Jobs › Wintrust

Senior Cloud Solutions Architect

Wintrust · Rosemont, IL · $117,000–$158,000 a year · Full time

Posted Aug 17, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about an architecture decision you made that turned out to be wrong. How did you find out and what did you do?

What they are checking: Honesty and willingness to revisit their own designs.

This is based in Rosemont inside a bank's own technology organization rather than a cloud vendor or consultancy. What draws you to that, and what would you want to know about the current estate?

What they are checking: Self-placement, and whether they ask about technical debt before joining.

What would you do

The posting names the Well-Architected Framework and asks you to maintain a cloud roadmap. How do you keep a roadmap useful when business priorities change every quarter?

What they are checking: Whether roadmaps are living documents to them or shelf decoration.

You would drive the transition to fully automated infrastructure using tools like Terraform, Pulumi or CloudFormation. What is the hardest part of getting a team off manual configuration?

What they are checking: The organizational half of infrastructure as code, which is where it usually stalls.

You would set standards and statements of direction for company IT architecture. How do you get engineering teams to follow a standard they did not write?

What they are checking: Adoption, which is the difference between an architect and a document author.

A team wants to ship something that works but does not fit the architecture you set. How do you handle it?

What they are checking: Where they bend and where they hold, which reveals whether they are practical.

About the work

This role covers architecture across Amazon Web Services, Azure and Google Cloud Platform. How do you decide which workload belongs on which platform rather than defaulting to one?

What they are checking: Real multi-cloud reasoning instead of a preferred vendor.

You would establish guardrails for resource provisioning to keep security compliance in place. Walk me through a guardrail you built and what it actually prevented.

What they are checking: Concrete preventive controls rather than policy language.

This is a bank running sixteen charters. How does financial services regulation change the way you design a cloud environment?

What they are checking: Regulated-industry architecture, not general cloud design.

Migration strategy here covers re-hosting, re-platforming and re-architecting. How do you decide which a given legacy workload deserves?

What they are checking: Cost and risk judgment, since re-architecting everything is not realistic.

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The full job description

As published by Wintrust.

