Outbound Sales Sequence Guide: Lead Targeting, Personalization & Follow-Ups

Outbound sales isn’t for the faint of heart.

You have to know how to research a prospect, how to segment your sequences, how to draft relevant messages with relevant content, how (and how often) to follow up to get a response. 

The list goes on.

But you know what? It’s not rocket science either. 

You just have to practice, iterate a thousand times, follow expert guides (like this outbound sales sequence one), and you’ll be well on your way to nailing your sales outreach.

What makes this guide so special?

We got sales leaders Florin Tatulea from Barley and Jack Wauson from Mixmax to co-host a webinar together, and then we extracted all the best bits from that webinar to create this guide.

If you’d rather just watch the full webinar recording (and by all means, we encourage you to), here’s the link: Outbound Sequencing Masterclass with Florin Tatulea & Jack Wauson

If you’d rather read the key takeaways, please proceed.

Outbound sales lead targeting

Mastering outbound sales begins with effective lead targeting. Here are key takeaways from the webinar about proper segmentation and identifying the right decision-makers.

Segmentation: Persona vs. use case

In the webinar, Florin stresses the importance of identifying whether to approach prospects based on personas or specific use cases. This decision varies depending on factors like the diversity of industries you're targeting, the range of products you offer, and the various use cases these encompass.

Here’s a template Florin shares that can be used when building your email sequences (above and below-the-line decision-making is explained in the next section):

Access the template here

Above and below-the-line decision-makers

A key takeaway from Florin is the concept of “above the line” and “below the line” decision-makers within a company. He highlights the need for different messaging strategies for each group. 

“Above-the-line” decision-makers, such as C-level executives, are more concerned with the overall business impact, while “below-the-line” individuals like managers focus on daily operational challenges.

Content creation & relevant messaging

Crafting compelling content is at the heart of successful outbound sales. And what’s compelling to one prospect might not be compelling to another. Here’s how you make it work.

Storytelling in sales emails

Florin advocates for storytelling in sales emails. He suggests a simple two-sentence structure:

• The first sentence should describe the current state or problem the prospect is facing, setting the context and resonating with their immediate challenges. 
• The second sentence is then aimed at illustrating how your solution can transform this current state into a more desirable future state.

This method is powerful because it directly addresses the prospect's pain points and immediately follows up with a solution, creating a narrative that is both relatable and solution-oriented.

Relevance over personalization

Florin and Jack focus on relevance in email content. In a world inundated with emails, breaking through the noise requires hitting on topics that genuinely matter to the prospect. 

While personalization (like mentioning a prospect’s hobbies or location) might catch attention, relevance to the prospect's needs and problems is key to closing deals. Effective sales teams should focus on "Why me? Why now?" by addressing relevant triggers and problems that the prospect is currently facing.

Here's what a relevant outbound sales approach looks like in a cold email:

Example of a cold email that nails relevance

While the primary focus should be on relevance, Florin and Jack acknowledge there’s still room for light personalization. They suggest using the PS statement at the end of the same email for this purpose. This approach keeps the email body focused on relevant content while the PS adds a personal touch without overwhelming the main message.

Optimizing timing and frequency in outbound sales sequences

The success of outbound sales often hinges on the perfect balance of timing and frequency. Here are pieces of advice Florin and Jack share in the webinar.

Optimizing sequence length and engagement

Discussing the ideal length of a sales sequence, Florin shares that his typically cover 20-21 business days with about 15 steps. Jack echoes this, noting that their sales sequences at Mixmax aim for 12 to 18 touchpoints. 

Both conclude that a sales sequence should be long enough to provide multiple opportunities for engagement, but not so long that it becomes intrusive or counterproductive.

The value in any response

Both speakers agree on the primary goal of a sales sequence: eliciting a response to gauge interest and guide future efforts. 

Jack emphasizes the importance of probing deeper into the reasons behind a “no,” suggesting follow-up calls to better understand the prospect's stance. Florin agrees with this view and explains that even a negative reply could offer valuable insights, like whether a prospect is using a competitor's solution. 

This perspective encourages seeing each response not as a setback, but as an opportunity to refine future approaches.

Setting up follow-up triggers

Jack highlights how modern sales tools like Mixmax’s sales engagement platform can greatly enhance the effectiveness of touchpoints in a sales sequence. Specifically, Jack discusses the use of engagement triggers, such as interactions with an email, to inform the timing of follow-up actions.

He explains that these triggers could include a prospect opening an email multiple times or clicking on links within the email. Such actions indicate a level of interest or engagement from the prospect. 

