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Remote Cobra Insurance Jobs in Milwaukee, WI (NOW HIRING)

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Remote Cobra Insurance information

See Milwaukee, WI salary details

$23.2K

$58.2K

$96.1K

How much do remote cobra insurance jobs pay per year?

As of Sep 5, 2026, the average yearly pay for remote cobra insurance in Milwaukee, WI is $58,222.00, according to ZipRecruiter salary data. Most workers in this role earn between $39,900.00 and $76,400.00 per year, depending on experience, location, and employer.

What is a remote COBRA insurance specialist?

A Remote COBRA Insurance Specialist is a professional who manages COBRA health insurance administration and compliance tasks from a remote location. Their main responsibilities include processing COBRA enrollments, communicating with employees about their rights and options, and ensuring that all legal requirements related to COBRA are met. They may work for third-party administrators, insurance companies, or directly for employers. This role is ideal for individuals with strong organizational and communication skills, as well as experience in benefits administration. Working remotely allows them to perform these duties from home or another location outside of a traditional office.

What are the key skills and qualifications needed to thrive as a remote COBRA insurance specialist?

To thrive as a Remote COBRA Insurance Specialist, you need a solid understanding of COBRA regulations, benefits administration, and compliance requirements, often supported by experience in health insurance or HR. Familiarity with benefits administration platforms, CRM systems, and regulatory compliance software is typically required. Strong attention to detail, customer service skills, and effective communication are crucial for managing sensitive data and assisting clients remotely. These competencies ensure accurate administration, regulatory compliance, and high-quality service for clients navigating complex insurance processes.

What are some common challenges faced by remote COBRA insurance specialists and how can they be managed?

Remote COBRA Insurance Specialists often face challenges such as keeping up-to-date with frequently changing regulations, managing sensitive client data securely, and ensuring clear communication with clients and employers across different time zones. To manage these challenges, it's important to stay current with industry updates through regular training, use secure digital tools for managing confidential information, and establish consistent communication protocols with your team and clients. Effective time management and a strong understanding of compliance requirements are also essential to succeed in this remote role.

What is the difference between Remote Cobra Insurance vs Remote Health Insurance Specialist?

AspectRemote Cobra InsuranceRemote Health Insurance Specialist
CredentialsTypically requires knowledge of COBRA regulations, insurance policies, and sometimes certifications in insurance or benefits administrationRequires knowledge of health insurance plans, customer service skills, and often certifications like AHIP or health insurance licenses
Work EnvironmentRemote, customer service or benefits administration setting, often within insurance companies or HR departmentsRemote, customer support or sales environment within insurance agencies or health plan providers
Industry UsageCommonly used in employee benefits and insurance administration sectorsUsed in health insurance sales, support, and benefits consulting sectors

Remote Cobra Insurance focuses on managing COBRA benefits and compliance, while Remote Health Insurance Specialist handles broader health insurance plans and customer support. Both roles are remote and require insurance knowledge, but they serve different aspects of health benefits administration.

What job categories do people searching Remote Cobra Insurance jobs in Milwaukee, WI look for?

The top searched job categories for Remote Cobra Insurance jobs in Milwaukee, WI are:

Remote Cobra Insurance jobs near you
Infographic showing various Remote Cobra Insurance job openings in Milwaukee, WI as of June 2026, with employment types broken down into 67% Full Time, 11% Part Time, 20% Contract, and 2% Nights. Highlights an 52% Physical, 3% Hybrid, and 45% Remote job distribution, with an average salary of $58,222 per year, or $28 per hour.

Director, Total Rewards (Remote, USA)

Optiv Security, Inc.

Milwaukee, WI • Remote

$123K - $168K/yr

Full-time

Medical, Dental, Vision, Life, Retirement

Posted 7 days ago

Job description

The Director, Total Rewards serves as a strategic leader responsible for the strategy, design, and development of total rewards. This includes leading the annual compensation review, managing effective base pay, developing variable and bonus compensation targets, health and welfare programs, a variety of rewards and recognition programs, and retirement plan for our expanding global workforce. This role will lead the total rewards strategy for Optiv by building a cohesive set of programs that align employees' needs to business strategy and enhance attraction and retention of our workforce. This role reports directly to the Senior Vice President of Human Resources (SVP, HR) and serves as a member of the Optiv HR Leadership Team (HRLT). The details below refer to compensation and benefits in multiple countries (USA, India, and Canada) with employees spread throughout.
How you'll make an impact

  • Partner with business leaders and HR leadership to develop global, strategic, total rewards strategy

  • Provide executive leadership with strategic total rewards program enhancements that will enable the attraction, development, and retention of talent

  • Design and recommend global compensation and benefits programs by assessing Optiv's future needs, reviewing competitor and general industry practices, and analyzing cost impact/effectiveness

  • Develop and coordinate communication strategies and activities designed to educate and inform Optiv about total rewards

  • Review benefit premium rate contribution, claims and utilization data on an annual basis; analyze and interpret data for trends, improvements, and efficiencies

  • Coordinate and lead the 401(k) administration and investment committee

  • Collaborate with Talent Partners, HR Business Partners and business leaders to understand their issues related to compensation and benefits. Provide counsel and build solutions appropriately (e.g. training for Managers on how to have a compensation conversation)

