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HR Total Rewards Specialist

TradewindMiddlebury, Connecticut, United StatesOnsite
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Tradewind Aviation is a leading Part 135 commuter and on-demand private charter operator with operational bases at the Waterbury/Oxford, CT (OXC), Westchester, NY (HPN), Stuart, FL (SUA) and San Juan, PR (SJU) airports. Founded by aviation enthusiasts in 2001 on the premise that all flights deserve the highest quality aircraft, crew, and service, Tradewind provides personal air travel—both private and scheduled service—throughout North America and the Caribbean.For more details visit www.flytradewind.com

ABOUT THE CANDIDATE / ROLE- 


This is an on-site position in Middlebury, CT. 


Tradewind is looking for a full-time, HR Total Rewards Specialist. This position plays a pivotal role in supporting payroll, benefits, and HR systems management. Our fast-paced environment requires an adaptable and skilled team member who enjoys using their math and Excel skills, has excellent attention to detail and proven, problem-solving abilities. The ideal candidate has experience with navigating complex systems, multi-state regulations, and evolving business needs. 

ESSENTIAL FUNCTIONS


  • Ensure accuracy in payroll processing, timesheet data analysis, and reporting, addressing discrepancies promptly.
  • Extract, clean, and analyze payroll and HR data using advanced excel functions (e.g., formulas, pivot tables).
  • Support benefits processes, including open enrollment, 401(k) contributions, invoice reconciliation, and employee deductions.
  • Create and run payroll-related reports and ad-hoc requests for data analysis.
  • Track and maintain benefits data and processes within HR operations, such as recruiting, onboarding, and special projects to ensure compliance and accuracy.
  • Work with HRIS (Paylocity) to generate reports, input data, and troubleshoot system issues.
  • Respond to internal HR-related inquiries via email, teams, and other communication channels.
  • Respond to external requests from state, federal or other sources (e.g., unemployment claims responses, annual surveys)
  • Assist in system training for team members and explore opportunities for process improvement.
  • Collaborate with cross-functional teams to understand data relationships and ensure alignment across departments.
  • Identify inefficiencies and recommend system or workflow enhancements.
  • Other duties as assigned.

Requirements

QUALIFICATIONS


  • Bachelor’s degree in human resources, business administration, or related field (preferred).

EXPERIENCE:


  • 3–5 years of HR experience, from a similarly-sized organization.
  • Exposure to payroll, benefits, and HR operations in a multi-state environment.

TECHNICAL SKILLS:


  • Strong proficiency in excel (e.g., data analysis, formulas, pivot tables, reports, HRIS).
  • Experience with various HRIS systems, especially Paylocity (preferred) or similar platforms.
  • Basic understanding of data relationships and reporting requirements.
  • Strong analytical and problem-solving skills.
  • Attention to detail with the ability to manage complex workflows.
  • 3-5 of experience working within an HRIS platform & processing payroll. 
  • Ability to work effectively in a fast-paced environment & meet deadlines.
  • Must maintain a high level of confidentiality.
  • Strong attention to organization, process documentation, written and verbal communication skills.

PHYSICAL REQUIREMENTS


  • Prolonged periods of sitting at a desk and working on a computer
  • Must be able to lift 15 lbs. at times.

BENEFITS


  • Competitive salary
  • Medical, Dental, Vision, FSA/DCA and 401(k) plan.
  • Paid Parental Leave
  • Fun, dynamic team with opportunities for rapid advancement
  • Travel benefits on various US and International airlines


Life at Tradewind

Thrive Here & What We Value1. Fun, dynamic team with opportunities for rapid advancement | 2. Competitive salary | 3. Medical, Dental, Vision, FSA/DCA, and 401(k) plan | 4. Paid vacation and sick days | 5. Paid Parental Leave | 6. Travel benefits on various US and International airlines</s> | Fun, dynamic team with opportunities for growth | Total Client Service Focus | Anticipating Client Needs and Exceeding Expectations | Safety Hazard Identification and Reporting | Professionalism in Handling Stressful Situations | Competitive Salary and Benefits Package | Paid Vacation, Sick Days, and Parental Leave | Medical, Dental, Vision, FSA/DCA and 401(k) plan. | Travel benefits on various US and International airlines. | Competitive Salary established pay scale including yearly increases and bonuses | Volunteer Pay: SIC - $450 per day | Per Diem: $3.21 Domestic and International per duty hour | Overnight Pay: $20 Domestic, $35 International | Flight Duty Pay: All legs flown over leg 6 is an additional $125 per leg | Team Member Benefits: United Healthcare Three-tier Medical PPO, Prescription, Vision, Dental (after 30 days) | Available Flexible Spending Healthcare Account – Medical and Dependent Care | Global Emergency Services | ZED fair travel is available on Delta, JetBlue, United, Spirit, and several other major & regional airlines (after 6 months) | Discounts on hotels, rental cars, wireless, shipping, and more | Position-Specific Benefits: Company paid uniforms | Paid housing when relocated away from the base | Cockpit Access Security System (CASS) | Known Crewmember (KCM) - available for purchase by team member | Pilots keep all hotel and frequent flyer points | Must be at least 18 years of age | Must be legally authorized to work in the United States. | International Candidates: Able to work and travel within and outside the United States and assigned territories freely. Hold a non-conditio nal, non-expired green card and legally authorized to work in the United States. Hold a valid unrestricted foreign passport with appropriate visas.</s> | Paid Parental Leave</s> | Medical dental, vision, FSA/DCA and 401(k) plan | Paid Maternity/Paternity Leave | 2. Committed to Learning and Growing with the IT Organization, Focused on Continuous Improvement | 3. Competitive Salary | Fun and dynamic team with opportunities for rapid advancement
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