The Complete Guide to Quantum Leaping Personalization at Scale


There is an existential crisis with personalization today. If you do it wrong, you alienate your customers. And even if you do a good job, you’re often ignored and risk being seen as an irritation.

You only have one shot of standing out, and that’s by doing a GREAT job and hyper-personalizing.

So, stop settling for good. I’m going to walk you through everything you need to know to hyper-personalize and take a quantum leap forward with your outreach.

So strap in as we cover:

Are you an Outreach user? Read: How to Do Personalization at Scale with Outreach

The Current State of Personalization

When I think about the state of personalization in 2020, I immediately think of {{curly bracket}} epic fails!

How many of you have been unceremoniously met with the following suddenly appearing in your inbox?

Dear {{}}

For some reason, a parameter failed, the curtain was pulled away, and all it did was remind you that this seller (and their company implicitly) is automating their outreach to you.

How did that make you feel?

Like a piece of meat? Like just another number to be counted in the queue?

This is the downside of the modern Sales Assembly Line — both buyer and seller feeling like a cog in the wheel.

It’s time to stop the insanity, people!

The bright side of this is that it gives you an opportunity to stand out. AI and machine learning haven’t officially passed the Turing Test (even though I want to believe I have when it comes to email).

I was recently speaking with a CEO who posited,

“We are applying AI and ML to the wrong problem! Once machines can perfectly write emails, there will need to be a warning label on them.”

Instead we need to focus on using our own voices and words to send each prospect a unique message. AI can help scale this, but we need to be careful not to rely too heavily on it.

So, let’s learn how to change the game and personalize the right way.

Building the System

To scale your outreach you need to build a system to ensure your message gets seen.

If no one sees your email, then it doesn’t matter how long you spent painstakingly personalizing it, it won’t do you any good.

This is where you can use automation tools to your advantage. Use them to increase your contact rates in both email and traditional cold-calls by making sure they’re going to the right people. Sales Engagement Platforms are very helpful to increase your opens in email, and dialer technology is very useful with phone calls.

The system you set up becomes even more important once you begin doing outreach at scale, but I’ll go over that more later.

The 3 Parts of Personalization

Personalization, Relevance, and Timing are the three-headed Hydra of getting personalization right. They need to become your mantra impacting everything you write.

In this article, I’ll be focusing on personalizing and scaling your message, but timing and relevance are just as important.

And this is where 99% of sellers fall short.

Imagine I am selling you an amphibious vehicle.

Personalization issues: I didn’t know you hate the sea and get seasick.

Relevance: I didn’t realize you just bought another primary vehicle.

Timing: I didn’t realize you’d just taken out a second mortgage on your home and are saving for a wedding.

So, what do we do as sellers when this happens?

We start to blow hard on features, functions, and benefits (FFAB).

“Well, we’ve improved the core technology of the Amphibious Kit. You can go deeper in the ocean now, and it’s got a faster outboard motor. But wait, there’s more… We’ve launched sonar to detect oncoming boats, jet skis, and sharks.”

What’s the problem here?

We neglected to figure out — in advance or in discovery — if what we are selling is relevant or timely to the prospect. You can keep perfecting personalization all day, but if it’s not something the prospect intrinsically needs, they’ll never buy it.

Amazon is excellent at this. They are great at giving personalized recommendations based on what they already know you love. And because they track your buying habits, they give you the recommendations at the perfect time.

The Importance of Hyper-personalization

Most sellers focus on personalizing their content, but they often fall short of the hyper-personalization that is required to really stand out.

Go beyond the curly bracket to produce content that is so tailored a machine can’t touch you until 2035.

For example, if you listen to a podcast interview or webinar, and they are legion now that we are all nearly remote in the crisis, you can pull a very specific section to reference.

“Hey Prospect, I noticed you talked about the challenges of scaling remote sales organizations at minute 4 and 14 seconds. Our intranet integrates with all your legacy systems to augment their functionality whilst keeping everyone connected with one-click boosting morale and esprit de corps. Learn how Some Hot Tech Startup increased productivity by 115%.”

Let me walk you through a real-world example.

A while back, I was leisurely, and randomly, reading a Wired magazine when I overheard the CMO of a major hotelier talking about keyless entry into their rooms via mobile app. This seemed space age to me, so I called her desk line using DiscoverOrg and got her message machine.

I left a quote and some thoughts I had about how they could optimize this from a customer perspective. I told her that when I book the stay, I should be prompted to download the app. The app should track me with GPS and immediately alert me when I’m near the property — so it’s top of mind.

If I already have the app and have checked in digitally, it should link me to the specific section of the app with my virtual key. I walk into the hotel, walk to the room number, and *click* the door opens.


Even when these massive companies invest in tech like this, it’s often hard to get customers to download and use the app, much less adopt it. This, I thought, would be an excellent way to solve this problem.

