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.

Principal Partner Account Manager, Heartland Region

Company: Cloudflare

Location: Chicago, IL

Posted Jan 24, 2025

Cloudflare, a leading company in the Internet infrastructure sector, is seeking a seasoned partner sales professional for its Chicago office. The role involves building and managing a network of resellers and systems integrators to expand the company's sales reach. The ideal candidate should have extensive experience in software/SaaS/security sales and channel management, with a proven track record in developing a partner ecosystem. The position offers a competitive salary, incentive compensation, and equity participation. Cloudflare is known for its commitment to protecting the free and open Internet, offering initiatives like Project Galileo and 1.1.1.1, and is an equal opportunity employer.

Managing Consultant, Services Business Development - Global Digital Platforms

Company: Mastercard

Location: Chicago, IL

Posted Jan 24, 2025

Mastercard is seeking a Managing Consultant for Global Digital Platforms in their Services Business Development team. The role involves driving growth of strategic digital partnerships, managing client relationships, and generating sales opportunities. The ideal candidate should have significant B2B sales experience, particularly in SaaS, data & analytics, or cybersecurity solutions. They must possess strong analytical skills, excellent communication abilities, and a customer-first attitude. The role requires managing end-to-end sales processes, leading pitches, and collaborating with stakeholders. Mastercard offers a competitive salary range of $132,000-$206,000 along with comprehensive benefits.

Personal Banker - NEW BUILD - Bridgeport - Chicago, IL

Company: Wells Fargo

Location: Chicago, IL

Posted Jan 24, 2025

Wells Fargo is seeking an Associate Personal Banker (SAFE) for their National Branch Network. The role involves delivering exceptional customer service, building relationships, and proposing appropriate products and services. The company is recognized for its supportive work environment, offering competitive salaries, robust benefits, and programs for work-life balance. The ideal candidate should have customer service experience, be able to educate customers on technology, and foster strong relationships. The position requires SAFE registration and compliance with the S.A.F.E. Mortgage Licensing Act.

Employment Investigator

Company: Meta

Location: Chicago, IL

Posted Jan 24, 2025

Shift Supervisor Trainee

Company: CVS Health

Location: Rockford, IL

Posted Jan 24, 2025

CVS Health is offering a Shift Supervisor Trainee position, an entry-level role designed to prepare employees for higher-level supervisory roles. The role involves working effectively with store management and crews, supervising activities, and ensuring smooth store operations. The company emphasizes a human-centric approach to healthcare, focusing on personal, convenient, and affordable solutions. Successful completion of the training program leads to eligibility for Operations Supervisor or Shift Supervisor positions, which involve leading store staff, driving store execution, and building customer loyalty through excellent service. The role requires deductive reasoning, analytical skills, and computer skills, with a flexible schedule including early mornings, overnight, and weekend shifts. Benefits include medical, dental, vision, 401(k), life insurance, disability benefits, well-being programs, education assistance, and PTO.

Fall 2025 Intern - Meshing (Masters)

Company: Ansys

Location: Evanston, IL

Posted Jan 24, 2025

Ansys, a global leader in engineering simulation, is offering an Emerging Talent program for students to gain experiential learning and structured job experiences. The program aims to convert interns into full-time employees. As an Emerging Talent Intern, you will work on the Meshing development team, researching, designing, and implementing mesh generation algorithms. You will also enhance the User Interface for pre-processing workflows and collaborate with expert professionals. Minimum qualifications include a degree in Computer Science, Mechanical, Aerospace, or related engineering field, and experience with object-oriented application features using C++ or C. Preferred qualifications include exposure to scripting languages, coursework in computational geometry and FEA, and knowledge of agile development methodologies.

Residential Support Specialist

Company: TruGreen

Location: Crestwood, IL

Posted Jan 24, 2025

Vice President; Securities/Prod Spec III

Company: Merrill

Location: Chicago, IL

Posted Jan 24, 2025

Bank of America is seeking a candidate for a role in the Foreign Exchange and Interest Rates market. The job involves monitoring the competitive landscape, creating client presentations, guiding junior bankers, and communicating market trends. Requirements include a Master's degree in a relevant field and 3 years of experience in providing risk management solutions, pricing derivatives, delivering market updates, communicating with senior stakeholders, and analyzing risks. The role requires 25% domestic and international travel and offers a salary range of $275,000 - $285,000 annually, with discretionary incentive eligibility.

Pharmacy Technician

Company: CVS Health

Location: Chicago, IL

Posted Jan 24, 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.

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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