We have funds on offer to the project to hire a contractor to update
the website.

Personally I think this is a fantastic opportunity, it would be great
to see the website afresh in coordination with the 4.0 release.

With no up-front defining goals or improvements specified, if we go
forth with the offer, how can we go about optimising such a
contractor's time? Achieving something we all accept and own can be
challenging. And I am aware this is a little at odds with how open
source typically operates, the closest I can think of is code bounties
which are usually easier to define and spec in advance. In those
situations the bounty hunter interfaces directly with the community.
In this situation, we want broader community involvement on something
as touching as the landing page to the project's website, while
optimising the contractor's time to their speciality.

If we want to take this on, how can we go about it?

My first suggestion to throw out there, is to tackle it incrementally
with a few checkpoints along the way: where we can pause and discuss
and bike-shed all we like without having to involve the contractor's
time.  It’s also worth keeping in mind the ongoing work on converting
the in-tree docs, its design changes and impact it will have on our
user base…

Some example of checkpoints are:
 * Various sketches presented and a straw poll from PMC (or the
broader dev group) (this could also be a 99design contest)
 * Initial prototype of selected sketch
 * Near completion of new website
 * Sign-off of final website (weighted to those actively involved in 2-3)

Do we want to do this?
Do we think it is feasible?
Is the above suggestion sound?
Do we want more/less/different checkpoints?

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