by Terrance Ellis | Dec 29, 2025 | Uncategorized
If you’re a dental billing vet who can keep claims moving, money posting clean, and AR from turning into a graveyard, Wisdom wants you. This is contract, remote, and flexible, but it’s not “casual.” They need someone experienced who can run point and get results.
About Wisdom
Wisdom pairs dental billing experts with custom-built technology to take the heavy lifting off dental practices and help them get paid faster. They’re a remote-first company with a distributed team across the U.S., and they’re building for growth after a fresh $21M Series A funding round.
Schedule
- Contract
- Remote
- Flexible hours
- Minimum availability: 8 hours per week during business hours (Mon–Fri, 8am–5pm CST)
What You’ll Do
⦁ Submit dental insurance claims accurately and on time, and follow up to drive prompt payment and resolve payer issues
⦁ Post insurance payments and adjustments, reconciling deposits with the PMS and investigating discrepancies
⦁ Manage insurance A/R by running aging reports, pushing collections forward, and spotting trends to improve cash flow
⦁ Serve as the primary point of contact for insurance-related questions with offices and insurance companies
⦁ Coordinate with dental offices to ensure correct coding and documentation for clean claim submission
What You Need
⦁ 5+ years of dental insurance claim submission, payment posting, and AR management experience
⦁ Strong knowledge of dental insurance plans, procedures, and coding
⦁ Excellent follow-up and problem-solving skills for complex billing situations
⦁ High professionalism around patient confidentiality and data security
⦁ Strong communication and relationship management skills (you’ll be dealing with offices and payers)
⦁ Experience with dental PMS platforms (Dentrix, Eaglesoft, or similar) and Google Workspace
⦁ Ability to reliably commit at least 8 hours weekly during standard CST business hours
Benefits
⦁ Flexible hours
⦁ Fully remote, distributed team environment
⦁ Tools, training, and community support for remote billers
⦁ Tech-enabled workflows designed to save time and help you earn more, faster
Straight talk: because it’s contract and they only require 8 hours minimum, this is perfect as a high-skill side lane, or for someone stacking multiple clients. If you’re rusty on follow-ups or you hate payer phone calls, this won’t be your vibe.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Dec 29, 2025 | Uncategorized
If you’re the benefits pro who can run Leave of Absence like a clean operation and still make people feel supported when life gets messy, Clover Health wants you. You’ll own LOA end-to-end, partner across Payroll and Legal, and help improve programs that touch every employee in a remote-first company.
About Clover Health
Clover Health is reinventing health insurance by pairing data and custom software with human empathy to help members stay healthier. They’re mission-driven, member-first, and measure success by the quality of life they improve. Their People Operations team is data-informed, employee-focused, and built to support a distributed workforce.
Schedule
- Full-time
- Remote (USA)
- Remote-first culture with a $1,000 office setup reimbursement
- Cross-functional collaboration with HRBPs, managers, vendors, Payroll, and Legal
What You’ll Do
⦁ Own Leave of Absence administration end-to-end, working directly with the absence management vendor
⦁ Act as the primary contact for employees, managers, and HRBPs for all leave-related questions and support
⦁ Support broader benefits operations: employee inquiries, open enrollment support, communications, and program troubleshooting
⦁ Administer 401(k) plan processes and support benefits billing
⦁ Manage workers’ comp processes and vendor relationships
⦁ Maintain strong relationships with carriers and benefits vendors and keep issues moving to resolution
⦁ Partner with Payroll and Legal as needed to ensure smooth, compliant execution
⦁ Contribute to PeopleOps projects and cross-functional initiatives as assigned
What You Need
⦁ 3+ years of Leave of Absence management experience
⦁ Benefits administration and/or HR operations experience with knowledge of key benefit programs (medical, disability, workers’ comp, retirement)
⦁ Strong comfort with HRIS systems (ADP preferred) and Google Workspace tools (Docs, Sheets, etc.)
⦁ Excellent written and verbal communication skills with a calm, service-first approach
⦁ Understanding of HR principles, practices, and procedures
⦁ Ability to spot process gaps and build cleaner workflows that scale
Benefits
⦁ Base salary range: $75,000–$85,000 (final pay based on equity, market, experience, and qualifications)
⦁ Remote-first flexibility with a $1,000 office setup reimbursement
⦁ Competitive base salary and equity opportunities
⦁ Performance-based bonus program and 401(k) matching
⦁ Comprehensive medical, dental, and vision coverage
⦁ Mental health support, No-Meeting Fridays, monthly company holidays, and flexible time off
⦁ Professional development funding, mentorship, and growth programs
⦁ Employee Stock Purchase Plan (ESPP)
⦁ Monthly cell phone and internet stipend
⦁ Paid parental leave for all new parents
This is a strong fit if you want real ownership: LOA is your lane, but you’re also close enough to the full benefits engine to influence how it runs long-term.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Dec 29, 2025 | Uncategorized
If you’re the person who can keep onboarding moving even when documents are missing, partners are slow, and everyone wants updates yesterday, this role fits. You’ll quarterback merchant onboarding and underwriting support, keep reporting tight, and make sure setups are accurate so clients go live clean.
