Manager, Legal Operations

What we offer

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• Participation in and financial benefit from our shared employee ownership program
• Hybrid work experience in downtown Chicago
• Career development and growth opportunities
• Ability to gain exposure to all areas of the business
• Great benefits including Medical, Vision, Dental and a 401k plan
• Annual discretionary bonus program
• Team oriented, fun and friendly work environment
• Immediate opportunity to make a large impact

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Position summary

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The Parking Spot is now hiring its first Legal Operations Manager to design, build, implement and manage the operational infrastructure of our in-house legal department. The department delivers legal, regulatory, government affairs, compliance, document management, transactional and real estate expertise across the company. This is a high-impact, high-visibility role working directly with the Chief Legal Officer to modernize how legal work gets done — from intake and staffing through contract lifecycle management, financial oversight, and performance measurement.

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This individual will serve as the operational leader for the department, driving process optimization, legal technology solutions, and contract administration, while assisting in outside counsel management, budget oversight, litigation support and compliance program support. This is not a maintenance role. The person we're looking for will inherit a partially built foundation and be expected to build, modernize, implement and own it.

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Key responsibilities

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Technology & intake transformation

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• Legal Technology: Lead the implementation, optimization, and administration of legal and compliance technology solutions, including intake system, matter management, contract lifecycle management (CLM), legal AI solutions, entity management, document management, and compliance systems.
• Intake Optimization: Build a scalable, automated system for incoming legal work. Research emerging legal technology and AI-enabled solutions to automate intake, routing, filing, playbook implementation, drafting when appropriate and closure. Drive visibility into supply vs. demand, identify skillset bottlenecks, and transition the department from manual staffing tracking to a data-driven model.
• Contract Lifecycle Management (CLM): Lead the implementation of the legal team’s CLM platform (Onspring). Evaluate platform capabilities, map cross-functional workflows with IT and business stakeholders and drive end-to-end implementation through to full adoption.

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Contract operations

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• Contract Lifecycle Administration: Support contract lifecycle management processes, including intake, tracking, execution, storage, obligations management, and reporting.
• Contract Visibility & Risk Tracking: Develop tools and processes that improve visibility into contract status, key obligations, renewal timelines, and risk areas.

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Legal operations & strategic execution

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• Standard Work & Lessons Learned: Develop and refine standard operating procedures, templates, playbooks, and workflow documentation to support consistency and scalability, embedding continuous refreshes and lessons learned into daily team operations.
• Knowledge Management: Establish centralized repositories and knowledge management resources that improve access to legal information and institutional knowledge.
• Strategic Execution: Identify and implement process improvements that enhance efficiency, reduce risk, and improve stakeholder experience.
• Legal Operations: Manage departmental projects and cross-functional initiatives, ensuring timely execution and stakeholder alignment.

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Executive advisory & functional leadership

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• Strategic Partner to the CLO: Act as a key operational advisor, identifying risks early and directing leadership attention toward friction points before they escalate into larger operational issues.
• Portfolio & Initiative Management: Oversee the department’s portfolio of strategic initiatives, representing the legal function in cross-company workouts and navigating matrixed teams effectively.

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Financials, vendor management & knowledge enablement

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• Budget & Resource Allocation: Own tracking, forecasting, and reporting for the legal department’s budget. Identify opportunities to improve cost efficiency while maintaining high-quality legal support.
• Outside Counsel Management: Oversee outside counsel engagement, billing guidelines, spend management, and performance evaluations, working toward an automated e-billing model.
• Knowledge Management & Negotiation Playbooks: Accelerate the creation of deal summaries and standard negotiation guides for contract staff—expanding coverage to complex agreements (e.g., PPAs, PSAs, and key commercial contracts) to enable business self-service.

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Knowledge, skills & experience required

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• Bachelor's degree required
• Paralegal Certificate or JD a plus, but not required
• 5+ years in legal operations, with demonstrated ownership of programs rather than participation in them
• Experience supporting an in-house legal department
• Experience building processes and standard operating procedures from scratch
• Hands-on experience implementing and managing an intake, matter management system and CLM platform; experience with Onspring specifically is a plus
• Experience managing legal department budgets and outside counsel billing
• Proven track record of building metrics programs and using data to drive decisions
• Track record of successful change management – able to champion technology adoption across the department
• Strong project management discipline — able to hold multiple workstreams, timelines, and stakeholders accountable simultaneously
• Communication style that works with lawyers, IT teams, and business leaders equally well
• Demonstrated ability as a collaborative partner that can see both the forest and the trees
• Someone who sees broken workflows as puzzles to solve, not problems to avoid

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Compensation details

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Any disclosed pay range is based on a consideration of neutral factors and criteria such as required qualifications, experience, education, skill, training, certifications, seniority, etc. The Parking Spot reserves the right to offer the selected candidate or applicant a salary at an appropriate level to be set and determined by the employer that is commensurate with the applicant’s qualifications, experience, education, skill, training, certifications, or seniority.

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Equal opportunity statement

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At The Parking Spot, we don’t just accept difference - we celebrate and seek it. We believe a diverse, inclusive, and equitable company is one where all employees, partners, and customers are welcome, supported, and valued. As a company in the travel industry, we witness the power of bringing individuals from different backgrounds and communities together. We treat all others with dignity and respect and stand firmly against racism and discrimination in any form. We intentionally develop diverse teams and relationships to ensure all voices are heard and to foster equal opportunity for all. We are committed to listening, learning, and growing because we know that our work is never done.