👋 Today, I’m handing the reins to my business partner Jack, who’ zooming in on what the lowest hanging fruit are in the newsletter ad sales world.

Sharing Revenews writing responsibility aside, let’s dive in! 🚀

Focus on the Low-Hanging Fruit 🍇

Hey there, my name is Jack Pilcher. I used to run sales for Chartr for two years before we were acquired by Robinhood. Now I run Ad Sales as a Service alongside Dan.

Today, I want to share some insights about selling ads for newsletters - specifically how to focus on the lowest hanging fruit, making your life easy and pockets heavy.

I'll start by saying this took me probably four or five months to properly figure out at Chartr. I spent a lot of time on fairly ineffective efforts, like converting newsletter readers into subscribers (which I'll mention later) and reaching out to people on LinkedIn at companies I thought were perfect fits. Looking back, that all sounds pretty silly when you're not doing the basics well.

What I'm about to talk about accounted for nearly 100% of our sales at Chartr in the last year, with about 30-40% coming from inbound.

😍 Inbound Leads - Bread and Butter

Obviously, inbound is the bread and butter. These leads convert the best because they're coming to you with live intent to buy. This should be your biggest focus.

Get back to them fast. Ideally within minutes, definitely within hours. Do not leave that kind of intent sitting for days, because they are the closest to taking action as soon as they message you. If you have this incredibly high-intent stream of people reaching out who are interested in your audience and content, get back to them quickly and they'll convert at a far higher rate.

🙋‍♂️ Be in the Market

After you've handled inbound promptly, the next highest-intent opportunity you absolutely should be doing is subscribing to the 5, 10, or 15 most relevant newsletters similar to your audience. Or use a data provider like WhoSponsorsStuff.

Every morning, spend 15 minutes scanning through all these newsletters, writing down who the advertisers are and where they're advertising. Then do some manual outreach.

Talk about the similarities between audiences and the advantages of your newsletter. Always lead with intent like "Hey, I saw you advertising in X, hope it went well for you" rather than just talking about yourself from the outset. People only have seconds to scan emails, so make sure you're talking about them and helping them toward their goals, rather than focusing on yourself - they don’t care. Obvs lean on past success and social proof.

🕺 Scale

Once you get a decent flow of leads coming in, start to automate this process. WhoSponsorsStuff is a great data source. OpenRates is another cheaper but not quite as complete option for finding out who's sponsoring which newsletters. You can start automating this with Clay, Apollo and Instantly/Smartlead.

Beyond the immediate newsletters, you can start enriching based on company websites and get AI to scrape each advertisers website to tell you which companies have customers who match your audience.

👋 Leverage Your Network

Depending on your network, this might actually rank higher than monitoring similar newsletters. If you come from an industry that overlaps with your newsletter's audience, you might have contacts through old colleagues and friends, which will get you advertisers.

If that's the case, that's obviously one of the most low-hanging fruits possible. 

For example, if you're writing a newsletter for CFOs and you have been a CFO for 10+ years, you already have a really good idea of the landscape and contacts you can reach out to.

If you’re starting from scratch, that’s no problem,m but this obvs doesn’t apply. Sorry.

👂 Podcast Sponsor Intent

Another great source of low-hanging fruit is other media intent, particularly podcast sponsors. I've used a tool called Sponsorable, which is a good cost-effective way to see who's sponsoring podcasts.

One caveat: a lot of these sponsorships go through podcast networks, so the marketers themselves may not have even signed off on that specific podcast. There's probably going to be less recognition of "oh yeah, I know that," but it's still a really great intent signal showing they're interested in this bucket of marketing.

🔎 Grow from within

Another approach (which I found hasn't worked as much in my experience, but I've talked to people who've seen success) is using a company like MegaHit to enrich your subscribers and tell you their job titles and companies. If they're in marketing or are founders/executives, and they love your content and their product customers are similar to your readers, that's absolutely worth pursuing.

I've heard a lot of people have huge success in this area. At Chartr, this is where I started, and in hindsight, it was a mistake. In the year running up to the acquisition, about 40-50% were from people buying similar newsletter placements. If you are thinking about this and haven’t already exhausted the 4 previous points, don’t bother. It's probably not going to solve your problem.

🤑 Funding signals

Companies that have raised capital are always good targets, but I would not reach out for a month or two after they've raised. As soon as they appear on Crunchbase, they probably get thousands of emails asking them for their money.

There's usually two or three months of strategy planning before they're actually looking at marketing channels. Wait a month or two so you don't get lumped in with all the SaaS outreach and marketing tool pitches.

That’s enough to go on - go get it.

Jack

P.S. Need help selling more sponsorships? Our agency Ad Sales as a Service helps media companies do just that.