Strong Leadership Skills Jobs in Chicago, IL

Entry‑level PM or Agile Coach: $80k‑$110k. Mid‑level Manager or Director of Product: $110k‑$150k. Senior Director or VP of Engineering: $150k‑$200k. C‑level (VP, CRO): $250k‑$400k, often plus equity and bonuses.

Core skills include strategic planning, stakeholder management, data analytics, and change management. Certifications such as PMP, SAFe Scrum Master, Certified ScrumMaster, Lean Six Sigma Green Belt, and ITIL Foundation boost credibility. Proficiency in tools like Jira, Confluence, MS Project, OKR platforms, and cloud dashboards (AWS, Azure, GCP) is increasingly expected.

Yes. Many tech firms offer fully remote, hybrid, or flexible schedules for leadership positions. Remote leadership requires strong communication tools (Zoom, Teams, Slack) and a proven track record of virtual team management and outcome delivery.

Start as a PM or Agile Coach, advance to PMO Lead or Operations Manager, then to Director of Product or VP of Engineering, and ultimately to C‑level roles such as COO, CRO, or VP of Strategy, where you shape enterprise-wide vision.

Digital transformation, AI integration, data‑driven culture, and sustainability initiatives are redefining leadership. Agile scaling frameworks (SAFe, LeSS), remote‑first team building, and cross‑functional collaboration are becoming core competencies for leaders.