Enrollment Operations Specialist

About Stride Stride helps independent workers access health, dental, and vision benefits. Stride is now part of Integrity, expanding the resources and capabilities available to the workers we serve. Position Details • Seasonal W-2 employment beginning October 12, 2026 • All Enrollment Operations Specialists are expected to remain through the December 31, 2026 CCA enrollment deadline. After December 31, the team will be reduced in phases based on enrollment volume and business needs, with individual assignments anticipated to end on January 15 or February 5, 2027. • $23.00 per hour • 40 hours per week, Monday-Friday, 8:00am-4:00pm PST • Non-exempt and overtime eligible; additional hours may be available or required during peak periods based on business needs The Role We are looking for detail-oriented professionals to join our Enrollment Operations team during Open Enrollment. This is a high-trust operational role responsible for accurately processing insurance enrollment activity and resolving issues that can directly affect a consumer's coverage. The work requires strong judgment, attention to detail, discretion, and the ability to follow established processes in a high-volume environment. Experience with ACA health insurance enrollment, Healthcare.gov, or state-based marketplaces such as Covered California is strongly preferred. Responsibilities • Review and process consumer enrollment, termination, and cancellation requests • Identify and resolve enrollment errors, discrepancies, and missing information • Follow established processes for handling enrollment activity and sensitive consumer information • Contact consumers when additional information or action is required • Research issues and coordinate with internal teams when appropriate • Escalate complex or high-risk issues with clear documentation • Maintain accurate records of enrollment activity and communications in Zendesk or similar systems • Identify recurring issues and communicate trends or process gaps to management • Support the Enrollment Operations team during periods of high volume Qualifications When reviewing resumes, we'll look for experience that indicates: • Experience managing detailed, process-driven work in which accuracy and timely execution were essential • Experience identifying discrepancies, researching issues, and determining or coordinating the appropriate next step • Experience following established processes and handling sensitive or confidential information • Experience maintaining accurate records and documenting actions and communications in business systems • Experience communicating directly with consumers or customers and coordinating with internal teams to resolve issues • Experience working independently in a high-volume environment with changing priorities • Experience using technology and digital tools to manage workflows, records, and communications, including learning new systems as needed Preferred Experience We'll prioritize candidates with resumes that indicate: • Experience in health insurance operations, broker services, member support, or enrollment processing • Experience with ACA enrollment, including eligibility, plan selection, or coverage changes • Experience using Healthcare.gov or state-based marketplaces such as Covered California • Experience using Zendesk or a similar CRM or support platform • Experience working in a high-volume Open Enrollment environment • Experience working effectively in a fully remote environment • Experience in a startup, small business, or similarly fast-paced environment where you were expected to take ownership and wear multiple hats What We'll Assess During the Interview During the interview process, we'll assess: • Critical thinking and problem-solving - the ability to assess a situation, identify relevant information, and determine the appropriate next step • Attention to detail - the ability to maintain accuracy under pressure • Judgment, discretion, and accountability when handling sensitive information and enrollment activity • Process discipline and independence - the ability to work with limited guidance while following established processes precisely • Written and verbal communication - the ability to document actions clearly and communicate effectively with consumers and internal teams • Comfort in a high-volume environment with changing priorities • Technical learning agility - the ability to learn and navigate new systems quickly • Ownership and adaptability - the willingness to take responsibility for work and respond effectively to new or unfamiliar tasks What Success Looks Like You process enrollment work accurately, consistently, and on time. You take ownership of your work, recognize when something is wrong, document your actions clearly, and escalate issues appropriately. Accuracy is critical in this role. Small enrollment errors can have significant consequences for consumers, and we expect every team member to treat that responsibility seriously. ...