Technical Project Manager

Company Description

Fairway IT Solutions is a complete technology solution provider dedicated to delivering reliable, professional IT services to businesses in the Chicagoland area. The company focuses on helping business owners eliminate technology challenges so they can concentrate on running and growing their organizations. A team of skilled IT professionals works closely with clients to design, implement, and support tailored technology solutions. Fairway IT Solutions offers a collaborative environment where technical expertise, client service, and continuous improvement are highly valued.

Job Summary

Fairway IT Solutions is seeking a Senior Technical Project Manager (TPM) to serve as the primary technical delivery lead for a portfolio of managed services clients. This role is delivery-focused: you will own the planning, scoping, and execution of client technology projects — M365 migrations, network and infrastructure refreshes, security rollouts, and vendor implementations — while maintaining account context to keep engineering, sales, and the client aligned. You are the person who turns a signed SOW into a completed, documented, client-approved project, on schedule and within scope.

The TPM is expected to personally execute a meaningful share of hands-on technical work — configuration, implementation, and troubleshooting tasks within their skill set — that is billed to the client as part of project delivery. Candidates should expect their calendar to include direct client-facing technical work, not just planning and status reporting.

Responsibilities

• Own end-to-end delivery of client technology projects: scoping, work breakdown, timeline, resource coordination, and go-live, from SOW handoff through project closeout.
• Translate sales-approved SOWs into actionable project plans; identify scope gaps or technical risks before kickoff and flag them to sales/engineering leadership.
• Coordinate internal engineers, field technicians, and third-party vendors (ISPs, hardware vendors, software publishers) to keep projects on schedule.
• Manage project RAID logs (risks, assumptions, issues, dependencies) and drive resolution of blockers.
• Run project status calls and provide clear, non-technical status updates to client stakeholders and internal leadership.
• Maintain accurate project documentation: network diagrams, configuration changes, licensing, and as-built documentation for handoff to the service desk/NOC.
• Track project budgets/hours against SOW and escalate scope creep before it erodes margin.
• Use the company PSA/PM toolset (e.g., Autotask) to manage tickets, project boards, and time tracking.
• Serve as the named technical point of contact for an assigned book of accounts between projects.
• Participate in technology business reviews (TBRs) alongside the account/sales team to present project outcomes and surface the next technology roadmap item.
• Identify and document upsell/renewal opportunities (hardware refresh cycles, licensing changes, security gaps) surfaced during project work and route them to sales.
• Act as an escalation point for project-related client concerns, coordinating with service delivery and support leadership as needed.

Hands-On Technical / Billable Work

• Perform hands-on configuration and implementation tasks directly — e.g., M365 tenant/Entra ID/Intune configuration, firewall (Meraki/Fortinet) staging and cutover support, server/workstation setup, and similar project tasks within scope of the SOW.
• Log all hands-on work as billable project time in the PSA, consistent with the same time-entry standards as engineering staff.
• Step in for basic troubleshooting or escalated project-related technical issues rather than routing every technical task to an engineer, where within skill level.
• Balance hands-on delivery work against PM/account duties so both billable utilization and project oversight targets are met — target utilization split will be set during onboarding based on client portfolio.

Skills

• 3–5 years of experience in an MSP, VAR, or IT consulting environment in a project management, technical account management, or senior technical coordinator capacity.
• Demonstrated experience delivering Microsoft 365 migrations/tenant work, network infrastructure projects (firewall, switching, Wi-Fi), or server refresh/replacement projects.
• Working knowledge of Entra ID, Intune, and core M365 licensing/administration.
• Familiarity with firewall/networking platforms such as Meraki or Fortinet, and server hardware (e.g., HPE) sizing and lifecycle basics.
• Comfortable performing hands-on technical work personally (not just delegating it) — this role carries a billable-hours component in addition to PM/account duties.
• Proven ability to manage 5–10 concurrent projects at varying stages without dropping details.
• Strong written and verbal communication — able to translate technical risk into business terms for non-technical stakeholders.
• Experience with a PSA or PM tool (Autotask, Streaty, Monday, or similar).
• Valid driver's license and ability to travel to client sites within the greater Chicago area.