Search for Director of Infrastructure roles in Chicago, with a focus on hybrid work environments, requiring 6+ years of experience, preferably in the insurance sector, and expertise in Microsoft 365 and Azure AD.

Okay, I've searched for Director of Infrastructure roles in Chicago within hybrid environments for candidates with over 6 years of experience in the insurance sector, and expertise in Microsoft 365 and Azure AD. I have found 23 positions for you.

Director of Infrastructure

Chicago, IL

Hybrid

6 years + Experience

Insurance

Can you help me to analyze the job description and company culture?

Sure. Here's the analysis:

Job Analysis:

The Director of Infrastructure is fundamentally hired to steer the transformation of a rapidly growing insurance company's IT infrastructure, ensuring it is modern, secure, and scalable. The primary responsibilities include overseeing endpoint management for over 3,000 devices, driving the adoption of Microsoft Entra ID, standardizing networking infrastructure, and managing enterprise-wide Microsoft 365 implementation. This role requires not just technical prowess, but also a strategic mindset to navigate the complexities involved in mergers and acquisitions, integrating new entities into the existing IT framework. Success in this role will look like achieving a seamless transition from legacy systems to standardized solutions, enabling enhanced operational efficiency and security across a multi-agency environment. Moreover, this position demands strong leadership and communication skills to effectively collaborate with various stakeholders, including IT, InfoSec, and business teams, underscoring the importance of building relationships and fostering a service-oriented culture in a dynamic setting.

Company Analysis:

Evolution operates within the technology recruitment consultancy industry, emphasizing a relationship-driven and quality-focused approach. As a fast-growing entity with a focus on Python and tech placements across various sectors, the company is well-positioned as a partner for both candidates and employers. The culture appears to prioritize innovation, collaboration, and continuous professional development, which reflects in their awards for training and support. For someone considering the Director of Infrastructure role, it's vital to understand that the company values adaptability and the ability to engage deeply with the communities they serve. This particular position will have a significant impact on shaping the IT strategy to support the company’s growth ambitions, as it engages not only with internal teams but also with newly acquired agencies. The role is strategic in nature and offers the potential for high visibility among leadership, making it crucial for the candidate to align with the company’s ambitious and collaborative culture to thrive.

Mock up some interview questions based on the job description.

Absolutely. Here are some mock interview questions that could come up:

Tell me about a time when you had to lead a major IT transformation project. What challenges did you face, and how did you overcome them?
Can you describe your experience with Microsoft 365 implementations? What were the key factors for success in those projects?
How do you approach collaboration with different teams, especially in a fast-paced and multi-agency environment?
Provide an example of how you've standardized infrastructure processes across multiple sites. What was your strategy?
How would you manage the transition from legacy systems to modern tools in a way that minimizes disruption?
What strategies would you employ to drive full adoption of Microsoft Entra ID within the organization?
Imagine you are facing resistance from a team regarding a new IT policy. How would you handle this situation?
Suppose you are tasked with consolidating various networking solutions into a streamlined architecture. What steps would you take to ensure this is successful?
Given the importance of security in this role, how would you prioritize security initiatives while managing infrastructure needs?
What excites you about leading infrastructure initiatives at a company in the insurance sector?
How do you keep yourself updated with the latest trends in IT infrastructure and security?
What do you see as the biggest challenge in overseeing endpoint management for over 3,000 devices?
If hired, how would you approach building relationships with newly acquired agencies to improve integration with the existing IT infrastructure?
What questions do you have for us about the cultural fit and work environment at this company?
What tools or methodologies do you find most effective for managing helpdesk workflows and improving service delivery?

Job Details

Overview Company

Director of Infrastructure

Evolution Recruitment Solutions, USA

2 days ago

Highlight

HybridFull-time6+ yearsDirector

Summary

Evolution USA is seeking a Director of Infrastructure to join their team in Chicago, IL. The role involves leading the design, standardization, and operational management of core IT infrastructure and services in a fast-growing insurance company.

About the Role

As Director of Infrastructure, you will oversee endpoint management across 3,000+ devices, drive full adoption of Microsoft Entra ID, standardize networking infrastructure, and own enterprise-wide Microsoft 365 implementation. You will collaborate with IT, InfoSec, M&A integration teams, and business stakeholders to ensure seamless delivery, security, and scalability of services.

About You

Required:

6+ years of experience in IT infrastructure leadership roles, preferably within mid-to-large enterprise environments.
Strong background in insurance, financial services, or similarly regulated industries.
Demonstrated success leading multi-site or multi-brand IT standardization, ideally in the context of M&A integration.
Deep expertise in Microsoft Intune, Microsoft 365, Azure/Entra ID, and endpoint security.
Experience driving network modernization and vendor consolidation projects.
Track record of hands-on leadership and excellent communication skills.

Benefits

Competitive compensation with high-impact visibility.
Strong benefits package.
Opportunity to influence infrastructure strategy and join a collaborative, no-ego tech leadership team.

Evolution Recruitment Solutions, USA

Evolution is an award-winning specialist tech recruitment consultancy with offices in USA, Singapore, Sydney, Germany and UK. Founded in 2000 we have helped thousands of technology professionals secure their next Permanent, Contract or Interim position with leading companies, ranging from SME to multinationals.

Here in the United States we are focusing on Python, placing candidates across the three pillars of Software Engineering, Data Engineering and Data Science. We engage and build relationships with the communities that we serve through a content led approach in the form of podcasts, articles and video marketing.

Our professional, relationship driven and quality focused approach provides a platform to build true partnerships with our clients and candidates.

Evolution have received multiple awards in recognition of the outstanding training, development and support we provide to our Consultants which in turn results in a higher level of service for both applicants and candidates.

Evolution could be a great place for you if you want to work for an innovative tech recruitment business that is ambitious and truly believes in collaboration.

Chicago, IL