Holidays Jobs in Chicago, IL

20,422 open positions · Updated daily

Looking for Holidays jobs in Chicago, IL? Browse our curated listings with transparent salary information to find the perfect Holidays position in the Chicago, IL area.

Sales Leader - Mid Illinois

Company: PNC

Location: Springfield, IL

Posted Jan 22, 2025

PNC is seeking a Sales Leader for its Retail Banking organization in Springfield, Illinois. The role involves leading and coordinating daily activities of team members, achieving business results, and growing customer relationships. The leader will manage risk, develop and oversee account and sales plans, and foster an inclusive workplace culture. Preferred skills include account management, client prospecting, and negotiation. The position requires a university degree, 8+ years of industry experience, and at least 5 years of management experience. The base salary ranges from $106,000 to $144,000, and PNC offers comprehensive benefits including health insurance, 401(k) match, and paid time off.

Operations Manager

Company: CVS Health

Location: South Elgin, IL

Posted Jan 22, 2025

CVS Health is seeking an Operations Manager to lead a store team, driving execution and performance while enhancing customer service. The role involves overall store management, sales and inventory management, employee staffing and development, and financial management. The ideal candidate will have strong leadership, communication, and analytical skills, and be able to work flexible hours. CVS Health offers competitive pay, comprehensive benefits, and opportunities for professional growth.

Sales Consultant

Company: CarMax

Location: Oak Lawn, IL

Posted Jan 22, 2025

Shift Supervisor Trainee

Company: CVS Health

Location: Monee, IL

Posted Jan 22, 2025

CVS Health is offering a Shift Supervisor Trainee position, an entry-level role designed to prepare employees for higher-level supervisory roles. The role involves working effectively with store management and crews, supervising activities, and ensuring smooth store operations. The company emphasizes a human-centric approach to healthcare, focusing on personal, convenient, and affordable solutions. Successful trainees can be considered for promotions to Operations Supervisor or Shift Supervisor positions, which involve leading store staff, driving store execution, and building customer loyalty through excellent service. The role requires deductive reasoning, analytical skills, and computer skills, with a flexible schedule including early mornings, overnight, and weekend shifts. Benefits include medical, dental, vision, 401(k), life insurance, disability benefits, well-being programs, education assistance, and PTO.

Pharmacy Technician

Company: CVS Health

Location: Aurora, IL

Posted Jan 22, 2025

Director Security Solutions Sales

Company: Mastercard

Location: Chicago, IL

Posted Jan 22, 2025

Mastercard is seeking a Director of Sales for the North American Services Team. The role involves leading a portfolio of key accounts, developing sales strategies, and driving revenue growth. The ideal candidate should have extensive experience in sales, particularly in the banking industry, and a deep understanding of cybersecurity trends. They must possess excellent relationship management skills, sales performance analysis capabilities, and a track record of quota achievement. The position offers a competitive salary range of $139,000 - $222,000 along with comprehensive benefits.

Store Associate

Company: CVS Health

Location: Marion, IL

Posted Jan 22, 2025

Senior Manager, Business Architecture

Company: CVS Health

Location: Northbrook, IL

Posted Jan 22, 2025

CVS Health is seeking a Senior Manager, Business Architecture for its PBM Caremark division. The role involves leading strategic initiatives to ensure durability, sustainability, feasibility, reusability, reliability, and standardization within the organization's architecture. The Business Architect will develop business architecture blueprints, identify and catalog business capabilities, and apply techniques like Capability Modeling, Customer Journey Mapping, and Value Stream analysis. Required qualifications include 2+ years of experience in business capability modeling and value stream analysis, 5+ years in architecture/management consultancy, and 2+ years of experience with enterprise Architecture frameworks. The role offers a competitive pay range and comprehensive benefits, including medical, dental, vision, 401(k), life insurance, disability benefits, well-being programs, and PTO.

Frequently Asked Questions

What are the typical salary ranges for Holiday roles by seniority?
Entry‑level Holiday positions start around $30k–$45k annually. Mid‑level roles, such as Inventory Analysts or Marketing Specialists, earn $45k–$70k. Senior positions—Retail Operations Managers or E‑commerce Platforms Administrators—can command $70k–$100k+ depending on experience and region.
What skills and certifications are required for Holiday positions?
Key skills include proficiency in POS and ERP software (e.g., SAP Retail, Oracle Retail), data analytics tools (Tableau, Power BI), and digital marketing platforms (Shopify, Adobe Commerce). Certifications such as Certified Holiday Operations Professional (CHOP), SAP Certified Application Associate – Retail, Salesforce Certified Administrator, and Google Analytics Individual Qualification are highly valued.
Is remote work available in the Holiday category?
Yes. Many Holiday roles, especially in e‑commerce platform administration, marketing strategy, and inventory analytics, support remote or hybrid work setups. Companies provide cloud‑based dashboards, virtual collaboration tools (Slack, Teams), and flexible scheduling to accommodate holiday peak periods.
What career progression paths exist within Holiday roles?
Professionals can advance from junior analyst or associate roles to senior analyst, then to managerial positions such as Operations Manager or Marketing Director. Additional growth opportunities include moving into cross‑functional strategy, data science for demand forecasting, or leading multinational holiday‑season initiatives.
What industry trends are shaping the Holiday job market?
The Holiday sector is increasingly driven by AI‑powered inventory forecasting, personalized gift recommendation engines, and sustainability in packaging. E‑commerce growth, especially on mobile platforms, fuels demand for digital marketing specialists. Companies also prioritize real‑time customer experience management, making roles in omnichannel retail and customer data platforms more critical.

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