Effective Email Outreach Takes More than Automation

Imagine you’re preparing for a meeting with a new prospect. What steps are you taking beforehand?

You’re probably doing some research on their organization and their particular position. Maybe you uncover a few recent milestones the business has reached or you find that the prospect recently received a promotion.

All of this information will obviously be helpful in moving your professional relationship forward. Why do we often fail to conduct this research before reaching out via email?

In this episode of the B2B Revenue Executive Experience, I check in with the CRO of OnCourse, Gessie Schechinger.

We discuss:

  • How to avoid becoming another automation junkie
  • Understanding the best email sequence timing
  • The biggest keys to effective email outreach

The right amount of automation

There’s no shortage of noise being streamed into our inboxes on a daily basis. You don’t want your reps simply adding to the pandemonium you know your peers are experiencing.

Never the less, it’s easier than ever to automate emails to be sent out on a whim. Convenient sequencing functions are quite literally turning us all into automation junkies and, therefore, ruining the customer experience.

The team at OnCourse has built its business around helping customers efficiently structure their outreach programs. The revolutionary CRM combines all of the necessary sales tools into one comprehensive piece of software. In other words, it eliminates the need for multiple apps that many times, don’t even talk to each other.

“It really is about how the tool is going to complement your existing business process.”


Email automation is just one of OnCourse’s capabilities. The thing is, since we’re so addicted to automation, it’s sometimes hard to see past email and leverage the rest of our CRM’s functions (something our prospects wish we’d learn how to do).

Gessie describes this paradox as sales reps and managers frankly not knowing what they don’t know. Specifically, with OnCourse, there are a lot of powers that sales pros don’t know they possess if they’re not properly trained in the platform.

To be candid, there are ultimately two components needed to ensure your sales reps aren’t morphing into automation junkies:

  1. They need to understand that effective outreach means approaching prospects from different angles. Not just email.
  2. They need to be properly trained in using 100% of your CRM. This is crucial for them to branch out into new tactics and leverage each capability of the software. If you don’t believe the majority of your CRM is worth learning, maybe it’s time for a new CRM.

“We’re in a place right now where you have to surround people from all sides to find out exactly
how they want to communicate.”


The right email sequence timing

Revisit our in-person meeting scenario. This is a great analogy for nailing down the best timing for your email sequences. You probably wouldn’t walk or log into the first meeting with no prior research and slap down a proposal.

The same goes for your email sequences.

Consider how you would want to be approached through email. You’d probably ignore the first one or two. But, after you notice the brand targeting you via other mediums, you might open the next email.

That’s as long as the prospector isn’t an automation junkie, sending you gobs of emails every day.

In Gessie’s example of what not to do, his team had realized the value in video embedded in emails. While this revelation wasn’t necessarily wrong, the cadence in which the team sent the emails was.

Being so enthusiastic about the video email, Gessie requested it be sent out straight away. It was and the response rate was ghastly. Why didn’t this work like Gessie had seen it work for other sales pros?

Because he unintentionally waltzed into the meeting and slapped down a proposal. Figuratively speaking, of course.

Through his research, Gessie had found that on average new prospects delete the first six emails you send if they don’t recognize your name. Ouch.

The lesson here? Warm-up to a new prospect before proposing anything. Even before sending out your cool, new video email. You want them to see it, right?

The right email content

Through all of this, we can take away one major piece of email outreach knowledge:

Research your prospects and their companies before contacting them.

By completing this one simple action, the content in your emails will be above and beyond that of any template material. Not to mention, the recipient will appreciate you taking the time to look them up before emailing them.

Teaching your reps to conduct research on their prospects prior to reaching out is one of the greatest sales tools they can acquire. Ideally, they already have a notion to do so.

Bits of information to look out for when researching a prospect include:

  • A recent promotion
  • A new business acquisition
  • A new executive
  • The expansion to another location
  • An individual or company-wide award
  • The launch of a new product
  • Recognition for growth

Additionally, Gessie points out that it’s important to demonstrate that you’re respectful of the recipient’s time. Make this awareness apparent throughout the content of your emails. Your prospect will appreciate the consideration of their time. Wouldn’t we all?

Final thoughts

Think of your email outreach as a meeting. Get to know your prospect. Feel out if it’s even a good fit in the first place.

By implementing the right CRM, training your reps on how to use it properly, and coaching them on how to conduct research, your team should be able to lock down email outreach and, eventually, happy customers.

This post is based on a podcast interview with Gessie Schechinger, CRO at OnCourse. To hear this episode, and many more like it, subscribe to the B2B Revenue Executive Experience.

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