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Remote Holiday Jobs in Wisconsin (NOW HIRING)

Staples, Inc.

Sales Account Manager

Burlington, WI · On-site +1

  • Medical

  • Dental

  • Vision

  • Retirement

  • PTO

... for remote work on Fridays. Staples is business to business. You're what binds us together. At ... floating holiday * 401(k) with company match * Medical, dental, vision, and wellness programs

Staples, Inc.

B2B Sales Representative

Bloomington, WI · On-site +1

  • Medical

  • Dental

  • Vision

  • Retirement

  • PTO

... for remote work on Fridays. Staples is business to business. You're what binds us together. At ... floating holiday * 401(k) with company match * Medical, dental, vision, and wellness programs

Staples, Inc.

Customer Service Representative

Burlington, WI · On-site +1

$17 - $23/hr

  • Medical

  • Dental

  • Vision

  • Retirement

  • PTO

... for remote work on Fridays. Staples is business to business. You're what binds us together. At ... floating holiday * 401(k) with company match * Medical, dental, vision, and wellness programs

State of Montana

Property Appraiser 2

Whitehall, WI · On-site +1

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

Sick leave- 12 days a year. * 11 holidays, including a floating holiday, which can be used any time ... Multitask and prioritize work under deadlines REMOTE/TELEWORK: This position may be eligible to ...

New

State of Montana

Property Appraiser 2

Whitehall, WI · On-site +1

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

Sick leave- 12 days a year. * 11 holidays, including a floating holiday, which can be used any time ... Multitask and prioritize work under deadlines REMOTE/TELEWORK: This position may be eligible to ...

New

Montana

Property Appraiser 2

Whitehall, WI · On-site +1

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

Sick leave- 12 days a year. * 11 holidays, including a floating holiday, which can be used any time ... Multitask and prioritize work under deadlines REMOTE/TELEWORK: This position may be eligible to ...

New

State of Montana

Property Appraiser 2

Whitehall, WI · On-site +1

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

Sick leave- 12 days a year. * 11 holidays, including a floating holiday, which can be used any time ... Multitask and prioritize work under deadlines REMOTE/TELEWORK: This position may be eligible to ...

Staples, Inc.

Inside Sales Representative

Bloomington, WI · On-site +1

  • Medical

  • Dental

  • Vision

  • Retirement

  • PTO

... for remote work on Fridays. Staples is business to business. You're what binds us together. At ... floating holiday * 401(k) with company match * Medical, dental, vision, and wellness programs

Staples, Inc.

Inside Sales Manager

Bloomington, WI · On-site +1

  • Medical

  • Dental

  • Vision

  • Retirement

  • PTO

... for remote work on Fridays. Staples is business to business. You're what binds us together. At ... floating holiday * 401(k) with company match * Medical, dental, vision, and wellness programs

Staples, Inc.

Inside Sales Manager

Pleasant Prairie, WI · On-site +1

  • Medical

  • Dental

  • Vision

  • Retirement

  • PTO

... for remote work on Fridays. Staples is business to business. You're what binds us together. At ... floating holiday * 401(k) with company match * Medical, dental, vision, and wellness programs

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Showing results 41-60

All JobsHoliday JobsRemote Holiday JobsRemote Holiday Jobs in Wisconsin

Remote Holiday information

See Wisconsin salary details

$17.4K

$60.2K

$147.9K

How much do remote holiday jobs pay per year?

As of Aug 16, 2026, the average yearly pay for remote holiday in Wisconsin is $60,152.00, according to ZipRecruiter salary data. Most workers in this role earn between $29,220.00 and $81,268.00 per year, depending on experience, location, and employer.

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 Wisconsin?

The most popular types of Remote jobs in Wisconsin are:

What are popular job titles related to Remote Holiday jobs in Wisconsin?

For Remote Holiday jobs in Wisconsin, the most frequently searched job titles are:

What job categories do people searching Remote Holiday jobs in Wisconsin look for?

The top searched job categories for Remote Holiday jobs in Wisconsin are:

What cities in Wisconsin are hiring for Remote Holiday jobs?

