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Remote Director Insurance & Risk Management Jobs in Chicago, IL

CIBC

Director, US IT Asset Management

Chicago, IL · On-site +1

$165K - $240K/yr

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

... risk and control oversight, and team leadership. This role will work across regional and enterprise ... Details on your work arrangement (proportion of on-site and remote work) will be discussed at the ...

CIBC US

Director, US IT Asset Management

Chicago, IL · On-site +1

$165K - $240K/yr

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

... risk and control oversight, and team leadership. This role will work across regional and enterprise ... Details on your work arrangement (proportion of on-site and remote work) will be discussed at the ...

Kone AB

Director, MP Delivery Operations

Lisle, IL · Remote

$201K - $264K/yr

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

Do you enjoy providing strategic oversight, risk management, and escalation support? * Does ... This is a remote position. Job Duties As our Director, MP Delivery Operations, you willbe ...

KONE

Director, MP Delivery Operations

Lisle, IL · Remote

$283K/yr

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

Do you enjoy providing strategic oversight, risk management, and escalation support? * Does ... This is a remote position. Job Duties As our Director, MP Delivery Operations, you will be ...

CNA

Risk Control Consultant, Virtual Center

Chicago, IL · On-site +1

$72K - $141K/yr

Under general management direction, works within broad limits of authority requiring a high degree ... insurance and risk control principles, practices and procedures including remote assessment ...

Stanley Consultants

Program Management Director

Chicago, IL · On-site +1

$207K - $284K/yr

Expertise in program governance, program controls, risk management, scheduling, and organizational ... Health Insurance. We provide a comprehensive insurance package including medical, dental, vision ...

Stanley Consultants

Program Management Director

Chicago, IL · On-site +1

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

... Remote, US | Salt Lake City, UT | West Palm Beach, FL Job type - Hybrid Requisition ID - 11281 ... Expertise in program governance, program controls, risk management, scheduling, and organizational ...

HUB

Management Liability Specialist

Chicago, IL · On-site +1

$60K - $100K/yr

  • Dental

  • Vision

  • Life

  • Retirement

... Directors, Officers, and Corporate Liability (D&O), Employment Practices Liability Insurance (EPLI ... This position has both hybrid and remote work options Salary: Disclosure required under applicable ...

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All JobsInsurance & Risk Management JobsRemote Director Insurance & Risk Management JobsRemote Director Insurance & Risk Management Jobs in Chicago, IL

Remote Director Insurance Risk Management information

See Chicago, IL salary details

$55.6K

$147.5K

$267.8K

How much do remote director insurance & risk management jobs pay per year?

As of Aug 15, 2026, the average yearly pay for remote director insurance & risk management in Chicago, IL is $147,501.00, according to ZipRecruiter salary data. Most workers in this role earn between $108,700.00 and $172,500.00 per year, depending on experience, location, and employer.

How does a remote director of insurance & risk management effectively collaborate with on-site teams and stakeholders across different locations?

As a Remote Director of Insurance & Risk Management, effective collaboration typically relies on leveraging digital communication tools such as video conferencing, project management platforms, and secure document sharing systems. Regular virtual meetings with cross-functional teams—including finance, legal, and operations—are essential for aligning on risk strategies and insurance matters. Building strong relationships and maintaining clear, consistent communication help ensure that risk management policies are understood and implemented company-wide, regardless of location. Many organizations also encourage periodic in-person meetings or retreats to strengthen team cohesion.

What does a remote director of insurance & risk management do?

A Remote Director of Insurance & Risk Management oversees an organization’s strategies to identify, assess, and mitigate risks, while ensuring appropriate insurance coverage is in place. This role involves analyzing potential threats to assets, developing risk management policies, and negotiating insurance contracts. Working remotely, they collaborate with various departments and external vendors to protect the company from financial losses due to unforeseen events. They also stay updated on industry regulations and best practices to maintain compliance and optimize coverage.

What is the difference between Remote Director Insurance & Risk Management vs Remote Insurance Underwriter?

AspectRemote Director Insurance & Risk ManagementRemote Insurance Underwriter
CredentialsTypically requires a bachelor's degree in risk management, insurance, or related field; professional certifications like CPCU or ARM are commonRequires a bachelor's degree in finance, economics, or related field; certifications like CPCU or ARe are advantageous
Work EnvironmentStrategic, leadership-focused role overseeing risk policies and teams, often in corporate offices or remotelyAnalytical role assessing insurance applications, often working remotely or in underwriting centers
Employer & Industry UsageUsed by insurance companies, corporations, and brokers for risk oversightPrimarily employed by insurance carriers and underwriting agencies to evaluate risks

While both roles involve insurance expertise and certifications like CPCU, the Remote Director Insurance & Risk Management focuses on strategic risk oversight and leadership, whereas the Remote Insurance Underwriter concentrates on evaluating individual insurance applications and assessing risk at the underwriting level.

What are the key skills and qualifications needed to thrive as a remote director of insurance & risk management?

To excel as a Remote Director of Insurance & Risk Management, you need deep expertise in risk assessment, insurance policy analysis, and regulatory compliance, often supported by a bachelor’s or master’s degree in finance, business, or a related field. Familiarity with risk management software, data analytics tools, and certifications like ARM (Associate in Risk Management) or CPCU (Chartered Property Casualty Underwriter) is typical. Strong leadership, strategic thinking, and effective communication are vital soft skills, especially when managing remote teams and collaborating across departments. These competencies are essential for minimizing organizational risk, ensuring compliance, and protecting company assets in a dynamic and distributed work environment.

