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Remote Principal Jobs in Chicago, IL (NOW HIRING)

We are seeking a full-time, remote Principal AI Architect. The Principal AI Architect role provides enterprise leadership for the design and delivery of end-to-end AI, Generative AI, and agentic AI ...

We are seeking a full-time, remote Principal AI Architect. The Principal AI Architect role provides enterprise leadership for the design and delivery of end-to-end AI, Generative AI, and agentic AI ...

Principal AI Architect - Remote

Lombard, IL · On-site +1

$125K - $170K/yr

We are seeking a full-time, remote Principal AI Architect.The Principal AI Architect role provides enterprise leadership for the design and delivery of end-to-end AI, Generative AI, and agentic AI ...

Senior Principal Solutions Architect Location-Type ... Remote (U.S. - Central or Eastern Time Preferred) Start Date Is: ASAP Compensation Range : $85-95 ...

UKG Principal Consultant

Chicago, IL · On-site +1

$120K - $150K/yr

UKG Principal Consultant Job Summary: Next Generation, Inc., an Equal-Opportunity employer, is ... This is a mostly remote position with occasional on-site visits to Chicago, Illinois. Job ...

UKG Principal Consultant

Chicago, IL · On-site +1

$120K - $150K/yr

UKG Principal Consultant Job Summary: Next Generation, Inc., an Equal-Opportunity employer, is ... This is a mostly remote position with occasional on-site visits to Chicago, Illinois. Job ...

Principal Software Engineer - IE06GE We're determined to make a difference and are proud to be an ... This role can have a Hybrid or Remote work arrangement. Candidates who live near one of our office ...

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Remote Principal information

See Chicago, IL salary details

$37.6K

$112.7K

$187.5K

How much do remote principal jobs pay per year?

As of Aug 23, 2026, the average yearly pay for remote principal in Chicago, IL is $112,690.00, according to ZipRecruiter salary data. Most workers in this role earn between $87,600.00 and $128,800.00 per year, depending on experience, location, and employer.

What is a remote principal?

A Remote Principal is an educational leader who manages and oversees a school or educational program primarily through online platforms rather than being physically present on site. Their responsibilities include supervising teachers, ensuring curriculum standards are met, facilitating virtual staff meetings, and supporting students and families in a digital environment. Remote Principals use technology to communicate, monitor progress, and address challenges unique to remote or hybrid learning settings. This role has grown in importance with the rise of online and virtual schools.

How does a remote principal effectively build and maintain strong relationships with teachers and staff in a virtual environment?

Building strong relationships remotely requires a proactive approach to communication and team building. As a Remote Principal, you’ll regularly schedule virtual meetings, use collaborative platforms, and foster open channels for feedback to ensure everyone feels connected and supported. Creating a sense of community through virtual staff lounges, team-building activities, and transparent leadership helps maintain morale and engagement. Effective Remote Principals also prioritize visibility and responsiveness, making themselves accessible for both professional guidance and personal check-ins.

What are the key skills and qualifications needed to thrive as a remote principal, and why are they important?

To thrive as a Remote Principal, you need strong leadership abilities, educational administration experience, and an advanced degree in education or a related field. Familiarity with virtual learning platforms, student information systems, and digital communication tools is typically required. Exceptional interpersonal skills, adaptability, and proactive communication set outstanding remote principals apart. These competencies are vital to effectively manage staff, support students, and ensure a positive virtual school environment from a distance.

What is the difference between Remote Principal vs Remote Project Manager?

AspectRemote PrincipalRemote Project Manager
Required CredentialsTypically requires advanced degrees (e.g., MBA, relevant certifications)Often requires project management certifications (e.g., PMP) and experience
Work EnvironmentStrategic leadership, high-level decision making, often involved in company-wide initiativesOperational focus, managing specific projects, coordinating teams
Employer & Industry UsageUsed in tech, consulting, and large organizations for strategic rolesCommon across industries for managing project execution

The Remote Principal generally focuses on strategic leadership and high-level decision making within an organization, often requiring advanced credentials. In contrast, the Remote Project Manager handles project execution, team coordination, and operational tasks. Both roles are vital in remote work environments but differ in scope and responsibilities.

What are the most commonly searched types of Principal jobs in Chicago, IL?

The most popular types of Principal jobs in Chicago, IL are:

What job categories do people searching Remote Principal jobs in Chicago, IL look for?

The top searched job categories for Remote Principal jobs in Chicago, IL are:

Infographic showing various Remote Principal job openings in Chicago, IL as of August 2026, with employment types broken down into 88% Full Time, 10% Part Time, 1% Temporary, and 1% Contract. Highlights an 91% Physical, 3% Hybrid, and 6% Remote job distribution, with an average salary of $112,690 per year, or $54.2 per hour.

