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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.

• 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.

• 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.

• 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 organization’s mission, vision, values, and strategic goals across all verticals.

• Bachelor’s Degree in Information Technology, Computer Science, or related field. Advanced degree (MBA or Master's) 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.

• 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.