About One Inc
One Inc builds digital insurance payment solutions that give customers choice, control, and convenience across premiums and claims. Their Digital Payments Platform combines digital communications with electronic payment processing and disbursement to create a smoother payments experience. They’re one of the faster-growing platforms in the insurance payments space, moving billions annually.
Schedule
- Full-time, hourly (non-exempt)
- Remote (United States)
- Pay range: $26–$30/hour (final offer based on experience, location, and qualifications)
What You’ll Do
⦁ Coordinate collection of underwriting and onboarding documents to support merchant setup
⦁ Build strong relationships with customers, banking partners, and vendors connected to Payment Operations
⦁ Create and maintain reports that track payment issues, project status, and implementation dates
⦁ Monitor onboarding progress, communicate blockers, and help resolve issues as they come up
⦁ Partner with project managers to guide merchant onboarding and remove friction points
⦁ Assist with due diligence reviews to ensure applications are accurate and complete
⦁ Research and resolve merchant inquiries independently
⦁ Perform merchant setup and configuration accurately so each merchant is set up correctly
⦁ Update merchant files daily to ensure clean documentation and audit-ready records
⦁ Process onboarding applications quickly and coordinate issue resolution with underwriting and partners
⦁ Learn and apply the full merchant application and underwriting process across credit card and ACH processors
⦁ Lead resolution of merchant setup or configuration issues and take proactive steps to prevent repeats
⦁ Support additional operational needs as assigned
What You Need
⦁ Strong Microsoft Office proficiency (Excel strength is a big plus, expert-level preferred)
⦁ Solid organizational skills and ability to juggle a high volume of projects and priorities
⦁ Strong attention to detail with investigative and analytical problem-solving ability
⦁ Excellent written and verbal communication, both client-facing and internal
⦁ Comfort working within a project management framework
⦁ Bachelor’s degree in Business, Project Management, or related field (or equivalent experience)
⦁ Experience as an onboarding specialist or similar role (insurance and/or merchant services experience preferred)
⦁ Familiarity with Jira and Salesforce (desired)
⦁ Payments industry experience is not required but is a major plus
Benefits
⦁ Competitive hourly pay range: $26–$30/hour
⦁ Remote work environment
⦁ Role focused on growth, development, and cross-team collaboration in a fast-moving payments operation
This is a strong fit if you like operational ownership: tracking details, pushing progress forward, and making sure every onboarding is tight, documented, and client-ready.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Dec 29, 2025 | Uncategorized
If you’re the kind of benefits pro who can keep the trains running on time and still make employees feel taken care of, Payscale wants you. This is a hands-on, service-forward role supporting US and global benefits and leave programs where accuracy, confidentiality, and follow-through matter every single day.
About Payscale
Payscale is a compensation and pay data leader helping organizations turn pay into a competitive advantage using trusted data and AI-powered tools. Their suite of products supports thousands of employers, including many major U.S. brands, and they’re known for building tools that create confidence in compensation. They run a remote-first model designed for focus day-to-day and in-person connection a few times a year when it matters.
Schedule
- Full-time
- Remote (United States)
- Remote-first with occasional in-person events (typically a few times per year)
- Work from home or company-paid co-working space options
- Tech expectations: stable high-speed internet (100 Mbps recommended), dedicated workspace, device for MFA/2FA
- Note: currently unable to hire in Quebec, Northern Ireland, or Hawaii
What You’ll Do
⦁ Administer day-to-day benefits and leave processes (enrollments, terminations, claims, COBRA, FMLA, disability)
⦁ Serve as a primary point of contact for employee benefits and leave questions with clear, supportive guidance
⦁ Maintain accurate, confidential employee, benefits, and leave records
⦁ Support compliance with benefits and leave regulations and escalate issues when needed
⦁ Assist with 401(k) administration and support global retirement and pension programs
⦁ Partner with Payroll to ensure accurate deductions, contributions, and timely processing
⦁ Coordinate benefits billing, reconciliations, reporting, and approvals
⦁ Work with brokers and vendors to resolve issues and keep programs running smoothly
⦁ Review file feeds and reports, flag discrepancies, and take routine corrective action
⦁ Document procedures and support employee-facing communications related to benefits and leave
⦁ Identify small, practical process improvements while maintaining strict confidentiality
⦁ Provide backup support for a compensation analyst within the total rewards team
What You Need
⦁ 3–5 years of hands-on benefits and/or leave administration experience (or equivalent HR experience)
⦁ Working knowledge of US benefits and leave regulations (ERISA, FMLA, COBRA, HIPAA)
⦁ Experience administering benefits in ADP or a similar HRIS
⦁ Strong spreadsheet comfort and attention to operational detail
⦁ Service-first communication style and confidence answering employee questions
⦁ Experience working with brokers, vendors, or insurance carriers in a support role
⦁ Ability to manage recurring processes, deadlines, and follow-through in a fast-paced environment
⦁ Collaborative, approachable, reliable work style
⦁ Nice to have: exposure to self-funded medical plans
⦁ Nice to have: global benefits administration experience
⦁ Nice to have: CEBS, PHR, or SPHR certifications
Benefits
⦁ Salary range: $72.1K–$108.1K base (plus bonus eligibility)
⦁ Flexible paid time off
⦁ 14 paid company holidays (including 2 floating holidays)
⦁ Medical, dental, vision, disability, and life insurance covered up to 100% by Payscale
⦁ Unlimited infertility coverage through medical plans
⦁ Supplemental health options for you and your family
⦁ 401(k) with immediate, fully vested company match
⦁ 16 weeks paid parental leave for birthing and non-birthing parents
⦁ HSA options with company contributions each pay period
⦁ FSA options for pre-tax allocations
⦁ Annual remote work stipend for wellness or home office equipment
⦁ Learning and development resources, ERGs, volunteer hours, and a strong feedback culture
This is a great fit if you’re equal parts operator and helper: you can run clean processes, protect confidentiality, and still be the person employees trust when life happens and they need benefits to make sense.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Dec 29, 2025 | Uncategorized
This is a clean entry point into healthcare scheduling: you’ll book appointments, coordinate referrals, and keep patient info accurate in the electronic system. The “remote” comes with a catch: you have to live close enough to get to SSM Wisconsin sites for orientation/training.
