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.

Senior Associate Data Engineer

Company: Discover

Location: Riverwoods, IL

Posted Jan 21, 2025

Discover is inviting applications for a Senior Associate Data Engineer role, offering meaningful work from Day 1. The company values individuality and encourages growth, with a collaborative culture based on three core behaviors: We Play to Win, We Get Better Every Day & We Succeed Together. The role involves designing, developing, and maintaining data solutions using enterprise frameworks. The ideal candidate should have 1+ years of experience in Data Platform Administration/Engineering, knowledge of SQL, and familiarity with ETL/ELT tools. The position offers a competitive salary and benefits package.

Sales Management Trainee- Rockford, IL

Company: Enterprise Mobility

Location: Rockford, IL

Posted Jan 21, 2025

Enterprise Mobility is currently recruiting for its esteemed Management Training Program. This role offers a clear career path with opportunities in various fields such as sales, business development, customer service, retail management, and operations. The program includes comprehensive training, development, mentoring, and a culture of promotion from within. The position is based in the Rockford, IL/Loves Park, IL area and comes with a competitive compensation package, including a targeted 1st year annual compensation of $49,202.40. Benefits include health, dental, vision insurance, life insurance, prescription coverage, employee discounts, and a 401(k) retirement plan with company match and profit sharing. The company is a family-owned, world-class portfolio of brands with a global network of nearly 100 countries and over 2.3 million vehicles. As a Management Trainee, you'll learn various aspects of the business, including customer service, sales, marketing, finance, and operations, with a focus on putting customers first.

Pharmacy Technician

Company: CVS Health

Location: Mattoon, IL

Posted Jan 21, 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 comply with all relevant laws and regulations, and complete necessary training and certification requirements.

Target Security Specialist

Company: Target

Location: Bloomington, IL

Posted Jan 21, 2025

Construction Project Team Administrator

Company: Equinix, Inc

Location: Chicago, IL / Remote

Posted Jan 21, 2025

Equinix is a digital infrastructure company operating over 260 data centers across the globe. They offer various job opportunities, including Construction Project Team Administrator, with competitive pay ranges and benefits. The company values diversity, equity, and inclusion, and is committed to ensuring an open employment process for all individuals.

Salesforce Director [Pharma & Life Science]

Company: PwC

Location: Chicago, IL

Posted Jan 21, 2025

PwC is seeking a Salesforce consulting generalist with extensive experience in various Salesforce applications. The role involves providing consulting services, analyzing client needs, implementing software solutions, and offering training and support for effective utilization of Salesforce applications. The ideal candidate will possess a broad range of consulting skills, thought leader-level knowledge, and acumen in understanding client business problems and developing Salesforce technology-enabled solutions. They should also demonstrate success in roles assisting large organizations with improving performance of various business units, and have experience in supervising teams, leading client proposals, and developing client relationships. Prior experience in Financial Services or Pharma & Life Science Industry Advisory is preferred for certain roles.

Pharmacy Technician

Company: CVS Health

Location: Springfield, IL

Posted Jan 21, 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.

Senior Software Engineer

Company: Grainger

Location: Chicago, IL

Posted Jan 21, 2025

Grainger, a leading industrial distributor, is seeking a skilled software engineer to join their CIM Intelligence team. The role involves developing, testing, and deploying high-quality web applications using React, Next.js, and Java. The team is responsible for building and maintaining core customer data products, playing a crucial role in Grainger's customer strategy and data management roadmap. The ideal candidate should have 7+ years of experience in modern software engineering, proficiency in React.js, Java, and cloud-native solutions, and a strong understanding of distributed system design.

Director of Executive Experiences

Company: ServiceNow

Location: Chicago, IL / Remote

Posted Jan 21, 2025

US Channel Sales Manager

Company: Apple

Location: Chicago, IL

Posted Jan 21, 2025

Apple's Sales organization is seeking a seasoned professional to build, develop, and manage a sales structure, team, and strategies for expanding Apple's enterprise platform adoption. The role involves creating and implementing plans with cross-functional teams, leading strategic account planning, and driving growth through executive-level collaborations. The ideal candidate should have 10+ years of channel and enterprise sales experience, with a focus on developing and growing a $1B+ business. They should possess strong leadership, communication, and strategic problem-solving skills, along with a deep understanding of the enterprise landscape and Apple's adoption within it.

Scheme Operations Analyst

Company: Adyen

Location: Chicago, IL

Posted Jan 21, 2025

Adyen, a financial technology platform, is seeking a Scheme Operations Analyst. The role involves managing operational merchant risk, ensuring compliance with Card Scheme regulations, and driving process improvements. The ideal candidate should have at least 2 years of experience, be detail-oriented, and have strong collaboration skills. The position can be based in San Francisco or Chicago, with salary ranges of $95,000 - $125,000 in San Francisco and $80,000 - $110,000 in Chicago. Adyen values diversity and inclusivity, encouraging applications from all backgrounds.

Pharmacy Technician

Company: CVS Health

Location: Edwardsville, IL

Posted Jan 21, 2025

CVS Health emphasizes its commitment to human-centric health care, guided by the purpose of '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 comply with all relevant laws and regulations, and complete necessary training and certification requirements.

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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