How to send hyper relevant emails

Harrison was co-founder and Chief Commercial Officer of Paddle, and is now CEO of GoodFit. Harrison was also Paddle’s “first” in almost every step of the sales process - first sales rep, BDR, AE, Solutions Engineer, CSM, Account Manager - and developed all the functions and processes from first principles, and ended up being responsible for Paddle’s end to end commercial performance.

This post was originally published as part of an article series with Notion Capital

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Setting the scene

As someone who sent 1000s of emails for Paddle over the years, and having walked in the shoes of our BDRs, I was always intrigued as to how I could best deliver the best messages to prospects and potential customers.  Many years down the line, this topic, some of the technology and amazing companies that have spun out of this space are truly awesome, whether that be the sales engagement tools themselves, or adjacent tools like Loom & Vidyard. But I think there is more to come in the evolution of delivering compelling messaging and scaling our outbound teams. 

 In terms of an agenda…

• We’ll zoom out and talk about what effective GTM looks like in 2022 
• We’ll look at the state of the market - how did we get here? 
• Will look at some of the personalised emails I’ve received over the years 
• We’ll talk about the type of behaviour and performance these types of messages drive
• We’ll give you some examples of a new approach and the benefits it can yield
• Before chatting about the next steps
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Right customer, right time, right message.

Just zooming out. I posed a question in a recent webinar for Notion asking - what is the most effective thing we can nail as an account-based GTM team in 2022? We heard some great answers around driving activity, success with direct dials and more, but ultimately concluded that the formula delivering for winning sales or marketing touchpoints is:

• Getting in front of the right customers 
• …at the right time
• …with the right message 

The goldilocks formula for GTM if you like, but easier said than done. 

By right customers we mean mapping the market of customers you can truly sell to.

• Too much time is wasted on companies we disqualify 
• Or don’t meet basic criteria needed to be able to sell to them
• You want to start by mapping the market of every company we want to sell to, and who meets our minimum criteria for a buyer
• You can read more about this here

By right time… 

• We mean focusing our attention and efforts on those who are demonstrating the greatest need for our product right now
• We have a limited number of XDRs, ad-spend… especially in the year ’23 with hiring freezes taking place and budgets being cut
• As such we shouldn’t have our team determine which accounts they work, or enroll in campaigns at random
• Instead we should focus our efforts on those who have the highest propensity to buy
• You can read more about this here

By right message, we mean…

• Having mapped the market, and identified who’s most likely to buy, we want to deliver the most compelling messaging to that company and persona that we possibly can. 

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And this topic is what we are covering in this article.

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Where do we spend our time? 

Whenever I discuss “right customer, time, message” it's always interesting to understand where people spend their time.

1. People spend their time on “right customer” and mapping their market during a fundraise, or during FY23 planning, when building books of business 
2. Far less time seems to be spent on scoring & prioritisation, i.e. the “right time” element
3. Much greater amount of time spent on the “right message” topic and this is a permanent topic of conversations for BDRs, BDR Managers

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But why so much time on messaging?

I think one of the other reasons we spend so much time crafting these incredible emails - sequences, cadences, whatever taxonomy you use - is because of the state of the market.  The sales engagement market is absolutely booming.

• Outreach announced their Series E funding of $200m at a $4.4bn valuation, founded only 8 years ago
• SalesLoft is a direct competitor to outreach, slightly longer in the tooth.   Vista Equity took a majority stake in Salesloft at a $2.3bn valuation, a massive 23x revenue multiple
• Groove & Apollo & Reply.io & MixMax, between them have raised >$225m dollars

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All of these companies are doing a great job on two fronts. 

First and foremost, they have made it easier than ever to enroll target prospects or accounts into sequences as sales teams, though tend to focus on the sales side of the account based funnel vs. marketing.

And you can see the impact of this in the numbers:

• In 2020 we were up to >300bn emails being sent per-day, and saw a sharp rise throughout the pandemic (and not slowed down). 
•  >4bn users of email globally the same year
• So target prospects in business were, on average, receiving 121 emails per-day! 

The big takeaway here is obvious; our prospects’ inboxes are busier than ever before … 

It’s easier than ever to deliver an email sequence or cadence to prospects or accounts and as such it’s harder than ever to stand out from the crowd. 

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So how did the market react?

SalesLoft, Outreach and those in adjacent verticals like Gong and Mutiny, all started coaching people on how to send the best messages they possibly could, helping them stand out from the crowd. 

In particular what happened is that emails got personal. 

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People started sending what are known to many as “hyper-personal emails”.

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Why did they do this? 

1. We don’t like to be spammed 
2. We all like to think the email is coming from a human 
3. And maybe we want to be entertained or have our egos massaged 

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XDRs - I Love You - You are my people!

