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Remote Supervisor Jobs in Milwaukee, WI (NOW HIRING)

Gallagher

Supervisor

Waukesha, WI · Remote

Workers Compensation * Prior leadership experience: 1-2+ years of supervisory experience ... This role is eligible for fully remote work. How you'll make an impact Supervise: Lead and ...

CorVel Corporation

Claims Supervisor

Waukesha, WI · Remote

$73K - $113K/yr

This is a remote position. ESSENTIAL FUNCTIONS & RESPONSIBILITIES: * Supervises WC claims staff in their day-to-day operations * Assists Claims Manager with recruitment, interviewing, and onboarding ...

Corvel

Claims Supervisor

Waukesha, WI · Remote

$73K - $113K/yr

This is a remote position. ESSENTIAL FUNCTIONS & RESPONSIBILITIES: * Supervises WC claims staff in their day-to-day operations * Assists Claims Manager with recruitment, interviewing, and onboarding ...

Sehinc

Senior Civil Engineer - Supervisor

Milwaukee, WI · On-site +1

$120K - $140K/yr

You belong at SEH SEH is currenting searching for a Senior Civil Engineer - Supervisor to join our ... Hybrid work environment with potential to be fully remote Essential Qualifications: * Bachelor ...

Sehinc

Senior Civil Engineer - Supervisor

Pewaukee, WI · On-site +1

$120K - $140K/yr

You belong at SEH SEH is currenting searching for a Senior Civil Engineer - Supervisor to join our ... Hybrid work environment with potential to be fully remote Essential Qualifications: * Bachelor ...

BES Software

IT Specialist

Milwaukee, WI · Remote

Utilize remote monitoring and management software to efficiently troubleshoot and maintain software ... Maintain regular communication with team members and supervisors through email, instant messaging ...

New

HotRun Inc.

Field Service Engineer

Milwaukee, WI · Remote

This position is a remote position working from a home office and travelling to client's plants in ... This would include supervising the rigging in of the machine into the facility, leveling and ...

HotRun Inc.

Field Service Engineer

Milwaukee, WI · Remote

$90K - $120K/yr

This position is a remote position working from a home office and travelling to client's plants in ... This would include supervising the rigging in of the machine into the facility, leveling and ...

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How much do remote supervisor jobs pay per hour?

As of Aug 8, 2026, the average hourly pay for remote supervisor in Milwaukee, WI is $30.17, according to ZipRecruiter salary data. Most workers in this role earn between $21.30 and $35.96 per hour, depending on experience, location, and employer.

What is a remote supervisor?

A Remote Supervisor is responsible for overseeing a team or department while working from a remote location. Their duties often include managing workflow, monitoring performance, providing support, and ensuring that team objectives are met. They use digital communication and collaboration tools to stay connected with their team. Strong leadership, time management, and adaptability are essential skills for success in this role.

What are some common challenges faced by remote supervisors and how can they be addressed?

Remote Supervisors often face challenges such as maintaining team engagement, ensuring clear communication across different time zones, and tracking productivity without direct oversight. To overcome these hurdles, many organizations rely on structured check-ins, transparent performance metrics, and regular virtual meetings to foster trust and accountability. As a Remote Supervisor, being proactive in addressing concerns and providing support promptly is vital, as is leveraging digital tools to keep the team connected. Building strong relationships remotely and encouraging open communication can greatly enhance morale and team cohesion.

What are the key skills and qualifications needed to thrive as a remote supervisor?

To thrive as a Remote Supervisor, you need strong leadership, organization, time management skills, and prior experience in team management or a relevant supervisory role. Familiarity with project management software, remote collaboration tools (such as Slack, Zoom, or Microsoft Teams), and performance tracking systems is often essential. Exceptional communication, problem-solving, and conflict resolution abilities set successful candidates apart. These competencies are crucial for ensuring effective oversight, consistent productivity, and cohesive team performance in a distributed work environment.

