IT Lead

TailWind  Voice & Data is seeking an experienced Information Technology Lead to serve as the internal owner of our technology operations. In this role, you will manage our relationship with an external Managed Service Provider (MSP), oversee business-critical platforms, and lead a small internal team that includes Stage & Configuration. You will be the bridge between our business and its technology ecosystem  holding vendors accountable, delivering data-driven insights to leadership, and driving continuous improvement across all systems and processes. This is a high-ownership role that requires strong technical fundamentals, sound judgment, and the communication skills to translate complex technology topics for non-technical stakeholders.

• Health & Wellness Benefits-  Medical, Dental, Vision, Basic Life Insurance, Healthiest You! and several supplemental benefit options
  
• Retirement-  Matching 401(K) to help plan for the future 
  
• Time Off- Accrued PTO, Paid Holidays, Floating Holiday, Birthday PTO
• Compensation - $65,000 to $80,000 DOQ 

About the Role: 

1. Leadership/Management/Accountability (“LMA”) – Manage a designated team of IT members, including Stage & Configuration. This includes involvement in hiring, evaluating, training, mentoring, correcting, promoting, and terminating current and prospective team members based on TailWind’s core values and standard policies and procedures. It requires conducting Quarterly Conversations with each team member.
2. MSP & Vendor Relationship Management- Serve as the primary internal point of contact for the external IT company (MSP). Hold the MSP accountable to service level agreements (SLAs), response times, and deliverables. Know when to intervene and assist. Manage technology vendor contracts, renewals, and service agreements. Serve as the escalation authority when the MSP fails to meet expectations. Evaluate vendor performance and make recommendations for changes when necessary. Having clear ownership between inside and outside resources.
3. Systems & Platform Oversight- Own and oversee all business-critical platforms including CRM, RMM, Microsoft 365, and Active Directory. Manage user access, permissions, and system configurations across all platforms. Oversee employee onboarding and offboarding from a system and access perspective. Drive software upgrades, system cutovers, and new platform rollouts. Develop & maintain an accurate database of software licenses and cloud subscriptions to ensure compliance and cost-effective utilization of resources.
4. Asset Management & Lifecycle Planning- Conduct & Maintain equipment inventory, oversee ordering, and manage laptop replacement programs. Ensure systems are properly integrated, maintained, and aligned with business needs.
5. Reporting & Data Analytics-. Lead, own, and manage the reporting pipeline from technology platforms to organizational leadership. Assist with the design, development, and automated reports from ERP, CRM, RMM, and other business systems. Utilize SQL and database knowledge to query, validate, and interpret data. Deliver clean, accurate, and actionable insights to department managers and leadership. Ensure data integrity across all managed systems and report outputs. Identify trends and anomalies in system data and communicate findings proactively.
6. User Support & Relationship Based Service- Deliver responsive troubleshooting and "help desk" support to employees, prioritizing issues that directly impact productivity of the employee or client needs. Engage staff with empathy and clarity, fostering a professional culture where technology is viewed as a bridge to success rather than a barrier.
7. Continuous Improvement- Actively participate in improving IT support processes and policies. Identify recurring issues and suggest changes like updates to image configurations, user training needs, or new support tools to reduce future problems. Help enforce IT security policies and best practices such as proper data handling, regular updates/patching through day-to-day support and user education, as well as documentation. Demonstrate familiarity with Change Management principles, including assessing risk, coordinating approvals and ensuring changes are properly communicated and documented to minimize disruption to business operations.  Communicate technology strategy and status clearly to non-technical leadership.
8. Cyber Security & Disaster Recovery- Identify and assess vulnerabilities from both digital threats (cyberattacks, ransomware) and physical threats (outages, natural disasters). Ensure backups are current, secure, immutable, and protected from ransomware to guarantee reliability during restoration. Develop, document, and regularly test incident response and disaster recovery plans.
9. Other Duties as Assigned
   

Core Values

• Dynamic
• Work Ethic
• Smart and Talented
• Accountable
• Pace
• Client Focused

Competencies

• Vendor & Relationship Management
• Systems Ownership & Accountability
• Data Literacy & Analytical Thinking
• Problem Solving & Escalation Management
• Strategic Thinking & Planning
• Organization & Attention to Detail
• Communication & Stakeholder Management

Required Education & Experience

• 3–5 years of experience in IT management, systems administration, or related field.
• Experience working in a small to mid-sized organization with a lean IT structure.
• Proven experience managing an MSP or external IT vendor relationship.
• Strong working knowledge of Active Directory and Microsoft 365 Admin Center
• Proficiency with Windows 11 and the Microsoft 365 ecosystem, including Microsoft Business Central.
• Experience with RMM (Remote Monitoring and Management) platforms.
• Experience with CRM platforms and managing automated reporting workflows.
• Solid understanding of databases and SQL for reporting and data validation.
• Experience with equipment inventory management and procurement oversight
• Experience building and managing a data warehouse, data analytics and delivering executive level reporting.
• Strong decision-making ability and comfort with escalating to management and leadership.
• Strong communication skills and business acumen to align business objectives.
• Demonstrated ability to manage employee onboarding and offboarding from a systems perspective.
• Familiarity with IT governance and compliance frameworks.
• Industry relevant certifications preferred (CompTIA, Microsoft, ITIL, etc.).
• Solid understanding of the whole IT landscape with an emphasis in data driven thinking.

Salary : $65,000 - $80,000