Hi, I’m Sky
I didn’t start in ops. I started at Chipotle, where I became one of the youngest service managers in the northeast region shortly after turning 18. Before I had the vocabulary for it, I was building teams, holding standards, and figuring out how to make things run when the pressure was on.
Then came Bryant University, where I picked up the frameworks to understand what I’d already been doing intuitively. Then a vertically integrated cannabis MSO, where I worked my way into project management and eventually served as right hand to the COO. I owned the execution of large-scale retail projects, drove process optimization across retail and manufacturing, and learned what it actually looks like to hold a lot of moving pieces together without dropping them.
I’m good at this work. That’s not a hedge…
it’s the honest reason Working With Sky exists.
WWS was already in motion before any of this— different name, early shape, something I kept coming back to. A wellness retreat to Thailand is what made me get serious about it. I came back with more clarity than I left with. A month or two later I was laid off, and just like that it became the whole thing. Best thing that ever happened to me— for me, not to me.
Working With Sky exists because founders deserve access to the kind of operational thinking that usually only lives inside larger organizations… without the overhead, the bloat, or the strategy engagements that never quite make it to implementation.
The Microfirm
Working With Sky is intentionally small. I cap active client work at 3-4 engagements at a time… not because I can’t handle more, but because more would mean less. Less attention, less depth, less of the kind of partnership that actually moves things forward.
When I take on a client, I’m genuinely in it. I know your business, I know what’s in motion, I know where the friction is. That’s only possible because I protect the capacity to actually show up that way. You’re not getting a stretched version of me working off a checklist. You’re getting a real partner who has the space to think about your business.
The work is better this way. The relationship is better this way. And honestly, I do better work this way too.
If you’re interested, don’t wait to reach out. There may be a waitlist.
How I Work
Every engagement runs async-first. That’s not a limitation— it’s a deliberate choice. Most of what we need to communicate doesn’t require a meeting, and defaulting to calls for everything wastes time on both sides. Async keeps things moving without adding to your calendar. When we do meet, it’s structured, purposeful, and worth showing up for.
ClickUp is the operating system behind every engagement.* Your project lives there— tasks, timelines, status updates, decisions, all of it. You have full visibility at all times and can drop a comment on anything, anytime. Nothing lives in my head or in a thread somewhere. It’s all in one place, and it’s always yours to see.
On the thinking partner piece— I own the plan, the systems, and the execution infrastructure. I flag things you haven’t thought of yet, push back when something doesn’t add up, and show up as a real sounding board for operational decisions. But the decisions are always ours. My job is to make sure you’re making them with the right information, the right structure, and someone in your corner who has actually thought it through.
Already running in another system? I can work with that.
The priority is visibility and consistency, not which tool we use to get there.