Remote-First Company Jobs in Chicago, IL

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Looking for Remote-First Company jobs in Chicago, IL? Browse our curated listings with transparent salary information to find the perfect Remote-First Company position in the Chicago, IL area.

Statistical Analyst, ISS (Entry Level)

Company: American Property Casualty Insurance Association

Location: Chicago, IL

Posted Jul 11, 2025

Under general supervision, the entry-level Statistical Analyst position will review, correct, and approve company data submissions for one or more insurance…

CDL-A Truck Driver - Regional OTR

Company: G&D Integrated

Location: Chicago, IL

Posted Jul 11, 2025

Company drivers earn up to $105,000 per year. G&D Integrated is now hiring Class A CDL Truck Drivers in the Joliet, IL area for *Regional OTR routes* that get…

Senior Manager, Software Engineering, Back End (Go/Python/Java, Node, Jenkins, AWS, DevOps)

Company: Capital One

Location: Chicago, IL

Posted Jul 11, 2025

Capital One will consider for employment qualified applicants with a criminal history in a manner consistent with the requirements of applicable laws regarding…

culinary chef manager - Starbucks Reserve Kitchen

Company: Starbucks

Location: Chicago, IL

Posted Jul 11, 2025

Drive the implementation of company programs by developing action plans and directly motivate and instruct kitchen teams to implement and meet operational and…

Data Analyst - Insurance

Company: WAHVE

Location: Chicago, IL

Posted Jul 11, 2025

Compile and prepare data for customer analysis. *Experience* *working in a data analysis role in the insurance or financial services industry – *_*required*_.

Commercial HVAC Preventative Maintenance Technician

Company: BGIS

Location: Chicago, IL

Posted Jul 11, 2025

Subject to drug, background, and driver’s license checks. Maintaining the company service vehicle, tools, and inventory stock while adhering to company driving…

CDL-A Truck Driver - Regional OTR - Up to $105k/yr

Company: G&D Integrated

Location: Chicago, IL

Posted Jul 11, 2025

Company drivers earn up to $105,000 per year. G&D Integrated is now hiring Class A CDL Truck Drivers in the Joliet, IL area for *Regional OTR routes* that get…

CDL-A Truck Driver - Regional OTR - Comprehensive Benefits

Company: G&D Integrated

Location: Chicago, IL

Posted Jul 11, 2025

Company drivers earn up to $105,000 per year. G&D Integrated is now hiring Class A CDL Truck Drivers in the Joliet, IL area for *Regional OTR routes* that get…

IT Project Support Specialist (Remote - IL)

Company: Tanager, Inc.

Location: Chicago, IL

Posted Jul 11, 2025

May consider college degree in IT field in lieu of experience. This position involves direct communication and support to ensure readiness to cut over remote…

CDL-A Truck Driver - Regional OTR - Home Weekly

Company: G&D Integrated

Location: Chicago, IL

Posted Jul 11, 2025

Company drivers earn up to $105,000 per year. G&D Integrated is now hiring Class A CDL Truck Drivers in the Joliet, IN area for *Regional OTR routes* that get…

Customer Service Agent - Full Time

Company: MedSpeed

Location: Elmhurst, IL

Posted Jul 11, 2025

Handle a large number of calls daily without losing enthusiastic voice and attitude, answering all calls promptly and efficiently.

Staff Product Security Engineer - AI

Company: Match Group

Location: Chicago, IL

Posted Jul 11, 2025

Experience with various prompt engineering techniques and AI models to effectively develop tooling. Bachelor’s Degree in Computing Science or related field.

Frequently Asked Questions

What are typical salary ranges by seniority for Remote-First roles?
Junior Engineer: $70k‑$90k; Mid‑Level: $90k‑$120k; Senior Engineer: $120k‑$160k; Lead Engineer: $160k‑$200k; Principal Engineer: $200k‑$250k. Remote‑First companies often add a 5–10% cost‑of‑living adjustment for high‑cost regions, making these bands competitive globally.
What skills and certifications are required for Remote-First positions?
Technical: AWS Certified Solutions Architect, Google Cloud Professional Data Engineer, Terraform Associate, Docker Certified Associate, Kubernetes Administrator, React, Node.js, Python, Go. Soft: asynchronous communication, remote collaboration with Slack/Zoom, documentation in Confluence, and experience with GitHub Actions for CI/CD.
Is remote work fully available for all positions?
All listed roles are 100% remote with no on‑site requirement. Companies provide a 24‑hour coverage model, allowing team members in different time zones to overlap for core meetings and support windows.
What career progression paths exist in Remote-First companies?
Typical path: Junior → Mid → Senior → Lead → Technical Manager → VP. Promotion criteria include delivery quality, cross‑team mentorship, contribution to open‑source projects, and participation in internal learning hubs like remote‑first bootcamps.
What industry trends affect Remote-First companies today?
AI‑driven collaboration tools, outcome‑based performance metrics, distributed DevOps practices, emphasis on continuous learning, and remote‑first security frameworks (Zero Trust, VPNless access) are shaping the landscape. Companies are investing in these areas to reduce latency, increase resilience, and attract top talent.

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