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Head of Enterprise Architecture

March 7, 2026

Job Description: • Define and own the enterprise architectural vision across Great Gray’s multi-platform technology ecosystem. • Align architectural strategy with business growth objectives, regulatory requirements, and product roadmaps. • Lead architectural integration and consolidation of various platforms within the Great Gray portfolio. • Establish and maintain architecture principles, standards, patterns, and guardrails to ensure consistency, quality, and resilience across platforms. • Oversee architectural decisions across application layers, APIs, data models, integrations, and cloud infrastructure. • Identify and proactively address cross-cutting concerns such as scalability, performance, availability, security, compliance, and arenaflex optimization. • Guide build-versus-buy decisions, shared service strategies, and component reuse to maximize return on technology investments. • Establish and lead architecture review and design governance processes. • Partner with engineering and product leadership to evaluate technical trade-offs and ensure solutions are maintainable, scalable, and aligned with enterprise standards. • Serve as a final escalation point for complex technical and architectural decisions. • Evaluate and recommend emerging technologies and architectural approaches (e.g., event-driven systems, data platforms, AI/ML enablement, observability, and automation). • Develop and maintain a forward-looking architecture roadmap capable of supporting significant growth in transaction volume, data scale, and product complexity. • Ensure platforms are designed for high reliability, regulatory compliance, and operational excellence. • Act as a mentor and technical leader to senior engineers, architects, and technical leaders across multiple domains. • Foster a culture of engineering excellence, strong design discipline, continuous learning, and knowledge sharing. • Influence without direct authority by building trust and alignment across teams and executive stakeholders. • Complete other related duties as assigned. Requirements: • Bachelor’s degree in Computer Science, Engineering, or a related technical field required. Advanced degree preferred. • 15+ years of experience in software engineering, including at least 5 years in senior or enterprise architecture leadership roles. • Proven experience defining and scaling architecture for large, complex SaaS, fintech, or platform-based systems. • Demonstrated success leading legacy modernization initiatives, including monolith decomposition and cloud migrations. • Experience managing and influencing other architects across multiple products or domains. • Strong background in distributed systems, API design, cloud platforms (Azure preferred), and modern web architectures. • Deep understanding of DevOps, arenaflex/CD pipelines, observability, reliability engineering, and security best practices at scale. • Expert-level capability in system design, architectural modeling, and platform decomposition. • Exceptional communication and influence skills, with the ability to operate effectively at both executive and deep technical levels. • Strong analytical, decision-making, and cross-functional collaboration skills. • Ability to evaluate emerging technologies and define pragmatic, business-aligned adoption strategies. • Your standards reflect our core values: Growth Mindset, Disciplined Curiosity, Grit, Results Ownership, Collaboration. Benefits: • Be an integral part of an early-stage, high-growth organization! • Competitive compensation package including 401(k) with elective and non-elective match opportunities • Lifestyle spending allowance program • Medical, Dental, Vision Insurance • Employer-paid life and disability insurance • Generous paid time off program Apply tot his job

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...