Before we dive any further worth calling out that the XDRs job is one of the hardest in the company.  The best are relentless, amazing, people and I’m proud to have walked in their shoes in the early days at Paddle

XDRs are a company’s first impression, speaking directly to your target customers and key stakeholders. 

They are also any company’s pipeline of talent.  At least 3 XDRs we hired at Paddle have gone on to launch their own successful businesses, and some have moved into VC. No shame in being an incredible SDR and sticking in the role either. 

My co-founder at GoodFit I hired straight out of university into a lead development rep (LDR) role. Essentially, a full-time researcher into commercial data for the business.  He hit his quarterly target in just four weeks. After which, we ran a company hackathon in which he built a way to programmatically gather data instead of manually researching. Largely because his peers were so unhappy doing it. Years down the line, he’s now supplying data to some of the biggest, best, companies out there. 

TL:DR - XDRs, I love you, and you are the lifeblood of any b2b org.

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Personalisation Today 

In order to stand out, our BDR teams are trying all sorts to get attention. 

• Putting our names on digital signage
• Or a piece of paper they’ve been able to edit digitally

• Or highly personalized linkedin requests
• Delivering messages to buyers via Spotify playlists

The best example I found was this playlist example from a recruiter:

Pretty entertaining.

One cold email stuck with me from way back in 2018.

An AE from a company I know very well, who went on to become a BDR Manager, then GTM Consultant, and now full P&L responsibility for >100 staff.  

Firstly he referenced I’m from Bedford;  not strictly true, I went to school there.  I imagine he saw this on LinkedIn - kudos for the research. Next - he saw I am into the band The Libertines, which would have had to take some time to research! 

Funnily enough, I replied to this outreach and gave them my office address for the book.  He sent me a book on the Libertines, which sits proudly on display in my lounge even today. 

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How does receiving an email like this make us feel? 

Emails like this make us feel like a human sent them, who cared enough to have looked into us, perhaps made us laugh/brightened our day, but certainly caught our attention. 

Perhaps they even made me feel guilty for not booking a meeting!

Or…probably some mixture of all of the above? 

Whilst I think we need to evolve the way we’re sending outbound email, delivering that feeling to the recipient remains super important in order to drive a response and book that meeting.

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Next question to ask ourselves is who is delivering these messages and how do we compensate them?

Most commonly teams have dedicated XDRs sending these personalised emails.  People call them weird and wonderful things: Sales Development Rep; Business Development Rep; New Business Associate.

At some point, the efficiency gain is there for this to be someone’s full-time job, as per the predictable revenue setup popular for many years now.

How do we quota these reps? Most commonly, one of the following: 

• Sales accepted leads? 
• Sales accepted demos? 
• Sales accepted meetings? 

In doing so, what happens is that your XDRs will optimise for hitting the target. So if we set targets that encourage high response rates and meetings booked, that’s what our teams will focus on and optimise for, whereas less care and attention will be taken on what happens to that opp later down the funnel.

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How do we solve for this?

Let’s think back to how we were feeling when we received that personalised email.

1. The rep made us laugh
2. They’d spent time researching us and our interests
3. Maybe we feel a bit guilty because they’d sent us a free book? 

So why did we book the meeting after receiving this email? 

We book the meeting based on an emotional response vs business need.  

We’re happy to give something back to the rep who worked hard, so sure we can give them 15 minutes, why not.  

But here’s the catch. We get a good response to meetings, but a large drop-off after that initial meeting because there is no actual need for the product from the respondent.

I’m not saying the companies who book meetings after sending a personalised email don’t ever convert. Of course they do…. 

The question I’d like you to ask yourselves is… Is there a better way?

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From hyper-personal to hyper-relevant.

So here’s the challenge: Can we book meetings for those who have a need for our product?  

Better yet, can we do so without negatively impacting response rates and meeting booked rates? 

This idea is the move from hyper-personalisation to hyper-relevance. 

What do we mean by hyper-personalised?  Delivering messaging personalised to the recipient, their interests and background.

What do we mean by hyper-relevant? Delivering a message based on the observable need of the business. 

In terms of driving great response rates, we need to accurately identify the pain the customer is feeling right now and be able to accurately articulate how we solve that pain.  The better we can do those two things, the better the response rate. 

We spend so much time trying to put names on digital screens, and build humorous playlists for our prospects. However, nothing can overcome finding the right customer, at the right time, i.e when they have the greatest need for your product, and articulating how we solve that need (i.e right message).

Doing that trumps a smart subject line, email tip or trick every time.

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So how can companies integrate hyper-relevant messaging into their outbound campaigns?

