How to Turn Your Outbound Sales Efforts Into a Strategic Advantage

I. What is Strategic Outbound Selling?

Strategic Outbound takes the old practice of sending emails and making cold calls to spark interest in your product or service and evolves it into a very targeted, data-driven approach. It requires laying the groundwork to identify the right target accounts and buyer personas more likely to have an appetite for your offering and using a personalized approach to engage these individuals with relevant and educational content.

When applied intentionally, Strategic Outbound allows you to engage the C-suite and other senior-level decision-makers more effectively to initiate the early stages of a complex sale. 

At ML, we have practiced Strategic Outbound Selling for over 20 years. We recommend this approach if your sales process meets the following criteria:

• Your product or service requires a complex sales process.
• Your buyers are typically senior executives all the way up to the C-suite.
• Your average deal size is six figures or more, with a long sales cycle, and tends to include multiple stakeholders.

II. How to Build a Strategic Outbound Sales Program

This Playbook contains four steps to turn your outbound sales program into a strategic market advantage.

Four Steps to a Strategic Outbound Sales Program

1. Cultivate a clean and comprehensive prospect list that covers your total addressable market (TAM).
2. Build trust by crafting relevant messaging for your audience that speaks to their issues and needs.
3. Proactively follow up with leads that react to your message to engage and move them forward to a dialogue.
4. Set goals, use data to measure results, and adjust your approach based on what you learn at every step of the process. 

Build a B2B Prospect List of Qualified Leads Through Personalized Outreach

Do a quick search on “How to Build a B2B Prospect List,” and you’ll find no shortage of articles advising you to take these steps:

1. Create an Ideal Customer Profile and Buyer Personas.
2. Understand the business value your offering provides your ICP and buyer.
3. Use that knowledge and a trusted data source to pull a list of target accounts and individuals to engage.

And while all of those steps are part of the right starting point, it takes a certain amount of expertise and strategic insight to build the best target account list. At ML, we believe there is an important fourth step that is often overlooked. We recommend personalized outreach to validate your list of suspects before you begin working on converting them into qualified prospects.

This is especially true if your offering involves a complex sales cycle. These are often long, require engagement with multiple stakeholders, including senior executives, and often include decisions from the C-suite.

The extra effort to confirm you are targeting the right people at the right organizations will result in a qualified list and turn your prospecting efforts into a strategic sales tool. This step is essential to creating a predictable revenue model.

“I am often asked, ‘what is the ideal length for an email message?’ and ‘what subject heading gets the best open rate?’ My response is always, ‘None of that matters as much as making sure you are putting your message in front of the right audience.’”

Lara Stewart Triozzi CEO and Founder

How to Turn Your Suspect List into a Qualified B2B Sales Prospect List

At ML, we have performed audience development (also known as prospecting or target account list building) for over 20 years as part of our account-based marketing services. We have learned that the process starts with the best data sources (we use many, including ZoomInfo) to build a preliminary list of accounts and individuals with titles that match your buyer personas. However, we have also learned that regardless of the source used, typically only about 70% of the data will accurately reflect the full scope of your total addressable market.

This is due to several factors:

• People move around.
• Buying teams have gotten bigger.
• You cannot use title alone to determine who owns a corporate initiative or has purchasing authority.

Take the time to organically validate your carefully curated audience. This is the important fourth step we mentioned earlier that many companies overlook. Doing this will pay off in four ways:

1. Engage the right audience
2. Obtain the best intel from your data
3. Focus on accounts that provide the most opportunity
4. Preserve your brand integrity

1. Engage the Right Audience

While building the best list requires time and resources, you’ll be able to leverage your marketing outreach better and get to your desired outcomes faster. It will ensure you do not waste valuable time and effort engaging the wrong audience.

2. Obtain the Best Intel From Your Data

You can use the metrics to truly test which messages work, and which don’t because you can rule out that it’s being ignored by someone who is not a relevant prospect.

3. Focus on Accounts That Provide the Most Opportunity

A focused effort ensures your budgets and sales resources are targeting prospects with the most need for your offering and will allow you to capture the best intel to influence your go-to-market strategies and product roadmaps.

4. Preserve Your Brand Integrity

Staying highly targeted helps protect your reputation, preventing your email outreach from getting flagged as spam because you are sending irrelevant information to your audience.

Make the Right First Impression

If your sales are complex and require engaging senior executives, we recommend using experienced sales team members to perform list validation through telephone outreach.

