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How to approach cold emailing

Finding the balance between efficiency and quality

Happy Monday & welcome to the second edition of Revenews! Not sure I am quite allowed to post ‘consistency is key’ memes yet. But we’re getting there.

The structure of this newsletter is flexible right now, but here’s the format so far:

  1. Main educational topic on ad sales & newsletter monetisation.

  2. Industry news & articles, not just sales related.

  3. Product recommendations, requested by a few people!

  4. Inbox Banter, some newsletter related funny stuff. Just cos.

📢 Please let me know if you think I’m missing something!

Crowd-sourced-feedback aside, lets dive in! 🚀

  1. The best way to approach your outreach

  2. Email like Mr Beast

  3. Do you use WhoSponsorsStuff?

  4. Inbox Banter

Excited Ric Flair GIF

How to structure cold outreach

First, let’s start super basic, sales can be either inbound or outbound. Within these, there’s a few approaches which can blur the lines, such as demand generation, lead generation, referrals, etc.

From my experience the two most effective ways to generate leads and close sponsorship deals are the most simple: outbound sales and inbound forms (‘advertise with us’ links).

Today, we’ll be looking at outbound email, for most newsletters it’s the most scalable, trackable and reliable approach. Of course, if a founder has a massive social media following, then that might be your best bet.

To automate or not to automate?

As always the answer in nuanced 🤔

Automation is a close second to AI as the buzz word of the century, it has become a lot more effective (and cheaper) in the last few years! This, coupled with the fact that outbound sales is a very time consuming endeavour, has made sales & outreach automation huuuuge.

Here’s how I think about automation in outbound sales.

On the right you have manually typing out emails from scratch every time, which is soo 2004. On the far left you have plugging in 10s, 100s or even 1000s of contacts into a fully automated, unsegmented sequence. Both of the extremes are not where you want to be operating.

🐌 The far right is far too time consuming, not trackable, and not necessarily even the most effective.

✋ The far left may be time efficient, but there is no way that all the contacts will relevant or accurate. Plus the message will be generic, and likely to fall on deaf ears. You’ll inevitably get a lot more, ‘please unsubscribe’ emails, redirected to spam, and quickly ruin email deliverability, not to mention putting out the wrong message for your brand.

Whilst there is no judgement here, personally when I’ve done this approach, I’ve struggled to sleep at night, as I felt more like a spammer than a salesperson.

🤑 The Green Zone

There are two set-ups that optimise the trade off between efficiency and quality:

  1. Various fully automated sequences, typically segmented by industry. Tweak the audience stats, case studies and the general language of the email to suit the buyer. Input contacts into the relevant sequence at a click of a button, or two.

  2. Partially automated, but manually edited sequences. Also segmented, but segmentation is less important here due to the manual editing. Have the templates and sequences fully pre-built, but just before you input a contact, add some custom personalisation about the business or the individual. The human touch.

If done correctly, both of these can be very efficient processes, whilst fostering quality sales conversations. Plus, most CRMs offer excellent tracking features for both of these.

Reply rates are of course a great way to determine success, but it’s also important to take note of how many replies are positive, and might lead to business. This is more subjective, but something to bear in mind.

A useful perspective to have…

Assume your prospects are scouring your emails for any evidence that it’s an automated email. If they spot something which gives them that feeling, they’ll quickly send it to trash. Try not give them any excuse to hit that delete button.

How to segment

Typical categories I’ve found useful

Whether they’re fully automated or partially edited each time. The above categories have proved foundational to effective outreach.

You can go much more granular with your segmentation, which should increase reply rates, if done correctly. There is the risk of segmenting too much and overcomplicating operations unnecessarily. Find the splits that make sense for you, and narrow down until each email reads as if it’s genuinely typed with the prospects business in mind.

Another useful way to segment sequences and prospects is by scenario. Adjusting the wording to fit situations, such as:

  • You saw them advertising in XYZ

  • They recently got funding, avoid opening with “Congrats on the funding!”

  • The contact got a new role

  • You have a strong case study with a competitor

Hubspot & Salesforce have great sequence sending features. My personal favourite is Apollo.io, the LinkedIn integration makes is super easy to use, the free version is genuinely useful, and the pricing is extremely fair!

🏆 Benefit of partially editing your emails

This of course allows for personalisation, above auto populated fields, which in my books doesn’t really count. Effective personalisations include:

  • The channel you saw them advertising in

  • Insight on, or a question about, their LinkedIn, Twitter or blog post

  • Insight on the company, or a comment on recent news, especially if you’re customer

These types of genuine notes, allow for personalisation that simply isn’t possible via automated fields. Reply rates will increase, and prospects will appreciate that you’ve taken the time to do a little bit of old fashioned typing.

FAQs

🎬 How should I start ?

Even before the very first email, its worth creating some templates. Not only because its more efficient. But It’ll give you some form of comparable & trackable results, enabling you to optimise and adjust.

👍 What is a good reply rate?

Depends, if you’re in a super small niche or have huge brand recognition then it can be easier to get higher reply rates. My rule of thumb is:

  • <5% and something is wrong

  • 5-10% is OK, nothing drastically wrong, but room for improvement

  • 10-20% really solid, well done

  • 20%+ outstanding, don’t change a thing! You might be in a great niche with huge demand. Regardless, if this is you, send me your templates! 😉

✉️ What’s the best approach to subject lines?

I’ve found that keeping it short and sweet is best. 2-4 words that describe the topic/opportunity is ideal.

I’ve seen mixed results with personalisation/names in the subject line, if it works for you, keep doing it.

✍️ How do you write a great cold email?

I will probably do a dedicated newsletter on this. Here’s the best practises:

  • Concise, no fluff, simple language (under 150 words)

  • Try to talk more about the prospect rather than about yourself

  • Use question-based call to actions

Act professionally, talk casually.

Bonus tips 📈

Take pictures of ads that you see in physical channels such as in the Tube/Metro, relevant magazines, include these in your outreach, ideally in the email body not as an attachment.

Check out Lavender’s blog & Will Allred’s LinkedIn content on how to write cold emails. The Lavender product wasn’t for me, but their cold emailing ethos and guidance is spot on.

Newsletter News

📝 Interesting article on whether newsletter length is linked to success (hint: it is)

🤯 Learn how Mr Beast achieves 10 clicks per subscriber!

Product Recommendations

A lot of people have asked me if I’ve used WhoSponorsStuff. Yes, I’ve used it at a previous role (Director of Partnerships).

Keeping tabs on a select group of newsletter for outreach is a great idea, WSS makes it’s a lot quicker & easier. It is fairly expensive, so if you’re just starting out, perhaps do this manually to start with, and consider purchasing it when your deal sizes justify it. From my experience the platform does pay for itself pretty quickly, both in terms of deals closed, and time saved.

WhoSponsorsStuff haven’t paid me for this, all of my product recommendations come from genuine experiences and opinion. I will however use a referral link if I can find one! Which in this case I have.

Inbox Banter

If you receive an email about tinned meat, don’t open it.

It’s Spam!

Thanks for reading!