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.

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.

Shift Lead

Company: Walgreens

Location: Bolingbrook, IL

Posted Jan 24, 2025

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 Reps 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.

Outside Sales Representative

Company:

Location: Naperville, IL

Posted Jan 24, 2025

Shift Lead

Company: Walgreens

Location: Peoria, 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.

Tax Manager, Property Tax Payments

Company: Walgreens

Location: Deerfield, IL

Posted Jan 24, 2025

The job involves leading a remote payments team responsible for processing daily property tax payments and handling month-end accounting activities. Key responsibilities include reviewing and approving tax payments, responding to internal payment queries, providing analysis on payment issues, and communicating with landlords and stakeholders. The role also encompasses managing tax processes, implementing tax savings strategies, developing staff, supporting audit functions, and collaborating on tax and accounting issues. The ideal candidate should have a Bachelor's degree and at least 2 years of experience in public accounting, corporate tax, or accounting, with strong skills in Microsoft Office applications and leadership experience.

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 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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