About SSM Health Dean Medical Group
SSM Health is a large healthcare system with clinics and hospitals across multiple states. Dean Medical Group is their Wisconsin physician group, and this team supports centralized operations for patient access and scheduling.
Schedule
- Full-time (40 hours), remote after orientation/training
- Day shift
- Must live within commutable distance of SSM Wisconsin locations for onboarding/training
What You’ll Do
- Collect scheduling details from patients and referring provider offices to confirm and schedule services
- Coordinate referrals and scheduling with other providers and services
- Obtain approval for schedule changes/cancellations when needed
- Maintain and update provider contact information
- Enter appointments, instructions, and patient details into the electronic medical system accurately
- Follow site-specific protocols and keep documentation current for compliance
- Help with other assigned duties as needed
What You Need
- High school diploma/GED or 10 years of work experience
- No experience required (big plus if you’re pivoting careers)
- Comfort with frequent keyboarding/data entry and phone communication
- Ability to follow detailed workflows and protect patient information
Benefits
- Comprehensive benefits package
- Paid parental leave (eligible team members: 1 week, pro-rated by FTE)
- DailyPay option for eligible hourly team members (fees may apply)
- Upfront tuition coverage through FlexPath Funded (eligible team members)
Here’s the gut check: this job is perfect if you want “stable, structured, day shift, remote-ish” and you’re good being the steady voice on the phone. If you hate repetitive tasks or can’t stand scheduling rules, you’ll be miserable.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Dec 29, 2025 | Uncategorized
This is a telehealth billing + AR role for someone who can live inside Athena, untangle claims fast, and keep patients informed without making them feel like they’re being sent to collections. You’ll troubleshoot, follow up, audit for trends, and help tighten the revenue cycle while protecting the patient experience.
About Midi Health
Midi Health provides virtual care focused on women 40+, supporting perimenopause, menopause, and other midlife health needs with a compassionate, modern approach. They’re building a digital-first care model that blends clinical quality with a strong patient experience.
Schedule
- Fully remote (WFH)
- Shift options: Monday–Friday 11:00 AM–7:00 PM ET or 8:00 AM–4:30 PM PT (includes 30-min unpaid lunch)
- Must be authorized to work in the U.S. without current or future visa sponsorship
What You’ll Do
- Use the Athena platform to troubleshoot and resolve claims for telehealth services, ensuring compliance with internal coding guidelines, payer rules, and regulations
- Coordinate with the clinical team to confirm insurance coverage, eligibility, and benefits before telehealth visits
- Help patients understand financial responsibility and payment options available through Midi
- Manage and collect patient accounts receivable (AR), including follow-up on balances, denials, and unpaid claims
- Participate in audits/reviews of billing data and documentation to identify errors, discrepancies, and revenue cycle trends
- Work with insurers and third-party billing vendors to resolve disputes, negotiate payment arrangements, and optimize telehealth reimbursement
- Track and adhere to KPIs and internal revenue cycle metrics
- Join cross-functional projects to improve patient experience, streamline RCM workflows, and implement tech improvements
What You Need
- 2–3 years of medical billing and coding experience
- 2–3 years of patient AR collections experience
- Experience with Athena (or similar billing platform), including statements, payment plans, and balance negotiations
- Familiarity with Zendesk or similar support platforms
- Strong knowledge of CPT, ICD-10, and HCPCS guidelines
- Telehealth billing experience strongly preferred
- Sharp attention to detail and strong problem-solving instincts
Benefits
- Hourly rate: $23–$25/hour (based on experience)
- Fully remote work-from-home setting
- Contract role (no benefits listed in the posting)
Interview Process
- Recruiter interview (30 min)
- Hiring manager + Billing Specialist interview (30 min)
- Department leader interview (30 min)
- Functional leader final interview (30 min)
Quick reality check: this role wants a billing person who can talk to humans. If you’re strong in Athena + claims troubleshooting and you can explain money stuff without sounding cold, you’ll be dangerous here.
Happy Hunting,
~Two Chicks…
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