Mastering Outbound Sales: Strategies, Triggers, and Campaigns

One of the most frequently asked questions we encounter is, “How do I create a robust strategy for my sales campaign sequence program?”

Gray Norman joined us on The Monthly Meta Podcast to break down this intricate topic into digestible pieces to help navigate the ins and outs of strategizing a successful sales campaign.

Building an Effective Sales Campaign Sequence Strategy

1. Understanding Your Core Use Case

The journey towards a successful sales campaign sequence begins with understanding your core use case – the one area your business shines brightest in and brings the most significant benefits to customers. Focusing on this use case, especially when time is of the essence, allows you to tailor your message accurately and efficiently.

2. Highlighting the Pain and Value

The next stage involves constructing your message around the pain that your product or service addresses and the value it delivers. Your call script should open the conversation by asking probing questions, fishing for potential pain points, and then seamlessly tying those pains back to the value your product or service offers. This method is effective whether dealing with a company that specializes in a single area or one that offers multiple services.

3. Using Case Studies for Credibility

To enhance your credibility when communicating with prospects, incorporating case studies into your campaign is an excellent strategy. A good case study effectively ties together the use case, the pain, the value, and real-life evidence of how your product or service solved a problem.

4. Implementing and Refining Your Strategy

Once you’ve crafted your sequence and call script, it’s time to get your campaign out there. Monitor the responses and gauge the effectiveness of your script. Is it flowing smoothly? Are you asking the right questions? Refinement is a continuous process, and you should always strive for constant improvement. 

5. Adopting a ‘Bite-Sized Chunks’ Approach

In building your sales playbook, it’s crucial to break your process down into bite-sized chunks. Instead of drafting an exhaustive playbook that might quickly become outdated, create flexible, small sections that can be updated or changed as necessary.

6. Capitalizing on Triggers

When crafting a campaign, strive to align it with relevant triggers. While having a benchmark campaign that targets the ideal persona is vital, significantly more success can be achieved by building messaging around a trigger event. For example, a new hire at a management level may not be immediately willing or able to implement changes, but a newly hired VP might. These individuals are often expected to initiate changes and might have a budget allocated for this purpose.

7. Customizing Pain and Messaging Based on Trigger Events

Finally, your campaign should adapt its pain and messaging based on different trigger events. Depending on the nature of your product, you’ll need to identify situations where the pain your product addresses is most potent. For instance, a company that sells employee onboarding software might find a significant opportunity in a rapidly growing company where a new VP has been appointed. 
Remember, each client is unique. Understanding their specific pain points and needs will allow you to craft a compelling sales campaign sequence that speaks directly to them. Through this process, ensure that you include strong evidence of the value of your product, case studies for credibility, and metrics for added legitimacy. This comprehensive approach will help set your sales campaign sequence strategy up for success.

Targeting and Identifying Triggers: The Key to Successful Sales Campaigns

In my 11 years of sales experience, I’ve come to realize that one aspect often overshadows others: targeting. Believe it or not, targeting can be even more crucial than messaging. Sending a decent message to the perfectly targeted prospect can yield better results than sending an excellently crafted message to a mediocre audience. The reason? Relevance. We must ask ourselves: why is this specific account or contact more likely to make a purchase right now?

Identifying Triggers

One way to ensure the relevance of your targets is by identifying triggers, events, or circumstances that might increase the likelihood of a prospect purchasing your product or service. If you’re scratching your head and thinking, “It kind of depends,” you’re not alone. Identifying triggers can sometimes seem daunting, but it doesn’t have to be.
To begin with, think about all the aspects that an SDR would research manually about an account and then find ways to automate and scale that process. For instance, certain triggers are relatively straightforward to spot. Rapid employee growth or recent funding, for example, are two strong signals that a company might be in a position to invest in your product or service.