Some companies look to save money by using junior staff to prequalify opportunities, but in a complex sale, the people making calls must know how to navigate through organizations to identify the right decision-makers, something only experienced professionals know how to do well.

In addition, more experienced professionals can start a conversation if they reach someone on an initial call, something that should often happen if you have used a reliable data source to pull your suspect list.

ML has carefully cultivated a team of seasoned sales and marketing professionals. Our corporate culture, especially our flexibility to work from anywhere, has helped us attract the best and brightest individuals with decades of experience speaking with senior executives across multiple industries. We understand complex B2B sales.

Your sales program should include a process for identifying and confirming the right decision-makers at your target companies. This process should be designed to generate a reaction, include a way to capture market intel, and advance prospects to the next stage of the sales cycle.

A process that identifies potential opportunities and establishes interest allows your sales team to focus on the latter stages of the sales cycle and achieve greater returns by allocating their time to qualified, actionable sales opportunities. And knowing the activity is laser-focused on the right decision-makers at the right companies, you can track metrics and extrapolate them to build a predictable revenue model.

Create Relevant Email Messaging, Call Frameworks, and Great Content

What Compels You to Take a Call from a Sales Rep?

Most executives receive multiple calls and emails every day from sales executives wanting some of their time.

That salesperson has just seconds to grab attention. So, what can you do to separate yourself from the pack?

At ML, we use Strategic Outbound strategies to get the attention of the C-suite and senior executives. We carefully craft messaging (delivered by phone and email) that reflects issues of relevance and includes valuable supporting content that educates or informs the reader.

Building Trust with Messages and Great Content Enables B2B Prospecting

According to Forbes in its Article “How to Use Content Marketing To Build Trust,” trust is crucial to growing revenue. Therefore, your message and content must create trust, and a great way to do this is by educating your readers with industry insights or doing a deep dive into a specific topic. In other words, if you can help a busy executive meet their corporate mandates, they will want to speak with you. Building trust is at the heart of everything we do at ML.

“… if you can help a busy executive meet their corporate mandates, they will want to speak with you."

Stephen Kirkpatrick Senior Sales Content Manager

How Do You Know What Messages Will Resonate?

Your value proposition should intersect with your ideal customer profiles. If you feel you have those two things aligned but your message is not resonating, you need to re-evaluate. Consider conducting a market research project to understand better the top-of-mind topics the buyers in your target market care about most.

Lara Triozzi, ML’s CEO, says, “Two things matter when crafting messaging intended to get a prospect’s attention: relevance and timeliness. The more relevant you can be to topics that are top-of-mind to your audience, the more likely they are to pay attention. And more importantly, the more likely they are to see you as a thought leader.”

Writing an Effective B2B Email

“Is email marketing dead?”

That question seems to crop up every year, and our answer is: not if you apply Strategic Outbound tactics to ensure your emails are relevant to the person you target and provide value to begin building trust.

To be enticing while building immediate trust, messaging must be about the problems your offerings solve for your target audience. This is why aligning your ideal client profiles with your value propositions is so important.

At ML, we use these resources to create talking points and emails that highlight a client’s differentiators and convince potential buyers to move the conversation forward. We conduct client discovery meetings before beginning a project and use this time to answer questions and validate any assumptions made about their ideal client profiles and value propositions.

When it comes to sales emails, less is often more. For example, most of our team’s emails aim to be 150 words or less with limited page breaks. Given that so many decision-makers consume emails via smartphones, if a message simply looks too long, it can cause some hesitancy to engage.

You also want to highlight the digital asset you’re offering. If the email copy lacks a personable, educational, and problem-solving tone, the chances of your prospect clicking a link significantly shrinks.

Subject Lines That Grab Attention

When crafting a subject line, we have found that these three themes generally perform well:

1. Reflect a business pain your reader is experiencing and looking to resolve.
2. Mention a benefit that your reader would like to create for their company.
3. Educate about a subject specific to their role or business.

In the spirit of building trust, make sure that the body of the email message and supporting content provide the reader with the material teased in the subject line. We all are on somebody’s email list, and we know what type of subject lines resonate with us as professionals. We have learned that subject lines that create a reaction tend to be short and informative.

A compelling subject line is essential. You may have a relevant message, but that message will be missed without a persuasive subject line.

Therefore, we recommend keeping subject lines brief and aligned with your overall message. Other best practices include:

• Use first names, company names, or “you/our.”
• Ask relevant questions.
• Leverage brackets strategically.
• Reference statistics/numbers.

A speaker from a recent HubSpot conference recommended the resource “Subjectline.com.” We have found the site to be helpful.

