I’m Sky
Working With Sky exists because I spent three and a half years inside a fast-growing company watching good ideas die in the gap between “someone should really build that” and anyone actually building it. I led an 18-month software implementation there… vendor research, stakeholder wrangling, the whole nine… and by the end I knew two things for certain— I was good at this and I never wanted to do it as an employee on someone else’s org chart ever again.
I got laid off in February 2026.
It felt less like a setback and more like the permission… or push… I’d been waiting for.
Working With Sky went full-time the very next day.
What I Actually Do
I turn the chaos in your head into a plan; whether you execute it or I do is up to you.
I’m not a consultant who leaves you a deck, and I’m not a VA who needs one handed to them.
I’m the whole operating system that runs either way.
Some founders already have the infrastructure, people, tools, documentation, but nobody’s holding the whole picture together. Others don’t have the infrastructure yet, and the work won’t get built unless someone’s actually in it, building. I work with both. The engagement looks different depending on which one you are, but the core of it doesn’t change: you stop being the only person who knows where everything stands.
I hold 2-3 Embedded Ops Partnerships at any time, by design. This isn’t a volume business.
It’s a handful of businesses, led by really cool people, who I am fortunate enough to partner with— and genuinely give a damn about.
How I Work
Ever heard of Human Design?
(If not, you have got to check it out… it will quite literally change your life).
Well, I’m a Projector— simply put: I don’t chase, and I definitely don’t do my best work under artificial pressure. I do my best work when I’ve actually been invited in, learned the business for real, and I’m trusted to hold it. That shows up in how I run engagements… async-first, ClickUp as the shared source of truth, nothing living only in my head or only in yours.
I run this business the way I want your business to run: with real systems underneath it, not just my own hustle holding it up. In the next six months, I will be walking two weeks of the Camino Portugués, unplugged, on purpose. If the business can’t run without me for two weeks, I haven’t actually built what I’m selling.
Why This Work
I studied team and project management at Bryant University, first-generation, first in my family to finish. I hold a CAPM, a PMO-CP, and a Six Sigma Black Belt, credentials that matter less to me than the fact that I’ve actually run the thing, not just studied it. Before any of that I was managing a Chipotle at 18. I’ve been the person holding the operational picture together since before I had a name for it.
I built Working With Sky because I don’t think you should have to choose between someone who thinks and someone who builds. You shouldn’t have to hire twice to get both halves of the job done.
Before Working With Sky Existed
The 18-month software implementation up above— vendor research, stakeholder wrangling, the whole nine, is the exact project this is about:
"Sky took an extremely organized approach, keeping up with Gantt charts and keeping all relevant stakeholders in the loop at every step. When problems arose, she stayed calm and collected while everyone else was lost in the chaos. We got exactly what we wanted: cleaner data across all locations, reduced our tech stack from three software subscriptions to one, and saw labor costs drop at our retail locations as a result."
— Abby Walsh, Optimization Manager
And two more, from that same chapter:
"Sky quickly became the point of coordination that kept everything moving. She understood how the business actually worked, not just how it looked on paper, and that allowed her to guide my developers toward changes that produced real efficiency, not just activity. She did not just manage tasks. She orchestrated people, context, and priorities so the work landed cleanly inside the organization. That is rare."
— Matthew Chambers, Founder, FixFinder"
“When Sky gets assigned a project, everything gets tighter and more organized, and deadlines actually get met. She holds people accountable with grace, communicates clearly so no one is left wondering what to do next, and takes her work seriously enough that you can genuinely hand something off and trust it's handled."
— Liam Treacy, Director of Enterprise Production
A different angle on the same chapter, this one’s about being managed by Sky directly:
"Sky took what felt like an overwhelming mountain of work and turned it into a clear, confident plan. No matter how stuck I got, she was fast to respond and always had my back. She has a way of making you feel like your project is her top priority, even when she's managing everything else at the same time."
— Abby Spessard, Technical Writer