  • Own and evolve our Total Rewards programs and scalable strategy targeted at retaining Optiv's competitive position, engagement, and retention

  • Provide subject matter expertise and accurately interpret, counsel, communicate, and educate HR Business Partners, managers, and executives on pay decisions, policy and guideline interpretations, and job evaluations

  • Manage payroll and benefits for the India entity of 650+ employees

  • Direct the benchmarking efforts associated with the rewards mechanics and elevate our understanding of competitiveness

  • Collaborate with Finance and executive leadership to build and manage cyclical and non-cyclical compensation budgets. Ensuring we generally have what we need

  • Responsible for analysis, design, compliance, communication, implementation, administration, monitoring and reporting of health, life, disability, and other benefit programs

  • Oversee all vendors, consultants and outsourced relationships for the department

  • Provide oversight and guidance of internal procedures to ensure compliance and consistency. Ensures that all welfare and retirement plans (health, dental, vision, life, disability, FSA, 401(k), etc.) meet legal, regulatory and audit compliance (ERISA, 5500 Filings, SPD's, SBC's, COBRA, FMLA, HIPAA, ADA, ACA, GINA, etc.)

  • Evolve current salary pay band structures that integrate job bands, grade levels, and promotion guidelines into the total rewards programs

  • Lead all global compensation processes (base and variable pay, merit, promotions, bonuses) including plan design, market competitiveness, distribution and sign off

  • Focus on health and welfare plan management that includes strategic and tactical planning as well as ongoing administration of the plans and open enrollment cycles

  • Supervise renewals, census, maintenance of enrollment, application, and claims records for all benefits plans

  • Maintain expert knowledge of benefit laws/regulations, provide oversight and guidance of internal procedures to ensure compliance and consistency.

  • Partner with brokers and insurance carriers to create and implement annual wellness initiatives; analyze ROI regarding the programs

  • Propose policies and procedures to ensure that the company's total reward programs support business objectives, are fair and competitive, and are legally compliant

  • Participate in M&A due diligence; manages the M&A comp and benefit integration process including job profile integration, compensation integration, and FLSA review/determinations

  • Complies with all policies and standards

  • Perform other duties as assigned

What we're looking for

  • Bachelor's degree in Human Resources, Business, Finance or other related areas, Master's Degree preferred

  • Demonstrated experience in total rewards design and implementation

  • Demonstrated compensation experience in the following areas: executive compensation, compensation committee management, base salary, market pricing, variable pay and performance management, job evaluation, data analysis, research, and cost modeling

  • Demonstrated benefit experience including knowledge of health and welfare plans, Leaves and time off practices, and retirement plans. Global exposure preferred

  • 10+ years of relevant experience: Compensation, HR and Benefits with half of those years managing people, processes and technology

  • Understanding of HR principles, laws, and practices

  • Technical understanding of HR Systems, how they work together and the downstream impact of data quality. Workday experience preferred

  • Ability to understand, balance, and articulate both tactical and strategic planning issues

  • Strong project management skills with proven track record, including ability to manage diverse cross-functional teams and multiple projects

  • Must possess excellent written/verbal communication, presentation, and facilitation skills

  • Effectively translates quantitative and qualitative data into actionable insights, strategies and plans and can articulate data visually and in an understandable manner

  • Effective at leading, and communicating with leadership, but with a willingness to play a 'hands-on' role with key projects and workstreams

Salary Range Description

$148,100.00 - $197,300.00 Annual

The Hiring Range provided for this role is informed by (but not limited to) various factors including responsibilities of the position, work experience, education/training, internal peer equity, geography, as well as other market influences when extending an offer. The disclosed range has not been adjusted for these factors. This role may also be eligible to participate in a variable incentive-based bonus plan. Optiv offers a comprehensive compensation and benefits package, of which salary is a component.

Job Application Window

This position accepts applicants for a minimum of 4 business days after the job posting date and will remain available until an applicant has been selected for the position.


What you can expect from Optiv

  • A company committed to our inclusive value through our Employee Resource Groups
  • Work/life balance
  • Professional training resources
  • Creative problem-solving and the ability to tackle unique, complex projects
  • Volunteer Opportunities. "Optiv Chips In" encourages employees to volunteer and engage with their teams and communities.
  • The ability and technology necessary to productively work remotely/from home (where applicable)

EEO Statement

Optiv is an equal opportunity employer. All qualified applicants for employment will be considered without regard to race, color, religion, sex, gender identity or expression, sexual orientation, pregnancy, age 40 and over, marital status, genetic information, national origin, status as an individual with a disability, military or veteran status, or any other basis protected by federal, state, or local law.

Optiv respects your privacy.By providing your information through this page or applying for a job at Optiv, you acknowledge that Optiv will collect, use, and process your information, which may include personal information and sensitive personal information, in connection with Optiv's selection and recruitment activities. For additional details on how Optiv uses and protects your personal information in the application process, click here to view ourApplicant Privacy Notice. If you sign up to receive notifications of job postings, you may unsubscribe at any time.

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