Intent-based and Research Tools

Investing in intent-based and research tools can prove immensely beneficial in helping you identify these triggers. Tools like LinkedIn and CrunchBase offer a wealth of valuable information, such as funding announcements and hiring trends. For more advanced triggers like product launches or company acquisitions, you might need to consider more specialized tools that can aggregate and analyze data at scale.
Static and Temporal Triggers
Triggers don’t always need to be time-sensitive events. Static triggers – unchanging facts about a company that indicates potential interest in your product – can be equally, if not more, important. For instance, if your product is a tool that aids companies working with Java, spotting a company hiring Java engineers could be a promising trigger. This approach isn’t tied to a specific event or timing; it’s a continuous signal that such a company might benefit from your product.
In contrast, temporal triggers are time-sensitive and only relevant for a certain period. A recent funding round is an example of a temporal trigger; it indicates a temporary signal of the company’s readiness to invest. However, this signal is only relevant for a limited time post the funding round, after which its importance diminishes.
Both static and temporal triggers are significant and play different roles in forming an effective sales campaign. A balanced combination of the two forms an excellent foundation for a sales strategy that ensures you target the right people, with the right message, at the right time. Thus, focusing on targeting and identifying triggers can help to improve the efficiency and effectiveness of your sales campaign significantly.
Relevance: Mastering Sales Copy
Crafting a compelling sales copy requires a delicate blend of skill, experience, and art. In my journey to mastering this craft, I’ve found that relevance often outweighs even the most persuasive language. The more hours I’ve poured into this, the more I’ve realized that tools like ChatGPT are best suited for enhancing relevance rather than just crafting charming messages.
Irrespective of how personalized your sales copy might be, it loses its impact if it fails to resonate with the recipient. Personalization without relevance equates to wasted time and effort. The power of an email lies in its relevance, and you don’t necessarily need exhaustive personalization to achieve that.

That being said, the relevance-personalization equation can change depending on the nature of your company. If you have a limited pool of prospective clients, perhaps just 50 companies, it might be worth investing more time in personalization. However, if you have a broader audience, relevance should take precedence.

The Pitfalls of Excessive Personalization

As we endeavor to stand out in a crowded inbox, personalization can sometimes lead us astray. For instance, an email that mentions the recipient’s alma mater or their favorite stadium snack might seem well-researched and individualized, but it fails if it doesn’t connect with the recipient’s current needs or interests.

To illustrate, I once received an incredibly personalized email from Gong. It referenced my pilot training and used an immersive flight scenario to draw me in. As engaging as the email was, it didn’t resonate with my professional needs. Gong’s services didn’t integrate with any of our tech. The email, while arguably the best I’ve received, was irrelevant.

Similarly, Chili Piper sends wonderfully written emails that I enjoy reading, but their product simply doesn’t align with my current needs. The effort they’re putting into engaging me as a potential customer would be better directed elsewhere.

Striking the Right Balance

Focusing on the right accounts and tailoring your messaging to them is a more productive endeavor than creating highly personalized emails for a random set of prospects. Remember the trifecta for successful outreach: right message, right time, and right person. As long as you get two out of these three elements right, you’re likely to gain traction.

For instance, if it’s the right time and the right person, they’ll probably respond positively even if your content isn’t perfectly personalized. If a company is in need of a SOC 2 audit, and you email the right person at the right time with a straightforward message like “Hey, I do SOC 2 audits,” chances are you’ll secure a meeting.

As you plan your market outreach with new campaigns, aim for a balance between personalization and relevance. Strive for relevance first, and then use personalization to enhance that connection. Remember, relevance resonates; relevance delivers results.

Refining Your Sales Development Process

Tweaking, tuning, testing, and iterating. It may sound like a mechanical process, but it’s the secret sauce to a successful sales development strategy. This process isn’t just about logging into your instance of Apollo or Outreach and making random changes. It’s about empowering your Sales Development Representatives (SDRs) to fine-tune their approach and discover what works best.

 Empower Your SDR Team

One of the critical debates in the sales industry is whether to use a standardized sequence or let SDRs create their own. While a uniform sequence can provide a consistent message, allowing SDRs to create their own sequences brings the benefit of individual creativity and personal experience.
Creating content isn’t a one-time activity either; it’s a process of continuous refinement. As a rule of thumb, I recommend revisiting your written content after a couple of days, refining it, and making real-time edits even during client presentations. In essence, strive for conciseness while continuously improving your copy.

Embrace A/B Testing and Aspirational Conversion Rates

Your sales strategy should always be rooted in continual testing and learning. A/B testing allows you to identify successful calls to action and improve on them. Sometimes, an email written by an SDR that doesn’t seem compelling at first glance might perform exceptionally well because it brings a fresh perspective.