Measure and Evaluate

As with every aspect of your sales and marketing programs, it is critical to evaluate the performance of your messaging and content at regular intervals. Because we are passionate about data, we track in HubSpot how emails perform to ensure we meet forecasted goals. Regular analysis will surface intel concerning what is performing, what isn’t, and content that may need some tweaking. We talk more about this in our blog Data and the Art of the Pivot.

Pro-Actively Follow up to Engage and Convert

In previous sections, we discussed developing a list of suspects and turning them into validated leads. We then discussed how to get the attention of a busy executive with relevant messaging and content.

Now it’s time to focus on getting your prospects to engage in a conversation by employing multitouch, multi-channel outreach.

Outreach and Engagement as a B2B Marketing Best Practice

This high-touch method involves multiple touchpoints to develop leads and move them toward a sales meeting.

Many companies underestimate the importance of phone calls in driving the early stages of their sales program. Calls are an essential component of Strategic Outbound Selling. Your email outreach should focus on warming up your audience, and making them more receptive to your call.

Your call framework should reinforce the messages in your emails. Whether speaking to the executive, their gatekeeper, or even their voicemail, get to the point quickly and re-state your compelling message. Leave your contact information but always follow up with a personalized email.

Previously, we discussed the value of having experienced sales professionals make calls, especially if your sales are complex and require engaging senior executives. When they connect, these skilled team members will converse most effectively with your target audience.

They also understand that you must reach out by phone and email numerous times. It’s the rare outreach that is successful on the first attempt (though not impossible!).

To convert prospects to a sales meeting takes multiple touchpoints. The actual number depends on various factors. Our experience conducting Strategic Outbound for over 20 years shows that it currently takes an average of 6 to 8 touchpoints just to reach a prospect and a total of 10 to 12 touchpoints to move a complex sales lead to a meeting.

3 Tips for Successful Outreach and Engagement

Before you begin, determine the proper outreach schedule. It’s a delicate balance between staying top of mind and being overly persistent to the point that your prospects start to ignore you.

In our experience with executivelevel and C-suite leads, once you’ve made contact, your goal is one of two outcomes:

• Prequalify and move the lead forward to a discovery meeting
• Collect intel and move to a nurture cycle if the timing is not right

Once they are in a nurture cycle, your ongoing cadence should be no more than one email per month to stay top of mind, and it should provide something of value versus just asking for a meeting. Phone followup should cycle every 90 days unless the prospect increases their engagement, in which case, you should follow up right away.

Of course, this cadence of touch points can differ based on many factors, including industry norms, the level of need in the market, and brand awareness. Be sure to analyze results and pivot your outreach based on your findings.

Here are three tips to help you create a successful outreach and engagement program.

Tip One: Begin Your “One-Way Dialogue”

“One-way dialogue” sounds like an oxymoron. But when it comes to Strategic Outbound Selling and B2B prospecting, we assure you it is not. The term “dialogue” signifies a “written or spoken exchange between two or more people.” So, a dialogue is happening when they react to the content you are systematically sending. You just aren’t privy to their side of it.

The result is an educated buyer who has developed an interest in your product or service because they have recognized your ability to solve a relevant need

Tip Two: Continue to Clean Your Data

You dedicated time, energy, and resources to building and validating your prospect list. Make sure you are keeping it up to date and capturing changes. Software like HubSpot makes it easy for your team to maintain and update contact information in real-time as they uncover insights. LinkedIn is invaluable for discovering where they landed when a prospect leaves a company

Tip Three: Measure Reactions and Personalize Your Outreach in Response

As prospects open and click through emails, it’s time to personalize the engagement. For example, perhaps a prospect responded to outreach by downloading a white paper, subscribing to a blog or thanking you for your call but saying the timing isn’t right to speak. The relationship-building process has begun. It is time to move those engaged leads deeper into the pipeline.

HubSpot can automate the process of sending content based on audience reactions. However, an experienced sales executive knows how to take that further. They will incorporate those reactions into emails and conversations, working the intel into the prospect’s experiences and challenges.

Is Your Strategic Outbound Selling Strategy Paying Off?

Your activity should generate consistent results at this stage of your strategic outbound program. If not, it’s time to analyze your data to understand where you need to improve. For example, are you focused on the wrong accounts or individuals? Perhaps your messaging is off, or you are sharing content that isn’t relevant.

Set Goals, Measure Results, Report Outcomes

How Does Data Impact your Outbound Selling Strategy?

