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.

Senior Solutions Engineer, Majors - Chicago

Company: Cloudflare

Location: Chicago, IL

Posted Jan 31, 2025

The Solutions Engineer role at Cloudflare involves building and maintaining long-term technical relationships with key stakeholders in strategic accounts. The role requires strong communication skills, experience in managing technical sales within large accounts, and a deep understanding of Cloudflare's solutions. The engineer will drive technical conversations across various lines of business, empower customers in their security and network transformation journeys, and represent Cloudflare at industry events. Desirable skills include proficiency in internet security technologies, networking, HTTP technologies, Zero Trust Network Access, SASE concepts, cloud computing, and scripting or programming experience.

Manager IT Solutions Engineering

Company: Ahold Delhaize USA

Location: Chicago, IL

Posted Jan 31, 2025

Ahold Delhaize USA is seeking a Solutions Engineering Manager to lead teams of software engineers and system analysts. The role involves building and delivering high-performing IT products, driving engineering best practices, and modernizing existing tech stacks. The manager will be responsible for hiring and developing talent, leading design and implementation of application platforms, and ensuring efficient and scalable applications. They will also manage budgets, technical personnel, and vendor performance. Preferred qualifications include a Masters Degree, Agile methodology experience, and retail or grocery industry experience.

Sr. Director, Strategic Product Portfolio

Company: Inspira Financial

Location: Chicago, IL

Posted Jan 31, 2025

Inspira Financial is seeking a Sr Director Product Portfolio Lead to develop a vision and strategy for a portfolio of products, ensuring alignment with business objectives and driving profitability. The role involves analyzing market trends, customer needs, and competitive dynamics to identify opportunities for innovation and growth. The ideal candidate should have 7-10 years of experience in the health and benefits industry, strong communication skills, and the ability to assess complex markets and competitive environments. The position offers a competitive salary of $190,000 - $215,000 per year.

Technical Project Manager I

Company: Vail Systems, Inc.

Location: Chicago, IL

Posted Jan 31, 2025

Vail Systems is seeking a Technical Project Manager to oversee the entire project lifecycle for innovative enterprise voice communication solutions on web and mobile channels. The ideal candidate should have a strong background in project management frameworks and agile methodologies, knowledge of customer service ticketing processes, IVR, and VoIP applications. The role involves partnering with engineering, product, operations, and support teams to establish project scope, timeline, and success metrics. The candidate will also manage communications, ensure documentation, and define support and maintenance procedures post-project completion.

Data Specialist, Level II

Company: Morningstar

Location: Chicago, IL

Posted Jan 31, 2025

The role of Level II Specialist in the Data and Data Product organization involves providing second-level support for complex product and data issues, working with various teams to ensure timely resolution, and contributing to process improvement. The ideal candidate should have 1-2 years of experience in a quality operations analyst or customer support role, extensive knowledge of Morningstar products and data, and strong problem-solving, organizational, and analytical skills. Morningstar offers comprehensive benefits, including financial, physical, emotional, and social health programs, a hybrid work environment, and a competitive base salary range of $54,093 - $91,977 annually.

Senior Product Owner

Company: CNA

Location: Chicago, IL

Posted Jan 31, 2025

The job description outlines a Senior Product Owner role at CNA, which involves supporting Agile Scrum teams, prioritizing team backlogs, and driving content via prioritized user stories. The role requires strong leadership, collaboration, and domain knowledge. The Senior Product Owner is expected to be a thought leader in Scrum ceremonies, fostering continuous improvement, and building customer insights into the planning and execution process. The role also involves analyzing metrics, recommending changes, and inspiring team members. The ideal candidate should have a Bachelor's degree, at least five years of Product Owner experience, and familiarity with Agile methodologies. CNA offers a competitive benefits package and is committed to providing reasonable accommodations.

LAN & WLAN Americas - Team Lead

Company: Caterpillar

Location: Peoria, IL

Posted Jan 31, 2025

Caterpillar Inc is seeking an experienced Team Leader for Americas LAN and WLAN teams. The role involves managing daily activities, ensuring smooth operations, and contributing to defining the global LAN/WLAN strategy. The ideal candidate should have a computer-related or engineering-related degree, at least 3 years of experience in working with business unit customers, and fundamental knowledge of LAN and WLAN technologies. The position offers a competitive salary, benefits, and opportunities for career growth.

Head of Marketing Operations

Company: Morningstar

Location: Chicago, IL

Posted Jan 31, 2025

The Head of Marketing Operations role at Morningstar is a key leadership position responsible for developing and leading a world-class marketing operations function. The role involves building scalable processes, managing critical infrastructure and tools, overseeing marketing performance measurement, and optimizing the end-to-end marketing workflow. The role requires at least 12 years of experience in marketing operations, marketing technology, or related functions, with at least 5 years in a leadership role within a large matrixed enterprise. The role offers a comprehensive compensation package, including a 401k match, stock ownership potential, health benefits, wellness incentives, and various leave programs. Morningstar's hybrid work environment allows for remote work with regular in-person collaboration.

Specialist Platform Support Engineer

Company: iManage

Location: Chicago, IL

Posted Jan 31, 2025

iManage is seeking a Platform Support Engineer for their Chicago office. The role involves being a data-driven problem solver, collaborating with customer-facing teams, and advocating for users. The company offers a flexible working policy, a supportive team culture, and comprehensive benefits. The ideal candidate has 47 years of experience in a technical escalation role, with expertise in distributed cloud services and REST APIs. iManage is committed to diversity and inclusion, encouraging applicants to apply even if they don't meet every qualification.

People Operations Intern

Company: iManage

Location: Chicago, IL

Posted Jan 31, 2025

iManage offers a paid internship program in People Operations, starting June 2nd and ending August 8th. The program includes project-based activities, team building, and learning opportunities. Interns will work on various projects, gain exposure to different aspects of iManage, and collaborate with team members. The role requires a bachelor's degree in HR, business, or a related field, excellent communication skills, and proficiency in Microsoft Office Suite. iManage values diversity and encourages applicants with a growth mindset to apply.

Associate Platform Support Engineer

Company: iManage

Location: Chicago, IL

Posted Jan 31, 2025

iManage is seeking a Platform Support Engineer for their Customer Reliability team in Chicago, IL. The role involves developing deep technical knowledge of the iManage platform, collaborating with customer-facing teams, proactively assisting internal teams and customers, and advocating for users. The ideal candidate has a Bachelor's degree in computer science or information technology, experience with distributed cloud service technologies, and familiarity with log aggregation and monitoring tools. iManage offers a flexible working policy, competitive salary, comprehensive benefits, and opportunities for career growth and learning.

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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