Cities in Wisconsin with the most Remote Holiday job openings:

Remote Holiday jobs near you
Infographic showing various Remote Holiday job openings in Wisconsin as of August 2026, with employment types broken down into 84% Full Time, 9% Part Time, and 7% Contract. Highlights an 100% Remote job distribution, with an average salary of $60,152 per year, or $28.9 per hour.

Customer Sales Account Manager

Staples, Inc.

Pleasant Prairie, WI • On-site, Remote

Full-time

Medical, Dental, Vision, Retirement, PTO

Re-posted 27 days ago

Staples rating

5.8

Company rating: 5.8 out of 10

Based on 634 frontline employees who took The Breakroom Quiz

427th of 734 rated retailers

Job description

This position is a minimum of 4 days in the office at our Lincolnshire, IL location with flexibility for remote work on Fridays. 

Staples is business to business. You’re what binds us together.

At Quill, we make it easy for businesses to get the products they need to succeed.  We help organizations of all sizes simplify purchasing while delivering an outstanding customer experience.

We're looking for motivated, sales-driven professional who enjoy building relationships, solving customer challenges, and closing business. As a Category Inside Sales Specialist, Print & Promotional, you'll work with existing and prospective customers, uncover opportunities, recommend solutions, and help drive revenue growth. If you're competitive, goal-oriented, and energized by earning incentives for your success, this role offers an exciting opportunity to build your sales career with a trusted industry leader.

Why Join Quill?

  • Competitive base salary plus incentive opportunity
  • Established brand with a strong reputation and loyal customer base
  • Career development and growth opportunities within sales
  • Collaborative team environment with ongoing coaching and support
  • Opportunity to make a direct impact on customer success and company growth

What You'll Do

  • Convert leads and opportunities into profitable sales while delivering exceptional customer service.
  • Partner with Account Managers and Key Account Managers to support high-value customer accounts and strategic projects.
  • Manage inbound and outbound opportunities across multiple lead channels, including web, chat, and sales-generated leads.
  • Build relationships with customers to identify needs and recommend tailored solutions.
  • Maintain a healthy sales pipeline and accurately track opportunities within CRM systems.
  • Collaborate with cross-functional partners including sales teams, merchants, and vendors to deliver customer solutions.
  • Increase customer spend and share of wallet through consultative selling and trusted advisor relationships.
  • Consistently achieve or exceed sales, revenue, and margin goals.

What You Bring

  • A competitive spirit and passion for achieving results.
  • Strong communication, negotiation, and relationship-building skills.
  • Confidence engaging customers and influencing purchasing decisions.
  • Ability to thrive in a fast-paced, performance-driven environment.
  • Strong organizational and time management skills.
  • Resilience, persistence, and a positive attitude when facing challenges.
  • Customer-focused mindset with a commitment to delivering value.
  • Desire to learn, grow, and contribute to team success.

Basic Qualifications

  • Minimum 1 year of sales, business development, customer service, or related experience.
  • Strong verbal and written communication skills.
  • Proven ability to influence, present, and engage customers effectively.
  • Self-motivated with a track record of meeting goals.
  • High School Diploma or GED.

Prefered Qualifications

  • Experience selling or supporting print and promotional products and solutions.

What We Offer

  • Competitive base pay plus incentive opportunity
  • 112 hours of PTO
  • 7 paid holidays plus 1 floating holiday
  • 401(k) with company match
  • Medical, dental, vision, and wellness programs
  • Associate-led Business Resource Groups
  • Employee discounts across Staples and retail offerings

  • Professional development and career advancement opportunities

The salary range represents the expected compensation for this role at the time of posting.  The specific base pay may be influenced by a variety of factors to include the candidate's experience, skill set, education, business considerations, geography, and internal equity.   Some roles may also be eligible for overtime pay, in accordance with federal and state requirements.   

At Staples, “inclusion” is an action word. It represents what we do to ensure that all employees feel valued and supported to contribute to their fullest potential. When we operate inclusively, diversity naturally follows. This is why we work hard to foster an inclusive culture, as we seek employees with unique and varied perspectives and areas of expertise. The result is a better workplace and innovative thinking that helps us exceed our customers’ expectations – through the power of the people behind our iconic brand. Staples is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, age, sex, sexual orientation, gender identity, national origin, protected veteran status, disability, or any other basis protected by federal, state, or local law.

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