A chat with the sales lead at Chartr

Welcome to a belated Revenews, last week I was in bed sick most days!

🇬🇧 Hear from Jack Pilcher who led ad sales at Chartr and helped bring them to be acquired by Robinhood/Sherwood Media.

Big newsletter deals aside, let’s dive in! 🚀

1. How Chartr does ad sales

2. Affiliate opportunity for newsletter people

3. Newsletter News

4. Worst joke I’ve ever seen

I sat down with Jack Pilcher, Associated Director of Client Partnerships at Sherwood Media, previously CRO at Chartr

Why you should listen to him?

I’ve known Jack for around a year, he’s been keeping a full ad calendar and decent rates through a tough market. Plus, in December Chartr was acquired by Sherwood Media (Robinhood’s media LLC).

Chartr punch above their weight in terms of revenue & campaign performance.

I’ve spoken to numerous brands directly who’ve said their Chartr campaign was hugely successful.

Of course, there are various acquisition-related topics that he can’t talk about.

I’ve extracted the most valuable parts of our chat for you today.

🥇 Introduce yourself, Chartr and touch on the acquisition if you want to…

Hi everyone, I’m Jack and I headed up revenue at Chartr. Chartr was recently acquired by RobinHood and we’re now part of Sherwood Media, with a couple of big launches coming up this year. Exciting stuff.

Before joining Chartr, I headed up sales in the Americas at AirFinance Journal, a big B2B media and data provider in the aviation finance space. 

I loved what Chartr was doing and managed to get chatting with the Founder David through a mutual connection.

So from July ‘22 up until December 23, at the point of acquisition, we were a one-man sales team. Including everything from getting leads together, to outbound, to negotiating, closing and managing ad ops. 

📣 Wow, that’s awesome, remind me how many subs and sends per week you have/had.

When I joined we we were twice a week and we incrementally increased to four. We now have over 500k subs.

📣 What was the sales set-up before you joined? Was there a little bit of founder-led sales?

Yes. David, Chartr’s founder, did everything (very well might I add). But all ‘ad ops’ were organised in his calendar and mostly based on inbound requests. Nicholas had joined in January that year, and they just started trying outbound, but hadn’t quite cracked it yet.

I had no experience setting up outbound systems prior, so from August to January (2023), whilst manually selling ad space, we set up our outbound systems. This was a steep learning curve for us, a lot of blog-reading and talking to people. But in the six to nine months after we’d ‘finished’, it bought us literally hundreds of leads. All from cold outbound. *Mic-Drop*

That was how we managed to increase the number of ad slots that we sold, and we were always booked out. That was our bread and butter, roughly 70% of revenue was from cold outbound email/LinkedIn.

The rest was a mix of inbound and utilising ad-hoc connections or relationships.

📣 What does partnerships at Chartr look like? The process from lead gen to executed campaign?

We'd use Open Rates or Who Sponsors Stuff to tell us what was in the market. Before that, we literally just subscribed to all similar newsletters and manually tracked who was sponsoring what.

Using a proper data provider enabled us to systematise outreach better. Every week or two I’d check out recent sponsors, and pick the right ones. Depending on who their target audience was, we’d input our corresponding audience stats, similar brands that we’d worked with before, and perhaps shareable data on renewals or performance. 

Beyond that, once we got a reply and they’d checked out our media kit, we’d hop on a call. We’d make the pitch by working out the expected ROAS and how many clicks would we need to send to reach their CAC. Based upon their average on-page conversion/CAC, and our average CTR. Once this was done, it was a pretty short sale cycle, I'd say two weeks approximately.

Looking back, we absolutely crushed the part of reaching out to brands sponsoring other newsletters. Our focus was pretty broad across tech, personal finance and consumer applications, so we weren't siloed into a niche. Obviously, we had our data visualisation niche, and we did do some partnerships there, but now I think we could have done more investing in those relationships.

The pitfall of being bootstrapped and a one-man-department is that we obviously needed that ad revenue to survive. Which can foster a bit of short-termism into your partnership outlook.

Had we had a little more wiggle room, here’s something I’d do more of:

I’d frame it more as a: “Hey, we're in the same area, we should get to know each other!” 

 Not just, here’s our media kit, you wanna buy some ad placements?

Every other non-media company right now is trying to build, or acquire, a media arm for marketing. Sometimes an acquisition makes sense, conversely, sometimes they’d much rather spend 5-10% of the acquisition price on a year-long exclusivity deal, for example.

These types of deals just don’t materialise in a quick turnaround pitch and 4-week sales cycle. So slowing down and building these relationships early is a key thing that I’d recommend to incumbent newsletter entrepreneurs.

📣 What’s the most important thing for a sustainable sponsorship operation? 

If you have a small team, which most newsletters do, get a good lead gen system. A robust and somewhat automated outbound system.

Design efficient, focused and effective systems/processes so that you are consistently reaching out to relevant companies. Put care into your messaging, make it concise, sensible and TAILORED.

Because Chartr sponsors a lot of other newsletters, I get a lot of emails that are clearly not actually tailored to me, or our business model. They’re blanket templates designed for any company sponsoring a newsletter. Without proper personalisation you’re just not going to get good results, people can tell a mile off.

But before any of that, this only works if you have a great product. I.e. great content, that people pay attention to.

It’s completely impossible to run a profitable and sustainable advertising business if you can’t show that you have engaged and happy readers.

My chat with Jack was so offensively jam-packed with value, that cramming it all into 1 newsletter would be a severe injustice.

So there will be a part 2 of this conversation, where we talked about:

• Deliverability

• Why most newsletters will fail

• How to avoid bottom-barrel pricing

• Outlook for ad sales

I don’t like a cliffhanger, but here we are. 🧗‍♂️

If you’d like to chat with Jack, slide into his DMs on LinkedIn, he is always happy to help!

📰 Newsletter News

🥳 The Newsletter Conference has been announced!

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🤷‍♂️ Why most newsletters suck for media buyers.

🤖 Tech companies are committed to addressing AI-generated misinformation

📊 How this chap grew 35k subs on LinkedIn

🤣 Inbox Banter

I’m trying to reduce my email storage, but it’s hard to delete old messages.

I’m just too attached!