Below are some examples of how companies could use hyper-relevancy in their outbound messaging.

All of these I’ve written myself for the purposes of this article. I’m not affiliated with any of the companies (bar Paddle), and each has been written based on assumptions around their value propositions and ideal customer profile. 

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Case study #1: Paddle

Paddle is contacting folks based on an observable need: “seen you’re getting >25% traffic outside HQ in the US, but only supporting English + USD.”

This is the observable need “Paddle” has identified in the recipient’s company. It’s this need which has led me to contact you. 

“We help companies like X optimise for this traffic,” this is our explanation of how we can help, potentially layering in social proof. 

Here “Paddle” are explaining that they are relevant to the problem at hand, they can help convert traffic better. The recipient has a need, and Paddle has a solution.

Paddle could then deliver a closed question CTA: “Can I show you 30 second Gif of the checkout in action?” 

One thing I have seen across many companies is that closed question CTAs, which require no thought, work very effectively. 

In the companies I work with, the goal of the first email is to elicit a response. In B2B Sales, you’re not going to educate buyers around your entire solution/value prop over email, so we need to get them on the phone to do so. 

Some companies go straight-in for meetings booked on the initial email. This rarely works. However, what we’ve seen in the past is that once a prospect has responded to an email, chances of booking a meeting go up exponentially.

Try to keep your email as simple as possible and easy to reply to as a yes/no.

Then push for the meeting on the 2nd email.

That being said, the main thing to take away here is that we’re outreaching to a company based on an observable need for our product. Indicated by traffic, currencies, languages in this case. 

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Case Study #2: Sticking with Paddle.

A similar idea - but even more specific and even more relevant. We went a little deeper with these internationalisation sequences given how well they were working…

“We’ve seen >10% of traffic coming from China…”

“But you don’t support yuan, mandarin or Alipay” 

The above is what I noticed about you, made clear in the very first line of the email. What’s the impact of that observation? Worse conversion for you and your company. CTA? “Can I show you how your checkout would look optimised?”

If you can make the CTA non-committal (eg. 30 seconds) and a closed question, this tends to help with responses. 

If you can make the CTA a “Show you” this also works well. If they say “yes” you can quickly pivot this to a “...better yet why don’t I show you over a call/zoom?” 

Remembering our initial goal is an email response, our main goal is a call since very few buy without one.

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Case Study #3: Workato. 

Workato were picked at random, but as far as I understand they help other companies with integrations. An iPaaS solution of sorts, helping roll out integrations for a product, and how data flows between those integrations. 

What relevant message could Workato send? 

Starting with the observable need: “See you have a bunch of open jobs for devs, which mention integrations.”

Next, proof they can solve that pain/need: “Here’s how we helped devs roll out integrations super quickly using our solution.” 

Lastly, a closed CTA to elicit a response: “Can I show you a clip of just how easy integration is?”

Broadly speaking, hiring data is a great indicator of need.  Quite often we have to educate someone around a need, but if someone is hiring to solve a problem - they know they have it. 

If our product helps them solve that problem then we are off to a great start.

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Case Study #4, Sticking with Workato… 

Observable need: “I see customers complaining about integrations for your product on G2.” 

Indication or proof we can solve that need: “Here’s how Workato helps you roll out those integrations, quicker, better, faster, easier.”

Closed CTA: “What’s your most requested integration? I’ll show you in 30 seconds how we support it.”

This is very different to some CTAs I’m sent… which ask

“Is this of interest”, “Do you want to hear more?”, which is the very opposite of easy to reply to in my opinion. The more effort and thought the busy exec needs to put into that response, the more likely they won’t reply. So try to avoid this mental block. 

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Case Study #5: Deel

Last but not least in company examples we have Deel, an employer of record solution - helping companies hire globally in a compliant way. 

Observable need: “I noticed you are hiring across 4 locations as well as remotely right now.”

Proof we have expertise around the need: “When people do this — they struggle with compliance.”

Closed CTA: “Can I send you a clip of how we help you convert contracts into one that works globally?” 

I am unsure if contracts that work globally is the best message for Deel, but the structure around how to apply hyper relevance in your emails remains the same.

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What does this mean from a funnel perspective?

When we think about those examples or case studies, the emails still feel human and bespoke, like the XDRs have done their homework. Of course there is no reason you can’t introduce elements of humor or education, for example, stats on performance vs. peers.

Most importantly … the message is about what a company is demonstrating a need around, vs. a message which is purely personal. 

These hyper-relevant messages evoke the same reactions and feelings as those that are personalised, but typically yield better end-to-end funnel performance. 

