66degrees

Technology

EnterpriseArchitect

$225–350k ~AI est. Chicago, Illinois, United States
Market Sentiment
HIGH DEMAND

Neural analysis suggests this role is
optimal for Mid+ candidates.

The Brief

“Enterprise Architect at 66degrees. Skills: Legacy modernization, Cloud architecture, AI transformation, Enterprise architecture. Partner with stakeholders to scope modernization. Plan large-scale modernization initiatives”

What You'll Achieve.

Quantifiable outcomes; Reduction of risk; Reduction of cost; Early cash flow realization; Accelerate development velocity

Industry & Context.

Technology
Problems you'll solve

Technical debugging; Root cause analysis

What They're Looking For.

Must Have

12+ years experience designing systems, 12+ years experience operating systems, 12+ years managing transformation programs, Grew career from legacy systems, Bachelor's degree or equivalent experience

Nice to Have

GCP/AWS Customer experience, Experience with COBOL, Experience with JCL, Experience with DB2, Experience with monolithic systems

What You'll Do.

Partner with stakeholders to scope modernization

Plan large-scale modernization initiatives

Lead technical decomposition of systems

Ensure functional parity

Analyze extractable processes

Build incremental value realization plans

Build cash flow forecast

Collaborate with leadership teams

Ensure secure approaches

Ensure reliable approaches

Ensure scalable approaches

Prevent technical debt

Accelerate development velocity

Oversee training teams

Ensure production releases tested

Own recommendation for release go-live

How You'll Work.

Team & Collaboration

Client executive stakeholders; Client CFO team; Client Security leadership; Client Networking leadership; Client Data leadership; Client CXO team

Communication Scope

Executive presentations; Strategy sessions

Process & Methodology

Roadmap planning, Release management

Full Job Description

Overview of 66degrees 66degrees is an end-to-end AI transformation partner that guides enterprises from complex business challenges to clear, quantifiable outcomes. Our company is the culmination of several successful firms, each a leader in its own right in cloud, artificial intelligence, and data. This convergence of talent and expertise is how we help businesses reach their own "inflection point," where chaotic data becomes a strategic asset, complexity becomes clarity, and AI becomes an engine for growth. Our ultimate vision is to be the catalyst for a future where every business operates as an intelligent enterprise, with autonomous systems unlocking human potential. At 66degrees, we believe in thriving through challenges and winning together. These values not only guide us in achieving our goals as a company but also for our people. We are dedicated to creating a significant impact for our employees by fostering a culture that sparks innovation and supports professional and personal growth along the way. Overview of Role As an Enterprise Architect, you are a strategic modernization leader with technical credibility. You bridge the gap between high-level Google Cloud (GCP) value engineering and the hands-on delivery of modernized legacy estates. Utilizing the 66degrees "Paradigm" accelerator, you will lead clients through the reduction of risk and cost for mainframe rewrites, translating decades of complex business logic—often buried in COBOL or ERP code—into scalable, cloud-native architectures, ready for AI. This is a career defining moment in the industry and this role puts you in the center. Responsibilities Strategic Solutioning: Partner with client executive stakeholders to scope and plan large-scale legacy modernization initiatives. Legacy Archaeology Assessment: Lead the technical decomposition of complex, multi-phase transaction systems to ensure functional parity between legacy source code and extracted business logic and data processes. Planning: Lea

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