Mixmax call task based on “email open” trigger

Using this information, sales teams can time their follow-up calls or additional emails more effectively, increasing the chances of a successful connection.

Importance of A/B testing in sales emails

Jack and Florin emphasize the importance of A/B testing for various elements of sales emails, such as subject lines, opening lines, and calls to action.

Florin mentions that subject lines are one of the easiest aspects to A/B test. He advises keeping them concise, usually within two to four words, and directly related to the topic. Florin also shares a strategy of leveraging the first names of direct reports in the subject lines to make them sound more relevant and researched, thereby increasing open rates.

Jack adds to this by discussing the significance of the opening line of an email. He agrees that simplicity in subject lines often results in better open rates, and that the first line of an email is crucial for maintaining the recipient's interest. 

The first line acts as a preview seen in the inbox and, along with the subject line, determines whether the recipient will open and engage with the email.

Both experts agree that subject lines should sound almost as if they were sent internally, to create a sense of relevance and immediacy. They also discuss the balance between being too creative and too straightforward, suggesting that sometimes the most effective subject lines are those that are simple and direct.

Reviewing sequence reports

Data is everything when it comes to improving your outbound sales strategy, otherwise you’re just shooting in the dark and hoping for the best. Here are some tips on how to review and analyze your sequence reports to boost engagement.

Quarterly sequence analysis

Jack mentions that at Mixmax, the sales team conducts a quarterly analysis of their sales sequences. This regular review helps them understand what strategies are working and what needs to be adjusted for the upcoming quarter. 

The quarterly timeframe provides a balance between having enough data to analyze trends and being responsive to changes in the market or strategy.

Incorporating SDR insights

Florin highlights the value of including insights from Sales Development Representatives (SDRs) in these reviews. At his previous company, they let sequences run for about three months and then had a sequence committee meeting that included SDRs, sales enablement staff, and managers.

This meeting was crucial for not only analyzing data but also for gaining ground-floor insights from SDRs, who might share observations about the sequence's practicality, effectiveness, and areas for improvement.

Tracking key metrics

Florin and Jack discuss the importance of tracking various metrics in sequence reports, such as:

• Reply rates: A reply, whether positive or negative, is valuable as it indicates engagement and interest, or at the very least, awareness of your outreach.
• Open rates: Provides insights into how effective the subject lines are in catching the attention of the prospects.
• Click-through rates (CTR): A high CTR indicates that the content of the email is relevant and engaging enough for recipients to take action, such as clicking on a link to learn more about the product or service.
• Meeting booking rates: While meeting booking rates are often a primary goal in sales sequences, Jack pointed out that this metric alone doesn't always provide the full picture of a sequence's success. He suggested that while it's important, it should not be the sole focus.

Mixmax has built-in reporting functionality that lets you easily track your email open rates, reply rates, click-through rates, bounce rates, and more:

Mixmax reporting feature

Wrap-up

The insights shared here are key to excelling in outbound sales and can dramatically improve your sales strategy.

Let's quickly bullet-point the essentials:

• Persona vs. use case lead targeting: This is a decision influenced by factors like industry diversity and product range.
• Above and below-the-line decision-makers: While C-level executives (above-the-line) focus on overall business impact, managers (below-the-line) are more concerned with daily operational challenges.
• Storytelling in sales emails: Use a two-sentence storytelling approach in emails, combining the current state or problem with a vision of a future state improved by your solution.
• Relevance over personalization: Focusing on topics that matter to the prospect, using personalization strategically for greater impact.
• Outreach timing and frequency: Florin’s sequences typically span 20-21 business days with about 15 steps, while Jack’s aim for 12 to 18 touchpoints. The goal is to elicit a response, with each type of response offering valuable insights.
• Follow-up triggers: Use of sales tools like Mixmax to enhance touchpoints in sales sequences, with triggers based on email interactions guiding the timing of follow-ups.
• A/B testing emails: A/B test elements like subject lines and opening lines to see what works and what doesn’t.
• Sequence analysis: Regular reviews (quarterly works for the Mixmax team) help identify effective strategies and necessary adjustments.
• Incorporating SDR insights: Including feedback from SDRs provides a practical perspective on sequences.
• Tracking key metrics: Tracking metrics like reply rates, open rates, and click-through rates is essential for understanding the effectiveness of your sequences.

Whether you choose to watch the full webinar (click the image above) for an in-depth exploration or rely on this guide for quick insights, you're on the right track. Keep practicing, keep iterating, and keep that expert guidance close – your sales outreach is bound for success.