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Remote Holiday Jobs in New Port Richey, FL (NOW HIRING)

E-Billing Coordinator

Tampa, FL · On-site +1

  • Medical

  • Dental

  • Vision

  • Retirement

  • PTO

The position may be fully remote and reports to the E-Billing Supervisor. The primary duties of the ... Generous Paid Time Off, Including a Floating Holiday * Paid Holidays * WorkWell Wellness Program

Mortgage Branch Manager

Clearwater, FL · On-site +1

$36K/yr

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

Remote in the Clearwater, FL area. Are you a top producer waiting for your chance to run your own ... Day (Floating Holiday) * Multiple PPO Medical Plans, as well as HDHP eligible plan. * Dental ...

Mortgage Branch Manager

Tampa, FL · On-site +1

$36K/yr

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

Remote in the Tampa, FL area. Are you a top producer waiting for your chance to run your own office ... Day (Floating Holiday) * Multiple PPO Medical Plans, as well as HDHP eligible plan. * Dental ...

Mortgage Branch Manager

Tampa, FL · Remote

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

Remote in the Tampa, FL area. Are you a top producer waiting for your chance to run your own office ... Day (Floating Holiday) * Multiple PPO Medical Plans, as well as HDHP eligible plan. * Dental ...

Software Developer I

Tampa, FL · Remote

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

This is a remote position supporting our Tampa, FL office . This role combines software development ... Holiday Pay * Unlimited PTO * Referral Program * Career advancement opportunities * Continuous ...

Benefits Specialist (Hybrid or Remote)

Clearwater, FL · On-site +1

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

... or remote Benefits Specialist position filled with many exciting opportunities! This role ... Paid time off and holiday pay * Education reimbursement up to five thousand two hundred fifty ...

Business Development Representative

Tampa, FL · Remote

$60K - $72K/yr

  • Medical

  • Dental

  • Vision

  • Retirement

  • PTO

This role operates with a remote work structure, but it is fundamentally a field-based sales ... We offer a competitive benefits package, including 6 paid holidays, 1 paid floating holiday and up ...

Inside Senior Property Claims Adjuster

Tampa, FL · On-site +1

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

USAA roles may offer remote or hybrid flexibility for active-duty military spouses consistent with ... or holiday work outside normal work hours. * May be assigned CAT deployment travel with minimal ...

Business Development Representative

Tampa, FL · Remote

$60K - $72K/yr

  • Medical

  • Dental

  • Vision

  • Retirement

  • PTO

This role operates with a remote work structure, but it is fundamentally a field-based sales ... We offer a competitive benefits package, including 6 paid holidays, 1 paid floating holiday and up ...

Inside Senior Property Claims Adjuster

Tampa, FL · On-site +1

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

USAA roles may offer remote or hybrid flexibility for active-duty military spouses consistent with ... or holiday work outside normal work hours. * May be assigned CAT deployment travel with minimal ...

Workday Absence & HCM Senior Analyst

Tampa, FL · Remote

$85K - $108K/yr

Maintain global annual holiday calendars and create background check packages * Manage Skills Cloud ... LI-SAW #LI-Remote POSITION REQUIREMENTS: Education Bachelor's degree in Human Resources ...

Business Development Representative

Tampa, FL · Remote

$60K - $72K/yr

  • Medical

  • Dental

  • Vision

  • Retirement

  • PTO

This role operates with a remote work structure, but it is fundamentally a field-based sales ... We offer a competitive benefits package, including 6 paid holidays, 1 paid floating holiday and up ...

Highway Design Build Project Manager

Tampa, FL · On-site +1

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

Paid Time Off and Flexible Holiday Program * Company Paid Disability (includes paid Maternity Leave ... Flexible Work Schedules (Hybrid or Remote, when possible) * Wellness Program for Physical and ...

Marketing Coordinator

Tampa, FL · On-site +1

$40K - $55K/yr

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

Paid Time Off and Flexible Holiday Program * Company Paid Disability (includes paid Maternity Leave ... Flexible Work Schedules (Hybrid or Remote, when possible) * Wellness Program for Physical and ...

