Keeping front of mind with your most important clients and prospects is an everyday challenge for B2B marketers. For many, a "newsletter" or roundup of trends across the industry makes good sense. It keeps your readers informed and gives you an opportunity to set your firm up as the leader of the discussion.

Newsletters are hard to do right. When to send it, how it should look and who to send it to are just a few of the hurdles marketers looking to set up a newsletter need to worry about.

I've searched through examples of successful newsletters in order to answer these questions and hopefully offer an example of who's doing it right. 

Because engagement matters most, I've not just chosen the biggest newsletters but have tried to focus on newsletters that have grown quickly in the last couple of years. These are all business based or expertise driven as well.

1. When to send? - VOX showing that options work

Vox are cheaters a bit in the newsletter market. As a media company, they've already done the hardest and most important part of a newsletter (getting together the content). 

They obviously have great writers and content creators, but something that Vox do particularly well is options. Vox have options for the type of content and frequency. Only want to receive health news once a week? No problem. Want to get a daily rundown of everything that's going on? Covered.

When it comes to when during the day or week to send your email, there are a number of different opinions. Here's a roundup;

Coschedule - either 6am, 10am, 2pm or 8pm; when readers are waking up, having their second coffee, their afternoon break or as they are unwinding later.

MailChimp - midmorning (10-12) on a Thursday; different times work for different industries and Thursday is only marginally ahead but something about Friday eve morning makes this the best time.

Smart Insights - Wednesday from 1am-12pm or 1-3pm; this is a really interesting read. Looking at over 100 of the biggest newsletters, the conclusion was that the best time to send is actually when others aren't.

2. How should it look? - Morning Brew are masters of curated content

"Become smarter in 5 minutes", this is the claim that New York based Morning Brew makes. A bold claim indeed but in fairness to them, their newsletter delivers. It's simple, includes a minimum of complicated design and follows a content first philosophy. 

As a result, it looks great on a mobile, is easily scannable and digestible and most importantly it gives the reader exactly what they want; valuable information.

All the newsletters on this list have that content over design approach. They are all simple, essentially being lines of text. But Morning Brew's 1,000,000 subscribers show that it works.

 3. Who to send it to? - MarketSnacks growing with signup swag

Your existing key clients and prospects should be your starting point, pull them from your CRM, bully your salespeople for their contacts and make it as easy as possible for new opportunities to be added as they are opened.

But how do you grow a newsletter among people you aren't already talking to? MarketSnacks give us the answer.

MarketSnacks was started by two friends to make business and financial news quick, clear and entertaining. Very quickly MarketSnacks were able to grow from nothing to an international sensation. Due in part to their signup swag.

If you invite 5 friends and they join MarketSnacks, they'll send you a snazzy sticker or two. The more signups, the better the reward. Somewhat surprisingly, simple rewards like VIP access, t-shirts and stickers work where perhaps other larger prizes would not.

From the people I've talked to that know the newsletter, they feel like they belong to a club, an "in crowd" and the simple swag is part of it. Like Apple a few years ago, having a market snacks sticker on your laptop is a status symbol.