Would you like to join an entrepreneurial HOA Management holding company that is acquiring and growing businesses for the long term?

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Are you excited by the challenge of building an outreach machine, and establishing yourself as a dealmaker with the “who's who” in a quickly evolving industry?

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Are you a sleeves-rolled, self-starter who wants the autonomy to set goals for yourself and an entire team – while pitching in wherever needed as we grow?

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What do we do?

****We acquire and operate Homeowners' Association Management companies (read: the folks who make sure your neighbors pay their HOA dues, hire the landscaper, and keep your condo building beautiful and structurally sound).

Why a “family of companies?”

We acquire small businesses, usually from their founders. They sell to us and not the big, national firms because they want to protect what makes them special: their people, culture, and deep connections to the local community. So we honor that: no layoffs, no rebranding, limited integration, and decentralized decision-making. Because we believe if you offer smart, empowered people big-company resources, they'll take advantage and grow just as fast as any top-down organization (and feel a lot more fulfilled in the process).

Job Summary

We are seeking a detail-oriented Paralegal – Operations Support to assist with legal and compliance matters related to property management. This role will support the operations team by managing contracts, regulatory filings, and compliance documentation while ensuring adherence to local, state, and federal real estate laws. The ideal candidate has experience in real estate or corporate law, strong organizational skills, and the ability to manage multiple priorities in a fast-paced environment.

Key Responsibilities

Legal & Compliance Support

• Maintain and organize legal documents, property records, contracts, and compliance files.
• Assist in drafting, reviewing, and managing lease agreements, vendor contracts, and service agreements.
• Ensure adherence to local, state, and federal real estate regulations, including Chicago-specific requirements.
• Support the preparation of compliance audits, licensing renewals, and regulatory filings.

Operational Coordination

• Serve as a point of contact for legal inquiries from vendors, property managers, and leadership.
• Assist in onboarding new properties by ensuring all legal and operational documentation is complete.
• Monitor contract deadlines, renewals, and compliance requirements for all managed properties.

Financial & Administrative Support

• Track and process invoices, vendor payments, and legal expenses.
• Support budget preparation related to legal and compliance costs.
• Collaborate with accounting and operations teams to ensure accurate financial reporting for property management activities.

Communication & Team Collaboration

• Act as a liaison between property managers, leadership, and legal counsel.
• Provide internal teams with updates on regulatory changes and compliance matters.
• Assist in the preparation of meeting agendas, minutes, and operational reports.

Qualifications

• Bachelor's degree in Paralegal Studies, Business Administration, Real Estate, or a related field preferred.
• 2+ years of experience in a paralegal, legal assistant, or compliance role (experience in property management or real estate law preferred).
• Strong knowledge of contract management, lease agreements, and real estate compliance.
• Familiarity with Chicago real estate regulations and local property laws is a plus.
• Proficiency in Microsoft Office Suite (Word, Excel, Outlook) and property management/legal software (e.g., Yardi, AppFolio, Clio, or similar).
• Excellent communication and organizational skills with attention to detail.
• Ability to work independently while collaborating with cross-functional teams.

What We Offer

• Fully remote position (applicants must live within 30 miles of Downtown Chicago).
• Competitive salary and benefits package.
• Opportunities for professional growth and development in the real estate legal field.
• A dynamic and collaborative work environment.