Account Executive

Hi, we're Oscar. We're hiring an Account Executive to join our Strategy 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 Account Executive is responsible for managing the full software sales cycle for small-to-mid market clients, from prospecting and discovery through contract execution and implementation handoff. This role partners with prospective customers to understand their financial and operational objectives, demonstrating how the Lucie Platform delivers measurable value through cost containment, risk mitigation, and administrative efficiency. The Account Executive collaborates cross-functionally with Solutions Architecture, Product, and Services teams to develop ROI-driven proposals, deliver compelling platform demonstrations, and ensure a seamless customer onboarding experience while maintaining accurate CRM records and serving as the voice of the customer. This position also ensures compliance with all applicable laws and regulations and performs other duties as assigned.

You will report into the Director, Business Solutions.

Work Location: This is a remote position based in the field, open to candidates who reside: Florida. Your daily work will involve a blend of work from your home office and frequent local 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: $55,890.00 - $73,355.63 per year. You are also eligible for employee benefits and participation in Oscar's unlimited vacation program.

Responsibilities:

• Manage the full software sales cycle for small-to-mid market clients, from outbound prospecting and discovery to contract execution.
• Leverage business acumen to understand a prospect's broader corporate financial goals, positioning our tech platform as a tool for cost-containment, risk mitigation, and administrative efficiency.
• Conduct compelling, data-driven platform demonstrations of the Lucie Platform.
• Maintain meticulous records of all sales activities, pipeline stages, and client communication within our CRM.
• Partner with internal solution architects and product teams to build and present comparative cost models that demonstrate clear ROI and software value to prospective clients.
• Act as a liaison between customer and Lucie to provide feedback including product features and overall satisfaction
• Work closely with the Services team to ensure a smooth onboarding and implementation experience.
• Compliance with all applicable laws and regulations
• Other duties as assigned

Requirements:

• 3+ years of professional sales experience
• Foundational understanding of the Affordable Care Act (ACA) Market
• Strong understanding of Field Market Organization (FMO's)/General Agents (GA's) and Agent workflows and behaviors

Bonus points:

Work experience:

• 5+ years of consultative B2B sales experience, preferably in SaaS, HR technology, benefits administration, or healthcare technology.
• Experience selling to insurance agencies, brokers, Field Marketing Organizations (FMOs), General Agencies (GAs), or employer groups.
• Working knowledge of CRM platforms (e.g., Salesforce, HubSpot) and sales engagement tools.
• Experience presenting software demonstrations and communicating complex technical solutions to diverse audiences.
• Demonstrated success building business cases and articulating ROI through data-driven sales presentations.
• Familiarity with the individual health insurance market, ACA enrollment processes, and broker technology platforms.
• Proven ability to collaborate effectively with cross-functional teams, including Product, Solutions Engineering, and Customer Success.

Education:

• Bachelor's degree in Business, Marketing, Healthcare Administration, or a related field, or equivalent combination of education and experience.