Head of Risk Management & Insurance

ATTENTION MILITARY AFFILIATED JOB SEEKERS - Our organization works with partner companies to source qualified talent for their open roles. The following position is available to Veterans , Transitioning Military, National Guard and Reserve Members, Military Spouses, Wounded Warriors, and their Caregivers . Unless specifically stated otherwise, this role is "On-Site"
Director, Risk Management
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 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.
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
Immediate opportunity to make a large impact
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.

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.
Bachelor's Degree required, preferably in Finance, Business Administration, Economics, or Risk Management

~ 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
• 15-20% travel may be required

______
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.

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.