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Remote Technology Strategy Jobs in Chicago, IL (NOW HIRING)

Paradigm

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 ... Partner with business and technology leadership to define AI strategy, roadmap, and execution ...

Huntington

Application Architect (IT)

Chicago, IL · On-site +1

$70K - $140K/yr

Minimum 7 years of experience in solution architecture, technology strategy, IT transformation, or ... Remote roles will also have the opportunity to come together in our offices for moments that matter.

Huntington

Application Architect (IT)

Chicago, IL · On-site +1

Minimum 7 years of experience in solution architecture, technology strategy, IT transformation, or ... Remote roles will also have the opportunity to come together in our offices for moments that matter.

Initio Capital

Technology Diligence Analyst

Chicago, IL · Remote

This is a remote, flexible role for candidates who are analytical, commercially curious, and comfortable moving quickly across business, finance, technology, and strategy topics. WHAT YOU MAY WORK ON

New

Sterling Engineering Inc.

Director of IT

Chicago, IL · On-site +1

... remote users. * Partner with operational technology teams to support secure IT/OT integration strategies. End User Technology & Collaboration * Oversee enterprise endpoint management, mobile ...

Initio Capital

Investment Strategy Analyst

Chicago, IL · Remote

This is a remote, flexible role for candidates who are analytical, commercially curious, and comfortable moving quickly across business, finance, technology, and strategy topics. WHAT YOU MAY WORK ON

K1X

Data Engineer

Chicago, IL · On-site +1

$118K - $141K/yr

... and technology strategy. About The Role We are seeking a Data Engineer to design, build, and ... Fully Remote Opportunity * Healthcare Benefits and 401K * Growing Startup Culture

K1X

Data Engineer

Chicago, IL · Remote

$117K - $140K/yr

... and technology strategy. About The Role We are seeking a Data Engineer to design, build, and ... Fully Remote Opportunity * Healthcare Benefits and 401K * Growing Startup Culture

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Showing results 21-40

All JobsTechnology Strategy JobsRemote Technology Strategy JobsRemote Technology Strategy Jobs in Chicago, IL

Remote Technology Strategy information

See Chicago, IL salary details

$55.6K

$103.9K

$154.5K

How much do remote technology strategy jobs pay per year?

As of Aug 21, 2026, the average yearly pay for remote technology strategy in Chicago, IL is $103,937.00, according to ZipRecruiter salary data. Most workers in this role earn between $68,500.00 and $139,100.00 per year, depending on experience, location, and employer.

What is the difference between Remote Technology Strategy vs Remote IT Consultant?

AspectRemote Technology StrategyRemote IT Consultant
CredentialsTypically requires a degree in technology, business, or related fields; certifications like PMP or TOGAF are commonOften holds certifications like CompTIA, Cisco, or Microsoft; may have specialized technical certifications
Work EnvironmentFocuses on strategic planning, technology roadmaps, and aligning tech with business goals; involves collaboration with leadershipProvides technical support, troubleshooting, and implementation services; works directly with clients or internal teams
Industry UsageUsed across industries for planning and aligning technology initiatives remotelyCommonly engaged in technical projects, support, and consulting remotely in various sectors

Remote Technology Strategy professionals focus on high-level planning and aligning technology with business objectives, often working with leadership. In contrast, Remote IT Consultants provide technical support and implementation services. Both roles require relevant certifications and can be performed remotely, but their core responsibilities differ significantly.

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

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

What are popular job titles related to Remote Technology Strategy jobs in Chicago, IL?

