Winning By Design
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Winning By Design

The Personalization Lie: 4 Easy Steps to Write Epic Emails at Scale

Don’t confuse personalization with relevance.

Just because you put in my {first_name} and noticed I worked at {company} as {job_title}, it does not mean I want to check out your free trial or meet with you for 15 minutes. But if you have insights that may help me specifically do my job better, by all means! Share how you can help.

Video: Salesman Podcast with Will Baron

If You Want Success, Figure Out The Price, Then Pay it — Thomas Oppong

Sales is NOT Just a Numbers Game

The conclusion from the famous report authored by Dr. James Oldroyd is you need 8–12 touches within 14 days to optimize the value of every lead. That single recommendation has been incorrectly interpreted to assume that all touches are equal, and that tools that allow reps to blast out lots of emails is the best sales approach.

It discounts the need to actually be valuable, and instead rely purely on volume based tactics that often result in pissing off the majority of your Total Addressable Market (TAM).

Figure 1: Traditional sales and marketing emails are much more likely to be considered spam because of lack of relevance

Right Intent, Poor Execution

Unfortunately, this high-volume advice has led to many eye-rolling, stomach-churning emails executives get in their inbox 124 times per day from well-intentioned but self-centric salespeople just trying to stand out:

Figure 2: Email highlighting a creative attempt at being funny that in reality is sales-centric without any value to recipient.

Brief History: How did we get here?

In 1971, the first email was sent by the Department of Defense using ARPANET. Twenty-one years later in ’92, Unica became the first marketing software to combine CRM data with email marketing. But it wasn’t until 1999 when Eloqua defined the marketing automation category. By the mid-2000s, the breakthrough of cloud technology led to the birth of many great companies like Hubspot, Marketo, Act-On and Pardot. It became easy and affordable for companies to send out personalized emails based on CRM data. One thing led to another, and now there are many great sales automation tools like Yesware, ToutApp, SalesLoft, Outreach and ZenProspect.

All great technology is subject to abuse. To over-simplify, adding a customer’s name 15 years ago made them more likely to engage with the marketing/sales message because they felt like “wow, this person took the time to write to me.” This has continued to be refined and more targeted to the benefit of customers and prospects.

Unfortunately this type of outreach has been so abused, many governments have passed legislation like CAN-SPAM and CASL to protect our inboxes with penalties up to $10 million.

Sales vs. Marketing

During the rise of sales automation, powerful tools usually reserved for marketers to allow large-scale customer communication have now found their way to frontline sales professionals without proper training of how to use them effectively.

Worse, there is tons of bad advice about “great results” from 1,000 dials/emails per day without consideration that your TAM is not infinite. In today’s connected world, the price of negative customer experience can result in permanently ruining opportunities to partner together. And if you really made them mad, they could tweet about it and ruin thousands of other opportunities.

Salespeople aren’t spamming to be jerks on purpose. They just haven’t been trained properly on how to communicate with customers.

Figure 3: The most prolific sales trainer in the world: Google

Here are the 4 Steps to Write Epic Emails — Relevance at Scale

Like every great song or movie, a great email follows a certain structure. There is not enough time in the day to write a hyper-personalized email to everyone you need to communicate with while running a business. The advice below should be applied thoughtfully depending on the scale you’re trying to reach out to. For practical advice like how to keep it short and [an-outdated] template, check out this post.

1) Understand your customer

Each email you send is a request for your recipients time. Don’t waste it by talking about yourself. If they don’t already know you, they don’t care. What they do care about is if you can help solve their problems, or make them look great in front of their team.

Most of us mistake trying to be valuable by talking about what we can bring to the table, or lead with social proof to demonstrate we are worthy of time. These emails have a lot of “I”-statements, and some sort of pitch.

A perfect elevator pitch is spam without compelling context.

Make your communication efforts based on what your customer cares about.

Practical Email Tip 1: Review your email, and convert “I-Statements” to “You-Statements”. A common writing mistake is to just convert “I noticed on LinkedIn” to “Noticed on LinkedIn”. This is just bad grammar! Change to something about them — and make sure it passes the “So what?” test. “Your recent blog post on restructuring sales teams was very insightful…”

Figure 4: Title-Totem-Pole showing Value Drivers by Persona

The best email you could send to a CEO will look much different than the best email you would send to a manager. Their pain-points are much different, and therefore the message you send should address what they care about.

Simple ways to implement this is to break down your ideal customers by personas. This could be based on their job title, or function and is simplified in figure 2 above. Research and understand your what are their common pain points, and things they care about.

