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Vice President of Technology

Winter Services

Job Location:

Milwaukee, WI - USA

Monthly Salary: Not provided by the employer

Posted: 26 September 2026 (Yesterday)

Application Deadline: 24 December 2026

Vacancies: 1 Vacancy

Job Summary

Seeking a strategic hands-on technology leader to oversee enterprise technology IT operations infrastructure cybersecurity and end-user support for a growing organization. This executive will drive technology strategy lead IT team(s) manage vendor partnerships and ensure reliable secure and scalable technology operations that support business growth while managing expenses.

Key Responsibilities Vice President of Technology:

Responsible for the evaluation of current technology and the future strategic planning/development of technology infrastructure information system assets data management and enterprise security.
Lead IT operations infrastructure networking and cybersecurity functions including managing day-to-day operations managing endpoint devices MDM and disaster recovery plans
Ensure system reliability security and business continuity through implementation of cyber security policies meeting industry regulations and standards creating SOPs and enforcing policies.
Establish the objectives for operations maintenance and enhancement of the IT systems and a plan for continuous improvement of the service levels.
Develop and manage the IT operating budget and capital budget technology roadmap capital planning licensing renewals inventory control and cost-control initiatives.
Evaluate and manage technology vendors managed service providers software partners contracts service level agreements and technology-related procurement.
Provide executive-level leadership & project management for major system & software implementations ensuring appropriate planning change management communication testing training adoption and post-implementation evaluation.
Partner with department leaders to identify opportunities for automation process improvement reporting data integrity workflow optimization and enhanced user experience.
Management and streamlining of company uploads/downloads related to customer portals to ensure billing data integrity and optimal workflows with NetSuite
Remain current on and drive continuous improvement and adoption of emerging technologies. (AI AEO vs SEO etc)
Direct help desk and end-user support services.

Supervisory Responsibilities Vice President of Technology:

Lead mentor and develop IT staff and technology partners to ensure high-quality support accountability collaboration and professional growth.
Assign prioritize and assist with department work projects support requests and operational responsibilities.
Participate in hiring onboarding training performance evaluations corrective action and employment decisions in accordance with company policy.
Establish performance expectations and standards for department employees to achieve or exceed performance metrics.
Develop succession planning and cross-training strategies to support operational continuity and reduce single points of failure.
Foster a culture of continuous improvement service-oriented IT that balances security compliance responsiveness innovation and practical business support.
Represent the technology function in executive board client vendor audit compliance and strategic planning discussions as requested.

Other Expectations Vice President of Technology:

Strong ability to be a hands-on leader as well as handling executive level job responsibilities.
Demonstrate a collaborative approach to supporting clients employees leaders and business partners.
Maintain confidentiality and protect sensitive company employee and client data without compromising daily productivity.

Proven ability to lead teams manage vendors and communicate effectively with executive stakeholders.

Ability to clearly articulate complex systems and system strategies with team members to build support and understanding of objectives.

Ability to evaluate risk make sound recommendations and balance security requirements with business needs.
Strong analytical problem-solving project management and decisive decision-making skills.
High degree of integrity discretion confidentiality and professionalism.
Act as a trusted advisor and technology leader who promotes accountability transparency and practical solutions.
Support the aggregate organizations mission vision values and strategic goals across all verticals.

Education and Experience Vice President of Technology:

Bachelors Degree in Information Technology Computer Science or related field. Advanced degree (MBA or Masters) preferred.
Certifications such as ITIL PMP CISSP Security Microsoft ERP or BI-related credentials are a plus
10 years of progressive IT leadership experience.
Strong background in infrastructure networking cybersecurity and IT operations.
Experience managing cloud and hybrid Microsoft environments across all aspects of IT.
Knowledge of ERP platforms business intelligence tools and system integrations. (PowerBI NetSuite Etc)
Proficiency with Microsoft Office Suite and related business collaboration security and reporting tools.
Proficiency with Customer Management Portals including but not limited to Corrigo Coupa Fexa FM Pilot and Service Channel.
Strong working knowledge of Data Warehouse Data Lake SnowFlake or equivalent.
Experience implementing and managing customer-facing web and mobile applications
Highly proficient in contract negotiations contract maintenance and vendor management.

BENEFITS:

Competitive salary based on experience
Medical and dental insurance benefits
Company-sponsored Group Term Life & Short-Term Disability insurance
401k retirement plan with company match
Paid vacation and holidays

Winter Services LLC is an equal opportunity employer that takes pride in creating a diverse and inclusive workplace. The company complies with all applicable federal state and local fair employment practices law. Winter Services strictly prohibits and does not tolerate discrimination against employees applicants or any other covered persons because of age race religion color creed disability familial status sex (including pregnancy childbirth breastfeeding and related medical conditions) sexual orientation gender gender expression gender identity genetic information marital status national origin ancestry veteran or military status or any other characteristic protected by federal state or local law.

Required Experience:

Exec

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