Even seasoned sales professionals can fall into the trap of sounding too “salesy” in their emails. To avoid this, periodically take a step back, refresh your approach, and strive to sound more relatable and less like a salesperson.

Shedding Egos and Encouraging Creativity

The art of tweaking and testing requires letting go of ego. You might come across a call script or a strategy that doesn’t resonate with you, but that doesn’t mean it won’t succeed. Sometimes, the best-performing strategies are those that seem least likely to succeed initially.

When it comes to testing new strategies, it’s crucial to maintain an open mind. Remember, no one is the omniscient master of sales development who can predict what will work perfectly. This attitude of open testing and refinement can lead to outsized returns in terms of reply rates. 

Pushing Back Against Resistance

One common challenge is encountering resistance from clients who are skeptical about trying out new strategies. In such cases, it’s essential to stress the importance of data-driven decisions. If a client is reluctant to test a new approach, ask them what data they have that conclusively proves it won’t work. Often, there is none.

Moreover, it’s essential to realize that marketing to prospects who are unfamiliar with your product or problem requires a different approach. Unlike nurturing known leads, you’re trying to educate these prospects and draw their attention to a problem they may not even realize they have. This unique situation requires a distinct messaging approach that can resonate with the unacquainted.

Mastering the art of sales development involves a cyclical process of tweaking, tuning, testing, and iterating. It’s a process of empowering SDRs, shedding egos, embracing testing, and constantly refining your messaging to better resonate with your prospects.

 Crafting the Right Messaging for Cold Prospects

Successful marketing strategies often stem from a deep understanding of your target audience and their unique needs. What works for one segment may not necessarily resonate with another.
This is particularly true when differentiating between prospects who are familiar with your brand and those who are not. The messaging needs for these two categories can be vastly different, requiring distinct approaches in your outbound strategy.

Understanding the Difference in Messaging Needs

If you’re prospecting to people who are already familiar with your product – perhaps they’ve downloaded an asset or attended a webinar – your messaging should be nurturing. They are already on a journey with your brand, so your job is to guide them along this path, offering them additional insights about your product or service, showcasing features, and creating an atmosphere that helps them feel more connected to your brand.

On the other hand, when targeting individuals who have no idea who you are or what you do, your messaging must take on an entirely different tone. Here, your prospect may not even realize that they have a problem that you can solve. Therefore, your primary goal becomes educating them. You must clearly articulate the pain points they may be experiencing and present your solution as an efficient way to alleviate this pain.

Addressing the Misconceptions about Branding

A common misconception in this realm is the overemphasis on maintaining a “brand voice” even when reaching out to cold prospects. This can be counterproductive. The truth is, when you’re engaging with someone who is unfamiliar with your brand, there is no “brand voice” to maintain in their perception because they don’t yet know your brand. What’s more important is to create an initial impression that your brand understands their challenges and has a solution.

 The Goal: Qualifying for Pain

Your initial outreach should focus on qualifying the pain point rather than bombarding the prospect with information about your product or brand. The email you send should be tailored to highlight their potential pain point and introduce your solution subtly. It should read something like, “Hey, I think this could be relevant to you because of X reason. Am I far off?” Rather than pushing your product upfront, you’re inviting a dialogue and presenting an opportunity for them to explore a potential solution to their problem.
In essence, when reaching out to cold prospects, the focus should shift from brand promotion to pain identification and resolution. It’s about connecting on a human level, empathizing with their challenges, and offering a solution that can make their lives easier. This approach not only improves the prospect’s experience but also increases the chances of converting a cold lead into a potential customer.


Successful sales and marketing strategies require a nuanced understanding of your target audience, the appropriate messaging, and the willingness to test and iterate. It’s important to empower your teams to make adjustments and foster a culture where creativity and new approaches are encouraged.
The focus should always be on relevancy, which may involve personalization for some companies or honing in on the right message for others. When reaching out to cold prospects, the key is to identify pain points, offer solutions, and spark meaningful dialogue rather than just promoting your brand. Remember, the goal is to be relevant and helpful and build a genuine connection that can eventually turn a prospect into a customer.
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