Technology Project Manager in Pewaukee

Job DescriptionJob Description

Technology Project Manager

Are you the person who steps into chaos and turns it into execution? Do you thrive in fast-moving environments where priorities shift, expectations are high, and outcomes matter more than process?

Our continued growth has created the need for a Technology Project Manager to join our team.

2W Tech works with cutting-edge, state-of-the-art technology solutions and services. This role is built for experienced project leaders who can operate at a high level inside our PMO, owning delivery, driving accountability, and helping shape how projects get executed across the organization.

This is not a sit-back-and-coordinate role. You’ll own a high volume of projects, drive execution across teams, and step in when things go off track. You are expected to operate as a leader, not just a project manager.

Some of the areas you’ll be responsible for include:

• Microsoft Azure infrastructure and migrations
• Microsoft 365 environments
• IT architecture and infrastructure projects
• Security and managed services initiatives
• ERP and integrated technology implementations

You don’t need to be the deepest technical expert (we’ve got those). But you do need to be someone who can lead, connect the dots, and drive results across technical teams.

This position is onsite at our Pewaukee, WI HQ.

If this is your next gig, you’ll need to:

• Manage and drive execution across 20–30 concurrent IT and infrastructure projects
• Own delivery from kickoff through completion, timelines, scope, and outcomes
• Lead cross-functional teams and hold resources accountable to commitments
• Communicate clearly and confidently with internal teams and senior leadership
• Operate effectively in environments where tools, priorities, and processes are evolving
• Make decisions, remove blockers, and keep projects moving without perfect information
• Help with resource planning, prioritization, and capacity management across the PMO
• Identify and implement improvements in how projects are delivered (builder mindset required)
• Step in, escalate, and “break glass” when projects are off track
• Influence stakeholders and manage expectations, even at senior levels

What we’re looking for:

• 5–10+ years of experience in an IT organization, with 3-5+ years leading people and projects
• Proven track record of delivering results in complex, fast-paced environments
• Excellent problem-solving skills and ability to operate under ambiguity
• Strong experience within the Microsoft ecosystem (Azure, M365, infrastructure)
• Ability to manage and prioritize a high volume of concurrent work without losing control
• Strong leadership presence and confidence working with senior stakeholders
• Self-motivated, organized, and accountable with an ownership mindset

Bonus points if you:

• Have experience improving PMO processes, tools, or delivery frameworks
• Have led infrastructure modernization or cloud transformation initiatives
• Bring an entrepreneurial or “builder” mindset to scaling delivery organizations
• Have experience in consulting, managed services, or client-facing delivery environments

Is this you?

If you’re looking for a role where you can own outcomes, lead from the front, and help build a high-performing delivery engine, click the apply now button.