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.
Same two pieces of work, drawn tighter. Project-based means we define the scope up front and I commit to fixed deliverables at fixed prices against it, instead of an open-ended retainer.
The trade is deliberate, and worth naming plainly: a fixed price needs a fixed scope, so this version is narrower on purpose. The design system gets cut to a defined v1, and the sales proposal work splits into phases with a checkpoint between each one. Where the work could grow, we name it up front and decide together rather than letting it creep. You trade some flexibility for a number you can plan around.
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.
Two weeks of listening, across the sales side and the ICs. The output is written: a set of findings, a risk map, and a recommended direction to build against.
This is also where we catch the biggest scope risk early. If the IC data-entry problem turns out to be a workflow and integration problem rather than a design one, we flag it here and reassess Phase 3 before either of us commits to it. That's the first real off-ramp: you can stop after this phase with a clear picture in hand and owe nothing further.
The primitives and the icon set the tool actually needs, and nothing it doesn't. We define the icon inventory first and agree the count before I build, so the scope is set by what's genuinely required rather than a guess. Delivered as a v1, not a living system.
If you want it to keep growing into a fuller system after that, that's real work, and it moves to the hourly path rather than hiding inside this number.
The dense comparison surface, restructured from the current third-party tool and taken to a hi-fi prototype, built on the Phase 2 system. The near-term version is the deliverable: the one we agree the surface needs to do imminently.
The bigger question of how these comparisons could work tomorrow is part of the value, so those opportunities get surfaced and documented, then deferred to a later round as their own scope. Surfaces beyond the first, and the "tomorrow" build, are a change-order conversation billed at $175/hr, not assumed inside this phase.
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 →
Three phases, run in sequence, each priced on its own. The checkpoints between them are real off-ramps: you can stop after any phase and pay only for what's built. Where scope could balloon, we reassess before starting the next phase, not after.
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, and it holds either way we price the work.
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 work is tracking and whether the balance between the two efforts 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.
The fixed price buys a tighter, defined scope. Each phase below is scoped and priced on its own, with a checkpoint between them. Anything beyond the agreed definition, added surfaces or the deferred "tomorrow" work, is billed by change order at $175/hr rather than absorbed silently.
Two weeks. Findings, risk map, direction. Stop here and it's all you owe.
Primitives plus the agreed icon set. Inventory defined and count agreed before build.
Dense surface to a hi-fi prototype, built on Phase 2. Near-term version; opportunities documented and deferred.
Each phase priced on its own. The exits mean a clean stop costs only what's built.
Change-order rate: $175 / hr · Starts immediately, Phase 1 first · Billed through Design by Proxy LLC