Associate Director, Solutions Execution

Hi, we're Oscar. We're hiring an Associate Director, Solutions Execution to join our Insurance Product Development 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 Associate Director, Solution Execution is responsible for driving high-quality execution across Oscar’s insurance product lifecycle, with direct accountability for regulatory filing delivery, quality assurance, and cross-functional product program governance. This role serves as the operational backbone of Product Management, acting as the hub between Product Managers, downstream execution teams and third party vendors to ensure product decisions are translated into accurate, controlled and on time outputs. This role ensures that product intent, regulatory requirements, and operational execution are tightly aligned from early product definition through filing, implementation, and ongoing optimization efforts.

You will report into the Vice President, Insurance Product Innovation and Development

Work Location: This is a remote / work-from-home role. You must reside in one of the following states: Arizona, California, Colorado, Florida, Georgia, Illinois, Massachusetts, Michigan, Nevada, New Jersey, New York, North Carolina, Ohio, Pennsylvania, Texas, or Virginia. Note, this list of states is subject to change. #LI-Remote

Pay Transparency: The base pay for this role is: $180,504 - $236,911per year in New Jersey, New York, and California. The base pay for all other locations is: $162,453 - $213,220 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, and annual performance bonuses.

Responsibilities:

• QA Governance & Control Ownership

  • Own the QA execution framework & continuous validation and oversee QA process for product execution to ensure product designs and filing artifacts accurately reflect approved product intent

  • Establish and enforce quality thresholds, escalation criteria and remediation workflows for identified defects or gaps

  • Translate QA outcomes into actionable insights for Product Managers and leadership

  
  

  Product Validation Testing

  • Ensure testing reflects approved product designs, versions and regulatory requirements

  • Partner with Product Managers to confirm testing and ensure findings are properly logged, resolved and signed off

  • Ensure outputs are distributed to the right stakeholders at the right time

  
  

  Production, Publication & Version Control

  • Lead production and publication readiness, ensuring all extracts are pulled in accordance with the approved calendar and release schedule

  • Enforce system freeze windows, ensuring no unauthorized updates occur during critical extraction or publication periods

  • Own version control standards, ensuring correct versions are labeled, distributed and retained as the source of record

  
  

  Vendor & Escalation Leadership

  • Serve as the primary escalation point for third-party vendors supporting product execution and QA

  • Oversee vendor performance, capacity and adherence to quality and delivery expectations

  • Manage external vendors supporting filing related and QA processes to ensure product designs and filing artifacts accurately reflect approved product intent

  • Partner with product leadership and procurement on vendor optimization, performance management and risk mitigation

  
  

  Cross-Functional Leadership & Enablement

  • Act as a central hub for the product team

  • Lead and manage regulatory filings and quality assurance teams, setting priorities, performance expectations, and development plans

  • Own the end to end regulatory filing execution and serve as cross functional execution lead,, ensuring accuracy, compliance, and on-time submissions to internal teams across Oscar’s service area

  • Establish execution rhythms, track milestones, surface risks, and drive issue resolution

  • Support leadership decision making with clear, concise updates and recommendations

  • Mentor and lead associate level execution staff

  • Compliance with all applicable laws and regulations

  • Other duties as assigned

  
  

Requirements:

• 7+ years of experience in insurance product (IFP and Small Group) execution, regulatory filings, and related roles

• 3+ years experience managing people 

• 5+ years Hands-on experience with health insurance regulatory filing processes, noting significant familiarity with ACA and state regulatory filings / environments

• 4+ years of proven experience leading complex QA and production workflows

• 4+ years experience and strong understanding of controls, documentation standards and version management

• 3 + years of experience operating in close partnership with senior leaders, supporting execution through strong planning, prioritization, and operating cadence

• 3+ years project management Experience, managing complex stakeholder calendars, forums, and meeting rhythms to ensure critical work progresses efficiently and leadership time is used effectively

• 3+ years of Experience managing or overseeing third party vendors

• Travel up to 25% of the time

Bonus points:

• Bachelor’s degree or higher in business, healthcare or quantitative degree

• Experience with product development process, focused on individual and family plans

• Experience supporting senior leaders through cross-functional agenda setting, meeting preparation, and follow-through on key decisions