How do I sell newsletter sponsorships to banks, hospitals and big regional brands?

"For bigger companies, you lose deals because your price is too low. For small companies, you lose deals because your price is too high."

This is the most counterintuitive thing in local ad sales. A bank or a hospital won't run a contract through legal for $500. $1,000 a month is unremarkable to them.

Why do big companies turn down cheap sponsorships?

Because a small contract isn't worth the internal work. Somebody has to approve the vendor, set up payment, review creative. If the check is $600 or $700 a month, that effort isn't worth it to a big enough client and they pass.

Most of us walk in with a limiting mindset: "If I ask for $700, will they freak out?" With a large prospect, if they hesitate, check whether your price is too low before you assume it's too high. A commission rep I work with heard my rule for big brands: don't offer $500 a month, they'll turn you down. It needs to be two grand.

Which big organizations should I target?

"Don't go target the dry cleaner lady and her husband. Target the hospital chain, the college, the city, the visitors bureau, all the bigger industries where paying you a thousand bucks a month is not a big deal."

• Hospital systems and children's hospitals
• Banks and credit unions
• Colleges
• The city, the economic development department, the visitors bureau
• The power company or electric co-op
• Big regional retailers like a furniture destination store, or IKEA if there's one near you
• Insurance companies

Regulated industries like banks and insurance are especially good. They have the money and a hard time making content people care about. You solve that.

How do I reach them?

LinkedIn. Their marketing teams are there, and that's where you get $1,000 and $2,000 a month partnerships, because to them that's nothing. A small ad form on your site brings in $100 to $200 ads. Different door, different buyer.

What do I pitch them?

Awareness and coverage. Bigger brands are often less fixated on conversions. A children's hospital isn't saying "if we give you $10,000 we expect 27 sales." They want to get the word out. Regional players also want regional coverage, so two or three newsletters across a region beat one small market.

Go above and beyond on deliverables. Big partners get more than an ad: stories, social and video. One caution: you can't make a ton of videos about banks before people get annoyed. Save the heavy video for fun brands.

When should I start pitching them?

Once you have the audience to back it up. Start with readers and small businesses, because you can call or DM them and they'll answer. Nobody DMs a hospital marketing director on Instagram. Around 20,000 subscribers, with real website traffic and 10,000 to 20,000 social followers, start hitting up the hospital and the big companies.

Treat big partners as a supplement, not the only plan. Get the $1,000 a month checks, and keep doing everything else too.