Health Insurance Jobs in Milwaukee, WI

18,738 open positions · Updated daily

Looking for Health Insurance jobs in Milwaukee, WI? Browse our curated listings with transparent salary information to find the perfect Health Insurance position in the Milwaukee, WI area.

Field Sales Representative – Hiring Immediately

Company: Lee Company

Location: Wauwatosa, WI

Posted Nov 21, 2024

AmeriPro Roofing, a leading residential roofing contractor, is hiring Outside Sales Representatives in Milwaukee, WI. These representatives 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 a 4% 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 Representative

Company: Lee Company

Location: Wauwatosa, WI

Posted Nov 21, 2024

AmeriPro Roofing, a leading residential roofing contractor, is hiring Outside Sales Representatives in Milwaukee, WI. These representatives 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 a 4% 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.

Roofing Sales $65K-200K Total Compensation!

Company: Lee Company

Location: Menomonee Falls, WI

Posted Nov 21, 2024

AmeriPro Roofing, a leading residential roofing contractor, is hiring Outside Sales Representatives in Milwaukee, WI. These representatives 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 a 4% 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.

Management & Sales Training Program (Madison/Rockford)

Company: Lee Company

Location: Wisconsin Rapids, WI

Posted Nov 21, 2024

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.

Oil Sales and Service Rep II

Company: Lee Company

Location: Madison, WI

Posted Nov 21, 2024

Safety-Kleen in Madison, WI is seeking a Local Class B Route Driver. The role involves picking up waste oil and anti-freeze from various locations, including garages, automotive dealerships, and fleet maintenance facilities. Safety-Kleen, a Clean Harbors company, prioritizes health and safety, offering competitive wages, comprehensive health benefits, and opportunities for career growth. The job requires a Class B CDL, Hazmat and Tanker endorsements, previous route experience, and strong customer service skills.

Outside Sales Representative

Company: Lee Company

Location: Wisconsin Rapids, WI

Posted Nov 21, 2024

AmeriPro Roofing, a leading residential roofing contractor, is hiring Outside Sales Representatives in Oshkosh, Green Bay, and Appleton areas. 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, vehicle allowance, quarterly bonuses, full insurance benefits, and a 401K with a 4% employer match. 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.

Oil Sales and Service Rep II

Company: Lee Company

Location: Madison, WI

Posted Nov 21, 2024

Safety-Kleen in Madison, WI is hiring a Local Class B Route Driver. The role involves picking up waste oil and anti-freeze from various customer locations. The company offers competitive wages, health benefits, 401K, paid time off, training, and growth opportunities. A minimum Class B CDL is required, and previous route experience is preferred. Safety-Kleen is committed to excellence, environmental sustainability, and equal opportunity employment.

Roofing Sales Immediately Hiring

Company: Lee Company

Location: Brookfield, WI

Posted Nov 21, 2024

AmeriPro Roofing, a leading residential roofing contractor, is hiring Outside Sales Representatives in Milwaukee, WI. These representatives educate homeowners about storm damage entitlements for roofing, siding, and gutter projects. The company offers competitive compensation including draw advancement, commission on approved sales, and a vehicle allowance. Benefits include full insurance, a 401K with employer match, and a training & development program. The role involves prospecting, qualifying, and closing sales, managing a territory, and building relationships with homeowners. Qualifications include 2+ years of full-cycle sales experience, a reliable vehicle, and excellent communication skills.

Management & Sales Training Program (Green Bay)

Company: Lee Company

Location: Green Bay, WI

Posted Nov 21, 2024

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.

Field Sales Representative – Hiring Now

Company: Lee Company

Location: Wautoma, WI

Posted Nov 21, 2024

AmeriPro Roofing is hiring Outside Sales Representatives in Oshkosh, Green Bay, and Appleton areas. The role involves educating homeowners about storm damage benefits for roofing, siding, and gutter projects. The company offers competitive compensation, including draw against commission, commission on approved sales, vehicle allowance, quarterly bonuses, full insurance benefits, and a 401K plan with employer match. Key responsibilities include prospecting, qualifying, and closing sales, managing territories, and building relationships with homeowners. Qualifications include 2+ years of full-cycle sales experience, reliable vehicle, excellent communication skills, and a valid driver's license.

Oil Sales and Service Rep II

Company: Lee Company

Location: Madison, WI

Posted Nov 21, 2024

Safety-Kleen in Madison, WI is seeking a Local Class B Route Driver. The role involves picking up waste oil and anti-freeze from various locations, including garages, automotive dealerships, and fleet maintenance facilities. Safety-Kleen, a Clean Harbors company, prioritizes health and safety, offering competitive wages, comprehensive health benefits, and opportunities for career growth. The job requires a Class B CDL, Hazmat and Tanker endorsements, previous route experience, and strong customer service skills.

Management & Sales Training Program (Green Bay)

Company: Lee Company

Location: Appleton, WI

Posted Nov 21, 2024

The Sherwin-Williams Management & Sales Training Program is designed to prepare individuals for a Store Management role within 18-24 months. The program includes comprehensive training in all operations, client relations, and internal strategy, with the opportunity to grow the company's market share. It offers leadership development, professional networking, and limitless career opportunities. Sherwin-Williams values diversity and inclusivity, providing a supportive environment for personal and professional growth.

Frequently Asked Questions

What are typical salary ranges by seniority in Health Insurance?
Entry‑level analysts earn $55k–$75k, mid‑level roles $80k–$110k, senior positions $115k–$150k, and directors or VP levels range from $160k to $200k. Pay varies by region; for example, New York City salaries are often 20% higher than national averages.
Which skills and certifications are required?
Key technical skills include SQL, SAS, R, Tableau, and HL7 for data integration. Certification requirements often involve SOA or CAS actuarial exams, HIPAA‑compliance credentials, Guidewire Underwriting Certification, PMP for project managers, and financial certifications like CPA or CMA for finance roles.
Is remote work available in Health Insurance roles?
Yes—about 70% of positions offer fully remote or hybrid options. Major carriers such as UnitedHealth, Anthem, Humana, and CVS Health have formal telecommuting policies, especially for data‑analysis, product‑management, and compliance roles.
What are common career progression paths?
Typical trajectories move from junior analyst to senior analyst, then to manager, director, and VP. Progression often requires additional certifications (e.g., actuarial exams, PMP), cross‑functional experience, and proven leadership in projects like claims automation or value‑based care initiatives.
What industry trends should Health Insurance professionals watch?
Key trends include AI‑driven fraud detection, telehealth expansion, value‑based care models, regulatory updates to the ACA and Medicare Advantage, data‑privacy enforcement (HIPAA, GDPR), cybersecurity investments, and ESG‑aligned underwriting practices.

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