Dreamline's Outbound Guide - Confidential

Scale your sale pipeline with AI & leading methods

Acknowledgments

Hey there! This guide comes from Ethan Wade, our COO, and the awesome team at Dreamline Digital.

We've spent the last eight years experimenting with cold outreach, launching hundreds of campaigns, and sending millions of cold emails, all while constantly tweaking and improving our approach.

We've had the pleasure of working with over 100 B2B businesses, ranging from startups to Fortune 1000 companies.

The processes, workflows, and tools you'll find in this guide are pretty much how we do things at Dreamline. If you find it helpful, please feel free to share it. If you're interested in working with us, check out our to learn more about our services.

Introduction

Outbound Prospecting as an Acquisition Channel:

Finding new customers can be done in many ways, but outbound prospecting often gets a bad rap. Our prospects' inboxes are overflowing with messages every day (yours probably is, too!).

So, do we really want to add to the clutter? Despite the negatives, outbound prospecting has some distinct advantages over other acquisition methods:

1. Cost-Effective: Unlike digital ads, you don't need a huge budget.
2. Speedy Results: Unlike inbound strategies, you get quick results and feedback.
3. Minimal Networking Required: Unlike word-of-mouth, you don’t need a vast network of contacts or a slew of satisfied clients to start.

The Problem with Outbound Sales Today

Why do so few companies succeed with outbound sales?

Think about the messages flooding your inbox—most are impersonal, irrelevant, poorly written, and way too long. No one enjoys reading long, irrelevant messages.

Now, imagine this: You’re grappling with an issue in your business. Someone reaches out to you. The message is brief. The sender has done their homework. The message is direct and to the point. It hints at a solution to your problem.

How would you feel if every outreach you received was a solution to your problems? You’d probably appreciate it a lot more, right?

While we can’t overhaul the entire industry's outbound practices, we can make a positive contribution.The biggest issue with outbound is that most sellers don't know why they're reaching out to specific individuals.

You might not know for sure, but you should at least have a reason why someone is on your list.

This should be the foundation of your outbound efforts: Identify people and companies struggling with a problem you can solve. The first goal of this document is to show you how to identify problems at scale and reach out to companies that are most likely to need your help.

Then, we'll demonstrate how to make this process more efficient by leveraging sales technology and copywriting best practices.

Ingredients of Successful Cold Email Campaigns
- Segmented List: Prospects who can genuinely benefit from your solution.
- Concise Copywriting: Short, punchy messages that highlight your value proposition.
- Personalization: Tailored and relevant messages for each individual.
- Proof of Solution: Demonstrating your ability to solve the prospect’s problem.
- Deliverability: Ensuring your emails land in inboxes.
- Valuable Assets: Providing helpful, valuable content.

Chapter 1 | Generate a Prospect’s Account List

Identifying Companies with a Problem

In a perfect world, you could simply snap your fingers and get a list of all the companies struggling with the issue you solve. Unfortunately, we need to rely on guesswork and research.Some experts in the outbound field use the term "problem sniffing," which means identifying problems based on companies' public activities.

A great way to do this is by looking for 'trigger events.'Here are a few examples of trigger events:

1. Changes in the industry that might impact businesses
2. Hiring trends and headcount growth or reduction
3. Opening new office locations
4. Appointment of a new C-level executive
5. Launch of a new product
6. Increase in ad spend
7. Mergers or acquisitions
8. Fundraising events

These events often signal changing needs within companies—needs you might be able to address.

From Problem to Targeting

To understand how to derive potential issues from trigger events, let’s explore a couple of scenarios.

Scenario 1: Selling HR Software

Imagine you’re selling HR software that helps companies with high churn rates. High employee turnover is costly because hiring and training new employees is expensive. If your software can reduce churn, companies can save a significant amount of money.

Who should you target? Every company could benefit from reduced churn, right? So why not contact every CEO and pitch your solution? The problem is, most recipients won’t be receptive to your pitch. It’s not that your product isn’t helpful; it’s that they’re not experiencing the pain you’re addressing.

Your outreach will get ignored if it isn’t relevant. To find the right targets, start by analyzing your existing clients:
What made them reach out to you? What made them buy? Look for patterns in your sales data.

For example, our sales prospecting agency noticed that many companies scheduling calls with us were struggling with low deliverability. Knowing this, we can target companies with similar issues, such as those not properly configuring their email infrastructure or participating in email deliverability webinars.

