Jessica Chessare

HR & People Ops

Greater Chicago Area

About

Hi, I’m Jess 👋 a passionate people professional with over 7 years of experience supporting high-growth companies in building engaging, inclusive, and efficient workplaces. My HR journey has taken me through various environments, where I’ve led initiatives across the full employee lifecycle. At the heart of my work is a belief that employees thrive when systems, culture, and leadership are aligned. From launching HR tech platforms and streamlining onboarding programs to developing manager training and engagement initiatives, I love helping people love what they do! 🔹 Highlights:- Led a full digital transformation, transitioning from a PEO and modernizing all core people operations - Revamped onboarding and engagement programs, boosting satisfaction and connection- Developed and implemented org-wide performance management programs - Supported employee relations and compliance efforts across global and multi-state teams- Built and scaled people ops infrastructure in remote and hybrid environments I’m known for balancing strategic thinking with hands-on execution. Whether I’m improving HR workflows, coaching managers, or leading engagement, I show up with curiosity, collaboration, and a bias for action. 🎮 Outside of work, you’ll find me exploring the word climbing mountains, sailing, practicing yoga, hanging with my dog, discovering new music, volunteering, gaming, or learning something new.Let’s connect!

Experience

  • Caregiving at Career Break
    Jan 2025 - Present · 1 yr 7 mos

  • Human Resources Business Partner at Vail Systems
    Feb 2024 - Jan 2025 · 1 yr

    Served as a strategic advisor to business leaders to deliver effective HR solutions and support organizational goals. Partnered with Talent Management on performance management cycles, including compensation band updates, manager coaching, and calibration sessions; collaborated to develop and implement leadership development programs and employee engagement survey strategies to drive retention and high-performing teams. Built strong relationships across all organizational levels, coaching leaders on employee relations, performance management, and policy compliance to foster engaged teams and resolve complex issues. Developed and executed HR strategies based on employee feedback and team pain points, acting as the primary point of contact for employee relations and compliance; handled ad hoc duties including semi-monthly payroll and benefits administration to ensure seamless operations. Collaborated with cross-functional teams to implement an HR ticketing system (Atlassian/Jira), streamlining communication in a distributed environment, reducing response times to employee inquiries, and enhancing overall employee experience through efficient shared services support.

  • Senior People Operations Generalist at Loadsmart
    Nov 2021 - Nov 2023 · 2 yrs 1 mo

  • Human Resources Manager at Club Colors
    Feb 2019 - Nov 2021 · 2 yrs 10 mos

    As an HR department of 1 at Club Colors I oversaw and worked to develop scalable processes across all aspects of the HR & Recruiting function. I served as the strategic link between employees and their managers throughout the entire employee life-cycle. I worked closely with our top executives on strategic planning, including attending regular strategy meetings and developing strategic plan for HR department. Key highlights include > Worked with c-suite to research and select HRIS for automation and integration. Successfully transitioned the company from PEO system (trinet) to a single source HRIS/Payroll/Benefit administration system (Paycor). Full implementation and integrations within 3 months including training employees on use. > Successfully brought all recruiting internal while implementing key automation. Vetted and implemented internal ATS (workable/paycor/LinkedIn)while creatively marketing open roles to manage and complete hiring goals with 100% candidate placement < / = 35 days for entry and mid level roles. > Developed HR & TA Dashboard > Managed payroll. Reduced overall payroll errors to less than .05% annually by collaborating with accounting to streamline and automate the payroll process. Achieved by integrating various systems for semi-Monthly Payroll including commission and bonus’ for all employees (hourly & salary). >Successfully transitioned 20 new employees during M&A into the culture and processes of Club Colors. >Collaborated with Marketing to develop Employer brand strategy to attract top talent and ultimately maintain low turnover. Plan and executed employee events. >Maintained compliance for warehouse and corporate employees by staying abreast changes to employment law and updating policies/procedures. >Navigated through COVID19, layoffs, remote work, return to office, and necessary compliance requirements to meet the needs of our front-line workers.

  • Sr. HRA / Seasonal HRBP at Amazon
    Apr 2018 - Feb 2019 · 11 mos

    - Supported 400+ employees at all levels including executive leadership in analysis & resolution of issues, grievances, and conflicts. (GEMBA, Labor Planning, ETC.) - Eliminated discrimination and harassment risks by documenting & investigating internal and EEOC complaints for corrective action from beginning to end. - Developed and implemented safety policies and procedures which resulted in a reduction of workplace accidents from 10-12 a month to 4-5 a month. - Collaborated with Sr. Management to implement incentives and set clear expectations to improve employee attendance from 70% to consistently above 88% from September to December, leading to overall productivity improvements. - Used HRIS data analysis and charting to identify root causes of attrition, and implement strategies to combat which resulted in a 28% reduction of employee turnover. - Projected and allocated facilities monthly budget for employee engagement activities and facility resources. - Trained and developed two seasonal interns on HR and administrative functions. - Tracked programs closely to assess effectiveness and make proactive changes to meet frequently changing demands. -Trained all new employees during orientation