The sales messaging challenge - email quantity versus email quality

Posted March 22, 2016

Mark kosoglow headshot

By Mark Kosoglow

VP of Sales at Outreach

There is a catch-22 in sales messaging, specifically rep-written emails. Most sales teams have had to make a conscious decision as to which strategy they want to employ, and if they haven't, they are at the mercy of what their reps are defaulting to:

1. Sales reps can take the time to write targeted, high-quality emails, but they run out of time to send enough to hit their targets.


2. Reps send a ton of emails, but miss their target because the emails are so generic and bland that reply rates are compromised.

How does a sales rep balance email quality with email quantity?

It's incumbent upon the sales leader to create a well thought-out process that leverages workflow, research and sales automation. Below, I'll detail how the Outreach team tackles this sales messaging problem to execute, on average, 1,000 personalized emails per rep per week. I want to make sure I take a second to emphasize that our solution was built upon dozens of rep-to-rep conversations, failed ideas, rep input, meetings, and a total team effort to tackle this problem.

As a credit to groupthink, grit, and our sales development team, take a look at the sales activity of our 14 outbound-only SDRs over the past 5 weeks.

Record count chart

The Process

1. Decide on the type of customization you want to do.

Email customization must be solved for on 2 distinct levels: account and persona. For complete transparency, to date, we've only solved for account-based customization. We have plans to take a stab at mass customization at the persona level soon. This was a deliberate decision, so let me explain so you don't have to screw up like we did initially.

Account customization allows you to go faster as reps use "talking points" across multiple contacts in an account. Persona-based customization can also be applied across roles at multiple accounts. However, I find company-based challenges to be more compelling than role-based challenges. This may be a matter of opinion, though, as we found role value statements more difficult to construct in a way to get results. Ultimately, data showed us what worked best for us. If you don't have visibility on your messaging's effectiveness, this is an impossible task.

The best approach is to combine company-specific with role-specific challenges. I warn against tackling both initially, though, as the amount of content required is voluminous and can slow down your efforts...or derail them entirely. For example: if you have 7 account-level challenges and 4 personas you are targeting, you will need to produce 28 separate pieces of content to support your messaging.

2. Get the right accounts.

Our process begins with our account sourcing and assignment. We believe that the lifeblood of an outbound sales team is the accounts they work. High quality accounts are a necessity. You will not see as distinct an improvement in results if your team is sourcing and targeting subpar accounts. If you want to get fancy, you can call it ICP (Ideal Customer Profile), but if you are grinders like us, you call it "finding people that will probably buy your stuff."

You need 3 or 4 data points you can point to which your customers have in common, and I suggest at least one of them needs to be so spot-on it's scary in how common it is among your customers. This could be the presence of a certain title or technology, a threshold for the size of the department you sell to, or a revenue level that indicates the account will be able to pay for your solution. There are tons more, but defining 3 or 4 (and 1 killer) is key.

When these are known, only allow reps to source accounts possessing these data points. Better yet, do it for your reps. At Outreach, we have interns sourcing accounts under the guidance of our director of sales operations. Those account prospect lists are enriched, scrubbed, tiered, assigned then loaded into Salesforce. This control allows us to make sure reps have equal account loads in terms of quantity and quality.

3. Define prospecting guidelines and rules of engagement for your reps.

Clear and easy to understand rules around how reps should fill an account with contacts is essential to balancing email quality and quantity. Your sales reps wield a powerful weapon when prospecting. Not providing them a framework to follow means you are increasing your chances of unproductive, ineffectual prospecting.

Outreach sales reps use LinkedIn to find contacts at accounts assigned to them. They fill each account with as many viable prospects as possible. By "viable," I mean our reps are constrained by the prospects they are able to add to Salesforce. We have developed a search query that only returns prospects who we have agreed are most productive to engage. Only results of this search query are able to be added to Salesforce. Having your reps help develop this search query is key to their adopting its use.

Having tons of great contacts to target is great, but it is dangerous to target every contact at once. Many mail servers begin to flag sellers as spam if they feel like reps from your domain are hitting them with too many emails. We have a rule of engagement for an account and its contacts.

It tells reps to target 5 contacts in an account at a time, with at least 2 of them being management level or greater. We cycle through contacts as they drop out of our messaging (for positive or negative reasons) so reps are always in compliance with the rule. Our software platform also sends data to Salesforce that allows us to create reports, giving our reps instant, up-to-the-minute visibility into accounts that need additional contacts engaged.

