Technical Leadership Jobs in Chicago, IL

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Looking for Technical Leadership jobs in Chicago, IL? Browse our curated listings with transparent salary information to find the perfect Technical Leadership position in the Chicago, IL area.

Pharmacy Technician

Company: CVS Health

Location: Springfield, IL

Posted Jan 23, 2025

CVS Health emphasizes its commitment to human-centric health care, guided by a single purpose: 'Bringing our heart to every moment of your health.' The company aims to deliver enhanced, personalized, convenient, and affordable health care solutions. Pharmacy Technicians play a crucial role in this mission, supporting pharmacy teams to ensure smooth operations, accurate prescription fulfillment, and exceptional patient service. Technicians are expected to demonstrate empathy, genuine care, and a growth mindset, contributing to a safe, inclusive, and engaging team dynamic. They must complete a rigorous training program and satisfy all registration, licensing, and certification requirements.

Product Manager - Pangea (Hybrid)

Company: Enova

Location: Chicago, IL

Posted Jan 23, 2025

The job posting is for a Product Manager role at Enova International, a leading financial technology company. The role involves owning the success of key product initiatives, working closely with cross-functional teams to deliver customer-centric solutions, and driving business outcomes. The ideal candidate should have 4+ years of experience as a Product Manager or Product Owner in an agile environment, strong organizational and project management skills, and excellent communication skills. The role offers a competitive salary range of $87,000 - $126,000, along with comprehensive benefits including health, dental, and vision insurance, 401k matching, PTO, paid holidays, sabbatical program, and more. Enova International is committed to providing equal employment opportunities and fostering an inclusive culture.

Senior Adoption Change Management Consultant

Company: Reply

Location: Chicago, IL

Posted Jan 23, 2025

Valorem Reply is an award-winning digital transformation firm specializing in Microsoft technologies. They focus on data-driven enterprise IT modernization, customer experience, product transformation, and modern workplace solutions. The company's Modern Work practice comprises digital workplace experts who create exceptional employee experiences using Microsoft 365. As a Senior Adoption Change Management consultant, you will lead impactful technology change management projects, provide strategic thought leadership, and contribute to business development. The role requires a Bachelor's degree, 4+ years of change management experience, and proficiency in Microsoft 365 tools. The base compensation range is between $110,000 and $125,000.

Engineering Technical Services Manager

Company: Eaton

Location: Edwardsville, IL

Posted Jan 23, 2025

Senior Data Scientist - Retail Pharmacy Personalization

Company: CVS Health

Location: Chicago, IL

Posted Jan 23, 2025

CVS Health is seeking a machine learning expert to build predictive models for enhancing patient engagement and experience. The role involves deploying large-scale models, conducting A/B testing, collaborating with technical teams, and working with healthcare data. Required qualifications include 3+ years of ML/DL experience, proficiency in Python, SQL, and cloud-based ML frameworks, and strong Github and MLOps skills. A Master's degree or PhD is preferred. The company offers competitive compensation, benefits, and a supportive work environment.

Facilities Manager

Company: Grainger

Location: Lake Forest, IL

Posted Jan 23, 2025

Grainger, a leading industrial distributor, is seeking a Facilities Manager for its corporate headquarters. The role involves leading a team, maintaining facilities, ensuring safety and cleanliness, and collaborating with various departments. The company offers competitive compensation, comprehensive benefits, and a positive work environment. Requirements include a Bachelor's Degree, 10+ years of experience, and technical knowledge in facilities maintenance.

Field Sales Consultant

Company: Sunrun

Location: Park Ridge, IL

Posted Jan 23, 2025

Sunrun is seeking a Field Sales Consultant to self-generate sales leads and conduct in-home presentations on solar products. The role involves creating effective sales strategies, providing an industry-leading customer experience, and building long-lasting relationships. The ideal candidate should have at least 1 year of sales experience, excellent communication skills, and comfort with technology. Sunrun offers a full benefits package, competitive salary, and performance incentives. The company is committed to diversity, inclusion, and belonging.

Senior Project Manager - Agency

Company: EVERSANA

Location: Chicago, IL

Posted Jan 23, 2025

EVERSANA INTOUCH is a leading global healthcare agency offering creative and media services, enterprise solutions, and data analytics. They specialize in connecting life science companies with consumers, healthcare professionals, and payers. The company values diversity and inclusivity, aiming to improve patient lives worldwide. They are seeking a Senior Project Manager with expert project management skills, pharmaceutical or advertising experience, and proficiency in PMO standards and processes. The role involves full lifecycle delivery and management of complex projects, leading the estimation process, and collaborating with various teams. The anticipated base salary range is $76,000 to $100,000.

