Senior Systems Engineer / Technical Project Manager

The Senior Systems Engineer / Technical Project Manager is responsible for leading multiple technical projects at the same time, designing practical technical solutions, supporting client technology planning, and providing hands-on technical execution across client environments. This is a client-facing MSP role for someone who is still actively technical and comfortable working directly in modern Microsoft, cloud, endpoint, networking, and security environments.

This role is not intended to be a purely advisory, executive, or coordination-only position. The ideal candidate has recent hands-on experience implementing, troubleshooting, and improving client systems, while also being able to assess client needs, design appropriate solutions, manage several concurrent projects, communicate clearly with clients, and make sound decisions in a fast-paced environment.

The successful candidate must be able to quickly evaluate technical requirements, design practical solutions, identify risks and dependencies, coordinate internal resources, manage competing project deadlines, and step in directly when technical work, validation, troubleshooting, or implementation support is needed.

BASIC QUALIFICATIONS

• 5+ years of professional IT experience in systems administration, systems engineering, network administration, technical project delivery, solution design, or a related technical role.
• Recent hands-on experience within the last 2–3 years supporting, implementing, and designing modern IT environments.
• Experience designing practical technical solutions for client environments, including scoping requirements, identifying dependencies, evaluating risks, and planning implementation steps.
• Experience managing multiple technical projects at the same time, including competing timelines, dependencies, resources, risks, and client expectations.
• PMP certification strongly preferred.
• Prior MSP or multi-client IT services experience strongly preferred.
• Strong practical experience with:
• Microsoft 365, including Exchange Online, Teams, SharePoint, and OneDrive
• Entra ID, including MFA, conditional access, user access, sign-in troubleshooting, and identity management
• Windows 10/11 and Windows Server environments
• Endpoint management, security tools, backup solutions, and cloud services
• Networking fundamentals, including TCP/IP, DNS, DHCP, VPNs, VLANs, firewalls, and wireless networks
• Experience leading or supporting technical projects such as Microsoft 365 migrations, security improvements, endpoint deployments, server upgrades, network changes, cloud implementations, client onboarding, or vendor transitions.
• Ability to make timely, informed decisions in a fast-paced technical 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.
• Experience with PSA, RMM, documentation, and project tools such as ConnectWise, HaloPSA, N-able, Hudu, IT Glue, Microsoft Planner, or similar platforms.
• Strong documentation, prioritization, follow-through, and organizational skills.

PRIMARY RESPONSIBILITIES

Technical Project Leadership

• Lead several technical projects at the same time from planning through completion, including scope, timelines, milestones, risks, dependencies, resources, and communication.
• Prioritize competing project demands and make practical decisions to keep work moving across multiple clients.
• Coordinate internal technical resources, client stakeholders, vendors, and third-party providers.
• Track project status, blockers, change requests, client decisions, deadlines, and follow-up items.
• Provide clear, timely updates to clients, internal teams, and leadership.
• Ensure projects are completed according to scope, security expectations, technical standards, documentation requirements, and client business needs.

Solution Design and Technical Planning

• Design practical, secure, and scalable technical solutions for client environments.
• Gather and clarify technical requirements, business needs, constraints, risks, and success criteria.
• Assess existing environments and recommend appropriate solutions across Microsoft 365, Entra ID, endpoint management, networking, cybersecurity, cloud services, backup, and server infrastructure.
• Identify project dependencies, implementation steps, resource needs, potential risks, and client impact.
• Translate solution designs into clear project scopes, technical plans, budgets, timelines, and implementation guidance.
• Review proposed solutions with internal technical resources to confirm feasibility, standards alignment, and supportability.
• Help ensure recommended solutions are realistic for the client’s environment, budget, security needs, and long-term operations.

Hands-On Technical Execution

• Participate directly in technical implementation, troubleshooting, testing, and validation when needed.
• Assist with Microsoft 365, Entra ID, endpoint management, backup, networking, cybersecurity, cloud services, and server infrastructure work as 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.
• Support technical escalations related to client projects, roadmap initiatives, and strategic remediation work.

Client Technology Planning

• Support client technology reviews, roadmap discussions, budget planning, and strategic planning meetings.
• Translate client business needs into practical technical recommendations, projects, budgets, and timelines.
• Identify risks and opportunities through assessments, ticket trends, lifecycle planning, security reviews, and client conversations.
• Help clients prioritize technology needs based on risk, business impact, urgency, budget, and long-term scalability.
• Communicate recommendations in clear business language while maintaining technical accuracy.

Fast-Paced Decision Making and Communication

• Quickly assess client needs, technical blockers, project risks, competing deadlines, and operational impact.
• Determine practical next steps when information is incomplete, timelines are tight, or priorities shift.
• Balance technical quality, business urgency, client expectations, budget, security, and resource availability.
• Communicate decisions, expectations, risks, and next steps clearly to clients, internal teams, vendors, and leadership.
• Escalate appropriately when issues require leadership, budget approval, or specialized technical expertise.

Documentation and Team Support

• Maintain accurate project notes, client roadmaps, solution designs, technical findings, 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, solution details, troubleshooting approaches, and best practices.
• Other duties as assigned.

Compensation & Benefits

• $95,000–$120,000/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