About Iyanna

Strategic PM leadership in a world where the human side still matters most

I'm Iyanna Trimmingham-Daniel: a PMP-certified program manager with over 15 years of delivery experience across government transformation, enterprise systems, and cross-functional programs. I built PM Pro Skillz because the hardest parts of this work have never been the tools or the plans. They've been the people, the politics, and the pressure that nobody prepares you for.

Get the Free Stakeholder Guide Start Here
Iyanna Trimmingham-Daniel
PMP Certified · MSc Project Management University of the West Indies · PMI Member

Delivery taught me more than any certification did

Over 15 years, I've worked across three very different delivery environments: government infrastructure programs in the Caribbean, enterprise digital transformation in the US, and independent consulting across businesses, nonprofits, and operational teams. The contexts were different. The underlying challenges were almost always the same.

"The plans were always there. The schedules made sense. The tools were in place. What I kept running into was everything else: the executive who wouldn't commit, the department heads who kept changing scope, the teams who didn't believe the change was real. Those weren't project problems. They were leadership problems."

Managing multi-year public sector programs in Saint Vincent and the Grenadines, including infrastructure projects, land titling initiatives, and a national data modernization effort covering nearly 1,000 employees, I saw firsthand what happens when political complexity, fragmented authority, and unclear mandates collide with delivery timelines. No certification prepared me for navigating that.

When I moved into the private sector and later led ERP readiness programs and SOP governance initiatives in the US, the names changed. The dynamics didn't. Stakeholders still said yes and meant maybe. Leadership still debated priorities while teams waited for direction. Change still met resistance.

PM Pro Skillz exists because that gap, between knowing how to run a project and knowing how to lead through the room, is exactly where delivery succeeds or fails. And almost no one is teaching it directly.

2009 – 2019 · Saint Vincent & the Grenadines
Operations Manager / PM / Business Analyst, Government of SVG

Led multi-year public sector programs totaling $25M+, covering infrastructure, regulatory compliance, and a national data modernization initiative. Navigated political complexity, multi-agency stakeholder dynamics, and high-visibility delivery pressure.

2019 – Present · Brooklyn, NY
Freelance Project Manager

Delivered project and operational consulting across a range of organisations, from growing businesses to nonprofits and operational teams in the US. Gained experience across sectors with varying levels of resource, structure, and cross-functional complexity.

2025 – Present
Project Manager, AP&G Catchmaster (Enterprise)

Leading enterprise SOP digitization, ERP readiness, and AI-assisted workflow programs. Building executive dashboards, process ownership frameworks, and change management infrastructure across finance, operations, and IT.

Now
Founder, PM Pro Skillz

Building a real-world platform for delivery leaders navigating the human challenges AI can't solve, stakeholder dynamics, competing priorities, executive pressure, and the strategic layer of delivery.

Four areas where delivery leaders need the most support

These aren't abstract frameworks. They're the recurring challenges I've seen derail otherwise capable PMs and the areas PM Pro Skillz is built around.

Stakeholder Leadership

Reading the room, managing power dynamics, navigating the disengaged sponsor and the difficult executive. Influence without authority. Getting people to commit when you can't force them to.

Strategic Prioritization

When everything is urgent and nothing is decided. How to surface trade-offs, force clarity, and make competing priorities visible in a way that gets leadership to actually choose.

Leading Through Ambiguity

Operating confidently in unclear environments. Helping teams move forward when direction from the top is shifting, scope is fuzzy, and everyone is waiting for someone else to decide.

PM Career Growth to Strategic Leader

How to move from tactical executor to strategic delivery partner. Executive presence, influence, visibility and the mindset shifts that separate PMs who advance from those who plateau.

If you recognize yourself here, you're in the right place

PM Pro Skillz isn't a generic blog or a certification prep site. It's built for delivery leaders who are technically capable and ready for the next level but need practical strategies for the human and strategic layer of their work.

  • Mid-to-senior delivery leaders hitting a ceilingYou're executing well but feel stuck below the level of influence you should have.
  • Program managers and transformation leadsOperating in politically complex, high-ambiguity environments with real stakes.
  • PMs moving into leadership rolesBuilding executive presence, influence, and strategic credibility alongside delivery skills.
  • Aspiring PMs and career changersBuilding a foundation that goes beyond tools and certifications from the start.

Not sure where to begin?

Every visitor's situation is different. Start with the challenge that feels most relevant right now and follow the path that fits.

Credentials
PMP, PMI MSc Project Management, UWI BSc Business, Andrews University Google PM Certificate AI Overview for PM, PMI PMI Member