If you'd like to talk to me directly, then you can email me at james dot stanier @shopify.com, ping me on Twitter @jstanier, or find me on LinkedIn: https://www.linkedin.com/in/jstanier/
Unless you have a very large following already, you're at the whim of the Medium editors to "elevate" content to the wider readership of the site, via the preexisting topics, or if you're really lucky, to feature your article on the front page.
* Edit: That doesn't mean you shouldn't! :-) However, you might get more readership - if that's what you're interested in - by writing pretty much anywhere, and just sharing it with the right communities.
I /think/ I know what you're talking about, but just in case this gets derailed in a back-and-forth and lost, then feel free to contact me on Twitter @jstanier or my email is in my profile - we can chat more easily there.
The target audience for the newsletter was decided as "the busy exec". Not too much text, lots of gifs of functionality that we've built, etc.
There's some separate newsletters we do as well - there's a fortnightly "what's going on in the backend" one, curated by our infrastructure teams that's aimed at engineers.
Currently the general case newsletter goes to Engineering, Product, Product Design, and the exec group. We don't think it's quite good enough for the staff@ mailing list yet, but maybe we're just being over-cautious. It's really hard to get the balance right.
The book assumes someone is interested in it or just started. I didn't cover landing the job, but that's a really interesting point.
Personally, I got promoted from within at the beginning of my management journey. Have you been applying to external companies? I wonder if others on here have more experiences in that area that they'd like to share.