If you don’t know what triggers your ideal customer profile (ICP) to take action, this is the most important question to answer. Spend time brainstorming with clients and identifying patterns in companies that would make them a great fit. If unsure, think of situations where the pain is likely to be stronger and build hypotheses to test.

Example Buying Signals for HR Software Let’s revisit our HR software example. Here are some potential buying signals:

Bad Employee Reviews on Glassdoor Companies with many negative reviews likely experience higher-than-average churn, making them more likely to need your software.

Partly or Wholly Remote Companies Remote teams can be harder to manage, and monitoring employee well-being is more challenging.

These companies could benefit more from your solution than in-person teams. By identifying these triggers and buying signals, you can create a targeted list of prospects who are more likely to need and appreciate your solution.Once you’ve built a few hypotheses, you want to confront them to the market.

It might be true that fully remote companies have more trouble monitoring employee well-being. But it might also be true that the C-level in these remote organizations care less because they haven’t ‘bonded’ as much with the employees.

There’s only one way to find out, and it’s by reaching out to these companies. The first step is finding the data.

Finding data on best-fit accounts

Now that we built the hypothesis that remote organizations are a great fit for us, the next question is how do we build a list with such companies?There are several ways to do this. The best we found was to look at companies hiring remotely. We’ll go deeper into data sources, but in this case, we’ve done that with .

They have a few integrations that let you find information on open job data. We figured that every company that had ‘Remote’ in their job opening had—at least—part of their team working remotely.

Chapter 2 | Target the right person within your target accounts

How to Think About People Targeting
Finding the right person to target within an organization is crucial for the success of your outreach. To make this decision, it’s essential to ask the right questions. Here are two of my favorite questions to guide this process:

1. "Find patterns among your best clients to guide your targeting." - Mary Grothe
2."Focus on those who truly need your solution." - Aaron Ross:

Alternatively, you could ask: Who would get promoted if the initiative was a success?

Criteria for Targeting
Here are some criteria to consider when deciding on your targeting:

1. Job Titles of Inbound Leads: Identify the most common job titles of your inbound leads.
2. Job Titles with Highest Close Rates: Determine which job titles have the highest close rates.
3. Typical Buyer Titles: Understand the title of the typical buyer of your solution.
4. Individual Users: Identify the individual users of your solution within the company.
5. Company/Department Size: Consider the size of the company or department you’re targeting.
6. Department: Know which departments your targets operate in.
7. Industry: Determine the industries your best customers are in.
8. Location: Consider where your target companies are located.

Steps to Target the Right Person

1. Analyze Your Best Customers:

Review your last 10 best customers and identify common attributes. What job titles, departments, personality and company sizes were involved? What industry were they in? Where are they located?

2. Identify Key Decision Makers:
Within your target accounts, identify the key decision-makers and influencers. These are often the individuals who would be most impacted by the success or failure of the initiative.

3. Use Data to Guide Targeting:
Use your CRM and analytics tools to find patterns in your existing customer base. Look for trends in job titles, departments, and other criteria.

4. Create a Persona Profile:
Develop a detailed profile of your ideal target persona. Include job titles, responsibilities, challenges, and goals. This profile should be based on the common attributes of your best customers.

5. Refine Your List:
Use your persona profile to refine your list of targets. Make sure each contact on your list matches the criteria you’ve identified.

6. Validate and Iterate:
Continuously validate your targeting criteria by monitoring the results of your outreach. Adjust your targeting as necessary based on what you learn.

By systematically identifying and targeting the right individuals within your target accounts, you can improve the effectiveness of your outreach and increase your chances of success.

Chapter 3 | Build your contact list

Building a list of people/companies hiring for many jobs is a great way to find organizations likely to be interested in recruitment services.

Here’s a step-by-step guide to creating such a list. Understanding the logic will allow you to adapt it to various needs:

1. You might contact companies recruiting for specific positions (e.g., Marketing Manager, if you specialize in certain roles).
2. You could choose another geography, industry, or size.
3. You might target different individuals within the organization (e.g., the Head of Department for the open position).

If you need help building these contact lists or running your prospecting campaigns, you can book a time with us here.

Step 1: Filter Your Target by Job Title, Industry, Geography, Company Size, and More

You can use a B2B database like Apollo to do the initial filtering.

