Supportive Leadership Jobs in Chicago, IL

29,604 open positions · Updated daily

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.

Shift Lead

Company: Walgreens

Location: Tinley Park, IL

Posted Jan 23, 2025

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: Naperville, IL

Posted Jan 23, 2025

Shift Lead

Company: Walgreens

Location: Skokie, IL

Posted Jan 23, 2025

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 Skokie, IL, and the salary range is $17 - $19 hourly.

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.

Store Manager Unassigned

Company: Walgreens

Location: Rock Island, IL

Posted Jan 23, 2025

The role involves learning Walgreens' operations and ways of working to lead full store operations, including front-end and pharmacy. The individual is responsible for completing an accelerated development track to Store Manager, shadowing or assisting the Store Manager, and overseeing store operations. This includes customer engagement, resolving complaints, and ensuring a positive customer experience. The role also involves operations management, business performance management, and people & performance management. The individual must be fluent in English, willing to work flexible hours, and have retail management experience. Preferred qualifications include PTCB certification, a Bachelor's degree, and managerial experience in retail or hospitality.

Outside Sales Representative

Company:

Location: Oak Park, IL

Posted Jan 23, 2025

Shift Lead

Company: Walgreens

Location: Arlington Heights, IL

Posted Jan 23, 2025

Maintenance & Engineering Director

Company: Diageo

Location: Plainfield, IL

Posted Jan 23, 2025

Diageo, a global leader in beverage alcohol, seeks a Maintenance & Engineering Director for its Plainfield site. This role is crucial as Plainfield is the key Innovation and Technical Center for Diageo North America, producing significant new product innovations. The incumbent will provide leadership in Engineering and Maintenance, overseeing CAPEX budgeting, project management, asset management, and environmental compliance. Key responsibilities include ensuring equipment reliability, making authoritative decisions on capital programs, and developing long-term site strategy. The role requires a Bachelor's degree in Engineering, at least 8 years of management experience in consumer product manufacturing, and strong technical, financial, and leadership skills.

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 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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