Chief Technology Lead – Strategy, Security & IT Operations

Insight Global

Milwaukee (WI)

On-site

USD 175,000 - 200,000

Full time

6 days ago

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Job summary

Insight Global seeks a strategic, hands-on Vice President of Technology to lead IT operations, infrastructure, cybersecurity, enterprise systems, and technology strategy on-site in Milwaukee. Partner with executive leadership to drive innovation, operational excellence, and scalable technology solutions across a growing landscape and snow management business.

The role requires a strong track record in IT leadership, cloud/hybrid environments, ERP/BI integrations, and vendor management.

Qualifications

Bachelor's degree required in IT, CS, or related field.
10+ years of progressive IT leadership experience.
Strong expertise in infrastructure, networking, cybersecurity, and IT operations.
Experience managing cloud and hybrid Microsoft environments.
Knowledge of ERP systems, BI tools, and integrations (Power BI, NetSuite preferred).
Experience with vendor management, contract negotiations, and enterprise technology planning.
Property management industry experience a plus.
Relevant certifications (ITIL, PMP, CISSP, Security+, etc.) are beneficial.

Responsibilities

Develop and execute the organization's technology strategy and roadmap.
Oversee IT operations, infrastructure, networking, cybersecurity, and disaster recovery.
Manage technology budgets, vendor relationships, software licensing, and procurement.
Lead major system implementations, upgrades, and technology initiatives.
Partner with business leaders to improve processes, reporting, automation, and data integrity.
Ensure secure, reliable, and scalable technology solutions across the organization.
Direct help desk and end-user support functions.
Stay current on emerging technologies and drive continuous improvement.