ZipRecruiter

Log In

2

Remote Chief Operating Officer Insurance Jobs in Chicago, IL

WEBIT Services

Virtual CISO (vCISO)

Naperville, IL · On-site +1

$100K - $130K/yr

Immediately escalate breaches, regulatory exposure, or media -sensitive incidents to the COO ... Benefits Company Paid Day-1 Health Insurance for employee Company Paid AD&D Insurance Company Paid ...

ServiceNow

Senior Enterprise Account Executive

Chicago, IL · On-site +1

$130K - $215K/yr

Develop relationships with multiple C-suite personas (e.g., CFO, CIO, COO, CDO) across all product ... Work personas (flexible, remote, or required in office) are categories that are assigned to ...

ServiceNow

Senior Enterprise Account Executive

Chicago, IL · On-site +1

$130K - $215K/yr

Develop relationships with multiple C-suite personas (e.g., CFO, CIO, COO, CDO) across all product ... Work personas (flexible, remote, or required in office) are categories that are assigned to ...

Crescendo

Senior Content Marketing Manager

Chicago, IL · On-site +1

Remote About Us Crescendo is the only AI-Native Customer Experience solution designed to run AI and ... You write the content that makes a COO at an insurance company feel like we built this for them.

previous pagenext page

Showing results 21-40

All JobsChief Operating Officer Insurance JobsRemote Chief Operating Officer Insurance JobsRemote Chief Operating Officer Insurance Jobs in Chicago, IL

Remote Chief Operating Officer Insurance information

See Chicago, IL salary details

$42.8K

$155.8K

$277.6K

How much do remote chief operating officer insurance jobs pay per year?

As of Aug 6, 2026, the average yearly pay for remote chief operating officer insurance in Chicago, IL is $155,761.00, according to ZipRecruiter salary data. Most workers in this role earn between $114,900.00 and $190,600.00 per year, depending on experience, location, and employer.

What is the difference between Remote Chief Operating Officer Insurance vs Remote Insurance Underwriter?

AspectRemote Chief Operating Officer InsuranceRemote Insurance Underwriter
Required CredentialsLeadership experience, industry knowledge, often MBA or similarLicenses, underwriting certifications, industry knowledge
Work EnvironmentExecutive leadership, strategic planning, cross-departmental oversightAnalyzing applications, assessing risk, decision-making within underwriting guidelines
Employer & Industry UsageInsurance companies, large brokerages, industry leadership rolesInsurance carriers, underwriting firms, risk assessment departments

The Remote Chief Operating Officer Insurance focuses on strategic leadership and overall operations management within insurance organizations, requiring executive experience. In contrast, the Remote Insurance Underwriter specializes in evaluating insurance applications and assessing risks, typically requiring underwriting-specific certifications. Both roles are vital in the insurance industry but differ significantly in responsibilities and required credentials.

Can a remote chief operating officer insurance work remotely?

A remote Chief Operating Officer (COO) in the insurance industry can work remotely, especially with the increasing adoption of digital communication tools and cloud-based management systems. Success in such roles often depends on strong leadership skills, industry knowledge, and the ability to coordinate teams virtually, with many companies offering flexible or fully remote arrangements.
What are the most commonly searched types of Chief Operating Officer Insurance jobs in Chicago, IL? The most popular types of Chief Operating Officer Insurance jobs in Chicago, IL are:
What are popular job titles related to Remote Chief Operating Officer Insurance jobs in Chicago, IL? For Remote Chief Operating Officer Insurance jobs in Chicago, IL, the most frequently searched job titles are:
What job categories do people searching Remote Chief Operating Officer Insurance jobs in Chicago, IL look for? The top searched job categories for Remote Chief Operating Officer Insurance jobs in Chicago, IL are:
What cities near Chicago, IL are hiring for Remote Chief Operating Officer Insurance jobs? Cities near Chicago, IL with the most Remote Chief Operating Officer Insurance job openings:
Remote Chief Operating Officer Insurance jobs near you

Virtual CISO (vCISO)

