Ultimate Guide to Sales Email Personalization 2020

Of late, I’ve become enamored of the insanely valuable content Becc Holland has been producing on email personalization. While she may not realize it, her approach builds on the shoulders of giants, esp. M. Jeffrey Hoffman who pioneered a similar approach at his firm BASHO Strategies circa 2002.

In the post, I’m going to prospect Becc leveraging her and Jeff’s techniques.

To set context for what I’ll improve upon, let’s start with the following well-optimized but still generic email:

The email is well-optimized in the following ways:

• Length: The email is short and sweet – just 56 words.
• Subject: SalesLoft data science has found that 1-word subject lines have the highest reply rates. Moreover, one should use sender’s company name in the subject line rather than the prospect’s first name or company name.
• Salutation: SalesLoft data science has also found that “Hey” is *currently* outperforming Hi, Hello, or the prospect’s name alone.
• Hook (paragraph 1): We looked at SalesLoft’s best & worst performing templates. Those combining social proof with positive business impact performed best. Those framing problems or challenges performed worst.
• Value Prop (paragraph 2): Using the same best/worst approach, we found WHAT (“… platform …”) + HOW (“… to ensure consistent execution…”) language was most effective.
• Call-To-Action (paragraph 3): The best/worst analysis actually showed CTA wording has relatively little impact on the reply rate. I like this one because it offers value and implies that this won’t just be a painful discovery call.

After running this email for a while, we used more data science (cosine similarity) to check the reply rate versus the amount of personalization our SDRs were applying. Consistent with our prior study, we found personalization of at least 20% of email content yielded a nearly 2x increase in reply rate.

Everyone knows they should personalize. However, what people are really hungry for is how to personalize. This is where Becc, building on Jeff’s and others’ work, steps in with the following premises (ranked from most to least effective):

1. Prospect-created content
2. Prospect-engaged content
3. Prospect self-attributed traits
4. Prospect demographic information
5. Prospect company information
6. Prospect persona

Prospect-Created Content

Examples of prospect-created content include articles or posts on LinkedIn as well as conference, podcast, or webinar appearances.

Prospecting Becc, I’m lucky she is super-active on social media. In particular, she is heavily invested in her (must-watch) Flip The Script series.

Let’s break this down.

The most important thing about this email is there is no way a machine could have generated it because of all the little details. A machine would not have known to abbreviate Flip the Script as FTS (I’m not even sure Becc does but that’s OK). A machine would not have pulled specific and relevant detail from minute 23 of session 3.

The other critical detail is the segue linking the choice of streaming music services to the choice of sales engagement platforms.

IMPORTANT: Amatuer personalization fails to link the personalized prospect premise to the sellers’ solution. For example, I received the following email recently:

I’m not into rep shaming and I want to give the rep props for his attempt at personalizing. I use this email merely as an example to illustrate what happens when one fails to link personalization to product. Here, there is no link between NJ Devils hockey or my hometown and his solution (sponsoring a sales & marketing event). The phrase “Anyhow…” is not segue.

It is neither here nor there but I’m not a hockey fan. I am hyper-active on LinkedIn so this rep could have targeted me much more effectively.

What would better segue have looked like? How about: “While sponsoring the Devils might be shrewd for Prudential, I’m betting you’ll get more bang for your buck targeting sales & marketing professionals at our upcoming summit.”

Prospect-Engaged Content

If I could not find prospect-created content for Becc, then I’d turn to prospect-engaged content such as comments, shares, or likes on LinkedIn. These three categories are not created equal. Since comments take the most amount of prospect effort, you should start there.

As it turns out, Becc does like a lot of other content but does not comment often. Precisely because the segue will be a stretch, I choose this comment of hers: (It also helps that Becc worked at G2 so I’m guessing she knows Ryan directly).

Here is how I would personalize:

Prospect self-attributed traits

Self-attributed traits are found in the Headline, About, and Experience sections of your prospect’s LinkedIn profile.

Becc’s headline (Head of Sales Development at Chorus.ai) and background image don’t give me much to work with.

Similarly, Becc’s experience section does not provide any detail.

I strike pay dirt in her About section

Here is how I’d leverage this:

Prospect demographic information

Hopefully, you will have been able to personalize with prospect-created content, prospect-engaged content, or prospect self-attributed traits.

Personalizing using prospect demographic information falls into the “something is better than nothing” category. As with the prior examples, the key here is to show that a human (you) put in real time and effort.

Demographic information includes career experience, education, volunteer experience, recommendations given or received, accomplishments, hobbies, etc. Much of this can be found to varying extents in LinkedIn or via web search.

Here, you want to look for legitimate commonalities if possible. As it turns out, Becc and I have very little in common. We do have a whopping 1,064 mutual connections but I’m not a big fan of referencing that since it is impersonal.

Here, I leverage a recent recommendation Becc received from her former colleague.

Prospect company information

For people who have a limited web footprint, your next best hope is to leverage information about their company. This may include press releases, financial disclosures, executive hiring, M&A, blog posts or other content marketing, website copy, etc.

Here, I personalize using a tagline from Becc’s company’s homepage. I included an image of the website for two reasons. First, SalesLoft data science shows including one highly-relevant image boosts the reply rate. Second, there is a good chance your prospect has not been to their company’s homepage recently.

Prospect persona

Worst case, if you do not have a relevant prospect or prospect company premise, then you can at least personalize on their role as follows.

Final Thoughts

There is a bit of a trade-off between the degree of email personalization and the amount of activity any rep can complete. While each organization will need to decide the right mix, all signs seem to be pointing at consistent personalization being table stakes as prospects ignore un-personalized and dynamically-personalized (i.e machine personalized) emails.