Outreach’s Best Practices for Personalizing Emails

By Meghan Donovan & Lauren Sawyer

Purpose

Customizing emails is a powerful way to connect with prospects, but to be effective, it requires consistency and scalability. At Outreach, we use standardized guidelines to compose, edit and review content. This allows reps to creatively catch a prospect’s attention while saving time and aligning messaging. This article shares Outreach's recommendations regarding:

• Sentence format for personalizing emails
• The 8 criteria for editing personalized emails
• Content management for each Outreach persona
• How to measure success to maximize effectiveness

Intended Audience

• Outreach admins
• Outreach users

Overview

When writing emails, it's easy to copy and paste, click send, and realize later that you forgot to update the recipient's name. We've all been there, but with Outreach’s blueprint feature, it's preventable.

A blueprint acts like an email template that uses built-in best practices and variables to prevent an email from being sent before it’s customized.

The first email in a sequence is the best for personalization because it is usually the start of your relationship with a prospect. The research and messaging used in this email can open the door for further communication, such as connecting on LinkedIn or a phone call.

Before sending an email

A personalized subject line or introduction can go a long way with a customer. Plus, it’s proven to increase open and reply rates. By crafting a message that you believe resonates with the customer, you’re building connection capital and increasing the likelihood of booking a meeting. This small touch is an invaluable tool for your team to see a return on their time investment.

We recommend this format for personalizing manual emails:

• Subject line: Capture interest, build curiosity or promise useful information
• Sentence 1: A piece of account research that is current and relevant to the prospect
• Sentence 2: Elaborate on risk and potential pains
• Sentence 3: How your organization solves that specific risk and pain
• Sentence 4: A proof point that addresses their risk or what is common in the industry
• Sentence 5: Call to action (CTA)

After composing an email using the above structure, it’s time to edit. Here are our recommended guidelines:

• Creative subject line
  • Include the prospect’s name when possible
  • Include a simple call to action
  • Make sure it ties into the body of your email and, preferably, the personalization
  • Use a maximum of 4-5 words
• Use punctuation like a professional 
• Don’t use emojis, however, this may vary by industry
• Value proposition: Tailor the value statement to the prospectʼs specific risk and pain.
• Be clear: Use conversational language instead of technical terms or abbreviations.
• Be brief: Limit the total word count to fewer than 150 words.
• Proofread: Read emails out loud, or use typing assistant software like Grammarly.
• Save successful emails: When a cold email gets a positive response, it can be saved to use as a template for future emails. It can be helpful to share these results in training sessions or simply to celebrate great work.

These guidelines can not only be used in prospecting emails but also can be used in follow-up emails with marketing qualified leads (MQLs). This will help keep prospects’ top priorities at the heart of the conversation.

Sequence settings for personalization

Customized content encourages customers to open emails. Making a few adjustments to sequence settings will further improve communication.

• Change the Hour and Minute within the times sent, not just the day, to avoid the prospect of receiving emails at the same time every day.
• Adjust the sequence schedule when targeting different regions, territories, and countries.

Example of a personalized email

Note: This email isn’t perfect! We used Sales Hacker’s cold email grader and it received a score of 91%. That’s a high mark, but there’s room for improvement. This example can be used as an exercise to identify ways to strengthen the content further.

Reviewing content

Before sending your email, review it one final time to ensure you’ve used each best practice. You can evaluate your work using Outreach’s rubric below.

Scoring email personalization

This rubric can also be used to provide actionable feedback to content creators. Note: Outreach strongly recommends A/B testing subject lines as well as changing the first sentence of emails in a sequence to further evaluate the success of content.

Check out more writing examples on Sales Hacker, “10 Sales Email Templates to Escape the Spam Folder.”

After sending an email

While the above guidelines will strengthen your email quality initially, ongoing content management ensures that best practices are maintained. With Outreach’s sequence settings and sequence reporting, you’ll continue to improve communication and determine what’s working to optimize performance.

Never forget a prospect at the end of a sequence

Sequences use emails to move the prospect through the sales funnel. If they reach the final sequence step without responding, it’s time to consider what action to take next. Add a generic task as the last sequence step as a reminder to revisit the prospect when they are unresponsive.

Content management

Auditing content ensures that your resources are well organized and up-to-date, which saves reps time. They will no longer have to go through the hassle of searching for an invite to a conference that’s already over. Instead, keep content fresh by archiving anything out of date. Every member of the team has a part to play when it comes to content management.

Individual content creators

• Recognize when you can clone a sequence for another use case to save time.
• Review sequence states for any changes in fails, bounces or pauses.
• Use a naming convention with the last modified date.
• Review privacy settings are appropriate for the intended use. For example, if one person is using a sequence, the sequence should be set to “Private to Owner.” If a whole team will use the sequence, set to “Others can see and use it.”

Admins

• Monitor usage rates of content on a regular basis to identify individual/team gaps.
• Review sequence states for any changes in fails, bounces, or pauses.
• Archive or lock content no longer in use – do NOT delete it, as that also removes the associated data.
• Standardize best practices to drive operational excellence.
• Use data to identify your best-performing content.
• Adjust user permissions to limit content creation, if necessary.

Content committee

• Review content older than 3 months.
• Draft content and oversee the adoption of new or edited emails and sequences.
• Drive content and sales strategy alignment.
• Help users understand what content they should use.

Learn how to create and maintain a content committee on Sales Hacker, “Build a Content Committee for Ultimate ROI on Content Companywide."

Using Outreach reporting to measure success

Speaking to a prospect’s specific problem takes analysis that only a rep can provide. However, Outreach’s Sales Execution Intelligence and reporting provide insights on gauging the success of that personalization. 

A/B testing

While customized content is proven to increase open and reply rates, it’s crucial to understand what personalization is resonating with prospects. A/B testing helps identify the specific details that are driving the pipeline. 

Outreach recommends these best practices:

• Test one variable within a template/sequence at a time. There should be as few variables as possible for accurate reporting.
• Create or clone new templates before starting an A/B test. At the start of an experiment, the sequence should not have been sent to a customer before. (So deliveries will read “0.”)
• Always A/B test what you want to change before implementing it across your sequences.
• Deliveries on each template should be at least 2,000 for the experiment to be statistically significant.
• Test on multiple sequences at the same time.
• Add an A/B test to the first half of the sequence to increase your chances of a reply.

Measuring email performance

Start your assessment by evaluating the previous two quarters. This helps account for seasonality, and it ensures there is enough data to draw statistically significant conclusions. Report and measure sequences on benchmarks on a month-over-month basis.

Industry Standards

Note: These are general guidelines and best practices vary by industry.

Outside of reporting, customers will also point you toward improvement. Review sequence steps for positive responses and clone high-performing personalizations accordingly. You can also address concerns from objections by updating customizations.

The Power of Internal Insight

While Outreach teams use all of these best practices and metrics, it’s important to add your own personal touch. As a rep, use your experience and listen to your gut on what might work. As a manager, ask reps what is or is not resonating and use their feedback to support others on your team. As an admin, use rep feedback and email performance to guide your content committee. By combining structure and insights (both technological and human!), your emails will resonate with customers and increase rep efficiency. 

As personalization is all about the person behind it, join the conversation on Sales Hacker to share the unique ways you customize emails.

Additional Resources:

• Outreach University: Personalizing Emails Workshop