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 getting their hands dirty and building it. I initiated & led an 18-month software implementation there — vendor research, stakeholder wrangling, the whole nine — and by the end I knew two things for certain… 1) I was good at this and 2) 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 shove… 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, and then I run it... whether that's one defined project with a real finish line, or everything you've got going at once, with no single bounded thing to point to.
Most people reach for a tool, or a coordinator to execute day to day. But a tool doesn't build a plan, and no one can run a plan that isn't there yet.
I build it and I run it, so it's not just organized… it gets done.
If it's one bounded thing, that's The Trailhead.
If it's everything all at once, that's Walking the Skyline.
Walking the Skyline stays capped at 2 active clients max by design; The Trailhead flexes with how many projects are actually in motion and at what complexity level. Either way, 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.
"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
Why This Work
I studied team and project management at Bryant University, first-generation college student, first in my family to graduate. 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.
"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