direct mail, and collateral deliverables.

Bonus points:

• Familiarity with design industry and best practices.
• Experience with design or production tools.

Hi, we're Oscar. We're hiring a Senior Motion Designer to join our Brand team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless 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:

As a Senior Motion Designer, you will work as a member of our small but mighty internal creative team to bring our brand to life and push our visual language. You will be heavily involved throughout the creative process—from requirements gathering and brainstorming to design crits and production support. With the guidance of our Creative Director and Creative Leads, you will drive your own projects while collaborating with other creatives and marketers to ensure that all deliverables are on strategy and on brand.

You will report into the Creative Director, Brand.

Work Location: This position is based in our New York City office, requiring a hybrid work schedule with 3 days of in-office work per week. Thursdays are a required in-office day for team meetings and events, while your other two office days are flexible to suit your schedule. #LI-Hybrid

Pay Transparency: The base pay for this role is: $149,040.00 - $195,615.00 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses.

Responsibilities:

• Own the execution of motion design for 360° marketing campaigns, delivering high-quality online video, social video, instructional and product videos, animated spot graphics, and modular motion systems
• Execute sophisticated motion design craft across motion graphics, kinetic typography, and animated illustration, applying strong animation fundamentals, visual storytelling, and sound design
• Partner closely with the creative director and creative leads to translate concepts into compelling motion narratives, developing storyboards, animatics, motion tests, and production-ready assets
• Bring conceptual ideas to life through hands-on design and animation, solving creative problems independently while collaborating with internal partners and external agency teams
• Apply subject matter expertise in kinetic branding, developing, maintaining, and governing motion standards, guidelines, and a template library to ensure brand consistency and quality across all assets
• Manage end-to-end project delivery, overseeing video and audio editing, asset optimization, and providing best practices for platform-specific specs, compression, and accessibility.
• Present executed work clearly and confidently to internal stakeholders, articulating creative decisions and incorporating feedback. 
• Compliance with all applicable laws and regulations. 
• Other duties as assigned. 

Requirements:

• 6+ years of motion design and animation experience, in-house or at a recognized creative studio.
• Proficiency in Adobe After Effects, Premiere Pro, Photoshop, and Illustrator. (Figma and Cinema 4D a plus).

Bonus points:

• Strong design portfolio demonstrating expert proficiency in motion graphics, kinetic typography, and animated illustration, with mastery of design and animation fundamentals.
• Proven ability to own projects from concept through final delivery, including storyboarding, animation, editing, and finishing.
• Strong visual storytelling and conceptual thinking skills, with high level of craft, attention to detail, and understanding of timing, pacing, hierarchy, and rhythm.
• Ability to confidently present creative work and articulate design decisions to a range of internal stakeholders.
• Proficiency in video and audio editing, sound design, and asset delivery for multiple platforms and formats.
• Experience building and evolving motion brand systems, and owning motion governance to ensure assets align with brand principles across campaigns.
• Advanced 2D animation skills required; 3D animation experience preferred.
• Strong written and verbal communication skills in English. (Spanish is a plus).