Create a matrix in excel or google sheets with ideas around

  • What they do — day in the life
  • Value Proposition you can most help with that applies to their role
  • Emotional and Rational Pain Points
  • Titles of similar roles you may see on LinkedIn (i.e. Director of Sales and Sales Director mean different things)

2. Identify value you can share

Don’t tell them you can help, prove it. Give them something that they’ll find valuable so they want to have a conversation with you. Henry Schuck, CEO of DiscoverOrg wrote an impressive post highlighting Will Elmore’s sales effort and insight to start a conversation. TL;DR: Don’t expect a meeting with a CEO without providing value first.

You can’t repeatedly earn extraordinary results without putting in the effort, being deliberate and measuring outcomes.

Link to a blog post, video, or case study that is relevant to them by persona, industry or recent event like raising funding. Easy right? Take it to the next level and share with them why it’s valuable to them specifically (Tip 2 below). Build a spreadsheet that is updated quarterly with relevant links by industry and persona. It’s perfectly fine that you send insights NOT created by your company like HBR articles. If it’s relevant, they’ll associate your brand with the value you deliver.

Figure 5: Create a spreadsheet with value-adding resources for your customers.

Use these in your emails over time — don’t send all 3 articles you think could be relevant in 1 email — space it out in order to deliver value over time.

Practical Email Tip 2: Always point to the part that is relevant in the blog, video or report that you are sharing. Save them time, and increase the likelihood they read what you send them by pointing out a specific part. “Here’s a video on effective speaking techniques that made me think of our conversation, specifically 6:21 where Julian speaks about pace…”

3) Scale your relevance efforts

If time was no issue, of course hyper-personalized emails would be the optimal approach. But to balance effectiveness with efficiency, use tools to maximize your effort.

The research that you’ve done about the person you’re emailing doesn’t need to be repeated before each email. Store your snippets in a way that make them easy to enter intro your email.

Many inside sales teams build sequences or cadences in a X*Y format (where X=number of touches, and Y=number of days). So an 8*14 would be 8 touches (email or call) over 2 weeks. Research everything you need before you start the sequence.

Make sure your emails are relevant by building your sequences with specific personas and by verticals in mind. Adjust language and linked blog posts/videos to be relevant to the recipient. Depending on your outreach objectives, a rough guideline is to spend 90–180s on each contact to find at least 3 unique insights for each person you plan to send a cadence/sequence to.

Check out what Adrian from Liftoff does when he’s researching and building out custom snippets he can insert into email templates. Each column will be a piece of information that is pulled into the sequence at some point. For example, “Custom 5” column represents which page of a white paper study is most relevant to that persona.

Figure 6: Building snippets to be used in email templates. Click here for example. Note that data listed here is hypothetical.

A simplified email template using Figure 4’s custom snippets shown above would then look like this:


Hi {first_name},

{custom 1}.

Based on your priority to have customers {custom 3}, please find best practices that {custom 2} has been leveraging in the past few months: {custom5}.

Is that relevant to you?

Thank you, Adrian


Even though you may send out 25 of these emails at the same time, as long as it is segmented by a specific persona in a specific industry/vertical, the email will be much more likely to be relevant because of the research you’ve done. Without segmentation, the same email could easily be considered spam.

Practical Tip 3: Every email doesn’t need to have a meeting request. Instead ask if what you sent was valuable, if they’d like to have a conversation to learn more or simply with gratitude for them reading your email. If you are valuable, the meetings you earn will be plentiful and engaging.

4) Start small and A/B Test

Before you focus on scaling your email efforts, first make sure your emails are good as 1-to-1 emails before testing them out in small batches. Test your emails to make sure they resonate with your customers before you send it out to your full customer list.

Figure 7: Test your email in small batches before sending it out to the world.

Practical Tip 4: Don’t optimize Vanity Metrics like open or reply rates without context. Look for conversions and pipeline generated after a completed sequence. It’s common to try and close a meeting in 1 email attempt — instead, measure meetings over a multi-step sequence since those will usually have more educated and engaged customers.

If you are only looking to maximize open rates, imagine tricking your customer with the following subject line: “Our next meeting Tuesday at 2:30”. The open rates will be amazing! But the customer probably reads it, then gets angry. They think at first “I forgot about this meeting — who is it with again?” *Click → open email. Then when they realize it’s a meeting request with a stranger sales person: “Aargh! I’ve been tricked! It’s just a sleazy salesperson.” And then they’ll never do business with you in the future.

Point of the story — if you’re only looking for great open rates or reply rates, you may be missing the important goal: starting conversations that lead to helping customers solve their problems.


Sales organizations need to evolve to meet customer’s expectations. The SaaS business model is unforgiving to pushy sales tactics that get the customer to sign a deal without ever achieving their desired outcome. The increasing number of competitors with similar features means that sales professionalism will now be the key differentiator.

If you want to start more conversations through better emails, focus on relevance, not personalization. Your customers will thank you for it, and reward you through great conversations and if you play your cards right, a few long-term partnerships.



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