Manager, Legal Operations

The Parking Spot • Chicago, IL

15d • $100,000 - $120,000 • Hybrid

About The Position

The Parking Spot is hiring its first Legal Operations Manager to design, build, implement, and manage the operational infrastructure of its in-house legal department. The department provides legal, regulatory, government affairs, compliance, document management, transactional, and real estate expertise across the company. This high-impact, high-visibility role works directly with the Chief Legal Officer to modernize legal operations, including intake and staffing, contract lifecycle management, financial oversight, and performance measurement.

The Legal Operations Manager is the department’s operational leader, driving process optimization, legal technology solutions, and contract administration while supporting outside counsel management, budget oversight, litigation support, and compliance programs. The role inherits a partially built foundation and is expected to build, modernize, implement, and own the department’s operating processes and systems.

The position is full-time and offers a hybrid work experience in downtown Chicago. The stated salary range is $100,000–$120,000 per year.

Requirements

• Bachelor’s degree required.
• At least 5 years of experience in legal operations, with demonstrated ownership of programs rather than participation alone.
• Experience supporting an in-house legal department.
• Experience building processes and standard operating procedures from scratch.
• Hands-on experience implementing and managing an intake system, matter management system, and CLM platform.
• Experience managing legal department budgets and outside counsel billing.
• A proven track record of building metrics programs and using data to drive decisions.
• A track record of successful change management and the ability to champion technology adoption across a department.
• Strong project management discipline and ability to hold multiple workstreams, timelines, and stakeholders accountable simultaneously.
• Ability to communicate effectively with lawyers, IT teams, and business leaders.
• Demonstrated ability to be a collaborative partner who can understand both broad objectives and operational details.

Nice To Haves

• Paralegal Certificate or JD.
• Experience with Onspring.

Responsibilities

• Lead implementation, optimization, and administration of legal and compliance technology, including intake, matter management, contract lifecycle management, legal AI, entity management, document management, and compliance systems.
• Build a scalable, automated intake system for incoming legal work, including research into emerging legal technology and AI-enabled solutions for automation, routing, filing, playbook implementation, drafting where appropriate, and closure.
• Improve visibility into legal work supply and demand, identify skillset bottlenecks, and move staffing tracking toward a data-driven model.
• Lead implementation of the legal team’s Onspring CLM platform, evaluate its capabilities, map workflows with IT and business stakeholders, and drive adoption.
• Support contract lifecycle processes, including intake, tracking, execution, storage, obligations management, and reporting.
• Develop tools and processes to improve visibility into contract status, obligations, renewal timelines, and risk areas.
• Develop and refine standard operating procedures, templates, playbooks, and workflow documentation, incorporating ongoing updates and lessons learned.
• Establish centralized repositories and knowledge management resources for legal information and institutional knowledge.
• Identify and implement process improvements that enhance efficiency, reduce risk, and improve stakeholder experience.
• Manage departmental projects and cross-functional initiatives, ensuring timely execution and stakeholder alignment.
• Advise the Chief Legal Officer on operational risks and direct leadership attention to friction points before they escalate.
• Oversee the department’s strategic initiative portfolio, represent the legal function in cross-company workstreams, and navigate matrixed teams.
• Track, forecast, and report the legal department’s budget and identify opportunities to improve cost efficiency while maintaining high-quality legal support.
• Oversee outside counsel engagement, billing guidelines, spend management, and performance evaluations, working toward an automated e-billing model.
• Develop deal summaries and standard negotiation guides for contract staff, expanding coverage to complex agreements such as PPAs, PSAs, and key commercial contracts to enable business self-service.
• Support litigation and compliance program operations.

Benefits

• Participation in and financial benefit from the shared employee ownership program.
• Hybrid work experience in downtown Chicago.
• Career development and growth opportunities.
• Exposure to all areas of the business.
• Medical, vision, and dental benefits.
• 401(k) plan.
• Annual discretionary bonus program.
• Team-oriented, fun, and friendly work environment.
• Immediate opportunity to make a large impact.

What This Job Offers

• Job Type: Full-time
• Career Level: Manager