As shown in the example below, we went a bit broad in the targeting and used the following filters:

1. Job Titles: Talent Acquisition Director, HR Director, Head of People, Head of Human Resources, Head of Talent Acquisition
2. Location: Worldwide excluding India, Pakistan, Philippines, Nigeria, and Brazil (80% of our list is US-based)#
3. Employees:
Companies with 100 to 1000 employees

We also added a condition in Apollo that the company needed to have at least one open job in the US. Since Apollo's job data aren't very precise, we will use Clay to find the exact number of active job openings.

Example Filter Setup in Apollo Job Titles:
Use the filters to include titles like Talent Acquisition Director, HR Director, Head of People, Head of Human Resources, and Head of Talent Acquisition.

1 Location: Exclude certain countries if necessary and focus on your target regions (e.g., primarily the US).
2. Company Size: Set the filter for companies with 100 to 1000 employees.
3. Active Job Openings: Ensure there is at least one open job in the US.

After setting up these filters in Apollo, export the list and uto refine the data further. Clay can help you find the exact number of active job openings, ensuring your list is accurate and targeted.

Step 2: Export the Results into a .CSV File and Import into Clay

Once you’ve refined your filtering criteria in Apollo, follow these steps to export and prepare your list for further enrichment in Clay.

Exporting from Apollo

1. Apply Filters:
Ensure you’ve applied all necessary filters such as job titles, location, company size, and the condition for active job openings.

2. Export the List:
In Apollo, go to your filtered list of contacts. Select the contacts you want to export. Click on the export button and choose to export as a .CSV file.

STEP 3: Find number of active jobs opening

Clay's UI looks like most Spreadsheet tools. Once you import your .csv file into Clay, your initial list should like the below:

As you'll see, despite looking like most Spreadsheet tools, Clay has some unique capabilities that will allow us to find all the interesting data we're looking for. If you haven't heard about the tool before, I urge you check them out: https://www.clay.com/

The next step is to find the number of active jobs openings inside of our target companies.

Our initial file included information such as the company name and the website where each of our HR/TA/People director works. We will use one of Clay's built-in integration to look for active jobs openings.

As you can see below, you have the option to filter jobs openings by Job Title. In this case, I typed 'Sales Director' for the sake of the example. If I had ran the search with the specific keyword; we would only have gotten active jobs openings for 'Sales Director' roles.On the file above, I didn't target by specific job title, so Clay's integration found all the jobs it could.

STEP 3: Find number of active jobs opening

Clay's UI looks like most Spreadsheet tools. Once you import your .csv file into Clay, your initial list should like the below:

Because we're only interested in companies that are hiring a lot, I filtered my search to only include companies with 10+ open roles:

Once we've filtered down our Head of TA/HR in companies we want to go after, all is left is to find their email addresses.

Chapter 4 | Contact prospects at scale

When your contact lists consist of thousands of contacts, the implications are:

1. Time Constraints: You won't have the time to manually reach out to each contact.
2. Opportunities: There are a lot of potential new clients to engage!

Before diving into sales engagement platforms to automate your outreach on a massive scale, consider these points:

- Your potential clients receive hundreds of messages daily.
- They can sense when your approach is impersonal and automated.

To achieve a decent conversion rate, you need to stand out. We've started this process by targeting companies based on specific needs and identifying the right person within those companies.

This approach is already better than 99% of the outreach out there.However, we can push this further. For example, by leveraging ChatGPT inside Clay to personalize our outreach at scale.

Making Each Outreach Message Unique
The goal is to make each outreach message feel unique and personal. You want your recipient to think, "There is no way this was for someone else."Here's an easy way to personalize your outreach at scale:

Leveraging Trigger Events or Public Information
Use trigger events (like active hiring) or publicly available information (such as LinkedIn bios or company summaries) to personalize your outreach.One effective method is using job descriptions for open roles as an input. Based on the job description, you can prompt ChatGPT to summarize the key needs for the hire and complete a sentence like: "I saw you were hiring a {job title} that specializes in... {AI-personalization}."