Inside Senior Property Claims Adjuster

Tampa, FL · On-site +1

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

USAA roles may offer remote or hybrid flexibility for active-duty military spouses consistent with ... or holiday work outside normal work hours. * May be assigned CAT deployment travel with minimal ...

Airport Senior Project Manager

Tampa, FL · On-site +1

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

Paid Time Off and Flexible Holiday Program * Company Paid Disability (includes paid Maternity Leave ... Flexible Work Schedules (Hybrid or Remote, when possible) * Wellness Program for Physical and ...

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Showing results 1-20

Remote Holiday information

What is a remote holiday?

A Remote Holiday job is a seasonal or short-term position that allows you to work from home or any location with internet access. These jobs are typically available during holiday seasons and may involve customer support, sales, marketing, or virtual assistance. Many companies hire remote workers to handle increased holiday demand, offering flexible schedules and temporary contracts.

What are the typical daily responsibilities of a remote holiday specialist?

As a Remote Holiday Specialist, your day usually involves communicating with clients to understand their travel preferences, researching destinations, and assembling customized holiday packages. You’ll book flights, accommodations, tours, and other travel services using specialized booking platforms, all while ensuring seamless coordination. Responding promptly to client inquiries, handling changes or cancellations, and providing travel advice are integral parts of the role. Collaboration with travel suppliers, hotels, and sometimes other team members is also common to ensure every client receives a tailored vacation experience.

What are the key skills and qualifications needed to thrive in the remote holiday position, and why are they important?

To excel as a Remote Holiday Specialist, you need strong customer service, travel industry knowledge, and excellent organizational skills, typically supported by experience in hospitality or travel planning. Familiarity with online booking platforms, CRM systems, and reservation management software is essential for daily tasks. Strong communication, problem-solving, and attention to detail are valuable soft skills that help build client trust and satisfaction. These competencies are vital for effectively managing holiday arrangements, resolving client issues, and delivering high-quality remote service.

What are the most commonly searched types of Remote jobs in New Port Richey, FL?

The most popular types of Remote jobs in New Port Richey, FL are:

What job categories do people searching Remote Holiday jobs in New Port Richey, FL look for?

The top searched job categories for Remote Holiday jobs in New Port Richey, FL are:

What cities near New Port Richey, FL are hiring for Remote Holiday jobs?

Cities near New Port Richey, FL with the most Remote Holiday job openings:

Infographic showing various Remote Holiday job openings in New Port Richey, FL as of August 2026, with employment types broken down into 73% Full Time, 19% Part Time, and 8% Contract. Highlights an 100% Remote job distribution.

Benefits Specialist (Hybrid or Remote)

FrankCrum

Clearwater, FL • Remote

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Re-posted 25 days ago


FrankCrum rating

7.4

Company rating: 7.4 out of 10

Based on 6 frontline employees who took The Breakroom Quiz

221st of 492 rated business services


Job description

FrankCrum is a Top Workplace!
FrankCrum, voted by its employees as a Top Workplace in Tampa Bay for more than 10 years in a row, is a Professional Employer Organization (PEO) based in Clearwater, Florida. FrankCrum employs approximately 500 people who serve over 4,000 businesses by offering a full range of HR services, including payroll, employee benefits, HR consulting services and workers’ compensation insurance. Our PEO is a family culture that encourages people to feel at home, collaborate, and respect each other and we live by our Pillars of Excellence which are Integrity, Prosperity, and Affinity!
Click here to learn more about FrankCrum!
The Role You'll Play to Create Success
We are thrilled to announce a full-time and onsite, hybrid or remote Benefits Specialist position filled with many exciting opportunities! This role contributes to the mission of FrankCrum by administering complex worksite client employee benefit programs.