Data analysis and reporting help elevate traditional outbound sales tactics to a Strategic Outbound program that is a market advantage. By applying data-driven decision-making to your sales programs, you will get in front of the right decision-makers faster. At ML, we have embedded data analysis and reporting into our services for over two decades and learned these valuable lessons.

Lesson One: Set Measurable Goals

Without goals, it’s virtually impossible to perform data analysis and reporting in a meaningful way. In addition, clearly defined goals ensure everyone on your team is focused and aligned to a common objective. Setting goals allows you to identify your strengths and areas for improvement. Striving toward defined goals that everyone shares sets you up for greater success.

Lesson Two: Include Quantitative and Qualitative Goals

To best gauge the performance of your B2B outbound program, be sure to set quantitative and qualitative goals.

What are Quantitative Goals?

Simply put, quantitative goals are objective and are tied to numbers. From a B2B sales perspective, quantitative goals and their corresponding data help you understand how your leads are progressing. This allows you to predict outcomes better. Here are a few examples of quantitative goals you might set for a lead generation program:

Examples of Quantitative Goals

• # of touches to reach a prospect
• # of touches to book a discovery meeting
• # of discovery meetings needed to hit opportunity pipeline goal
• # of opportunities needed to hit sales target based on closing ratio 

What are Qualitative Goals?

Qualitative goals are subjective and can be harder to track. Qualitative data includes the intel we pick up from conversations. This can provide insight into how your audience responds to your offering. It can help inform strategy and confirm whether you are on the right track or in need of a pivot.

Examples of Qualitative Goals

• Validating titles that have the greatest need for your product offering
• Identifying competitive intel
• Feedback on pain points that cover similar themes to highlight emerging trends

Lesson Three: Invest in a Solution to House Your Data

What are you doing with all the data you collect? At ML, we use HubSpot to manage data. HubSpot is an effective tool that every MLer uses to track every interaction. It is safe and secure and easy to use.

Full compliance with capturing data is critical to measuring results. We have seen many instances of insightful data not being effectively used to inform sales strategies because it’s simply not captured consistently. This is often the case for clients with new sales teams or that have gone through a merger or acquisition, and data is housed in disparate systems

Often companies will invest in a CRM and sales tracking systems only to find that not all of their team members have adopted usage. Avoid letting your sales team use spreadsheets that only they can access, or worse, keep the data only in their heads.

At ML, one of the first things we do for new clients is create a HubSpot portal to house lead data. Through this process, combined with our regular reporting, our clients see how essential information is to revenue generation. They see how to gather the intel their sales (and other) programs generate and learn how to establish similar in-house programs. Sharing data management best practices is one of our highest priorities.

Lesson Four: Analyze and Report Regularly

Data analysis and reporting should occur regularly. Data will inform your activities and responses and improve decision-making. Regular reporting will show how your leads progress and how the market responds to your value proposition. You can spot trends early and take necessary action fast. This includes re-evaluating your goals or pivoting to achieve them.

Technology can assist with analysis. For example, the ML team uses Power BI to quickly and easily pull data together to visualize our performance against project goals.

For each client program, we track about 30 standard quantitative metrics. Thanks to HubSpot and Power BI, we can access those metrics in seconds. 

We continually review what we are learning from conversations to analyze qualitative data. For example, we read discussions in bulk to see trend consistencies like keywords or competitor mentions. Then we try to use that information to shape messaging and responses to help us meet objectives.

Lesson Five: Build a Repeatable Process

Incorporate your learnings across your organization to get the full advantage of your investment in a Strategic Outbound Selling program. Much of the intel you collect may also influence other lines of business, including Customer Experience, Support, and Marketing.

The insights will help you create a repeatable, evolving sales program and build a sales pipeline that is predictable and scalable.

III. The Best Outbound Strategy Is a Team Effort

We have one more recommendation to elevate your outbound efforts, and that is to have experts on your team who can take ownership of each cornerstone element necessary for a successful program. At ML, we call this the “Diamond Approach.” We have senior personnel held accountable for the elements that are central to success, and they work together to achieve a common goal:

• Client Services is responsible for the STRATEGY and focused on the GOALS
• Account Operations is responsible for the REPORTING and focused on the DATA
• Marketing Communications is responsible for the MESSAGING and focused on the MARKET REACTION
• Our Specialist Team is responsible for the EXECUTION and focused on the INTEL

Consider taking a collaborative approach to revenue generation, just like we did with this Playbook (did you notice we had four team members contribute?).

Combined with the four steps to Strategic Outbound covered here, you are almost sure to get in front of your buyers faster to close more deals.