Senior Technical Project Manager / vCIO

Enterfusion•Orlando, FL

1d•$110,000 - $130,000•Hybrid

About The Position

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

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.

Nice To Haves

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.

Responsibilities

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.
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.
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.
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.
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.