1/31/26 WFH Leads: 3 New Remote Jobs Paying $20–$25/hr in Edtech, Healthcare & Mental Health
These billing & support-based remote roles include a contract position and two full-time opportunities
DAILY LEADS
1/30/20264 min read
Customer Support Representative at Outschool (contract)
Outschool is a disruptive online learning platform that reimagines the traditional education system by offering live, engaging, and small-group classes for kids. By connecting over one million learners with a global community of teachers, they provide a dynamic supplement to traditional schooling that focuses on curiosity and human connection. Their mission is to ensure every learner can navigate the future with resilience, leveraging a platform that has seen massive growth and now incorporates cutting-edge AI tools.
Job Details:
Multichannel Support: Act as an expert in Outschool’s inner workings, primarily managing high-quality support conversations via chat and email.
Complex Issue Resolution: Investigate and resolve sensitive or ambiguous customer inquiries with sound judgment and empathy.
Internal Triage: Handle escalated support situations, ensuring they are addressed or moved to the appropriate internal team when necessary.
Operational Agility: Follow established workflows while quickly adapting to new products, software tools, and evolving company policies.
Team Support: Take on additional customer experience tasks as needed to maintain smooth operations during high-volume periods.
Requirements:
Strong written communication skills with a distinct "customer-first" mindset.
Proven ability to work independently and make decisions within defined guidelines.
A quick learner who thrives in fast-changing environments and adapts well to new software features.
Availability to work a flexible schedule (35-40 hours/week) that includes one weekend day.
Benefits:
Remote Support: Fully remote work for candidates in the U.S. and Canada, including support for home office setup and internet.
Connection Stipends: Weekly meal budgets provided to help remote team members stay connected and energized.
Shared Success: Competitive hourly pay with a culture that values professional development and DEI learning.
Family Perks: Access to annual budgets specifically for your children to take Outschool classes.
The listed pay range for this role is $20-$25 per hour according to the job description.
Billing and Claims Associates at Talkspace
Talkspace is a leading virtual behavioral healthcare provider on a mission to democratize therapy by making it accessible and affordable for everyone. With over two million members served, they prioritize a diverse and inclusive environment where mental health is the top priority. This role sits at the intersection of healthcare operations and white-glove customer service, ensuring members feel supported through the often-confusing world of medical insurance and claims.
Job Details:
Billing Advocacy: Use internal resources to educate clients on billing and claims procedures, resolving escalated inquiries regarding enrollment errors, refunds, and superbill requests.
Claims Management: Conduct outbound calls to insurance payers to obtain member EAP authorizations and discuss specific claim submissions on a case-by-case basis.
Complex Investigations: Resolve sensitive inquiries that require deep-dive investigations, ensuring every interaction leaves the client feeling understood and supported.
Special Operations: Participate in departmental projects involving charge disputes, medical records requests for billing, and the drafting of billing affidavits.
Process Improvement: Recommend updates to the internal knowledge base and correspondence templates to improve team productivity and the overall client experience.
Internal Collaboration: Serve as a Subject Matter Expert (SME) for the Client Support team, providing status updates on payer issues and assisting with training new hires.
Requirements:
2+ years of experience in health insurance claims or a healthcare support environment (email/chat/phone).
Deep knowledge of Behavioral Health terminology (CPT Codes) and insurance benefits (copays, coinsurance, and deductibles).
Proven ability to comply with PHI and HIPAA guidelines while handling sensitive patient data.
Familiarity with payor portals and third-party healthcare clearinghouses; experience with Zendesk and Jira is a plus.
Strong communication skills and a typing speed of 50-60 wpm.
Ability to work remotely while maintaining an Eastern Time (ET) schedule.
Benefits:
Day-One Coverage: Comprehensive medical, dental, and vision plans that start on your first day of employment.
Retirement Planning: 401(k) savings program with a company match of up to 4%.
Wellness Focus: Monthly wellness stipends to promote self-care and regular team-building wellness workshops.
Talkspace Perks: Free access to Talkspace products for you and one household member, plus additional discounts for friends and family.
Remote-First Culture: A flexible, distributed work environment with a focus on work-life harmony.
The listed pay range for this role is $22-$24.50 per hour according to the job description.
Customer Support Specialist at Wheel
Wheel is the hidden engine powering the modern virtual care revolution. They provide a premier platform and a nationwide network of clinicians that allow the world's most innovative companies to deliver high-quality healthcare at scale. By blending cutting-edge technology with an intuitive consumer interface, Wheel is making "seeing a doctor" as easy as ordering a meal on an app. They are a high-growth, mission-driven team that values smart problem solvers and collaborative thinkers.
Job Details:
Second-Level Support: Triage and respond to complex Tier 2 Zendesk tickets that require deeper investigation beyond standard scripts.
Multichannel Communication: Answer incoming calls from a diverse group of stakeholders, including clients, patients, and pharmacies.
Technical Troubleshooting: Handle sensitive situations and complex technical issues, de-escalating when necessary to ensure a smooth patient experience.
Engineering Liaison: Vet and submit JIRA tickets for the Engineering and Operations teams to help fix systemic bugs and platform issues.
Cross-Functional Collaboration: Work closely with internal teams to solve high-priority issues that impact the quality of virtual care delivery.
Requirements:
2–5 years of experience in a high-volume, fast-paced customer support role.
Expertise in Zendesk is a must for this specific position.
Exceptional verbal and written communication skills with a proven ability to manage escalations.
Strong "people skills" rooted in empathy, patience, and the ability to build trust quickly.
Experience in the healthcare industry is a significant plus.
Benefits:
Financial Security: Access to a 401(k) program with company matching and stock options to give you a stake in Wheel's growth.
Comprehensive Health: Full Medical, Dental, and Vision insurance, plus Short and Long-Term Disability coverage.
Work-Life Balance: Flexible PTO and dedicated Parental Leave to ensure you can prioritize your family and well-being.
Remote-First Perks: A fully remote role with additional programs and perks designed to keep a distributed team connected and supported.
The listed pay range for this role is $22-$25 per hour according to the job description.
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