Senior Technical Project Manager / vCIO

JOB DESCRIPTION

The Senior Technical Project Manager / vCIO is responsible for leading client-facing technology strategy, managing technical project delivery, and providing hands-on technical leadership across client environments. This role combines project ownership, client advisory, solution design, practical technical execution, and fast-paced decision making in a dynamic MSP environment.

This position requires someone who can quickly assess technical needs, client priorities, project risks, and business impact, then determine the right next step without unnecessary delays. The ideal candidate brings prior MSP experience, strong technical judgment, excellent communication skills, and the ability to lead projects while also stepping in directly to troubleshoot, validate, or assist with technical work when needed.

This role serves as a trusted technical advisor for clients and a dependable internal resource for project execution, technical planning, roadmap development, and escalation support. The successful candidate must be comfortable moving between executive-level client conversations, internal technical coordination, and hands-on work across Microsoft 365, Entra ID, cloud services, cybersecurity, endpoint management, networking, backup, server infrastructure, and business systems.

Requirements

BASIC QUALIFICATIONS

• 5+ years of professional IT experience in managed services, systems administration, systems engineering, network administration, technical project management, or a related technical role.

• Prior experience in an MSP or multi-client IT services environment strongly preferred.

• Hands-on experience supporting and implementing:

• • Microsoft 365, including Exchange Online, Teams, SharePoint, and OneDrive
  • Entra ID, including MFA, conditional access, identity, sign-in, and access troubleshooting
  • Windows 10/11 and Windows Server environments
  • Networking fundamentals, including TCP/IP, DNS, DHCP, VPNs, VLANs, firewalls, and wireless networks
  • Endpoint management, security tools, backup solutions, and cloud services

• Experience managing or leading technical projects involving infrastructure, Microsoft 365, cybersecurity, endpoint management, cloud services, network changes, vendor transitions, or client onboarding.

• Ability to assess technical issues quickly and make sound decisions in a fast-paced environment.

• Strong troubleshooting skills and ability to assist directly with complex technical issues when needed.

• Strong customer-facing communication skills, including phone, video, and in-person client meetings.

• Ability to explain technical concepts clearly to business owners, executives, users, vendors, and internal technical teams.

• Strong project coordination, documentation, prioritization, and follow-through skills.

• Experience with PSA, RMM, documentation, and project management tools such as ConnectWise, HaloPSA, N-able, Hudu, IT Glue, Microsoft Planner, or similar platforms.

• Comfortable balancing urgency, risk, budget, client expectations, technical standards, and resource availability.

PRIMARY RESPONSIBILITIES

Technical Project Management

• Lead assigned technical projects from planning through completion, including scope, timelines, milestones, risks, dependencies, and communication.
• Coordinate internal technical resources, client stakeholders, vendors, and third-party providers to keep projects moving.
• Track project status, blockers, change requests, client decisions, and follow-up items.
• Ensure projects are completed according to scope, security expectations, technical standards, documentation requirements, and client business needs.

vCIO and Client Technology Strategy

• Serve as a strategic technology advisor for assigned managed services clients.
• Lead client technology reviews, roadmap discussions, budget planning, and strategic planning meetings.
• Translate client business goals into practical IT recommendations, projects, budgets, and timelines.
• Identify risks, gaps, and opportunities through assessments, ticket trends, security reviews, lifecycle planning, and client conversations.

Hands-On Technical Leadership

• Provide hands-on technical leadership for client projects, assessments, escalations, and strategic initiatives.
• Assist with solution design, implementation, troubleshooting, testing, and validation when needed.
• Work with engineers and technicians to resolve technical blockers and maintain project momentum.
• Validate that completed work meets scope, documentation, security, and quality expectations.

Fast-Paced Decision Making and Communication

• Make timely, informed decisions in a fast-paced MSP environment with competing priorities.
• Quickly assess client needs, project risks, technical blockers, and operational impact.
• Determine practical next steps when information is incomplete, timelines are tight, or priorities shift.
• Communicate decisions, expectations, risks, and next steps clearly to clients, internal teams, vendors, and leadership.

Documentation and Team Support

• Maintain accurate project notes, client roadmaps, recommendations, meeting notes, and follow-up items.
• Ensure relevant documentation is stored in the company knowledge base.
• Contribute to project templates, client review processes, checklists, and internal standards.
• Support service desk and project team members by sharing technical context, troubleshooting approaches, and best practices.
• Other duties as assigned.

NICE TO HAVE

• Prior experience as a vCIO, Technical Account Manager, Senior Systems Engineer, Service Manager, Project Manager, or technical lead in an MSP environment.
• Experience leading QBRs, technology business reviews, roadmap meetings, or IT budget planning sessions.
• Experience with ConnectWise PSA, HaloPSA, Hudu, N-able, Microsoft 365, Azure, Entra ID, Intune, Fortinet, UniFi, VMware, Hyper-V, or similar MSP tools and technologies.
• Experience with Microsoft tenant onboarding, baseline configuration, security hardening, or tenant-to-tenant migrations.
• Intune and endpoint management experience.
• Cybersecurity assessment, remediation planning, or compliance support experience.
• Experience mentoring technicians or coordinating technical work across service and project teams.
• Certifications such as PMP, CAPM, ITIL, Microsoft certifications, CompTIA Security+, Network+, or similar credentials.

ON-CALL & ON-SITE EXPECTATIONS

• On-site visits are occasional and based on client or project needs.
• Candidate must be able to visit client sites in the Continental U. S. when hands-on work, project discovery, implementation, or client meetings require it.
• This role may assist with urgent project-related issues or escalations when needed.
• After-hours work may occasionally be required for planned maintenance windows, project cutovers, migrations, or client-impacting initiatives.

ABOUT US

Enterfusion has been in operation since 2008 and has been growing robustly to become a leading managed service provider with a focus on mid-sized corporations and state agencies. Our core philosophy is to leverage our experienced staff and vendor relationships to provide leading innovative technologies for our clients while maintaining cost effectiveness and reliability. Customer service is intrinsic to our operations, which creates a positive atmosphere of collaboration between clients and employees.

JOB TYPE

Salary, Full-time, Exempt

COMPENSATION

Annual salary of $110,000 – $130,000/year, dependent on experience, with paid vacation, health insurance plans, retirement program, disability insurance, and life insurance.

HOURS

This is a full-time exempt position which is expected to work 40 hours per week. Additional hours may occasionally be required based on client needs, project deadlines, planned maintenance windows, or urgent technical priorities.

JOB LOCATION

Downtown Orlando: candidate must be located in Metro Orlando.

Benefits

Compensation & Benefits

• $110,000–$130,000/year
• PTO accrual begins after 90 days and increases over time
• Health insurance (Florida Blue plans; Enterfusion covers 60% of employee premium)
• 100% company-paid dental, vision, and life insurance
• Short- & long-term disability
• SIMPLE IRA with company match
• Certification/training reimbursement