What are popular job titles related to Remote Director Insurance & Risk Management jobs in Chicago, IL?

For Remote Director Insurance & Risk Management jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Remote Director Insurance & Risk Management jobs in Chicago, IL look for?

The top searched job categories for Remote Director Insurance & Risk Management jobs in Chicago, IL are:

Remote Director Insurance Risk Management jobs near you
Infographic showing various Remote Director Insurance & Risk Management job openings in Chicago, IL as of August 2026, with employment types broken down into 72% Full Time, and 28% Contract. Highlights an 100% Remote job distribution, with an average salary of $147,501 per year, or $70.9 per hour.

(Senior) Sales Executive - Capital & Carolinas

Origami Risk LLC

Chicago, IL • On-site, Remote

$130K - $160K/yr

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Re-posted 15 days ago

Job description

Overview
As a Sales Executive you will be responsible for helping to expand the business by identifying new prospects and selling our suite of Integrated Risk Management (IRM) solutions. In this role you will maintain relationships with current clients, build and maintain relationships with new cleints and meet or exceed annual sales quotas. This is a geography-based role, covering North Carolina, South Carolina, Virginia, Washington DC, and Tennessee.
Starting base pay for this role is between $130,000 and $160,000. The actual base pay is dependent upon many factors, such as transferable skills, work experience, business needs, training, location, and market demands. The base pay range is subject to change and may be modified in the future. This role will be eligible for a bonus as well as competitive medical, dental, and vision benefits, wellness reimbursement, life insurance, and a 401(k) with company match. We offer vacation and sick leave benefits (under a flexible time off policy in most states).
Responsibilities
  • Develops a strong pipeline of prospective clients through personal introductions, referrals, RFPs and prospecting within your territory.
  • Works with prospective clients to introduce them to the features and capabilities of Origami Risk and to learn and understand their needs and concerns.
  • Leverages industry knowledge to offer advice and perspective to prospective clients during the sales process.
  • Prepares price quotes and statements of work that reflect the needs of each prospective client and the capabilities and standards of Origami.
  • Confirms or estimates potential strong competitors on each opportunity and devise a strategy to successfully compare and contrast Origami to each of them.
  • Networks with brokers, risk managers, and other members of the risk management and insurance community to identify prospective customers and enhance awareness of Origami Risk.
  • Develops, executes, and exceeds all goals within an annual territory plan.

Qualifications
  • Bachelor's degree required
  • At least 3 years of direct sales experience with demonstrated history of success selling SaaS solutions. To be considered for Senior, at least 7 years of SaaS sales experience.
  • Experience uses a highly consultative sales process, such as MEDDPICC.
  • Consistently carried and exceeded quotas on average with the market/industry.
  • Must possess domain knowledge consistent with a subject matter expert in the industry.
  • CRM experience required; Salesforce experience preferred.
  • Travel as needed for the role.

Benefits
  • Medical and Dental coverage available for employees, dependents, domestic partners, and spouses
  • Paid Time Off - Flexible options plus 10 paid company holidays where available**
  • All full-time positions are hybrid, with many eligible to be completely remote
  • Fully Paid by Origami Risk - Vision insurance, Short & Long-Term Disability Insurance, and Basic Life Insurance
  • Generous family leave options-including adoption and foster care placements
  • Pre-Tax Savings Accounts - Flexible Spending Account, Health Savings Account, Commuter Benefits, Dependent Care Savings Account
  • Retirement Savings - 401(k) with company match up to 4%
  • Employee Assistance Program (EAP) - Confidential & Free support offered to colleagues facing personal or work-related complications
  • Education Assistance Program - to help colleagues pursue industry/role-specific certifications
  • Wellness Benefits - reimbursement program to invest in healthy habits as well as support better colleague productivity and stress management
  • Additional coverages available - Pet Insurance, Critical Illness Insurance, and Voluntary Life & AD&D coverage

**Flexible PTO not available in California or the UK
Who We Are
Origami Risk delivers single-platform SaaS solutions that help organizations best navigate the complexities of risk, insurance, compliance, and safety management.
Founded by industry veterans who recognized the need for risk management technology that was more configurable, intuitive, and scalable, Origami continues to add to its innovative product offerings for managing both insurable and uninsurable risk; facilitating compliance; improving safety; and helping insurers, MGAs, TPAs, and brokers provide enhanced services that drive results.
A singular focus on client success underlies Origami's approach to developing, implementing, and supporting our award-winning software solutions.
Origami Risk is proud to be an equal opportunity employer. We thrive and benefit from diversity and are committed to creating an inclusive and equitable environment for all employees. We do not discriminate against any individual based upon race, religion, gender (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity, gender expression, color, sex, national origin, age, marital status, military or veteran status, disability, or any other characteristic protected by applicable law.
Caution: Be alert to recruiting scams. We have received reports of individuals impersonating Origami Risk recruiters to deceive candidates into disclosing personal information. These impostors use fake Origami Risk domain names and email addresses. Please double-check that any email address from an Origami Risk recruiter ends with origamirisk.com or talent.icims.com. And to confirm the legitimacy of any recruiting communication, feel free to email transparencycheck@origamirisk.com.

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