Open to opportunities

Michael Guiffreda

@michaelguiffreda

I deliver complex enterprise software implementations through disciplined planning, accountability, and proactive stakeholder communication.

United States

Message

What I'm looking for

I'm looking to lead complex, client-facing software implementations where I can own delivery plans, align cross-functional teams, communicate clearly with executives and customers, and proactively manage risk.

I've led 100+ concurrent software implementations at CentralSquare Technologies, owning project plans, schedules, delivery governance, and customer-facing communication across complex matrixed engagements.

I keep delivery teams and customers aligned by running recurring project calls, executive status reviews, and weekly reporting that surfaces risks, blockers, account changes, and overdue deliverables early. I've delivered enterprise initiatives valued up to $710,000 and use Microsoft Copilot to make reporting and documentation more consistent without consuming team bandwidth.

Earlier at CentralSquare, I translated complex requirements into implementation estimates supporting $43M in contracted services, and built scalable training for enterprise adoption and customer onboarding.

Experience

Work history, roles, and key accomplishments

Project Manager II

CentralSquare Technologies

Mar 2023 - Jan 2026 (2 years 10 months)

Owned project plans and delivery governance for 100+ concurrent implementations, serving as primary customer contact and driving accountability across matrixed teams. Produced weekly status reports and executive reviews, using Microsoft Copilot to streamline reporting.