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.

Outside Sales Reps Hiring Immediately

Company:

Location: Villa Park, IL

Posted Jan 23, 2025

Outside Sales Representative

Company:

Location: Bolingbrook, 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 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.

Field Sales Representative - Hiring Now

Company:

Location: Naperville, 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 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.

CDL A Local Delivery Driver- Freeport

Company: Sysco

Location: Freeport, IL

Posted Jan 23, 2025

Sysco Baraboo, LLC is seeking full-time CDL A Delivery Truck Drivers. The role involves safely operating a tractor-trailer and manually delivering various products to customer locations. Drivers build relationships with customers and are expected to be flexible for overtime, weekends, and holidays. Benefits include excellent pay, paid vacation, ongoing training, career growth opportunities, comprehensive healthcare, and retirement benefits. Sysco is the global leader in foodservice distribution with over 71,000 colleagues and 333 distribution facilities worldwide.

Transportation Clerk

Company: Sysco

Location: Danville, IL

Posted Jan 23, 2025

Roofing Sales Hiring Now Training Provided

Company:

Location: Joliet, 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 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: Oak Park, 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, offering them protection at reduced costs. The company stands out due to its fully staffed departments, enabling sales reps to focus on sales without administrative burdens. AmeriPro Roofing offers competitive compensation including 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. The role involves prospecting, qualifying, and closing new sales, managing a territory, conducting property inspections, and building customer relationships. Qualifications include 2+ years of full-cycle sales experience, a reliable vehicle, excellent 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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