One option is to create drip campaigns that can run automatically after creation. That way you've got content being fed to your audience on a schedule (X days from sign-up), and your overhead is much lower in terms of generating new content.

When you have something meaningful to say, you can send it out to the list ad hoc, but you're not on the hook to regularly generate new broadcasts.

I have a lot of experience setting up email marketing automation, as well as a strong technical background (I recently sold my marketing agency to take a full-time contract building custom web and native apps). On top of that, I'm also an experienced technical and non-technical writer (3 books and hundreds of articles under my belt).

If you're interested, I'd be happy to discuss some of your options for creating newsletter content that will continue working for you, rather than spending lots of time each week for single-purpose content. Drop me a line and we'll chat.

Good luck!

Sounds like you've got a number of wrenches in your gears: your boss's desire for creative/stylistic control, budgeting, project management, and bandwidth.

I've been a professional copywriter for about ten years now, so here's the first thing I'd say: if you're trying to find cheap talent AND meet your owner's standards AND hire only one person, then you've got a long road ahead of you.

I'd recommend hiring two different people for two phases: 1) raw content production (the most time-consuming part); and 2) editing, polishing, establishing brand voice.

You simply don't need top-tier talent to write your first drafts. I could help you find a good enough writer on Upwork.com who would charge $10-20/hour.

Where you want the heavy-hitter (who will be more expensive and will be worth it) is with the second phase, especially if you foresee needing the owner's greenlight before emails go out the door. Paying a premium to hire a pro will actually save you time and money in the end because s/he will be more likely to nail the first revision and will thus make fewer demands on the owner's bandwidth. Thus, you'll finish the emails faster and get them out into the wild faster where they will begin to create engagement and generate revenues faster.

That's another angle: how much is inconsistent email marketing costing the company right now? Thousands of dollars?

Here are the steps I'd recommend:

1. Brainstorm the various email drip campaigns.
2. Hire good enough talent to write the first drafts.
3. Bring in the expensive pro to polish them up.
4. Pay a virtual assistant to load up all of the drip campaigns.
5. Press play.

Happy to discuss in more depth on a call! I love this stuff.

Cheers,
Austin

Have you looked at ebyline?

After years of executing email marketing programs, AND leading content development efforts, I can tell you most companies already generate a lot of valuable content. Here is what I would suggest:

1) Consider an automated "drip" campaign. This takes the form of an on-boarding set of emails or a welcome-series of emails. These should be no less than 3 emails, and can be as many future emails as you think is relevant to your customers. You can do the same for existing customers by giving away a whitepaper or other useful document in exchange for an email opt-in. The opt-in should be followed by additional automatic emails that provide new and relevant content that strengthens your brand and helps the customer with a pain point.

If you can muster the investment and human resources to get it done, it will serve you for a long time. From time to time, you will need to invest in updating the creative, but it will allow you to get back to focusing on your regular business.

2) Explore current sources of content. Your sales team may be creating extensive powerpoints that you could re-purpose into an article for sharing over email. Your PR or media team (or agency) may also have content that can be re-purposed. The other possible source of content could be training materials. If you're providing customers with classroom or online training, consider recording and transcribing key training sessions, and hiring an editor to wordsmith and polish the transcription into actual useful content. A freelance transcriber will cost you pennies to the dollar (look in upwork.com), and with the core knowledge and expertise "written down", a freelance editor should be able to polish it up into a useful format. As you think about the power of re-using spoken content, consider other sources such as the owner's keynote presentations.

3) Use a freelancer. Once you have the core "facts" needed for a content piece, you should be able to hire a skilled freelance writer to handle the wordsmithing and polishing. You may want to craft a complete business and customer overview document to provide potential freelance writers. A good freelance writer who is provided with solid source material and the right background should be able to create good content for you.

Likewise, invest the effort into creating a brand style guide that documents your owner's writing aesthetics so you can empower good freelance writers to deliver what you need. This should all be part of an overall "brand styleguide" resource.

Finding and hiring an effective freelance writer/editor will take time and effort. But once you do, you'll find yourself with an invaluable resource that will be worth the initial effort. Like with any other hire, you'll want to interview freelancers carefully, test a few out with easy and quick projects, before settling on one that works for your needs.

Feel free to schedule a consultation phone call if you have follow up questions to my thoughts.