I share this fine-grain detail because of the following crucial rule…

Anything you personalize must be tied to the unique value proposition you’re attempting to solve for your prospective customer.

That’s the key to hyper-personalization.

Tie your personalization to the value the solution will create. (Make money, save money, reduce risk, answer to a new regulation. Steve Richard calls these demand types, and the last one is most potent!)

Scaling Your Personalization

Now let’s scale this puppy! But there are some serious speed limits we need to consider first. So, let’s look at those before you fly too close to the sun, Icarus!

Speed Limits

You can only send about 75 custom connect requests per-day in LinkedIn at the time of this writing. And you get about 50 InMails per month on LinkedIn Sales Navigator.

Gmail should be limited to around 150 outbound emails per day, per email sender (you can feather these by creating multiple email addresses and

If you are manually dialing, you are limited by the data set, so choose one with high-quality cell phone and direct numbers vs. switchboards (I recommend testing out several data sources in a bake-off to suss this one out).

AB Testing

Because you’re limited to only sending out so many emails and messages a day, you need to make sure you’re using the best possible message.

This is why AB testing everything is critical.

Honest Abe Lincoln was famous for saying, “Give me six hours to chop down a tree, and I will spend the first four sharpening the axe.” It’s the same with scaling your personalization strategy. You should run a sequence to 100 prospects with a few touches in order to test a new personalization mechanic before scaling it up to a thousand sends.

Obsesses over your ICP (ideal customer profile). Build out personas, and run cohorts for manual connection requests and touches inside LinkedIn.

Become a Power User

Learning to become a power user of your automation tools is key. This includes programs like Outreach, SalesLoft, Groove, and XANT, as well as dialing systems like Orum, ConnectAndSell, and ConnectLeader. Some of these systems offer trials to allow you to road-test them, and Outreach and Salesloft have online universities for basic onboarding and how-to learnings.

Learn how to leverage your Sequencer’s custom fields. And learn how to leverage your Sales Engagement platforms snippets. These are saved, shareable bits of templates that could be battle cards on competitors, for example.

Then as SDRs are programming sequences and cadences, they can just browse a library of great “fear, uncertainty, and doubt” (FUD) to drop in the emails as they are composing.

There are 35 custom fields in Outreach which allow you to pull in data of intent or technographic drops. Imagine if certain accounts are searching for Hadoop, you could prioritize these accounts and write custom sequences for them.

Lars Nilsson, the co-Founder of Sales Source, did this when running worldwide Sales Development for Cloudera. Technographics, firmographics, and psychographics form the bedrock of hyper-personalized email. By layering in all three, I do believe we passed the Turing Test at OutboundWorks in 2017. That is to say, prospects couldn’t tell our emails were written via AI-personalization injection rather than being manually pre-written by a human.

Determine the Level of Personalization

When you’re scaling personalization, you need to make a judgment call in an ABM model of just how much to personalize. Jeremey Donovan at Salesloft typically looked at a sample size of 6 million emails to determine how much of the email needs to be personalized. He found the answer is around 20%.

My personal philosophy is to separate prospects into a minimum of 2 Tiers. For the top 50 dream accounts, I am going to hyper personalize, maybe even touch them manually, and then set full automation on the next 150 accounts I’m working in any given quarter.

Let’s see how this might look:

This is fully automatable:

Hey {{first_name}}, I noticed that your headcount recently increased by {{custom_1 = employee increase}}. We find explosive growth poses integration challenges for RevOps. Based on our connection with {{insert_common_connection}}, it looks like we are both highly interested in the confluence of Sales and Marketing Operations.

This is adding hyper-personalization:

Hey {{first_name}}, We’ve been connected on LinkedIn since {{custom2 =}}. I noticed you love quantum physics and acoustic guitar. Based on your recent funding round of {{custom3 = funding amount}}, I thought we could get on a Zoom, get out our guitars, whiteboards with physics equations, riff on those oh… and maybe also talk shop about Revenue Operations, because we are both connected with Jeremey Donovan. Thanks, Justin

Automating LinkedIn

LinkedIn is more difficult to automate than email, and for good reason, but there are automated ways to approach LinkedIn connection requests, outbound sending, and interaction with replies. Companies like and AmpleMarket are working on this problem. But keep in mind, that these kinds of tools are potentially risky for two reasons.

First, tools that use chrome extensions violate the terms of service and are often detected (not to say every tool does this, but look out for scrapers and automators on LinkedIn). Using something like this can get your LinkedIn profile shut off.

The bigger issue, though, is that LinkedIn automation tech is often so wonky on the frequency it sends messages that it’s a dead giveaway.

I often receive bizarre LinkedIn automations that look like a really pitchy email with a bunch of bullet points followed by a near-immediate push reply:

2:05 PM – Hey Justin, Sounds like we are both interested in advertising technology, let’s connect! (looks normal)

2:07 PM – Thanks for accepting my request, at MegaCorp, we analyze all your ads so feature, function, benefit – 1000% ROI. Can we meet on Tuesday or Thursday?

