Human Resources Benefits & Operations Manager
Chicago, IL
Human Resources – Human Resources /
Full-time /
Hybrid
About JSSI
For more than 35 years, Jet Support Services, Inc. (JSSI) has been the leading independent provider of maintenance support, advisory services, software, and financial tools to the business aviation industry. With 6,000+ aircraft supported by maintenance programs and software platforms, JSSI leverages this wealth of data, scale, and innovation to drive cost savings and provide custom solutions that align to the interests of each client, regardless of make or model. Learn more at jetsupport.com.
JSSI products and services include:
Maintenance Programs. Hourly Cost Maintenance Programs to stabilize maintenance budgets, maximize aircraft availability and enhance residual value.
Parts & Leasing. Experienced product line specialized team who leverages our All-OEM inventory and global vendor relationships and go beyond parts sourcing to find optimal customer solutions.
Software: Traxxall and Conklin & de Decker. Powerful data platforms to help you make more informed decisions, from choosing the right aircraft to tracking your maintenance, inventory, and MRO projects.
Advisory Services. Objective insights and independent technical advice from a global team of technical advisors and ASA-accredited appraisers for virtually any business jet, turboprop or helicopter.
Aviation Capital. Customized asset-based finance solutions for business aviation.
Position Summary:
The HR Benefits & Operations Manager is responsible for overseeing the planning, administration, compliance, and communication of employee benefits programs worldwide, while also ensuring smooth execution of HR operations. This role ensures that all programs align with organizational goals, enhance employee experience, and remain compliant with applicable regulations. Additionally, this role manages HR systems, process improvements, and cross-functional initiatives to support the broader Human Resources strategy. The position will be based at JSSI’s Global Headquarters in Chicago, reporting directly the Vice President for Human Resources. The position requires an on-site presence a minimum of three days a week.
Duties and Responsibilities
- Benefits Administration:
- Manage and administer all employee (self-funded) benefits programs including health, dental, vision, life insurance, disability, HSA/FSA, 401(k), and wellness initiatives.
- Serve as the primary liaison with benefits brokers, insurance carriers, and third-party administrators.
- Lead annual open enrollment, including communication strategy, system configuration, and employee support.
- Ensure benefits programs comply with all local, state, and federal regulations (e.g., ERISA, HIPAA, ACA, COBRA).
- Collaborate closely with Payroll and Accounting to ensure accurate financial information, reporting, and compliance.
- Analyze benefit plans for competitiveness, cost-effectiveness, and employee satisfaction.
- Address escalated employee benefits questions and resolve complex issues.
- HR Operations:
- Oversee HRIS system administration including data integrity, reporting, and system improvements.
- Develop and maintain HR policies and procedures (i.e. FMLA, STD, PTO) to ensure consistency and legal compliance. Collaborate with local consultants or counsel to ensure policies adhere to relevant international regulations across regions.
- Drive key HR processes such as onboarding, offboarding, employee recordkeeping, and compliance audits.
- Collaborate with Finance and Payroll to ensure accurate and timely benefits-related transactions.
- Partner with HR leadership to drive continuous improvement in operational efficiency and employee service delivery.
- Support company-wide compliance with employment laws and regulations through documentation, training, and audits.
Desired Credentials
- Bachelor’s degree in human resources, Business Administration, or related field; master’s degree or HR certification (SHRM-CP/SCP, CEBS, PHR/SPHR) preferred.
- 5–7+ years of progressive HR experience, including at least 3 years in benefits administration or HR operations.
- Strong knowledge of employee benefits and related laws/regulations.
- Proficiency in HRIS systems (e.g., Workday, ADP, Paylocity, UKG) and advanced Excel skills.
- Strong analytical, organizational, and problem-solving skills.
- Excellent interpersonal and communication skills with a customer-focused mindset.
- Ability to manage multiple priorities in a fast-paced environment with high attention to detail.
- Experience managing vendor relationships and negotiating benefit contracts.
- Experience with multi-state and global HR operations and benefits.
- Experience with M&A due diligence and post-integration benefits harmonization is a plus.
At JSSI, we are committed to rewarding our team members with competitive and comprehensive compensation packages that reflect their contributions and talent.
For this role, the annual base pay generally ranges from $110,000 to $115,000, with the final offer determined by variable factors including but not limited to market location, job-specific knowledge, skills, education, and experience. In addition, your total rewards package may include an annual discretionary bonus plan, incentive or sales bonus plan, or other form of additional compensation, based on your role.
Additionally, for full-time employees based in the USA, Canada, or the Philippines, we are proud to offer a robust suite of benefits. This ranges from insurance offerings such as medical, dental, vision, retirement savings programs, among others, starting day one of employment. For a full overview of our offerings, visit the JSSI Benefits Page on our company website.
JSSI is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, national origin, disability, protected veteran status, or other characteristic protected by law.
JSSI does not accept unsolicited resumes from individual recruiters or third-party recruiting agencies in response to job postings. No fee will be paid to third parties who submit unsolicited candidates directly to our hiring managers or Recruiting Team.