Principal AI Architect - Remote

paradigm

Lombard, IL • Remote

Full-time

Re-posted 6 days ago


Job description

We are seeking a full-time, remote Principal AI Architect. The Principal AI Architect role provides enterprise leadership for the design and delivery of end-to-end AI, Generative AI, and agentic AI solutions, while also contributing hands-on technical expertise to prototyping, implementation, and architectural direction. This position requires deep expertise in enterprise software engineering, cloud architecture, AI/ML, and Generative AI, with responsibility for translating evolving AI capabilities into scalable, secure, and production-ready solutions. The role operates within regulated environments and is accountable for incorporating data privacy, security, governance, and responsible AI practices into solution design and delivery, particularly in healthcare or other sensitive-data domains. This position plays a key role in shaping Paradigm’s AI architecture, advancing the AI Center of Excellence (COE), and enabling consistent, governed, and scalable AI solution delivery across the organization.

RESPONSIBILITIES:  

AI Architecture & Solution Delivery

  • Architect and deliver end-to-end AI, Generative AI, and agentic AI solutions from concept through production
  • Apply hands-on expertise to build LLM-based systems, RAG pipelines, AI agents, and multi-agent orchestration solutions
  • Design AI platform capabilities including model selection, LLM routing, retrieval strategies, memory systems, and tool/function orchestration
  • Lead hands-on prototyping and proof-of-concepts to validate technologies and accelerate adoption
  • Ensure AI solutions are designed for performance, scalability, observability, privacy, and operational readiness
  • Define and drive architecture across multiple domains/business segments, ensuring alignment with enterprise strategy
  • Partner with business and technology leadership to shape AI roadmap, priorities, and execution strategy
  • Establish and promote architecture standards, reusable patterns, and best practices
  • Drive modernization initiatives to reduce technical debt and improve scalability, resilience, and performance
  • Implement and guide AI governance, security, responsible AI, and compliance practices
  • Ensure AI solutions are designed for performance, observability, privacy, and operational readiness
  • Collaborate across engineering, data, product, and business teams to deliver production-grade AI solutions
  • Mentor engineers and architects and effectively communicate AI concepts to technical and non-technical stakeholders

Leadership & Collaboration

  • Partner with business and technology leadership to define AI strategy, roadmap, and execution priorities.
  • Establish and promote architecture standards, reusable patterns, and best practices.
  • Mentor architects and engineers; build internal capability for AI solution delivery.
  • Communicate complex AI concepts effectively to both technical and non-technical stakeholders.
  • Leads adoption of AI-enabled tools within the team, ensuring effective integration into workflows. Coaches employees on appropriate usage, monitors impact on productivity and quality and identifies opportunities for process improvement.
  • Demonstrates a customer-first mindset by developing a broad and deep (where appropriate) understanding of Paradigm organization, products, operations, and customers. Prioritizes collaboration to meet customer needs and expectations and takes personal accountability for service quality.

Technology Strategy & Innovation

  • Continuously evaluate the evolving AI landscape (LLMs, agents, frameworks, tools).
  • Translate emerging technologies into practical enterprise use cases and capabilities.
  • Drive modernization initiatives to improve scalability, resilience, and performance.

QUALIFICATIONS:

  • 10+ years of experience in software engineering, architecture, and enterprise system design.
  • Proven experience delivering end-to-end AI/ML and Generative AI solutions in production environments.
  • Strong hands-on engineering capability with ability to operate across architecture, design, and implementation.
  • Deep expertise in LLMs, prompt engineering, RAG, embeddings, vector databases, and agent-based systems
  • Experience with agent frameworks and orchestration including multi-agent patterns and integrations
  • Strong programming experience in Python and building APIs, microservices, and distributed systems.
  • Experience designing and implementing solutions on cloud platforms (Azure preferred).
  • Experience with DevOps practices, including CI/CD, containerization, and scalable deployment of AI systems.
  • Familiarity with infrastructure-as-code (Terraform, Bicep) and Kubernetes-based deployments.
  • Strong understanding of data architecture and integration patterns supporting AI workloads.
  • Ability to evaluate emerging technologies and translate them into enterprise-scale capabilities
  • Solid knowledge of AI governance, risk, compliance, privacy, and responsible AI principles
  • Strong communication and stakeholder management skills.
  • Ability to influence decisions across engineering, data, and business teams.
  • Proven ability to mentor, guide, and elevate engineering and architecture teams.
  • Master’s or Bachelor’s degree in Computer Science, Engineering, Data Science, or a related STEM field.