Director, Risk Management

The Parking Spot • Chicago, IL

1d • Hybrid

About The Position

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 across over 40 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.

Requirements

• Bachelor’s Degree required, preferably in Finance, Business Administration, Economics, or Risk Management
• 8+ years of relevant experience in a corporate risk environment overseeing enterprise insurance programs and working directly with brokers, carriers, TPAs, and outside counsel
• Demonstrated ability to operate across functions, influence without direct authority, and balance strategic thinking with practical execution.

Nice To Haves

• Professional certifications preferred (e.g., ARM, CPCU, CRM).

Responsibilities

• Oversee the Company’s enterprise risk management activities, including identification, prioritization, monitoring, and mitigation of key operational, safety, insurance, regulatory, and reputational risks.
• Serve as a core contributor to the Company’s Risk Management Committee, providing data driven insights, risk trend analysis, and escalation of material issues.
• Develop and maintain risk reporting, dashboards, and key risk indicators to support senior management and Board‑level oversight.
• Help embed risk awareness and accountability into day-to-day decision‑making across the organization.
• Own the design, placement, and ongoing management of the Company’s insurance programs across all lines of coverage.
• Work closely with the Safety team and Operations leadership to support the development and execution of a strong, data driven safety program.
• Analyze incident and near miss data to identify trends and systemic risks.
• Partner with Operations and Safety on training initiatives, operational controls, and tools designed to reduce risk companywide.
• Serve as a key point of coordination following significant incidents, even where direct management responsibility resides elsewhere.
• Partner with the Legal and Compliance team on claims and litigation strategies.
• Continue to mature and formalize risk management processes, governance, and documentation, building structure where needed.
• Evaluate and leverage risk management and claims systems and tools (system‑agnostic) to improve visibility, analytics, and decision-making.
• Actively represent TPS in the insurance market, reinforcing the Company’s commitment to disciplined risk management, safety, and continuous improvement.

Benefits

• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Number of Employees: 251-500 employees