Comprehensive Health Benefits Jobs in Chicago, IL

69,983 open positions · Updated daily

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

Field Sales Representative – Hiring Immediately

Company:

Location: Wheaton, IL

Posted Jan 24, 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.

SAS in Jewel – Part Time Retail Merchandiser

Company:

Location: Park Ridge, IL

Posted Jan 24, 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. The job pays $15.80 per hour, provides paid training, and offers benefits including medical, dental, and life insurance. Candidates must be 18+, have reliable transportation, and a valid driver's license, capable of physical work involving lifting up to 25lbs.

Roofing Sales $65K-200K Total Compensation!

Company:

Location: Alsip, IL

Posted Jan 24, 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.

Management & Sales Training Program (Madison/Rockford)

Company:

Location: Freeport, IL

Posted Jan 24, 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.

Outside Sales Representative

Company:

Location: Naperville, IL

Posted Jan 24, 2025

Roofing Sales Immediately Hiring

Company:

Location: Joliet, IL

Posted Jan 24, 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 representatives to focus on sales. 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. Responsibilities include prospecting, qualifying, and closing sales, managing territories, inspecting properties for damage, and building customer relationships. Qualifications include 2+ years of sales experience, reliable vehicle, strong communication skills, and CRM experience.

Outside Sales Reps Hiring Immediately

Company:

Location: Plainfield, IL

Posted Jan 24, 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.

SAS in Jewel – Part Time Retail Merchandiser - Overnight

Company:

Location: Chicago, IL

Posted Jan 24, 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.

SAS in Jewel – Part Time Retail Merchandiser

Company:

Location: North Riverside, IL

Posted Jan 24, 2025

Outside Sales Representative

Company:

Location: Romeoville, IL

Posted Jan 24, 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 CRM experience.

Frequently Asked Questions

What are the typical salary ranges for Comprehensive Health Benefits roles at different seniority levels?
Entry‑level Benefit Analysts earn roughly $55k–$75k; mid‑level analysts and claims specialists average $75k–$115k; senior managers and actuarial consultants command $115k–$170k; directors of benefits typically receive $160k–$230k; and VP or Chief Benefits Officers can earn $200k–$350k, depending on company size and region.
What skills and certifications are essential for a career in Comprehensive Health Benefits?
Key skills include proficiency with Epic or Cerner EHRs, Workday and SAP SuccessFactors benefits modules, Salesforce Health Cloud configuration, and data analytics tools such as Tableau, Power BI, or SAS. Certifications like Certified Employee Benefit Specialist (CEBS), Certified Professional in Health Benefits (CPHB), Certified Compensation Professional (CCP), and compliance credentials (HIPAA, ACA, ISO 27001) are highly valued.
Can Comprehensive Health Benefits positions be performed remotely?
Many benefits roles—especially analyst, compliance, and technology configuration positions—can be fully remote with secure VPN access to cloud platforms. On‑site support is usually limited to system administration or audit visits, so hybrid or fully remote arrangements are common for 70% of open listings.
What career progression paths exist within Comprehensive Health Benefits?
Typical progression starts with Benefit Analyst, moves to Senior Analyst or Claims Specialist, then to Manager or Senior Manager overseeing teams and projects. From there, executives advance to Director of Benefits, VP of Benefits, and ultimately Chief Benefits Officer or Head of Total Rewards, with a typical timeline of 3–5 years per promotion in high‑growth firms.
What are the current industry trends affecting Comprehensive Health Benefits roles?
Digital transformation drives AI‑powered claims analytics and real‑time wellness dashboards. Telehealth integration, HRA technology, and value‑based care models push benefits teams to negotiate new provider contracts. Regulatory shifts around ACA reporting, HSA/FSA contributions, and HIPAA data security keep compliance specialists in high demand, while blockchain pilots for claims settlement are emerging in leading tech‑savvy employers.

Related Pages