Hi, we're Oscar. We're hiring a Senior Sales Executive to join our Sales 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 Sales Executive, you will be responsible for driving membership growth through the management of traditional insurance sales channels, as well as the pursuit of innovative sales strategies. On the traditional side, the Senior Sales Executive is in charge of  driving the broker strategy, ensuring insurance brokers across our coverage area have the information and tools to effectively understand and sell our product. On the creative side, the Senior Sales Executive is responsible for iterating on ideas to drive buzz at a local level and create partnerships with local organizations.

You will report into a Director, Sales.

Work Location:  

This is a remote position based in the field, open to candidates who reside in Tennessee. Your daily work will involve a blend of work from your home office and frequent travel for client meetings. Occasional travel may be required for team meetings and company events. #LI-Remote

Pay Transparency:

The base pay for this role is: $96,876.00 - $127,149.75 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, and sales commissions.

Responsibilities:

• Building and managing broker and GA (General Agent) relationships in the assigned geographic market and as required to support growth goals.
• Identifying distribution partners to invest in and building relationships over time.
• Training brokers and GA partners on our product.
• Representing our product in the market at local broker and community events, which may take place during evening and/or weekend hours.
• Identifying and testing new growth opportunities and sharing learnings with broader sales team.
• Partner with teams to build and improve tools and processes that make our product the easiest to work with in the market.
• Meeting or exceeding sales goals while providing great service to distribution partners.
• Providing local competitive intelligence and market research.
• Being the voice of brokers and consumers within our product.
• Compliance with all applicable laws and regulations. 
• Other duties as assigned. 

Requirements:

• 4+ years of healthcare industry in an outside sales role.
• 3+ years of experience presenting and communicating with stakeholders at all levels.
• Must be a licensed insurance professional.

Bonus points:

• Bachelor's Degree or 4 years of relevant experience.
• Proficient in Salesforce.

Travel Required:

• Up to 50%

How You'll Make an Impact: 

As a Senior Fullstack Engineer on the Distribution Team, you'll be instrumental in developing and enhancing the products that connect Cloudbeds' ecosystem to the world's largest distribution channels. You'll architect scalable solutions using modern technologies, contribute to our microservices migration, and ensure our platform delivers exceptional performance and security for thousands of properties worldwide. Your work will directly impact how hotels reach guests through integrations with major platforms like Booking.com, AirBnb and beyond.

Our Distribution Team:

We're the bridge connecting properties to the global travel ecosystem. Our team tackles complex integration challenges that directly impact revenue for thousands of hotels worldwide, from building rock-solid connections with major OTAs to ensuring every booking flows seamlessly and securely. We balance innovation with pragmatism: migrating legacy systems to modern microservices while maintaining the reliability our customers depend on. If you thrive on solving hard technical problems with real business impact and love the challenge of both building greenfield features and refactoring legacy code, you'll feel right at home here.

What You Bring to the Team:

• Design and implement robust backend features and improvements using PHP, with a strong focus on performance optimization and scalability for our distribution platform
• Build intuitive frontend experiences using React and Vue, ensuring seamless user interactions across the Cloudbeds ecosystem
• Architect secure solutions for handling financial transactions and sensitive personal data, applying security best practices throughout the development lifecycle
• Write clean, well-tested, and well-documented code with comprehensive test coverage (unit, integration, end-to-end) to maintain high quality standards
• Lead technical discussions on complex concepts and requirements with both technical and non-technical stakeholders, driving alignment on backend and frontend architecture decisions
• Contribute to our ongoing initiative to migrate core platform components into microservices, helping shape the long-term technical vision
• Re-architect and refactor existing legacy systems to align with modern standards and project requirements, demonstrating ownership and commitment to continuous improvement
• Mentor team members through pair programming and code reviews, promoting best practices that elevate code quality and team processes
• Collaborate with cross-functional teams to plan, build, and ship high-quality features that delight our global customer base

What Sets You Up for Success:

• 5+ years of PHP web application software engineering experience
• 5+ years of experience with JS frameworks, Vue.js and React are preferred
• Solid experience with modern JavaScript/TypeScript
• Strong hands-on experience with Docker and containerized development workflows
• Demonstrated expertise in performance optimization and expert knowledge of relational databases, indexing, and searching technologies
• Strong understanding of security considerations, particularly for applications handling financial transactions and personal data
• Experience with test automation across all levels (unit, integration, end-to-end) and a passion for quality-driven development
• Proven track record of taking ownership of projects and delivering results independently
• Business-level English fluency (verbal and written) and excellent communication skills for collaborating across a globally distributed, remote-first team

Bonus Skills to Stand Out:

• Experience designing and building microservices and/or micro-frontends
• Hands-on experience with PHP frameworks (CodeIgniter, CakePHP, Laravel, Symfony)
• Cloud and infrastructure experience with Kubernetes, AWS, Terraform, and Argo CD
• Experience working with event-driven architectures and messaging systems (e.g., Kafka)

Compensation: Depending on your skills and experience, you can expect your annual compensation to be between $145,000 - $165,000