2:08 PM – Justin?

Not kidding. This bot went around sending this with that 3rd jarring touch, and it even reached some threads I’m on. I instantly detected it as automation, but others remarked, “Wow, this seller is so pushy!

Needless to say, you don’t want this.

RELATED: The 3-Step Mantra to Modernize Your LinkedIn Lead Generation

The best way to get better at all of this is to start a Slack Channel in your own company where you tear down all the inbound emails you get — automated, manual, or otherwise — and collectively analyze them.

What do you love and hate about them?

Where did they go wrong?

Encourage all the executives on your team and your colleagues to share screenshots in the Slack Group whenever they actually take a meeting or respond. This is the fastest way to learn what works, via crowdsourcing.

What doesn’t work are templates, ordinary approaches, and basic curly brackets. Bullet points and overly neat writing are also big no-no’s.

Remember, it’s not marketing copywriting — it’s outbound sales.

One of the biggest mistakes I see on LinkedIn is treating it as a transactional channel. Salesforce data shows it takes 6 to 8 touches to create a viable lead. Why then, do most sellers — and it’s true if you think about your own inbox — connect impersonally and then pitch immediately. The Connect and Pitch culture on LinkedIn is so bad it’s a proverb.

And when reps get ahold of InMails (with the limit of 50 to preserve the community), they invariably copy and paste a beautiful template. Except that templates don’t work, however much you personalize them. Personalization is a holistic problem – grammar, syntax, tone, and intent.

Another problem I see is reps not using their full allocation of LinkedIn Sales Navigator InMails every month. And the reason for this is that it can feel like it doesn’t work. Getting one meeting from 50 InMails seems low. But you need to remember that using your Sequencer, you often end up sending hundreds to get that same one meeting outcome.

If you extrapolate the math and make sure it’s an apples-to-apples comparison, you’ll find LinkedIn InMails perform 30% better, which is the stat LinkedIn gave me on the phone with my rep the other day.

How to Stand Out

I believe I’m an authority on the topic of Personalization at Scale because I’ve done it wrong thousands of times.

So here are three tips that I’ve had to learn the hard way to stand out.

Use your own authentic voice

Just be you and write like you talk. Conversational approaches are King, Queen, and Ace because no one can mimic your true voice, and that shines through in your writing

Use pattern interrupts

Flex your poetic license to make the grammar different. You can tell by the way I write it’s unique syntax. I have my own style born out of millions of emails sent. This includes ‘funking the grammar’ as I call it, and emojis.

AB test

AB test on a pendulum, or spectrum, from formal to informal, emotional to dry, left brain to right brain (this would be scientific facts vs. emotional stories). Prospects buy on emotion and close on logic, so sometimes both are powerful.

Dare to be different! There needs to be a ten-year moratorium on “Hope you’re doing well, or just reaching out.

I once had a partner that signed all her emails with Lemmeno! Talk about standing out! I started to sign all my emails with Lemmeno and add a lemon emoji .

The more you AB test, the faster you’ll learn, iterate, and get smarter. As you scale your personalization and get various replies and results, keep that internal knowledge in a shared Google doc.

Advanced Personalization Is Coming

Whatever you do now. You always need to be aware of what’s coming on the horizon. That’s how you stay ahead. And right now, what’s on the horizon is something called Liquid Syntax.

Liquid syntax allows you to build in logic to your personalization. Imagine the curly bracket parameters above, but instead, they’re injected with scripting, so the following scenario is possible.

You send one email to 1,000 sales leaders, Director to VP, VP to CXO. The machine can line up the title in the database to the script parameters and dynamically deploy a different call to action (CTA) for each role!

Can you imagine? You can also utilize fall back logic like with personalized push messages in a wild variety of ways. “Hey John,” or if there’s no name in the database, just “Hey.” That’s the simplest form.

Luis Batalha, Founder at AmpleMarket, is working on futuristic ways to get the scripting technology to automagically scale personalization for you.

Check out for a portfolio of high-quality examples!

The more creative you are, and the greater level of effort, the more dramatic the result.

Be Buyer-Centric

Your messaging needs to be conversational, personalized, relevant and timely. And it needs to be deployed with enough frequency that they read it, but spaced out enough that prospects don’t feel like they’ve suddenly been placed on a mailing list they did not opt into.

It’s a delicate balancing act. And it’s difficult to get right. But above all, be unique and focus on giving the best experience to the buyer.

Your personal brand becomes everything as you scale your networks to the maximum (30K is the cap, and I’m just reaching 29K — I had 200K on MySpace in the heyday). It’s my personal belief that one should personalize connection requests because prospects “like” it. Modern sales is buyer-centric!

Whether you resist change or not, it is still a game of know, like, and trust.

Make it about them!

And remember… anything that doesn’t look like it’s possible to make with automation wins.

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