What are the most commonly searched types of Supervisor jobs in Milwaukee, WI? The most popular types of Supervisor jobs in Milwaukee, WI are:
What are popular job titles related to Remote Supervisor jobs in Milwaukee, WI? For Remote Supervisor jobs in Milwaukee, WI, the most frequently searched job titles are:
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What cities near Milwaukee, WI are hiring for Remote Supervisor jobs? Cities near Milwaukee, WI with the most Remote Supervisor job openings:
Remote Supervisor jobs near you
Infographic showing various Remote Supervisor job openings in Milwaukee, WI as of August 2026, with employment types broken down into 96% Full Time, and 4% Part Time. Highlights an 100% Remote job distribution, with an average salary of $62,752 per year, or $30.2 per hour.

Supervisor

Gallagher

Waukesha, WI • Remote

Full-time

Re-posted 9 days ago

Arthur J. Gallagher & Co. rating

7.7

Company rating: 7.7 out of 10

Based on 92 frontline employees who took The Breakroom Quiz

200th of 303 rated insurance

Job description

Introduction
At Gallagher Bassett, we're there when it matters most because helping people through challenging moments is more than just our job, it’s our purpose. Every day, we help clients navigate complexity, support recovery, and deliver outcomes that make a real difference in people’s lives. It takes empathy, precision, and a strong sense of partnership—and that’s exactly what you’ll find here. We’re a team of fast-paced fixers, empathetic experts, and outcomes drivers — people who care deeply about doing the right thing and doing it well. Whether you're managing claims, supporting clients, or improving processes, you’ll play a vital role in helping businesses and individuals move forward with confidence. Here, you’ll be supported by a culture that values teamwork, encourages curiosity, and celebrates the impact of your work. Because when you’re here, you’re part of something bigger. You’re part of a team that shows up, stands together, and leads with purpose.

Overview

Role specifics: 

  • Claims Background: Workers Compensation
  • Prior leadership experience: 1-2+ years of supervisory experience
  • Jurisdictional  experience: WI, IA
  • Licenses: IA
  • Location: This role is eligible for fully remote work. 

How you'll make an impact

Supervise: Lead and encourage a Workers Compensation claims team handling a variety of caseload sizes and complexities to deliver high-quality and efficient service. 

 
Promote Best Practices: Guide claims team to handle claims in accordance with GB’s Best Practices. 

 
Drive Talent: Take charge of adjuster hiring and training, encouraging a culture of performance and continuous improvement. 

 
Manage Workloads: Define team goals, motivate performance, and effectively manage workloads to ensure optimal efficiency. 

 
Utilize Technology: Harness the power of Gallagher's technology to enhance your team's efficiency and overall quality of service. 

 
Client Communication: Communicate with clients, carriers, and brokers in a professional, positive, and proactive manner. 

 
Prioritize and Develop: Effectively manage multiple competing priorities, identify coaching opportunities, and position team members for successful development. 


About You

Required Qualifications: 

  • High School Diploma
  • Minimum of 10 years related claims experience
  • Appropriately licensed and/or certified in all states in which claims are being handled
  • Knowledge of all team member related functions 

Desired:  

  • Bachelor's Degree 

#LI-KD1

#LI-Remote

#WorkersComp


Compensation and benefits

At Gallagher, we believe supporting our colleagues goes far beyond the role itself. For more information, visit our Benefits page.

  • Competitive compensation
  • Comprehensive benefits programs designed to support your well-being 
  • Career development opportunities and ongoing learning 
  • A collaborative, people-first culture with accessible leadership 
  • The opportunity to do meaningful work with global reach and local impact 

At Gallagher, we are dedicated to building an inclusive and authentic workplace. If your past experience doesn’t align perfectly, we encourage you to join our Talent Community to stay connected to additional career opportunities. At times, we will consider transferable skills from previous roles.

Gallagher is an affirmative action/equal opportunity employer (Minorities/Females/Veterans/Disabled)

Qualifications:

Required Qualifications: 

  • High School Diploma
  • Minimum of 10 years related claims experience
  • Appropriately licensed and/or certified in all states in which claims are being handled
  • Knowledge of all team member related functions 

Desired:  

  • Bachelor's Degree 

#LI-KD1

#LI-Remote

#WorkersComp

Education:UNAVAILABLEEmployment Type: FULL_TIME

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