Generous Benefits Package Jobs in Chicago, IL

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

SAS in Jewel – Part Time Retail Merchandiser - Overnight

Company:

Location: Chicago, IL

Posted Jan 23, 2025

SAS Retail Services is seeking a Reset Merchandiser. The role involves ensuring the latest products match the new plan, offering flexibility with Monday - Friday work, and opportunities for growth. Benefits include $15.80 per hour, no weekends, early access to earned wages, paid training, and customizable benefits. The ideal candidate is 18+, has reliable transportation, a valid driver's license, and can lift up to 25lbs.

Outside Sales Rep Now Hiring

Company:

Location: Plainfield, IL

Posted Jan 23, 2025

AmeriPro Roofing, a leading residential roofing contractor, is hiring Outside Sales Representatives in South and Southwest Chicagoland areas. These representatives educate homeowners about storm damage entitlements for roofing, siding, and gutter projects. AmeriPro Roofing stands out due to its fully staffed departments, enabling sales reps to focus on selling. The company offers competitive compensation including draw against commission, commission on approved sales, vehicle allowance, quarterly bonuses, full insurance benefits, and a 401K with employer match. Sales reps are expected to prospect, qualify, and close new sales, manage territories, inspect properties for damage, and build relationships with homeowners. Qualifications include 2+ years of sales experience, reliable vehicle, strong communication skills, and a smart phone. Industry knowledge and CRM experience are preferred.

Field Sales Representative – Hiring Immediately

Company:

Location: Downers Grove, IL

Posted Jan 23, 2025

AmeriPro Roofing, a leading residential roofing contractor, is hiring Outside Sales Representatives in West Chicagoland. These representatives will educate homeowners about storm damage entitlements for roofing, siding, and gutter projects. The company stands out due to its fully staffed departments, allowing sales reps more time for tasks. Compensation includes a draw against commission, commission on approved sales, a vehicle allowance, quarterly bonuses, full insurance benefits, a 401K with a 4% employer match, and a training & development program. Responsibilities involve prospecting, qualifying, and closing new sales, managing territories, inspecting properties for damage, and building customer relationships. Qualifications include 2+ years of full-cycle sales experience, a reliable vehicle, excellent communication skills, and CRM experience.

Outside Sales Representative

Company:

Location: Oak Park, IL

Posted Jan 23, 2025

Outside Sales Representative

Company:

Location: Alsip, IL

Posted Jan 23, 2025

AmeriPro Roofing, a leading residential roofing contractor, is hiring Outside Sales Representatives in South and Southwest Chicagoland areas. These representatives educate homeowners about storm damage entitlements for roofing, siding, and gutter projects. AmeriPro Roofing stands out due to its fully staffed departments, enabling sales reps to focus on selling. The company offers competitive compensation including draw advancement, commission on approved sales, vehicle allowance, quarterly bonuses, full insurance benefits, and a 401K with employer match. Sales reps are expected to prospect, qualify, and close new sales, manage territories, inspect properties for damage, and build relationships with homeowners. Qualifications include 2+ years of sales experience, reliable vehicle, strong communication skills, and a smart phone. Industry knowledge and CRM experience are preferred.

Retail Data Collector

Company:

Location: Oak Lawn, IL

Posted Jan 23, 2025

The company is hiring for the Retail Data Collector team, offering a competitive wage of $15.00 - $18.00 per hour, growth opportunities, and comprehensive benefits. They are looking for detail-oriented individuals who enjoy physical work, can lift up to 25 lbs, and have reliable transportation. The role involves handling product movement at retail, creating visually appealing displays, and contributing to optimal sales.

Management & Sales Training Program (Madison/Rockford)

Company:

Location: Sterling, IL

Posted Jan 23, 2025

The Sherwin-Williams Management & Sales Training Program is an 18-24 month entry-level position designed to prepare individuals for a Store Management role. The program includes 6-8 weeks of intensive training, followed by a typical 44-hour workweek. Participants will collaborate with store management, oversee a million-dollar business, and learn all aspects of operations, sales, and strategy. The training equips participants with skills for a successful career in management and professional sales, offering limitless career opportunities and leadership development. Sherwin-Williams values diversity and inclusivity, encouraging applications from all backgrounds.

Frequently Asked Questions

What are the typical salary ranges for Generous Benefits Package roles at different seniority levels?
Entry‑level benefits coordinators earn $55k–$70k, mid‑level benefits analysts $70k–$90k, senior benefits managers $90k–$120k, benefits directors $120k–$160k, and chief benefits officers $160k–$250k. Regional cost of living and company size adjust these figures; jobtransparency.com displays the exact range for each posting.
What skills and certifications are required for these roles?
Proficiency in benefits administration platforms (Workday, SAP SuccessFactors, Gusto, BambooHR) and data tools (SQL, Power BI, Tableau) is essential. Knowledge of ERISA, GDPR, and vendor contract negotiation is mandatory. Certifications such as CEBS, CBP, SHRM‑CP, HRCI‑SPHR, and PMP for project‑led benefit rollouts are highly valued.
Are Generous Benefits Package roles available for remote work?
Yes—approximately 70–80% of listings support remote or hybrid arrangements. Benefits technology specialists and analysts can perform duties from any location using secure VPNs, while some roles requiring on‑site compliance audits may require occasional office presence.
What are common career progression paths in this field?
Typical trajectories move from benefits coordinator → benefits analyst → benefits manager → benefits director → VP of total rewards → chief benefits officer. Specialists may also branch into benefits technology, wellness program design, or benefits analytics, each offering distinct growth ladders.
What industry trends are shaping Generous Benefits Package roles?
Current trends focus on benefit personalization, mental‑health coverage, flexible spend accounts, hybrid‑work benefit bundles, gig‑worker benefits, ESG‑aligned offerings, AI‑driven benefits optimization, and data‑driven decision making. Staying ahead of these trends enhances a professional’s marketability.

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