Director Operational Risk Jobs in Chicago, IL (NOW HIRING)

Director, Risk Management | Corporate

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.

Salary Range: $150000 per year - $170000 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:

As a Director of Risk Management, this role leads the Company’s enterprise risk and insurance programs and serves as the primary point of accountability for how risk is identified, managed, and transferred across the organization. 

This role is responsible for overseeing all risk management programs and initiatives, managing and negotiating the Company’s insurance programs (excluding employee benefits), and serving as the primary face of TPS in the insurance marketplace. The Director of Risk Management will work closely with Finance, Operations, Safety, Legal, and external advisors to ensure risk is managed thoughtfully, proactively, and cost-effectively. The Director of Risk Management will report to the Chief Financial Officer. 

The role is designed for a seasoned risk professional who combines strong technical risk and insurance knowledge with sound judgment, practical leadership skills, and a collaborative mindset. While the role requires strategic thinking, it is also hands‑on and execution oriented, particularly as the Company continues to mature and formalize its risk management processes. 

Key Responsibilities:

Enterprise Risk Management & Governance 

• 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. 

Insurance Program Management 

• 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 

Process Improvement & Market Engagement 

• 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. 

Knowledge, Skills & Experience Required:

• Bachelor’s Degree required, preferably in Finance, Business Administration, Economics, or Risk Management  
• Professional certifications preferred (e.g., ARM, CPCU, CRM).  
• 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. 
• 15-20% travel may be required 

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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.