How to Book a Meeting Over Email with Josh Garrison

What makes a great cold email? There are dozens of templates for email outreach, but before you craft a high-converting email, you need to understand the strategy behind it. Our latest podcast guest is an expert at prospecting, and he had plenty of insights to share.

Josh Garrison is the Head of Content Marketing at Apollo, an all-in-one sales intelligence platform with tools to help you prospect, engage, and drive more revenue. He joined the Predictable Revenue podcast to discuss how to book more meetings over email.

Strategy

Before we can create messaging or a sequence, we need to look at the overall Strategy of your go-to-market motion. For that, we recommend using the idea of the Crux from Richard P Rumelt:

Situation – outlines the relevant context of your potential customers
Diagnosis – defines the challenge that is holding them back from achieving their goals.
Guiding Policy – defines your approach to help them overcome their challenge.
Coherent action – defines how the guiding policy will be carried out.

Writing these down on paper or in a doc can be a helpful exercise for building understanding and empathy for the user across everyone that will be involved in the outreach. If you are an SDR, it is important to understand your company’s answers to the above before embarking on any sales outreach.

Strategy – see above.

Method – which styles/tactics/approaches will get the best result?

Messaging – what is the core message?

Why Effective Outreach Starts with Defining the Right Goal

The biggest mistake SDRs make is to approach their cold email outreach with the goal of booking a meeting or making a sale. Very few meetings will be booked after just one email, which is why it’s more important to focus on building a relationship with the prospect.

In the first few emails, your goal should simply be to start a conversation and determine if the prospect needs what you’re selling.

Give a straightforward introduction to who you are and what you’re selling, then ask if that seems relevant to them. If they say yes, you move forward and ask for the meeting.

Ideas to consider before you put pen to paper

Ask yourself what you are trying to accomplish with this sequence.
The email communication should act as a movie trailer, sharing as little as possible to get the prospect’s interest.
Remember that you’re not selling your product over email. Between 2-5% of people are looking for a new X; your strategy should recognize this.
The overall goal of a cold email is to establish a relationship and ask to see if they need what you have. Maintain a relationship with those relationships by not being annoying. Brevity is key here.
Your email should look like the buyer’s normal email traffic.
Good messaging is Relevant, Thoughtful, and Human.
Good messaging builds on your Hypothesis, Style, and Structure.
Don’t get too attached to your first version.
Send in small batches of 100-200 prospects, send them weekly, and try to launch them on the same day.
If you’re starting fresh, it can take months of iterations to really get this tuned.
The best day of the week and time of day is now.

How to Establish a Relationship Over Email

Think of your email outreach like a movie trailer–give the prospect just enough information that they want to learn more without giving away the film’s whole plot.

Another important factor to consider is what your prospect’s email inbox looks like. CEOs received hundreds of emails daily, and they can tell at a glance which ones are relevant and which are spam.

If you’re selling to the C-suite, keep it short and relevant. Most executives don’t have time to read a lengthy email with six paragraphs. The ideal length would be one sentence, but if you can get it down to three, that’s a great place to start.

Why You Should Always Leave a Voicemail After a Sales Call

Another underrated tip for email outreach is to follow up over the phone. Leave a voicemail introducing yourself and letting the prospect know you emailed but haven’t heard back. Very few sales reps will take the time for this additional step, but it can significantly increase the number of meetings you book.

The 3-sentence Email Outline for More Replies

A great cold email consists of three parts:

The subject line, which determines your open rate
The body copy, which determines your reply rate
And the call to action (CTA), which determines your conversion rate

Ideally, each one of those will be one sentence long. The subject line should let the prospect know who you are and why you’re reaching out, the body copy tells them why they should care (i.e. the core benefit), and the CTA makes an ask.

Tips for stronger CTAs

Again, remember that you don’t need to book a meeting on the first email. Try a “soft ask” first (i.e. asking if your product is relevant to them). Make the CTA its own paragraph so it stands out, and make sure you’re asking a question that’s easy to reply to.

Email outreach example

Hey Collin,

I’m Josh; I own a software company that helps salespeople sell more. I know you own a sales company and I think you’re leaving money on the table.

Are you looking to get more from your sales reps this quarter?

