Thanks for the time this week. Here's how I'm thinking about the work, where I'd start, and how I'd like to run it.
Two pieces of work, running side by side. The design system I can start on right away, it's fairly clear. The sales proposal project is less defined, and I'd rather understand it properly before I put a shape on it than guess now and be wrong.
That's why I'd run this as a retainer at an hourly rate instead of a fixed project. It lets me start the clear work immediately and let the rest come into focus as I learn. You're not paying for a number I made up to cover unknowns, and I'm not boxed into a scope that shifts the moment discovery starts.
The primitives exist, but they're not in a form the team can reliably reuse. I'd pull them together into something small and practical: clear guidance, a set of base components, and one source of truth everyone can point to.
It won't ever be "done," and it shouldn't be. The aim is a living system that stays useful as the product grows, and that another designer could pick up and run with if the team ever expands. For a team this size, small and dependable beats big and theoretical. I'd also work through iconography that matches the shape and form of the branding you already have.
The tool that helps close deals, assisted, with a real person guiding it, not self-serve. It matters more and I understand it less right now, so I want to open by listening.
The first couple of weeks are deep discovery, and it reaches past the sales side. I want to sit with the ICs too, the people handling the manual implementation and data entry across the different systems, since that's where a lot of the real friction tends to live. Shadowing how deals close, watching how the work gets entered by hand today, and finding where the process gets in the way.
I don't want to commit to a timeline past discovery yet. What the work becomes, and how fast, should come out of what I learn. We'd set the direction together once I have it.
The design system starts now and keeps going. The sales proposal project opens with discovery, then finds its own pace. Where they meet: once the sales proposal work needs real UI, it draws straight from the system I'm already building. That overlap is the reason to run them together.
Scroll the timeline sideways →
A few light rituals to keep things visible without turning into overhead. All of it flexible once we find a rhythm.
Thirty minutes to sync, clear blockers, and set priorities for the week. Kept short on purpose.
A short recording from me each week: what shipped, what's next, and any open questions. Easy to forward to anyone who wasn't in the room.
The design system doubles as living documentation, so the current state is always visible without me writing a status report.
A short look at how the retainer is being spent and whether the balance between the two projects still feels right, especially as discovery reshapes the sales proposal work.
Billed against hours worked, through Design by Proxy LLC.
Flexes up or down as the work asks for it.
Monthly, no fixed end date. Either side can adjust with notice.
Design system begins day one. The sales proposal project begins with discovery.