Wintrust provides community and commercial banking, specialty finance and wealth management services through its 16 bank charters and nine non-bank businesses. Wintrust delivers the sophisticated solutions of a large bank while staying true to the relationship-focused, personalized service of our community banking roots. We serve clients in all 50 states with more than 200 branch banking locations in Illinois, southwestern Florida, northwestern Indiana, west Michigan and southern Wisconsin and commercial banking offices in Chicago, Denver, Milwaukee, Grand Rapids, Mich., and in key branch banking locations throughout Illinois. Our people are the heart of our business and we are proud to rank consistently as a top place to work. Wintrust is a $66 billion financial institution based in Rosemont, Illinois, and listed on the NASDAQ Global Select Market under the symbol “WTFC.” Why join us? • An award-winning culture! We are rated a Top Workplace by the Chicago Tribune (past 12 years) and Employee Recommended award by the Globe & Mail (past 6 years) • Competitive pay and discretionary or incentive bonus eligible • Comprehensive benefit package including medical, dental, vision, life, a 401k plan with a generous company match and tuition reimbursement to name a few • Promote from within culture Why join this team? • This position has the opportunity to interface with and have a positive impact on multiple areas of Wintrust's business • We hold ourselves accountable to high standards, share wins, operate ethically, and have fun The Senior Cloud Architect helps to develop, maintain and govern Cloud architecture and the technology portfolio roadmaps across multiple Cloud application portfolios. Work across all architectural disciplines, including business (processes/activities/functions/information), application, data, integration, infrastructure, security and technology, and creates and maintains related best practices, patterns and reference architectures. The Senior Cloud Architect facilitates the development, implementation and maintenance of standards, guidelines and statements of direction for company IT system architectures, establishing a framework that constrains the design of systems for the purpose of integration of Hybrid Cloud systems and accessibility of data supporting various interdependent business processes and functions. Works closely with applications system architects, data architects, network technologists, business analysts and other stakeholders to ensure consensus on direction, in line with global strategies for future integration. Focus is often on establishing and maintaining a reusable Cloud architectural blueprint to reduce business costs, improve time-to-market of products and services, improved product quality, and customer satisfaction. Design, architect and implement new Cloud capabilities that address any gaps and provide integrated end to end scalable, enterprise-class services. Has a proven capability to analyze existing products and infrastructure, understand how to leverage existing investments and introduce best of breed, emerging Cloud infrastructures: IaaS, PaaS and SaaS across Microsoft Azure, Amazon Web Services (AWS), Google Cloud Platform (GCP) or other major cloud computing services. What You’ll Do • Architectural Blueprinting: Lead the design of scalable, highly available, and fault-tolerant systems and ecosystems in AWS, Azure and GCP. • Cloud Strategy: Develop and maintain the cloud roadmap, ensuring alignment with business goals and industry best practices (Well-Architected Framework) • Governance & Compliance: Establish guardrails for resource provisioning to ensure security compliance (HIPAA, GDPR, SOC2, etc.) and operational consistency. • Infrastructure as Code (IaC): Drive the transition towards a fully automated environment using tools (e.g. Terraform, Pulumi, or CloudFormation) to eliminate manual configuration drift. • Migration Orchestration: Lead the strategy for migrating legacy workloads to the cloud (Re-Hosting, Re-Platforming, and Re-Architecting). • CI\CD Integration: Partner with DevOps teams to integrate architectural patterns into automated deployment pipelines. • Performance tuning: Identify bottlenecks in current architecture and implement caching, CDN, and load-balancing strategies to optimize latency. • Technical leadership: Act as final escalation point for complex cloud technical hurdles. • Stakeholder Communication: Translate complex architectural decisions into business terms for C-suite executives and non-technical stakeholders. • Mentoring: Level up our Cloud Engineers through design reviews, pair programming and architectural workshops. • Contribute to the definition of architectural cloud strategies and plans for enterprise’s information technology. Conduct assessments, studies, and/or surveys to obtain data; analyzes data to advise and recommend cloud solutions. • Participate in key planning sessions to advise and clarify capabilities, limitations, and trade-offs of established enterprise architectures and technology in general. • Develop and maintain a strong understanding of enterprise’s businesses. Understand current and future needs of the business and align cloud technology roadmap to deliver upon those needs. • Identify, analyze, and communicate cloud architecture and integrations options and make recommendations to management. • Analyze project requirements with development teams and influence the appropriate technical design at the project level maintaining consistency with architecture vision. • Develop architectural diagrams that document project plans and production systems. • Develop documentation on recommended cloud solutions that would include relevant research, cost analysis data, risk information, implementation strategies and industry positions. Conduct industry research and evaluations in order to develop cloud solutions to resolve business needs. • Contribute to the Architecture Standards and Review Board (ASRB); ASRB capabilities, documentation and processes • Responsible for third-party vendor relationships related to area of responsibility. Qualifications • 10+ years of experience. 7+ years of experience in Software Engineering or System Administration, with at least 5+ years of Cloud Architecture experience. IT Cloud Architecture, Design, and Implementation utilizing Microsoft Azure, AWS, GCP. • Cloud Proficiency: Expert-level mastery of AWS, Azure and or GCP. Deep knowledge of core services (Computing, Storage, Database, Networking, Cloud Governance). • IaC Mastery: Proven experience managing production environments via IaC tools (e.g. Terraform, Ansible etc.) • Containerization: Deep expertise in Kubernetes (EKS/AKS/GKE) and Docker orchestration. • Networking: Strong understanding of VCPs, Subnets, Transit Gateways, DNS, and Hybrid-Cloud connectivity. • Multi-Cloud Experience: Experience designing redundancy across two or more cloud providers. • Serverless Architecture: Proven track record of deploying event-driven architecture using Lambda, Azure Functions, or Google Cloud Functions. • Deep understanding of cloud computing technologies, applications, and trends. • Strong cloud migration and cloud management skills with emphasis on cloud resource management and security. • Must have excellent written and verbal communication skills, along with interpersonal, customer service skills and leadership skills. • Strong knowledge of software development life cycle (SDLC), architecture frameworks, design patterns, and programming concepts. • Experience in designing and implementing enterprise-scale cloud systems and applications. • Experience in project management, including budget and time management. • Ability to work effectively in a fast-paced, dynamic environment with changing priorities. • Certifications or 10+ years of experience across a wide range of Information Technology disciplines. • Must have at least one of the following Certifications: • Professional level Cloud Certifications (e.g. AWS Certified Solutions Architect—Professional) • Certifications in Architecture Frameworks (e.g TOGAF, Zachman) Benefits Medical Insurance • Dental • Vision • Life insurance • Accidental death and dismemberment • Short-term and long-term Disability Insurance • Parental Leave • Employee Assistance Program (EAP) • Traditional and Roth 401(k) with company match • Flexible Spending Account (FSA) • Employee Stock Purchase Plan at 5% discount • Critical Illness Insurance • Accident Insurance • Transportation and Commuting Benefits • Banking Benefits • Pet Insurance Compensation The estimated salary range for this role is $117,000.00 - $158,000.00, along with eligibility to earn an annual bonus. Actual salaries may vary based on several factors, such as a candidate’s qualifications, skills and experience. From our first day in business, Wintrust has been proud to serve a variety of unique communities and people from all walks of life. To build a company that reflects the communities we serve, we believe that fostering a unique and inclusive workplace where everyone feels valued and empowered to succeed will support our ongoing success. Wintrust Financial Corporation, including community banking and financial services subsidiaries, is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, age, national origin, disability, veteran status, genetic information, and other legally protected categories.

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