Assistant Store Manager

Company: Staples

Location: Northbrook, IL

Posted Jan 23, 2025

Site Reliability Engineer Team Lead (Hybrid)

Company: Enova

Location: Chicago, IL

Posted Jan 23, 2025

Enova International is seeking a qualified candidate for a leadership role in the SRE team. The role involves leading day-to-day operations, collaborating with TechOps leadership, and mentoring team members. Responsibilities include balancing team activities, overseeing on-call rotations, and promoting operational best practices. Requirements include a Bachelor's degree in Computer Science or Engineering, strong IT infrastructure knowledge, and proven project management experience. The company offers a competitive salary, comprehensive benefits, and a values-driven work environment.

Product Manager

Company: Pangea Money Transfer

Location: Chicago, IL

Posted Jan 23, 2025

The job posting is for a Product Manager role at Pangea, a financial technology company. The role involves owning the success of key product initiatives, working closely with cross-functional teams to deliver customer-centric solutions, and driving business outcomes. The ideal candidate should have 4+ years of experience as a Product Manager or Product Owner in an agile environment, strong organizational and project management skills, and excellent communication skills. The role offers a competitive salary range of $87,000 - $126,000, along with comprehensive benefits including flexible scheduling, health insurance, 401k matching, PTO, paid holidays, sabbatical program, and more. Pangea values introspection, accountability, empowerment, excellence, and kindness, and is committed to providing equal employment opportunities.

Frequently Asked Questions

What are the typical salary ranges for Technical Leadership roles by seniority level?
Engineering Manager: $140k–$190k base, often topped with 10–20% bonus and 0.5–1% equity. Director of Engineering: $190k–$240k base, 15–25% bonus, 1–3% equity. VP/Head of Engineering: $240k–$320k base, 20–30% bonus, 3–7% equity. Adjustments for cost‑of‑living and company size apply; leaders in AI/ML or multi‑cloud sectors may see a 5–10% premium.
What core skills and certifications are essential for Technical Leadership positions?
Core skills: Kubernetes & container orchestration, Terraform or Pulumi for IaC, GitOps with Flux or ArgoCD, CI/CD pipelines (GitLab CI, Jenkins, CircleCI), cloud expertise (AWS, Azure, GCP), AI Ops (MLflow, Kubeflow), data platform architecture, security (CISSP, ISO 27001), cost‑optimization, and people management. Certifications that add credibility: Certified Kubernetes Administrator (CKA), Certified Kubernetes Application Developer (CKAD), AWS Solutions Architect Professional, Google Professional Cloud Architect, Certified DevOps Professional, and Scrum Master for cross‑functional leadership.
How common is remote work for Technical Leadership roles?
Approximately 65% of Technical Leadership openings allow full‑time remote work, 20% are hybrid (3–5 days on‑site), and 15% require on‑site presence. Remote roles often demand 24/7 coverage across time zones, so leaders use asynchronous OKR reviews, distributed retrospectives, and tooling like Slack, Zoom, Azure DevOps, and Jira to coordinate squads worldwide.
What are the typical career progression paths for Technical Leaders?
Typical trajectory: Engineering Manager → Director of Engineering → VP/Head of Engineering → Chief Technology Officer or Chief Architect. Lateral moves include Enterprise Solutions Lead, AI/ML Platform Lead, Technical Advisor, or Consulting roles. Advancement hinges on mastering cross‑functional strategy, earning advanced certifications, publishing technical roadmaps, and demonstrating measurable impact on product velocity and revenue.
What industry trends should Technical Leaders be aware of?
Key trends: AI/ML Ops integration for automated model deployment, serverless and Function‑as‑a‑Service for cost‑efficient scaling, multi‑cloud governance tools like Anthos or Terraform Enterprise, AI‑driven observability and predictive monitoring, edge computing for low‑latency services, data mesh and governance frameworks, automated security (SecOps), sustainability metrics for cloud usage, and remote‑first culture with distributed leadership practices. Leaders should adopt Kubernetes‑native ops, implement cost‑monitoring dashboards, and champion DevSecOps to stay competitive.

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