Step-by-Step Process

1. Extract Job Descriptions:
Gather job descriptions from companies on your contact list.
2. Summarize Key Needs: Use ChatGPT to read and summarize the key needs from these descriptions.
3. Create Personalized Snippets: Ask ChatGPT to create personalized snippets addressing the specific needs of each company.Example: "I saw you were hiring a Software Engineer who specializes in cloud infrastructure. We can help streamline your hiring process by providing pre-vetted candidates with cloud expertise."

Tools for Automated and Personalized Outreach
With a list of companies potentially interested in your solution, contact information of relevant people, and personalized snippets for each company, you can now reach out at scale in a way that feels personalized to each recipient.

At Dreamline Digital, we use the following tools:

- Instantly, Smartlead: (there are a bunch): used to  automate our outreach by email.
- HeyReach or Lemlist: To automate our outreach via LinkedIn.

Lemlist is particularly useful for multichannel outreach, allowing you to contact your leads via both email and LinkedIn, and even send voice notes at scale. Additionally, Lemlist offers strong integration options, making it ideal for sales teams needing: If you are using multiple accounts Lemlist can get very expensive for smaller teams. 

- Strong Hubspot or Salesforce integrations.
- A native phone dialing option.

By using these strategies and tools, you can efficiently manage large-scale outreach while maintaining a personal touch that resonates with your prospects.

Hey there! If you’ve made it this far, it’s clear you’re serious about mastering your outbound sales strategy.

I’ve skipped over some details in this guide—not on purpose, but because explaining everything thoroughly without turning this into a full-length book is quite a challenge...In the upcoming sections, I'll dive into sales copywriting best practices and how to set up an email infrastructure that keeps your emails out of the SPAM folder.

If you’re eager to discuss how to build a prospecting system tailored to your products or services, feel free to book a time with us using the link below 👇

Chapter 5 | Write high-converting messages

Now that we covered:

- finding companies demonstrating buying intent
- finding contact information of relevant people within these companies
- personalizing part of our messages using AI
- software for automating our outreach.

The question is... how are we going to write convincing messages so that our prospects want to meet with us?

Here are a few best practices to follow when writing your messages. Both to make sure they’re read by your recipient and they don’t land in the SPAM folder:

- Write messages as short as possible.
- Avoid adding links, images &/or documents.
- Individually personalize them for your recipients.
- Include several touchpoints, and follow-up a few times.
- Reach out across several platforms using various formats(send videos, reach out on LinkedIn, via Email...)

To help this process - you can use tools such as Lavender that rates your cold emails in real time.

Chapter 6 | Email Deliverability Infrastructure

The final, yet crucial step is to set up an email infrastructure that allows you to send emails at scale without landing in the SPAM folder.

Avoiding Spam Filters

Avoiding spam filters involves:

1. Content: Refrain from using links, images, and documents in your cold emails.
2. Volume: Avoid sending too many emails from the same inbox.

Best Practices

Limit Per Domain:
Send fewer than 50 emails a day per domain.

Separate Domains: Use different domains for outreach instead of your main domain. If too many people mark your emails as spam, it can severely impact your main domain, causing even important communications to land in the spam folder.

Setting Up Your Infrastructure

Here’s a brief overview of the necessary steps:

1. Create Multiple Domains and Email Accounts: Set up several domains and corresponding email accounts.Forward these new domains to your main domain in case someone tries to look you up.
2. Configure SPF, DKIM, and DMARC Records: Properly configure these records for each of your domains to ensure email authentication and improve deliverability.
3. Limit Sending Volume: Stick to sending 50 emails per domain per day to avoid triggering spam filters.
4. Use Email Warming Software: Employ email warming software to gradually build the reputation of your new domains, ensuring better deliverability.

Recommended Resources
Deliverability is a complex topic. For more in-depth information, check out this comprehensive article by Mailreach on how to prevent your emails from going to SPAM

Cost-Effective Sending Solutions
If you’re using multiple email inboxes, you can save money by choosing a sending solution that doesn’t charge per email profile. Consider using Smartlead, which allows you to use an unlimited number of email profiles.By following these steps, you can efficiently send 500+ emails a day while maintaining high open rates and avoiding the spam folder.

Chapter 7 | Building your sales stack for prospecting campaigns

Wrapping this up...This is all for now. I hope you learn a thing or two by reading this guide.

If you want to connect, don't hesitate to send us an invite on LinkedIn:

-> Madison Wade  (Co-Founder - CEO)
-> Ethan Wade  (Co-Founder - COO)

Thank you!