How to Design a High-converting Email Sequence

The best cadence for follow-ups:

According to a study by Backlinko, emailing the same prospect multiple times can double your response rate. Josh recommends a four-email sequence spread across three weeks:

Email 1: Initial outreach following the template above.
Follow-up 1: Reply to the same thread as the first email and restate the call to action.
Follow up 2: New email thread, same format as the first email, restate the benefit.
Follow-up 3: Reply to Follow-Up 2, and ask if solving this is a priority right now. Sign off with something funny in the PS note.

In the third follow-up, your goal should be to make the prospect laugh. If they haven’t responded to your other emails, this is your last chance to grab their attention, so don’t hold back. You can also mention any colleagues of theirs you’ve been in touch with.

The difference between “no” and no reply:

If a prospect responds and tells you they’re not interested, write them back and ask: “Is it okay if I check in six months from now and see if anything has changed?”. This creates a legitimate email exchange and makes it more likely they’ll remember you when you follow up.

How and When to Follow Up on Cold Emails

If you get no response, you can follow up on other channels, but don’t send more than three emails within 30 days, or you risk being flagged as spam. LinkedIn is a great tool for connection and can be used to warm up prospects before sending another call or email.

Lastly, if you try all of those channels and still don’t hear back, add the prospect to a new sequence that will restart in six months. They may not have been in a buying motion when you reached out initially, but by then, things could have changed.

The end of a fiscal quarter or new fiscal year is a great time to reengage cold prospects. Old contracts are ending, new budgets are being built, and you might catch them at just the right time.

Choosing Who to Target Within Each Account

The most successful email outreach campaigns target multiple contacts within the same organization–a technique known as multithreading, which can boost your response rate by 160%.

As an SDR, your first step should be to look back at past deals your company has closed. Whoever signed the agreement is your primary buyer.

Also, pay attention to the various stakeholders you communicated with throughout the sales process; these people represent other buyer personas, and they should go into a sequence as well.

Josh recommends having a separate sequence for economic buyers, champions, and influencers. Prioritize the champion first because they’re the best person for you to connect with in each account.

Don’t email all three of these personas simultaneously with the same message. Aim to stagger them at least one week apart, but if you receive a response from one, then pause on the others.

How to Choose Which Product Benefit to Lead With

Using the same strategy of looking back at closed deals, see if you can determine which benefits buyers respond the most to. This will help you decide which benefit to lead with in your prospecting emails.

When it comes to writing the email itself, make sure you explain the benefit as colloquially possible–in other words, make it easy to understand. Use the same language your prospects use to describe their pain points, and if you can, mention how your product will save them money.

Try writing your first draft of the email by hand. When you transcribe it onto the computer, you’ll be forced to rewrite it, and your writing will become stronger in the process.

Deciding Between a List-based vs. Account-based approach

List vs. Account-Based

A variety of SDRs tend to work Lists vs. being given a list of Accounts, and there is no right or wrong answer. List-Based is faster to implement, but Account-Based will have a better conversion rate; you can decide which is right for you now and can always change later.

Many new sales development teams start out with List-Based and then transition to Account-Based when they have more than a few reps.

List-Based

Using filters in a database to determine the accounts and contacts that will be added to a Sequence. A List-Based approach is best for large, wide-open markets, and quotas will be higher as a result.

Account-Based

Leadership decides ‘the list’ of accounts that represent your TAM and assigns an SDR a subset of them to work. The SDR is then given the flexibility to find the best way into the organization.

An Account-Based approach is best for companies with smaller markets and larger deal sizes because the conversion rate will be the most important metric.

If you don’t have a lot of data from past deals, create buckets for different buyer personas, create a sequence for each persona, and start testing. Take note of which sequences perform the best so you can narrow in your personas.

For example, if the sequence for the VP of Marketing performs the best, then start looking at which size company seems to be the best fit. From there, you can begin to optimize the email copy in the subject line, body, and call to action.

If you need help finding the right prospects or designing your sequences, reach out here to learn how we can help. Our sales development coaches can help you tailor your campaigns to reach the right people with the right message so your team always has a full calendar of meetings.

Final Thoughts on Prospecting Emails

Designing your email sequences doesn’t need to be complicated. If you start with the right goal in mind, keep things short and relevant, and follow a strategic cadence, you’ll see an increase in response rates.

If you want to connect with Josh to learn more about email outreach and prospecting, reach out via LinkedIn.

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