Prospects don’t take a meeting based on how they felt emotionally about the outreach and don’t take a meeting when they don’t have a need or a fit, they take the meeting by engaging with you around a topic and value proposition you actually solve. 

We can maintain the high response rates, and meeting booked rates, but see improved conversion later in the funnel through to actual revenue. hich of course translates to happy BDRs, CROs, Founders and their investors! 

Long-term this is even more important as your are winning ICP customers based on a need your product actually solves.

All-in-all, relevancy is a great iteration on personalisation.

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What’s the outbound recipe?

There aren’t any silver bullets to outbound email and I can’t emphasise enough, the most impactful thing to drive improved performance is contacting the right customers, at the right time, with a message based on needs.

When we zoom in on subject lines, or CTAs, we get into the grey areas of subjective views vs  objective success and statistical significance.  Meanwhile, the advice is often out of date by the time any of it’s shared or become widely known. 

But I do appreciate there’s an unrelenting, insatiable appetite for advice around the topic. So if there is a recipe to go back and try at home… here’s what I’d encourage you to try, evolve, and play with. 

1. Start with emails without pleasantries, or anything irrelevant, we’re all busy after all.

• Instead start with the observable need for the business - why you got in touch
• “I see you’re hiring for role X”
• “I see you’re getting negative reviews about Y”

2. Talk about the impact of the observation and proof around how you help solve it.

• When X observation is true, people struggle with Y
• When X observation was true for company Y, we helped them with Z
• Keep it short and sweet: case studies, content, longer form stuff comes later
• Let them be intrigued and ask “how” … that's a trigger for a call in itself which is our goal

3. Deliver a closed CTA at the end of the email that is easy to reply to as yes or no.

• The response to the outbound email is our goal
• Following that chances of booking a meeting go up
• Try to make the CTA one that involves “showing” the prospect something
• This can lead very quickly to a meeting — where you can do a better job of the “show”

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Some quickfire advice?

Here are some quick fire pieces of advice in trying to deliver hyper-relevant email or outbound email more broadly.

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Marketing Email

Your outbound sales emails should feel like they’re sent by a human, not marketing. People are more likely to respond if this is true.

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Data references

I run a company that provides data on companies, sometimes to a more granular level of insight into a company than the people working at it have! But there are always risks associated with programatically gathered data, and it is never 100% accurate.

Bear this in mind when referencing things you’ve observed about a business. 

Don’t run with “I see you’re hiring 567 open roles” …. say “over 500.”   

Don’t run with “I see you’re using NetSuite”… say “folks like you are typically using NetSuite”…. 

This protects you from angry respondents and remains human.

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Basing email campaigns on triggers 

Many people base their email campaigns on changes in data.  This is very effective, however the volume of these changes isn’t typically enough. Try to build campaigns based on what is currently true about a company, for example:

* Email them based on having over X employees, vs. a change in that figure

* Email them based on current traffic not a change in traffic 

This means you can run ever-green campaigns based on stuff being true for a company, vs. being reliant on the changes themselves. 

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Striking the balance between nurture and close

I see some sales folks insisting they need to send 10 emails before booking a meeting.

I appreciate some education may be needed before someone jumps on the phone, but strike the balance here and don't be scared to ask for the meeting. Hearing no’s are helpful to move onto new prospects. If we’re truly successful at identifying the right customers at the right time, and sending them the right message — we can be quite forthright in asking for their time. We’re solving a big need for them that’s a pain right now after all. 

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Nail your tone…

I see some emails written full of jargon, or alternatively with perfect grammar and punctuation. These emails are meant to be written by our XDRs, so keep them simple. The next stage in the process is literally getting on the phone and speaking to the XDR. For me -  a consistent tone of voice, communication style from email through to that discovery serves up the greatest experience.

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Allowing buyers to self-evaluate 

I’ve got some battle scars here from Paddle.  If you’re creating a category or offering a complex product, buyers will struggle to evaluate you, or compare you to competitors. And it's very hard for them to differentiate when given a brief homepage comparison between your company and your competitors. 

As a result, I got pretty obsessed about trying to not let the buyer self-determine whether they were a fit for my product, or self-evaluate whether they should take a meeting.  I didn’t link them out to loads of content, my absolute focus was getting them on the phone, and only after that supplementing with materials to support, further education etc.

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So what should we expect in the evolution from personalisation > relevancy?

Our emails should yield the same response and benefits that we’ve seen from personalisation. However, rather than optimizing for top-of-funnel leading indicators like responses and meetings-  we should see it more likely the interest is carried through to close and beyond. 

Employing these methods Paddle grew at 300% YoY for 5 years with outbound email as our sole channel, and we’ve since applied the same practices to many others. I’m excited to hear how it works for you!

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