Stride enables independent workers to reap the benefits of their independence.

We simplify the challenges of being self-employed by helping workers handle the complexities of insurance, finances, and taxes — in one convenient platform. Since we were founded in 2014, we have helped over 3.7 million workers save an estimated $5.4 billion on their taxes and monthly health insurance premiums.

Stride partners with over 100 leading companies like Uber, Amazon, DoorDash, and Instacart to provide their independent workers with access to our benefits platform. The company is backed by $96 million in capital from Venrock, New Enterprise Associates, Fidelity's F-Prime Capital Partners, Mastercard, Allstate and King River.

Stride is building the leading individual benefits platform, providing Health Insurance & Benefits for individual Americans and we're looking for a driven and ambitious product operations specialist to lead the execution of our enrollment processes.

You'll work with teams across the organization to ensure our members have a best-in-class portable benefits enrollment experience by submitting all enrollment requests during the Open Enrollment Period.

Responsibilities include but are not limited to:

Reviewing and processing consumer enrollment and cancellation requests
Triaging enrollment errors and implementing solutions to improve enrollment success
Escalating complex enrollment issues to management for review and resolution
Contacting insurance companies or state based exchanges for member or organizational questions
Contacting members to request additional information if appropriate
Supporting the Enrollment Operations team in any other ways necessary

Qualifications

When reviewing resumes, we'll be looking for experiences that indicate:

Strong organizational and process management skills — perhaps from roles where you've balanced competing priorities, kept operations running smoothly, or built systems to bring order to chaos.
Exceptional attention to detail — the kind that ensures accuracy and quality across every spreadsheet, email, and deliverable.
A calm, patient approach under pressure — maybe you've worked in fast-paced environments where clear thinking and composure were key to success.
A positive, can-do attitude — you bring optimism and energy to your work and the people around you.
Sound judgment and independence — whether you've made quick decisions on the fly or managed responsibilities with minimal oversight.
Comfort with technology and systems — you're fluent in Google Workspace (Docs, Sheets, Drive) and eager to learn new tools quickly.
The willingness to go the extra mile during high-volume periods — you understand that some seasons require an extra push, and you show up ready to make things happen.

We'll prioritize candidates with resumes that indicate:

A background in the health insurance industry — this could come from roles in member support, broker services, policy administration, or benefits coordination.
Hands-on experience with healthcare enrollment, operations, or billing — whether you've processed applications, supported open enrollment, or managed claims or billing workflows.
A genuine interest in public or digital health — maybe you've worked with a mission-driven startup, supported health access programs, or volunteered in community health initiatives.

Role Details

This is a seasonal contract role running from ASAP through January 31.
Compensation: $23.00 per hour
Schedule: Two available shifts — 9:00 a.m. to 5:00 p.m. PST or 9:00 a.m. to 5:00 p.m. EST
Status: Full-time, hourly contract
Start Date: Immediate

Helpful Information:

This resourcewill help explain Stride's Compensation Philosophy and compensation practices, and will answer some common questions you might have.

Stride's Compensation Philosophy utilizes a National Payscale, which is designed to fairly and equitably pay employees based on their performance and impact regardless of geographic location. For employees in the United States, our National Payscale leverages San Francisco Bay Area market data to determine our compensation bands for cash, commissions, or bonus (if applicable) and equity.

Unless otherwise noted, the cash compensation above is the total salary and does not include a bonus. In addition to cash compensation, all full-time Striders will be given stock options to participate in Stride's equity incentive program. We want all Striders to be an owner of the company, value that ownership, and be able to participate in any future positive outcomes for the company.

Individual compensation packages are based on a few different factors unique to each candidate, including their skills, experience, qualifications, and other job-related reasons. Our compensation ranges are designed to be competitive, equitable, and growth-oriented.

We know that benefits are also an important piece of your total compensation package. To learn more about what's included in total compensation, check out some of the benefits and perks Stride offers to all US-based employees.

At Stride, we believe in compensating Striders in ways that are true to their value in the marketplace, that inspire and motivate the team to execute our vision, that shape behavior toward productively building and sustaining Stride's culture, and that support the risks and rewards of a fast-growing technology company.

We know theconfidence gapandimposter syndromeare a real thing. This can get in the way of meeting incredible candidates, so please don't hesitate to apply — we'd love to hear from you!

Stride is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.

Stride Health jobs

Enrollment Operations Specialist (Seasonal Contractor)