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Contracts and Compliance Paralegal

HAI Group
HAI Group Salary
Cheshire, CT Full Time
POSTED ON 4/5/2026
AVAILABLE BEFORE 5/3/2026
Position Overview

The Contracts and Compliance Paralegal will play a critical role in supporting enterprise-wide compliance and effective risk management. This role will support contract review and management, vendor oversight, and the assessment of cybersecurity and information security risks. The Legal & Compliance Paralegal will work to ensure that HAI Group’s policies, procedures, vendor agreements, and vendor relationships align with applicable legal, regulatory, and security requirements. They’ll also support regulatory and legal research and essential filings for HAI Group’s companies. This role will workboth independently and as a team member for projects related to filings, audits, regulatory changes, legal and state-by-state research, contract review and vendor management.

The Contracts and Compliance Paralegal is a self-motivated, proactive professional with a strong ability to drive results. They demonstrate a commitment to ethics, integrity, and confidentiality while consistently upholding organizational values. Adaptable and flexible, they thrive in dynamic environments and effectively manage shifting priorities. This individual is a quick learner who applies new information with ease, takes ownership of responsibilities through to completion, and approaches challenges with a solutions-oriented mindset.

Essential Functions

  • Support the contract review process, including drafting, reviewing, and negotiating terms, leveraging HAI Group’s contract library to identify and mitigate organizational risks associated with contractual engagements and third-party relationships.
  • Support vendor management through analysis of vendor performance, contractual obligations, cybersecurity, artificial intelligence and information security risks.
  • Manage vendor and contract administration databases and related workflow systems.
  • Participate in legal and compliance research projects to support legal and regulatory initiatives and risk mitigation.
  • Support preparation of regulatory filings for HAI Group’s companies.
  • Support process to track and review a broad range of regulatory updates, ensuring accurate and consistent application across business operations.
  • Stay current on laws and regulations through review of publications and industry literature.
  • Perform other compliance or legal tasks as directed by the Assistant Director of Legal and Compliance.

Job Requirements

  • Bachelor’s degree
  • 5 years of paralegal or other experience in a comparable position, preferably with an insurance or financial services company.
  • Experience in contract review and lifecycle management, with the ability to identify and assess legal, regulatory, information security, and operational risk.
  • Must be legally authorized to work in the United States without the need for employer sponsorship

Knowledge, Skills And Abilities

  • Demonstrated knowledge of third-party and vendor risk management, including vendor due diligence, ongoing oversight, and contract controls.
  • Knowledge of insurance compliance programs, filing obligations, and governance structures.
  • Ability to interpret and consult on laws and regulations.
  • Experience managing and coordinating timely, accurate filings and responses to insurance regulators and other regulatory bodies.
  • Strong organizational and prioritization abilities.
  • Attention to detail combined with strong time management skills.
  • Proficiency in Microsoft Office Suite, with ability to leverage tools for efficiency and accuracy.
  • Proven project management skills, ensuring timely and successful completion of initiatives.
  • Excellent written and verbal communication skills for clear and professional interactions.
  • Ability to identify external and internal factors impacting legal and regulatory requirements.
  • Analytical and solutions-driven problem solver, capable of interpreting regulatory changes and consulting on the same.

Work Environment and Physical Demands

  • Inside climate-controlled office building
  • Prolonged sitting and using a PC
  • <10% Travel
  • Ability to lift 25lbs

  • Department Overview

    Enterprise Compliance provides organization-wide support to ensure operational compliance with external legal and regulatory requirements and internal policies. Our mission is to deliver excellence through critical thinking and collaboration, helping the organization navigate complex legal and regulatory issues, mitigate risks, and maintain compliance across all business operations.

    The department is responsible for enterprise-wide vendor management, including vendor onboarding, assessment and ongoing oversight, contract review and management, and the evaluation of cybersecurity, information security, and artificial intelligence risks to support responsible and compliant third-party relationships. We manage regulatory communications and ensure timely, accurate, and compliant filings with governing authorities. Enterprise Compliance also oversees the dissemination and interpretation of new or evolving regulations to promote company-wide awareness and understanding. We foster an ethical culture and an inclusive, compliance-focused work environment by maintaining robust systems and controls that identify and prevent noncompliance.

    Company Overview

    HAI Group® [1] , is the nation’s leading property-casualty insurance company founded by and dedicated to affordable housing organizations. While we are recognized as a pioneer of affordable housing insurance programs, insurance is not our only strength. We protect, preserve, and promote the sustainability of affordable housing with an array of products and services that support the challenges housing organizations face. Besides insurance, we offer risk management services, online training, and consulting services used by more than 1,500 housing organizations nationwide. Headquartered in Cheshire, Connecticut, HAI Group® was recognized as a Top Workplace from 2020-2025.

    Cultural Objective

    HAI Group contributes to a culture that creates a safe and healthy working environment and a space of inclusiveness and belonging for all by: exceeding our customers’ expectations, working collaboratively across the organization, embracing diversity, and demonstrating mutual respect and empathy.

    HAI Group Benefits And Perks

    • Bonus program eligibility
    • Annual merit program
    • Outstanding 401(k) program and non-elective contribution
    • Flexible work schedules
    • Generous paid time off, paid volunteer days and paid holidays
    • Medical, vision and dental Insurance
    • Company paid life, AD&D, short-term disability, and long-term disability coverage
    • HSA, FSA and dependent care options
    • On-Site wellness: Full gym and locker rooms, wellness initiatives, outdoor basketball and tennis court, picnic pavilion area
    • Tuition reimbursement and loan repayment
    • Professional development
    • Community outreach

    HAI Group is an Equal Opportunity Employer.

    HARRG Inc., reserves the right to fill this position at a level above or below the level included in this posting.

    No agency submissions please. Resumes submitted to any HAI Group employee without a current, signed, and valid contract in place with the HAI Group Recruiting team for this position will become the property of HAI Group and no agency fees will be paid.

    [1] HAI Group® is a marketing name used to refer to insurers, a producer, and related service providers affiliated through a common mission, management, and governance. Property-casualty insurance and related services are written or provided by Housing Authority Risk Retention Group, Inc.; Housing Authority Property Insurance, A Mutual Company; Housing Enterprise Insurance Company, Inc.; Housing Specialty Insurance Company, Inc.; Innovative Housing Insurance Company Inc.; Housing Investment Group, Inc.; and Housing Insurance Services, Inc. (DBA Housing Insurance Agency Services, Inc. in NY and MI).

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