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.

Field Sales Representative – Hiring Immediately

Company:

Location: Tinley Park, 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 valid driver's license.

Field Sales Representative - $60k - $200k Compensation

Company:

Location: Aurora, 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 reps more time for sales. Compensation includes a draw against commission, commission on approved sales, a vehicle allowance, quarterly bonuses, full insurance benefits, a 401K with employer match, and a training & development program. Responsibilities involve prospecting, qualifying, and closing 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 Rep Now Hiring

Company:

Location: Tinley Park, IL

Posted Jan 23, 2025

Outside Sales Representative (Training Provided)

Company:

Location: Springfield, IL

Posted Jan 23, 2025

The text describes a sales career opportunity with Platinum, a robust company that supports its salespeople with marketing, recruiting, customer service, and technology. Successful salespeople receive superior support and have the potential to earn $75,000-$100,000+ annually. The role involves traveling to meet with farmers and small business owners, receiving training in Platinum's reliable 10-step sales system, and identifying highly qualified leads. The company's team-based structure encourages motivation, accountability, and increased sales, with additional benefits like annual renewal income potential, generous bonuses, and luxury travel incentives.

Management & Sales Training Program

Company:

Location: Champaign, 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 customer service. Successful completion leads to an Assistant Store Manager position. The program offers leadership development, professional networking opportunities, and a clear career trajectory. Benefits include health coverage, retirement plans, and flexible time off. Sherwin-Williams values diversity and inclusivity, encouraging applications from all backgrounds.

Sales and Service Rep (Hourly)

Company:

Location: Alsip, IL

Posted Jan 23, 2025

Safety-Kleen in Dolton, IL is recruiting for a Sales and Service Route Driver position. The role involves driving a Class B box truck to provide onsite service for parts washer machines, collect hazardous waste, and sell products/services within a defined route. Clean Harbors, Safety-Kleen's parent company, is a leading provider of environmental, energy, and industrial services across North America. The job offers competitive pay, comprehensive health benefits, opportunities for growth, and a commitment to health and safety. Key responsibilities include maintaining safety, servicing machines, upselling products, and adhering to all regulations. Required qualifications include a Class B CDL, Hazmat and Tanker endorsements, basic computer skills, strong communication, and customer service skills. Clean Harbors is an equal opportunity employer.

Outside Sales Representative

Company:

Location: Aurora, IL

Posted Jan 23, 2025

Roofing Sales Immediately Hiring

Company:

Location: Bolingbrook, 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 reps more time for sales. Compensation includes a draw against commission, commission on approved sales, a vehicle allowance, quarterly bonuses, full insurance benefits, a 401K with employer match, and a training & development program. Responsibilities involve prospecting, qualifying, and closing 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 Rep Now Hiring

Company:

Location: Tinley Park, 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 valid driver's license.

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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