Supportive Leadership Jobs in Chicago, IL

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

Roofing Sales $65K-200K Total Compensation!

Company: Lee Company

Location: Joliet, IL

Posted Dec 20, 2024

AmeriPro Roofing is hiring Outside Sales Representatives in the South and Southwest Chicagoland 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. Sales support staff handles various stages of the job process. Key responsibilities include prospecting, qualifying leads, closing sales, and managing territories. Qualifications include 2+ years of full-cycle sales experience, reliable vehicle, excellent communication skills, and a valid driver's license.

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

Company: Lee Company

Location: Bolingbrook, IL

Posted Dec 20, 2024

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.

Roofing Sales Hiring Now Training Provided

Company: Lee Company

Location: Wheaton, IL

Posted Dec 20, 2024

AmeriPro Roofing is hiring Outside Sales Representatives in West Chicagoland 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. Sales support staff, training, and company-issued leads are provided. Qualifications include 2+ years of full-cycle sales experience, reliable vehicle, excellent communication skills, and a valid driver's license.

Shift Lead

Company: Walgreens

Location: Springfield, IL

Posted Dec 20, 2024

The role involves managing store operations, including opening and closing the store, handling cash, managing inventory, and ensuring a positive customer experience. Key responsibilities include managing deliveries, processing returns and refunds, maintaining store cleanliness, and assisting with pharmacy tasks. The position requires leadership experience, fluency in English, and knowledge of store systems. The role is based in Springfield, IL, and the salary range is $17 - $19 hourly.

Roofing Sales Immediately Hiring

Company: Lee Company

Location: Homewood, IL

Posted Dec 20, 2024

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.

Management & Sales Training Program

Company: Lee Company

Location: Mattoon, IL

Posted Dec 20, 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 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.

Roofing Sales Immediately Hiring

Company: Lee Company

Location: Romeoville, IL

Posted Dec 20, 2024

AmeriPro Roofing is hiring Outside Sales Representatives in the South and Southwest Chicagoland 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. Sales support staff handles various stages of the job process. Key responsibilities include prospecting, qualifying leads, closing sales, and managing territories. Qualifications include 2+ years of full-cycle sales experience, reliable vehicle, excellent communication skills, and a valid driver's license.

Shift Lead

Company: Walgreens

Location: Chicago, IL

Posted Dec 20, 2024

The role involves managing store operations, including opening and closing the store, handling cash, managing inventory, and ensuring a positive customer experience. Key responsibilities include managing deliveries, processing returns and refunds, maintaining store cleanliness, and assisting with pharmacy tasks. The position requires leadership experience, fluency in English, and knowledge of store systems. The role is based in Chicago, IL, with a salary range of $17 - $19 per hour.

Emerging Store Manager

Company: Walgreens

Location: Champaign, IL

Posted Dec 20, 2024

The role involves supervising customer service associates and designated hitters, managing the front end of the store, and making recommendations for overall operations. The individual is responsible for supporting the Store Manager in achieving company deliverables, managing store team members, and ensuring proper merchandising, protection of store assets, and improving store sales and profitability. They lead and manage store team members, including recruitment, hiring, performance management, and discipline. The role also involves engaging customers and patients, resolving complaints, and improving customer service metrics. Operations management includes supervising store activities, collaborating with external partners, and managing cash, inventory, and bookkeeping. The individual is accountable for business performance management, people and performance management, and training & personal development. They communicate regularly with team members and assist in planning and communicating company strategy.

Shift Lead

Company: Walgreens

Location: Riverwoods, IL

Posted Dec 20, 2024

The job involves managing store operations, including opening and closing the store, handling cash, managing inventory, and ensuring a positive customer experience. Responsibilities also include coaching team members, maintaining store cleanliness, and complying with company policies. The role requires leadership experience, fluency in English, and knowledge of store systems. Preferred qualifications include experience with store inventory control.

Shift Lead

Company: Walgreens

Location: Peoria, IL

Posted Dec 20, 2024

The role involves managing store operations, including opening and closing the store, handling cash, managing inventory, and ensuring a positive customer experience. Key responsibilities include managing deliveries, processing returns and refunds, maintaining store cleanliness, and assisting with pharmacy tasks. The position requires leadership experience, fluency in English, and knowledge of store systems. The role is based in Peoria, IL, and the salary range is $17 - $19 per hour.

Roofing Sales Immediately Hiring

Company: Lee Company

Location: Alsip, IL

Posted Dec 20, 2024

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.

Frequently Asked Questions

What are the typical salary ranges for Supportive Leadership roles at different seniority levels?
Entry‑level supportive leaders (Team Lead, Junior Coach) earn $60,000–$80,000 annually. Mid‑level managers ($80,000–$120,000) handle multiple squads and OKR ownership. Senior leaders (Director, Head of People) command $120,000–$170,000, while VP‑level roles range $170,000–$250,000, and CxO positions can exceed $250,000 depending on company size and region.
What skills and certifications are most valued for a Supportive Leadership position?
Key skills include emotional intelligence, coaching (ICF Associate Certified Coach), conflict resolution, data‑driven people analytics, and Agile facilitation. Certifications that boost credibility are SHRM‑CP/SCP, PHR/SPHR, PMI‑ACP, Certified ScrumMaster (CSM), and leadership programs like the Leadership in a Digital Age (LIDA). Practical experience with HRIS platforms such as Workday or SAP SuccessFactors and collaboration tools like Miro and Slack is also highly prized.
Is remote work available for Supportive Leadership roles?
The majority of supportive leadership roles are offered as fully remote or hybrid. However, senior positions that involve executive alignment or cross‑departmental strategy often require occasional on‑site presence for quarterly alignment meetings or leadership retreats.
What career progression can a Supportive Leader expect?
A typical trajectory moves from Team Lead → Manager → Senior Manager → Director → Vice President → CxO. Progression typically takes 2–4 years to reach a manager level, 3–5 years to a director, and 5–7 years to reach VP or executive roles, depending on performance and organizational size.
What are the current industry trends affecting Supportive Leadership?
Key trends include a heightened focus on employee experience and well‑being, AI‑driven people analytics for predictive engagement, inclusive and bias‑free leadership practices, remote‑first culture integration, and the adoption of digital coaching platforms that combine video, analytics, and real‑time feedback. Companies are also investing in continuous learning ecosystems to keep leaders updated on emerging technologies and leadership frameworks.

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