WEBIT Services

Naperville, IL • On-site, Remote

$100K - $130K/yr

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Posted 4 days ago

Job description

WEBIT SERVICES is a Managed Services Provider in Naperville, Illinois, servicing customers in the Western Suburbs of Chicago. WEBIT Services is looking for an experienced vCISO to join our team.
Are you a security leader who's just as comfortable in the boardroom as you are in risk management? WEBIT is looking for Virtual CISO to serve as a trusted, named security advisor for our managed security clients. A person who can translate technical risk into business strategy and help executives make confident, informed decisions about security posture.
This is a strategic, client facing leadership role. You won't be doing hands-on remediation (that is what our service desk is for) --- instead, you will own the big picture: security, planning, compliance posture, executive relationships, and driving real business value through structured, evidence-based assessments.
What You'll Do
Client Security Advisory
  • Serve as the named vCISO and trusted security leader for your assigned clients.
  • Own and maintain a comprehensive Security Roadmap, updated quarterly based upon assessment findings
  • Build and lead executive relationships, including quarterly briefings with C-suite and board members as appropriate
  • Partner closely with the vCIO team, providing quarterly reporting for each client.

Driving Growth Through Control Map Assessments
  • Conduct quarterly Control Map gap assessments using the NIST CSF 2.0 framework
  • Identify Net Revenue Retention (NRR) opportunities and articulate them in clear business language
  • Convert identified gaps into ScalePad Lifecycle Manager initiatives
  • Keep the vCIO team in the loop on client changes tied to NRR projects

Security Posture Oversight
  • Own patching compliance KPI's (95%+ within 14 days for OS, 90%+ within 7 days for third party, 100% of critical patches within 72 hours)
  • Monitor vulnerability remediation SLA adherence (95%= target)
  • Ensure full tool coverage across managed assets: Huntress, Threatlocker, ConnectSecure, and Datto RMM

Client Reporting
  • Deliver monthly security posture reports in plain business language--no raw scanner output
  • Lead quarterly Security Roadmap briefings with executive stakeholders
  • Provide a weekly internal posture summary to WEBIT leadership

Documentation
  • Keep thorough records of interactions, decisions, and action items in Autotask
  • Document NRR opportunities with clear business justification
  • Track risk acceptance decisions and their compensating controls

Escalation & Incident Response
  • Acknowledge security incidents within 1 hour
  • Coordinate response efforts with the service desk, keeping communication clear
  • Immediately escalate breaches, regulatory exposure, or media -sensitive incidents to the COO

Requirements
  • 5+ years of experience in a security advisory, CISO, or vCISO role - ideally within an MSP or managed security services environment
  • A relevant security certification (CISSP, CISM, or equivalent)
  • Proven ability to translate technical risk into business language for executives and board-level audiences
  • A track record of identifying and closing revenue opportunities through consultative client facing work
  • Working knowledge of the NIST CSF 2.0 framework or comparable compliance framework
  • Strong documentation habits and follow through

Nice to Have
  • Experience with Control Map or similar gap assessment methodologies
  • Familiarity with Autotask, ScalePad Lifecycle Manager or similar PSA/ITSM tools
  • Hands on exposure to Huntress, Threatlocker. Connect Secure, or Datto RMM
  • Experience leading incident response tabletops or post incident reviews
  • Background across multiple compliance frameworks (SOC 2, HIPPA, PCI-DSS, ISO 27001)

What Makes You Great at This
  • Strong executive presence
  • A consultative, relationship first approach to selling
  • Methodical, process driven mindset
  • Calm, sound judgement when incidents escalate
  • High accountability and documentation discipline
  • The ability to balance strategic advisory work with revenue goals

Why This Role Matters
As vCISO you'll close the gap between security risk and real business decisions for WEBIT's managed clients. You'll keep the security posture viable, actionable and understandable -- giving them a trusted named leader they can count on. It's a role where strategic thinking and genuine client relationships go hand in hand.
Benefits
Company Paid Day-1 Health Insurance for employee
Company Paid AD&D Insurance
Company Paid LTD& STD Insurance
Unlimited PTO after 90 days of employment
Employee Assistance Program
Dental Insurance
Vision Insurance
401k Plan
Life Insurance
Additional Information
Position is Full time salaried
Salary range $100,000 - $130,000/yr
Employee Ownership Eligible after 1 year of service

Apply