Jennifer Chesery
Vail
Summary
HR professional with extensive experience in onboarding compliance and HRIS management. Demonstrated success in conducting data audits and implementing inclusive programs that enhance employee engagement. Proven ability to improve internal communications and support talent acquisition strategies across diverse organizations.
Overview
3
3
years of professional experience
Work History
Human Resource Associate
Town of Vail Human Resources Department
Vail
03.2025 - Current
- Played a key role in Workday HRIS implementation, contributing to Phase I (HCM and payroll) setup, data migration, and employee transitions, and preparing for and creating Phase II (recruiting, onboarding, journeys and help, talent and learning)including job description updates and system configuration.
- Ensured HR data integrity across 300+ employees by conducting regular data audits, generating weekly HRIS reports, and performing detailed benefit reconciliation audits.
- Supported data-driven decision making by generating weekly HRIS reports, conducting regular data audits, and performing benefit enrollment reconciliations, ensuring accuracy and identifying trends to improve operational efficiency.
- Revamped the onboarding system to be more inclusive, welcoming, and educational; designed and delivered comprehensive orientations, custom welcome packets for relocating employees, benefits education, I-9/E-Verify processing, and compliance communicationsresulting in smoother integrations and broader new hire engagement.
- Developed targeted interview questions aligned with organizational core values for recruitment. for managers and directors aligned with the Town's core values; supported recruitment preparation in advance of Workday Phase II rollout.
- Coordinated offboarding processes by creating exit questionnaires and checklists and serving as the final point of contact for returning company property and documentation.
- Enhanced internal HR communications across platforms (newsletters, flyers, calendars, smart board bulletins, and HRIS updates) for 300+ employees, ensuring timely delivery of policy, labor law, and program information.
- Coordinated appreciation and engagement events (monthly breakfasts, ice cream socials, educational sessions) to improve employee recognition program, fostering morale and collaboration in a resort environment.
- Built and maintained spreadsheets for biweekly bill payments to insurance carriers and conducted weekly benefit reconciliation audits, ensuring accuracy and operational efficiency.
Human Resource Administrator
The Sonnenalp Hotel
Vail
01.2024 - 03.2025
- Led full-cycle onboarding for over 100 employees, including I-9 verification/E-Verify, ADP HRIS maintenance, orientations, pre/post communications, direct deposit and payroll data entry (hourly/salary inputs), and custom welcome packets for those relocating.
- Supported recruitment processes by posting jobs, updating job descriptions to emphasize accommodations and best practices, screening applications, scheduling interviews, and communicating with candidates to facilitate hiring.
- Developed and communicated HR policies, procedures, and compliance guidelines across channels to ensure consistent application of employment laws and best practices.
- Interpreted and communicated HR policies and procedures to employees, while maintaining up-to-date documentation on bulletin boards, HRIS, newsletters, and compliance updates.
- Upheld HR data governance standards in ADP through consistent auditing, accurate data entry, reporting, and system maintenance, ensuring payroll and benefits data integrity.
- Supported offboarding processes by developing exit questionnaires, creating standardized checklists, and serving as the final point of contact for returning company property and documentation, facilitating smooth transitions and gathering valuable employee feedback.
- Planned and executed employee appreciation programs and educational sessions to enhance morale and foster professional growth among staff.
- Directed internal communications strategy: revised bulletin boards, social media, flyers, HRIS homepage, monthly newsletters/calendars, and compliance updates on benefits, labor laws, policies, and events.
Resort Executive Assistant & HR & Administrative Support
Marriotts StreamSide
Vail
06.2023 - 01.2024
- Facilitated recruitment through on-site job fairs, payroll support, local wage/housing research, and event coordination in a competitive resort market to attract top talent.
- Managed orientations, I-9 documentation, policy updates, benefits education, monthly check-ins, celebrations, newsletters, and activities to enhance onboarding and associate engagement, improving employee experience and retention.
- Provided high-level administrative support to the General Manager and Association Governance Manager, including agenda preparation, sensitive communications, and record-keeping.
- Coordinated travel arrangements, on-property stays, daily itineraries, meal planning, and accommodations for board members to ensure seamless and productive visits.
- Served as Recording Secretary for four Board Associations, accurately capturing and maintaining detailed meeting minutes to ensure compliance, transparency, and follow-through on decisions.
Education
Bachelor of Arts - English Education
Montana State University
Bozeman, MTSkills
- HRIS systems (Workday, ADP)
- Onboarding management
- Inclusive program design
- New hire engagement
- Recruitment support
- Job description development
- Interview design
- Talent acquisition strategies
- Compliance management
- Employee relations
- Internal communications
- Benefits coordination
- Employee recognition
English Language Arts, Elementary and Foundations Teacher
- 2002 2023
- Built strong relationships with diverse stakeholders (students, parents, staff) to address challenges, deliver training/education, and foster positive environmentstransferable to employee relations, performance support, and training coordination.
- Designed and implemented programs, incentives, and creative solutions to improve engagement and outcomes, demonstrating project management, communication, and adaptability.
Timeline
Human Resource Associate
Town of Vail Human Resources Department
03.2025 - Current
Human Resource Administrator
The Sonnenalp Hotel
01.2024 - 03.2025
Resort Executive Assistant & HR & Administrative Support
Marriotts StreamSide
06.2023 - 01.2024
Bachelor of Arts - English Education
Montana State University