Manager, Legal Operations | Full-Time

With more than 25 years in business, The Parking Spot has grown into the largest near-airport parking company in the United States with over 2,000 valued team members spread across 70 locations nationwide. We are proud to offer an Employee Ownership Program, allowing every team member the opportunity to receive a direct financial stake in The Parking Spot’s success. As employee owners, every one of us plays a part in providing exceptional service to our guests across the country.

What makes working at The Parking Spot so special? We’ve built a culture of support, fun, and camaraderie that empowers us to be the most innovative company in the parking industry. As a nationwide business with a small business feel, there are endless opportunities within The Parking Spot to grow your career. Come join us and see how we leverage people and technology to deliver a superior product, outshine our competition, and find creative and innovative solutions to everyday problems.

Salary Range: $100000 per year - $120000 per year

What we offer:

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

Position Summary:

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.

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.

Key Responsibilities:

Technology & Intake Transformation

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.

Contract Operations

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.

Legal Operations & Strategic Execution

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.

Executive Advisory & Functional Leadership

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.

Financials, Vendor Management & Knowledge Enablement

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.

Knowledge, Skills & Experience Required:

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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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.

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.

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