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Chief Operating Officer

Chief Operating Officer

Hillside Title and EscrowNaperville, IL, US
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Overview

Are you a proven executive leader in the title insurance industry, ready to take on a high-impact role shaping the future of a trusted Chicagoland agency? We’re seeking an experienced Chief Operating Officer (COO) to oversee operations, drive growth, and strengthen client and partner relationships for a well-established title agency in the western suburbs of Chicago. As COO, you will serve as a strategic partner to ownership, providing visionary leadership and operational expertise across all facets of the business—including title production, escrow, compliance, and client services. This role is ideal for a results-driven leader who thrives in a fast-paced environment, is passionate about operational excellence, and has the ability to scale a respected title agency to new heights.

Compensation & Benefits

Base Salary : $150,000 – $180,000

  • Performance-based incentives
  • Comprehensive benefits package
  • 401(k)

Responsibilities

  • Provide executive oversight of day-to-day operations to ensure efficiency, accuracy, and compliance with Illinois and federal regulations.
  • Lead, mentor, and develop a high-performing management team across title production, escrow, and operations.
  • Drive organizational growth by identifying new business opportunities, improving operational processes, and implementing innovative technology solutions.
  • Partner with ownership on strategic planning, financial management, and long-term business goals.
  • Oversee financial performance, including budget development, forecasting, and profitability.
  • Build and maintain strong partnerships with real estate agents, lenders, attorneys, and other industry stakeholders.
  • Ensure compliance with ALTA best practices and escrow / trust account requirements.
  • Anticipate industry trends, regulatory changes, and market opportunities to position the agency for continued success.
  • Qualifications

  • Bachelor’s degree in business administration or related field (preferred).
  • 7+ years of senior management or executive-level experience in the title insurance industry.
  • Deep expertise in Illinois title laws, compliance, escrow / trust accounting, and industry standards.
  • Demonstrated success in scaling operations and driving profitability in the title industry.
  • Strong strategic thinking, leadership, and team development skills.
  • Excellent communication, negotiation, and relationship-building abilities.
  • Proficiency with title production / closing software and related real estate technology.
  • Compensation

    $130,000 - $150,000 per year

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