For Remote Technology Strategy jobs in Chicago, IL, the most frequently searched job titles are:

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

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

Remote Technology Strategy jobs near you

Lead Solutions Architect (Remote)

Inspira Financial

Oak Brook, IL • On-site, Remote

Full-time

Posted 10 days ago

Inspira Financial rating

7.8

Company rating: 7.8 out of 10

Based on 22 frontline employees who took The Breakroom Quiz

Job description

The Lead Solution Architect serves as a senior technical leader responsible for shaping architecture strategy, guiding cross-portfolio technology decisions, and ensuring alignment between business objectives and technology investments. This role provides architectural leadership across multiple product teams, programs, and business capabilities while establishing standards, reusable patterns, and long-term roadmaps that enable scalable, secure, and maintainable solutions.
The Lead Solution Architect operates as a trusted advisor to business and technology leaders, influences enterprise technology direction, mentors architects and technical leaders, and helps drive architecture consistency, governance, and engineering excellence across the organization.
Key Responsibilities
Architecture Strategy & Leadership
  • Define and evolve architecture roadmaps, target-state architectures, and strategic technology direction for one or more business domains.
  • Translate business strategy into practical technology strategies, architectural capabilities, and implementation roadmaps.
  • Provide architectural leadership across multiple concurrent initiatives, ensuring solutions align with enterprise objectives and architectural principles.
  • Evaluate emerging technologies, industry trends, and vendor capabilities to identify opportunities and risks.

Enterprise & Portfolio Architecture
  • Guide architecture decisions that span products, platforms, integrations, data domains, and shared services.
  • Resolve architectural conflicts, competing priorities, and cross-team design tradeoffs.
  • Ensure solutions support long-term business goals while balancing cost, risk, complexity, and delivery objectives.
  • Lead architectural planning for modernization, platform evolution, technical debt reduction, and operational resiliency.

Governance & Standards
  • Establish and maintain architecture standards, reference architectures, design patterns, and decision frameworks.
  • Lead architecture reviews and governance activities for strategic initiatives and high-impact technology decisions.
  • Promote consistency, reusability, supportability, and security across the technology landscape.
  • Drive use of architecture decision records (ADRs), standards, and documentation practices.

Risk Management & Operational Excellence
  • Identify and proactively address architectural risks, dependencies, constraints, and systemic weaknesses.
  • Ensure solutions appropriately address security, compliance, privacy, resiliency, recoverability, scalability, and operational support requirements.
  • Partner with security, infrastructure, operations, and engineering teams to ensure alignment with enterprise controls and operational standards.
  • Contribute to disaster recovery, business continuity, and platform resiliency planning.

Organizational Leadership
  • Mentor Solution Architects, technical leads, and engineering teams on architecture practices and decision-making.
  • Foster a culture of technical excellence, continuous improvement, and knowledge sharing.
  • Lead architecture communities of practice and contribute to architecture capability development across the organization.
  • Serve as a trusted advisor to senior technology and business leaders.

Business & Stakeholder Engagement
  • Partner with product, engineering, security, infrastructure, data, and business stakeholders to align technology investments with business priorities.
  • Communicate complex technical concepts effectively to both technical and non-technical audiences.
  • Influence strategic decisions through analysis of benefits, risks, constraints, and tradeoffs.
  • Support portfolio planning, investment decisions, and long-range technology strategy discussions.

Additional Interview Requirements:
As part of the evaluation process, candidates who progress beyond the initial screening will be required to complete a formal technical assessment to validate coding proficiency and technical competency.
Required Qualifications
  • Bachelor's degree in Computer Science, Information Technology, Engineering, or a related field, or equivalent combination of education and experience
  • 12+ years of experience in software engineering, solution architecture, enterprise architecture, or related technical leadership roles
  • Demonstrated success leading architecture across large-scale, cross-functional initiatives involving multiple systems, teams, and business domains
  • Deep understanding of application architecture, integration patterns, APIs, event-driven architectures, distributed systems, data architecture concepts, and cloud-native design principles
  • Experience establishing architecture governance processes, standards, reference architectures, and reusable patterns
  • Experience designing and governing solutions on modern cloud platforms, preferably Microsoft Azure
  • Strong understanding of security, compliance, resiliency, observability, and operational readiness practices
  • Exceptional communication, facilitation, stakeholder management, and influence skills

Preferred Qualifications
  • Experience in financial services or another highly regulated industry
  • Experience influencing enterprise technology strategy and multi-year roadmaps
  • Experience mentoring architects and leading architecture communities of practice
  • Familiarity with enterprise architecture frameworks, architecture repositories, and capability-based planning approaches
  • Relevant cloud, architecture, security, or integration certifications

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