Senior Document Writer – New Group Business (Remote)

If you’re the type who can take messy benefit inputs and turn them into clean, compliant plan documents without breaking a sweat, this is your lane. The work is detail-heavy, deadline-driven, and built around writing and quality control for medical, dental, and vision plan documentation.

About CVS Health
CVS Health is focused on building a more connected, convenient, and compassionate health experience, supported by large teams delivering health solutions at scale.

Schedule

  • Full-time (40 hours/week)
  • Remote
  • Application window expected to close: 02/26/2026

What You’ll Do

  • Draft, review, and edit medical, dental, and vision plan documents
  • Support new group business by producing plan documents and Summaries of Benefits and Coverage (SBCs)
  • Ensure accuracy, clarity, and consistency in benefit language and formatting
  • Manage priorities and deadlines in a fast-paced, high-volume environment
  • Collaborate as needed across teams while owning assignments end-to-end

What You Need

  • 2–4 years of extensive plan writing experience (self-funded or fully insured plans)
  • 2–4 years of experience in the health insurance industry
  • Proficiency with Microsoft Word, Excel, SharePoint, and Outlook
  • Strong attention to detail and accuracy
  • Independent, critical thinker who is deadline-driven and a self-starter

Preferred Qualifications

  • Knowledge of medical, dental, and vision benefits
  • Strong familiarity with benefit terminology
  • General understanding of compliance/regulatory topics (ERISA, HIPAA, ACA, COBRA)
  • Strong written and verbal communication skills
  • Strong time management and organization to meet or exceed deadlines

Benefits

  • Pay range: $18.50–$42.35/hour (offer varies based on experience, location, etc.)
  • Medical plan options, 401(k) with match, employee stock purchase plan
  • Wellness programs, counseling, and financial coaching
  • PTO, flexible schedules, family leave, tuition assistance, and more (eligibility varies)

Quick gut-check: this role is not creative writing. It’s precision writing with compliance gravity. If you enjoy rules, structure, and catching the “one wrong word that costs money,” you’ll probably thrive.

Happy Hunting,
~Two Chicks…

APPLY HERE.

Clinical Documentation Specialist – Remote

If you’re detail-obsessed and you care about getting the clinical story right, this role is a solid fit. You’ll support care and compliance by helping ensure documentation is accurate, complete, and aligned to standards, all from home.

About CVS Health
CVS Health is building a more connected, convenient, and compassionate health experience for individuals and communities. Their teams support care delivery and patient outcomes at scale, with a strong focus on quality, safety, and accountability.

Schedule

  • Full-time (40 hours/week)
  • Remote role (Work at Home, Illinois)

What You’ll Do

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What You Need

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Benefits

  • Pay range: $18.50–$38.82/hour (based on experience, location, and other factors)
  • Medical plan options, 401(k) with company match, and employee stock purchase plan
  • No-cost wellness programs plus confidential counseling and financial coaching
  • Paid time off, flexible work schedules, family leave, tuition assistance, and more (eligibility varies)

This posting is expected to close 03/27/2026, so don’t wait if you’re interested.

Happy Hunting,
~Two Chicks…

APPLY HERE

Senior Patient Communications Operations Associate (Oak Street Health) – Remote

This role sits right where patient experience meets systems and strategy. If you’re good at building CRM campaigns, tightening omni-channel journeys, and turning performance data into smarter outreach, you’ll help Oak Street Health keep patients engaged and supported throughout their care.

About Oak Street Health
Oak Street Health, part of CVS Health, delivers personalized primary care for older adults on Medicare with a value-based care model focused on quality over volume. Their goal is to simplify communication and proactively support patients through coordinated outreach that strengthens engagement and retention.