  1. Coordinates, administers, and supports benefits programs for multiple client companies, including health, dental, vision, life insurance, and retirement plans.
  2. Assists with benefits enrollment, eligibility tracking, changes, and terminations for worksite employees across diverse industries.
  3. Serves as a primary point of contact for client representatives, addressing benefits-related inquiries and issues promptly.
  4. Manages ACA compliance for multiple clients, including monitoring employee hours, determining eligibility, and ensuring accurate IRS filings (e.g., 1094-C, 1095-C), reporting, and deadlines.
  5. Oversees COBRA compliance and administration for client companies, ensuring timely distribution of COBRA notices to eligible employees and manages enrollments, terminations, and premium payment tracking for multiple employers.
  6. Manages and executes annual Open Enrollment (OE) processes for client companies, ensuring timely and accurate communication of benefits options to employees, and providing training and support to clients and employees on OE process.
  7. Educates client companies and their employees on benefits offerings, ACA requirements, and COBRA rights.
  8. Ensures compliance with federal and state regulations across all client benefit programs.
  9. Conducts regular audits of benefits data, processes, and documentation for accuracy and compliance.
  10. Clocks in and out consistently and accurately by using the electronic timeclock system for all time worked and does not perform any work when not clocked-in.

The Attributes We Seek
Keys to success in this position include knowledge of Federal and state laws regarding employee benefits and insurance. Experience in multi-company benefits management including ACA compliance and COBRA administration is needed. A minimum of three (3) years of experience in benefits administration, specifically within a PEO or multi-employer environment is needed. Bachelor’s degree in Human Resources, Business Administration, or related field preferred, high school diploma or equivalent is required.
Our Competitive Benefits
Along with this great opportunity, FrankCrum also provides exceptional benefits from top carriers including:
  • Health Insurance is zero dollar paycheck cost for employee's coverage and only one hundred and ninety five dollars a month for family!
  • Dental and Vision Insurance
  • Short Term Disability and Term Life Insurance at no cost to the employee
  • Long Term Disability and Voluntary Term Life Insurance
  • Supplemental insurance plans such as Accidental, Critical Illness, Hospital Indemnity, Legal Services and Pet Insurance
  • 401(k) Retirement Plan where FrankCrum matches 100% of the first 4% the employee contributes, and the employee is immediately vested in the employer match
  • Employee Assistance Program at no cost to the employee
  • Flexible Spending Accounts for Medical and Dependent Care Reimbursement
  • Health Savings Account funded by FrankCrum
  • Paid time off and holiday pay
  • Education reimbursement up to five thousand two hundred fifty dollars tax free per calendar year
  • PTO cash out
  • Tickets at Work
  • Access to the Alero Financial
  • Employee and client referral bonus programs

#LI-AC1
What's Special About FrankCrum
FrankCrum, a family-owned business-to-business entity since 1981 made of several companies: FrankCrum Corporate (a professional employer organization), FrankCrum Staffing, Frank Winston Crum Insurance Company, and the FrankCrum Insurance Agency - all based in Clearwater, Florida. This “family of employer solutions” employs more than 500 people who serve over 4,000 clients throughout the United States. FrankCrum employees are trained to deliver high value through exceptional customer service and treat clients and coworkers like family. By living by our Brand Pillars (Integrity, Affinity, and Prosperity) employees are recognized at quarterly events for exceptional customer service and milestones in tenure.
The FrankCrum headquarters spans 14 acres and includes a cafe, subsidized for employees. Menus include made-to-order breakfast, hot lunch options and even dinners that can be ordered to-go, all at very affordable prices. The cafe also hosts monthly birthday and anniversary celebrations, eating and costume contests, and yearly holiday parties. Through the input of its own employees, The Tampa Bay Times has recognized FrankCrum as a Top Place to Work for more than 10 years in a row! FrankCrum also supports several community efforts through Trinity Cafe, the Homeless Empowerment Program, Angel Tree, and Clearwater Free Clinic!
If you want to play this role to positively impact our client's day-to-day business, then apply now!
FrankCrum is an Equal Opportunity Employer that does not discriminate on the basis of actual or perceived race, color, creed, religion, national origin, ancestry, citizenship status, age, sex or gender (including pregnancy, childbirth and pregnancy-related conditions), gender identity or expression (including transgender status), sexual orientation, marital status, military service and veteran status, physical or mental disability, genetic information, or any other characteristic protected by applicable federal, state or local laws and ordinances.

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