4. Capture account research while prospecting contacts.

While finding prospects in the account, as the first step, our reps are required to use LinkedIn, company blogs, press releases, etc. to find news. This research helps them determine how to customize their emails to prospects in those accounts. Finding relevant facts that marry a business case with a value proposition of our product is very important.

As your reps research, they need to be able to capture account data in your CRM so that it flows through to the contact level (we use a Salesforce workflow rule). This will streamline the process by allowing them to enter the company information once and have it auto-populate for all contact records in that account. This saves us a ton of time because research is populated into dozens of contact records as they are added to the account during prospecting.

5. Craft email messages.

When we capture research about an account we classify it into a “bucket.” A bucket, or category, groups companies based on their current situation or status to see which triggers are getting the best results so we can tailor messaging to those buckets. More importantly, our list of buckets keeps reps focused on what bits of useful information to look for and how to deal with them once uncovered. An example of a “bucket:" If our research shows that the company is doing a lot of hiring in the sales department, this might indicate the account is dealing with aggressive sales goals and would benefit from a platform like Outreach. Other examples of buckets: good quarter result, bad quarter results, new product launching, new leadership hire, certain technologies being used, certain LinkedIn profile characteristics, and so on.

We use a spreadsheet that shows our reps for each bucket all of the points of customization that can be used while crafting custom emails to accounts in that group. Each bucket includes:

  • 4 or 5 open-ended questions a rep can ask to start an email (or a phone call!)
  • 2 or 3 value propositions a rep can make relating to the bucket
  • 1 or 2 case studies applicable to the bucket a rep can attach to or cite in an email
  • A related customer quotation reps use to allow our customers to sell on our behalf

This provides a lot of structure. Do your research, bucket it, and then, when you’re writing your email, go to the corresponding bucket and decide which bits and pieces you want to use to really customize that email. Structure is the friend of productivity.

You’re probably wondering where the buckets and corresponding documents come from. They are developed by the whole sales development team during monthly meetings. When a new bucket is identified, based on the research they are doing, they update it in the bucket spreadsheet. The reps create all aspects of the document and request the case study(s) from the marketing department. Reps are the people closest to the customer, and their group knowledge around what prospects want is invaluable.

Also, we fine-tune the document components for existing buckets during the monthly meetings based on what’s working and what’s not. The actual performance results of email components are shown in reports generated by Outreach.

6. Set up a sequence of touchpoints your sales team needs to use for every lead/prospect.

A sales automation platform (Outreach) is required to inject automation into your process. Depending on the goal, it might look something like this:

  • Day 1: Customized email written by rep
  • Day 1: Phone call
  • Day 3: Automated follow-up email that appends original email to bottom
  • Day 3: LinkedIn Connect
  • Day 5: Phone call
  • Day 6: Automated follow-up email that appends previous 2 emails to bottom
  • Day 10: Customized email written by rep
  • Day 10: Phone call
  • And so on…we usually make 18-20 touches within 3-4 weeks

You set up this sequence one time in Outreach, and then, reps use it each day with new prospects they find in their accounts. This methodology allows our reps to focus on adding more prospects into the system and completing activities the sequence generates for them (many activities, because they are automated, are performed without the effort or attention of a sales rep). Here’s the key to it all:  If a response email is received or a phone call is answered, our software knows this means you want to stop the process so no future messaging/activity is generated for that prospect until the rep decides what to do next with the email in their inbox or after they hang up the phone. 

It’s like building a muscle

In order to master the impossible task of balancing email quality and quantity, you have to build a muscle for it. People don’t just write really great emails really fast. We have to help them develop that muscle. The way we do it is through repetition and practice by using the Pomodoro method combined with coaching. Set a timer for 25 minutes. The rep does a task, and only that task. Then, set the timer for 5 minutes to record your production and review the results. Repeat. For example…spend 25 minutes writing custom emails. The first 25 minutes you might write 3 emails, then in the next 25-minute block its 2 emails,  4 emails in the next, 6 emails in the next, and so forth. Through repetition a level of competency is developed. Reps will get faster at writing high-quality emails. Practice makes perfect, so give your team a way to practice. Through this method you can coach your team on all aspects of the process, including the quality of their emails.

Companies that write the most high-quality emails will always outperform companies that can’t execute as well or as fast. So if you want to have a competitive advantage, you need to make sure your team is equipped with tools and methods that give them an advantage. I know this process has given my team an advantage. We are sending out hundreds of emails a week that, as a group, garner reply rates of 25% or more. Imagine building a sales machine that can get take 100 cold, outbound prospects, and in a week or two, get 25 of them to engage. Balancing email quality and quantity can do that for you.


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