Schedule

  • Full-time (40 hours/week)
  • Remote (listed as Chicago, IL/Remote; work at home in Illinois)
  • Cross-functional collaboration with operations, data, infrastructure, and strategy partners

What You’ll Do

  • Develop and manage CRM campaigns that improve patient engagement and retention
  • Build and execute automated and one-off campaigns across email, SMS, direct mail, and patient messaging
  • Provide first-line technical support for campaign performance and troubleshoot delivery/operational issues
  • Create dashboards and reports, generate insights, and recommend improvements
  • Design and run A/B tests to optimize messaging, timing, and channel mix
  • Serve as an SME on journey-based, data-driven communications and customer journeys
  • Partner with stakeholders to improve campaign effectiveness and align work to business priorities
  • Collaborate with technology teams to integrate new tools and capabilities (including AI-driven personalization)
  • Support additional projects and duties as assigned

What You Need

  • 2–5 years of CRM campaign management experience (healthcare or regulated industry preferred)
  • Hands-on experience with marketing automation platforms (Marketo, Pardot, HubSpot, Eloqua, or similar)
  • Strong knowledge of omni-channel marketing (email, SMS, direct mail)
  • Intermediate SQL or data-querying skills
  • Strong grasp of analytics, segmentation, and testing strategies
  • Familiarity with privacy and compliance standards (HIPAA, CAN-SPAM, CCPA)
  • Strong project management and communication skills
  • U.S. work authorization

Benefits

  • Pay range: $46,988–$112,200/year (based on experience, location, and other factors)
  • Eligible for a CVS Health bonus, commission, or short-term incentive program (in addition to base pay)
  • Paid vacation and sick time, plus 401(k) match options
  • Health, dental, and vision insurance
  • Leadership development opportunities and continuing education stipends
  • Flexible work environments and opportunities for growth and advancement

This posting is expected to close 03/30/2026, but strong roles like this don’t always wait around.

If you can build smart journeys, troubleshoot like a grown-up, and keep patient comms clean, timely, and effective, this is a strong move.

Happy Hunting,
~Two Chicks…

APPLY HERE

Senior Document Writer – Remote

If you’re the kind of person who can turn messy benefit details into clean, compliant plan language, this role is for you. You’ll help launch new business by writing and polishing medical, dental, and vision plan documents that employers and members actually rely on.

About CVS Health
CVS Health is building a more connected, convenient, and compassionate health experience for individuals and communities. Through its health solutions and benefit services, CVS supports millions of people while prioritizing safety, quality, and access to care.

Schedule

  • Full-time (40 hours/week)
  • Remote role
  • Deadline-driven work supporting new group business and plan document production

What You’ll Do

  • Draft, review, and edit medical, dental, and vision plan documents for new business
  • Create plan documents and Summaries of Benefits and Coverage (SBCs)
  • Ensure accuracy, consistency, and clear benefit language across documents
  • Apply benefit terminology and align content with compliance and regulatory expectations
  • Manage multiple deadlines in a fast-paced, changing environment while maintaining high quality

What You Need

  • 2–4 years of extensive plan writing experience supporting self-funded and/or fully insured plans
  • 2–4 years of experience in the health insurance industry
  • Proficiency with Microsoft Word, Excel, SharePoint, and Outlook
  • Strong attention to detail, accuracy, and the ability to work independently under deadlines
  • High school diploma or GED

Benefits

  • Pay range: $18.50–$42.35/hour (based on experience, location, and other factors)
  • Eligible for a CVS Health bonus, commission, or short-term incentive program (in addition to base pay)
  • Medical plan options, 401(k) with company match, and employee stock purchase plan
  • No-cost wellness programs plus confidential counseling and financial coaching
  • Paid time off, flexible work schedules, family leave, tuition assistance, and more (eligibility varies)

This posting is expected to close 02/26/2026, so don’t wait until it’s gone.

If you’re sharp with benefits language, organized under pressure, and you can spot errors before they become problems, this is a strong fit.

Happy Hunting,
~Two Chicks…

APPLY HERE

Administrative Support – Remote

If you’ve got real IT admin support miles under your belt and you can clear Public Trust, this one’s a legit lane. The big gate here is the clearance and the “5+ years supporting IT” requirement. That’s not fluff, they’ll screen hard on it.

About PingWind
PingWind supports federal government clients across cybersecurity, development, IT infrastructure, supply chain, and other professional services. They’re a VA CVE certified SDVOSB and SBA HUBZone company with offices in the DC/Northern VA area.

Schedule

  • Full-time, Remote
  • Public Trust required: Non-Sensitive / High Risk (Tier 4/6c)

What You’ll Do

  • Provide executive-level administrative support (calendar, coordination, comms)
  • Draft correspondence that reflects leadership’s intent and handles some technical context
  • Resolve complex admin issues and conflicts that can’t always be pushed to the executive
  • Track tasks and deadlines across multiple concurrent priorities
  • Coordinate documentation collection and team communications
  • Schedule travel as needed
  • Keep work aligned with leadership requirements and timelines

What You Need

  • HS Diploma/GED
  • 5+ years supporting Information Technology (this is the experience anchor)
  • Must have and maintain a Public Trust clearance (Tier 4/6c)
  • Strong organization, time management, and task tracking
  • Strong written and verbal communication
  • Comfortable handling sensitive workflows and executive communications

Preferred

  • Bachelor’s Degree

Benefits

  • 11 Federal Holidays
  • PTO accrued each pay period
  • Parental leave
  • 3 medical plan options (employer contribution)
  • Dental and vision
  • Company-paid short and long-term disability
  • Company-paid life and AD&D
  • 401(k) with matching and vesting
  • Continuing education assistance
  • FSA options (medical, dependent care, commuter)
  • EAP
  • Wellness perks (Calm Health app, WellHub/GymPass subsidy)
  • 529 college savings plan
  • Legal insurance
  • Pet insurance

Heads-up (backbone moment): if you don’t already have that Public Trust or you’re not clearly “IT admin support” for 5+ years, this posting will waste your time. Government contractors don’t bend much on those two.

If you want, paste your last 2–3 job titles + what you actually did (bullet style), and I’ll tell you straight if your experience reads like “5+ years supporting IT” or if we need to reframe it.

Happy Hunting,
~Two Chicks…

APPLY HERE.

Negotiation Specialist I – Remote

This role sits in the middle of operations and provider networks. You’ll negotiate one-off rates with out-of-network providers (or contract exceptions with in-network providers) so injured workers can start care on time. It’s a mix of fast problem-solving, persuasive communication, and clean documentation.

About One Call
One Call helps injured workers get the care they need when they need it. Their teams support care coordination and the operational work that keeps services moving.

Schedule

  • Full-time
  • Remote (remote-first)

What You’ll Do

  • Negotiate rates with out-of-network and in-network providers for prospective referrals using established guidelines
  • Execute short-term agreements (Single Referral Agreements) when the network can’t staff the referral at contracted rates
  • Partner with scheduling to secure a provider quickly and confirm services start on time
  • Locate viable out-of-network providers that match operational needs for specific referrals
  • Communicate One Call’s value proposition to providers to gain agreement and participation
  • Submit strong non-contracted providers to Provider Contracting for potential long-term contracting
  • Collect minimum provider qualification documents for Single Referral Agreements
  • Submit SRA requests to Provider Data Management
  • Maintain clean, clear, concise documentation and task notes
  • Communicate start dates and instructions with providers on negotiated files
  • Confirm Start of Care for negotiated files
  • Meet quality and turnaround time standards and support ad hoc requests as assigned

What You Need

  • Associate degree or 1–2 years of experience in lieu of a degree
  • Financial acumen with the ability to calculate margins using client and provider pricing
  • Comfort negotiating and handling confidential work independently
  • Strong verbal and written communication with concise, professional documentation
  • High attention to detail and solid problem-solving skills
  • General knowledge of workers’ compensation and negotiation principles (or the ability to learn quickly)
  • Ability to juggle multiple tasks and stay dependable in a fast-paced environment

Benefits

  • Remote-first flexibility
  • Time off: 18 days PTO minimum, plus 8 holidays and 2 personal days
  • Medical, dental, vision, pet insurance
  • 401(k) with match
  • Company-paid life insurance, short-term and long-term disability
  • Colleague Assistance Program (counseling and financial services)
  • One Call Foundation support for unexpected hardships

Compensation

  • Salary range: $19.04 – $28.56 per hour

Happy Hunting,
~Two Chicks…

APPLY HERE.