Scale your prospecting with software & AI
Outreach Ark’s Ultimate Cold Email Guide — Outbound Sales Playbook
Acknowledgements
This guide was prepared and written by Deepak Amirtha Raj and the team at Outreach Ark. It is the culmination of over 5 years of hands-on experience in outbound sales and cold outreach.
The insights shared here are drawn from countless cold outreach experiments, running hundreds of campaigns, sending millions of cold emails, and continuously iterating to refine our approach. These practical guidelines are designed to help you achieve success in your outbound efforts.
We encourage you to share this guide if you find it helpful. If you’re interested in partnering with us or learning more about our services, please visit our homepage.
Introduction
Outbound Prospecting: A Way to Find New Customers
There are lots of ways to find new customers, but outbound prospecting often gets a bad reputation. People get so many messages every day (your inbox probably does too!)... do we really want to add to that?
But outbound prospecting has some great advantages compared to other methods:
It doesn’t need a big budget like digital ads.
You can get results and feedback much faster than with inbound strategies.
You don’t need a big network or lots of past clients to refer you, unlike word-of-mouth marketing.
The Challenge with Outbound Sales Today
Many companies struggle to make outbound sales effective. Why does this happen?
Think about all the messages filling your email inbox. Most of them are too long, boring, and not relevant to you.
Do you enjoy reading long, unhelpful messages? No one does.
Now, imagine this scenario:
You’re facing a problem in your business.
Someone contacts you.
The message is brief.
The sender has done their homework.
Their message goes straight to the point, and it shows how they can help solve your issue.
How would you feel if all the messages you received were answers to your problems?
I bet you would appreciate that much more!
While it's hard to change how most companies do outbound sales, we can help improve things a little bit.
The biggest issue with outbound sales is that many sellers don’t really understand why they are reaching out to certain people. You don’t need to know the exact reason, but you should at least have a clear idea of why someone made it onto your list.
This should guide your outbound efforts 👇
You want to find people and companies that are dealing with problems you can help solve.
The main goal of this guide is to teach you how to identify problems on a large scale and reach out to the companies that are likely to need your assistance. After that, we’ll explain how to make this process more efficient by using sales technology and good writing techniques.
Key Ingredients of Successful Cold Email Campaigns
The best cold email campaigns usually have these key elements:
A focused [well segmented] list of prospects who can truly benefit from your solution.
Short and powerful copwriting that shows your value.
Personalized and relevant messages for each person.
Evidence that you can solve the prospect’s problem.
High deliverability rates, meaning your emails reach the inbox.
Valuable resources or information.
Chapter 1 | Creating a Prospect Account List
Finding Companies with Issues
Ideally, it would be great if you could just snap your fingers and get a list of all the companies that are having the same challenges you can help with. Sadly, we often have to make educated guesses instead.
I’ve heard some well-known people in the outbound sales field use the term “problem sniffing.” This means figuring out problems based on what companies are publicly doing. A smart way to do this is by watching for what we call ‘trigger events.’
Here are some examples of what these trigger events might be:
Changes in the industry that could affect businesses
Trends in hiring and changes in employee numbers
New office openings
A new executive hired at the company
The introduction of a new product
Increases in advertising spending
Mergers or acquisitions
Recent fundraising activities
These are just a few examples, but you get the idea. All of these events usually lead to changing needs within companies, and those are the needs you might be able to address.
From Identifying Problems to Targeting Customers
To understand how to spot potential issues based on triggers, let’s explore a couple of scenarios and how we think through these.
[1] Let’s say you’re selling online courses for startup founders.
One of the challenges you address is providing first-time founders with the knowledge and skills they need to succeed in their new ventures. Many startups struggle because they lack the right guidance, leading to failed projects and wasted resources. By offering your courses, you can help these founders gain essential insights that can lead to business success.
The business case here is clear. Founders can invest in your courses for a few hundred dollars, which can significantly improve their chances of building a successful startup and avoiding costly mistakes.
So, who should you target? Every founder could benefit from your courses, right? Why not gather contact information for every first-time founder and pitch them about your features?
The problem is that most recipients won’t pay attention to your offer. It’s not that your product isn’t valuable; it’s simply that they don’t feel an immediate need. Their inboxes are cluttered with messages, and if your outreach isn’t relevant, it’s likely to be ignored.
Who is Likely Experiencing the Pain? In an ideal situation, you would have a good grasp of the challenges facing your ideal customer profile (ICP). The easiest way to gather this information is to analyze your existing customer base or prospects and ask:
What motivated them to reach out to you?
What influenced their decision to enroll in your courses?
If you review enough customer feedback or inquiries, you’ll likely identify common trends. For instance, our course-selling company found that many clients who signed up recently were first-time founders who had just secured funding.
Not every startup founder needs help, but those who are inexperienced or recently funded often feel overwhelmed and in need of support.
Once we know this, the next question is, “How do I find first-time founders and startups that might need our courses?” We can look for indicators such as:
Founders who have recently received funding.
Attendees of startup-focused events or webinars.
Individuals identifying as first-time founders on networking platforms like LinkedIn.
If we can gather this information, we’ll know how to improve our outreach and increase our conversion rates.
Often, however, you might not immediately identify the trigger events that prompt your ICP to seek out help.
If you’re unsure, this is the most critical question you should address. We dedicate a significant amount of time brainstorming with clients to identify patterns within companies that would be a good fit for our courses. If they’re uncertain, we help them brainstorm situations where the need for guidance is likely to be higher. Based on this, we formulate hypotheses that we can validate or invalidate.
In our earlier example of selling courses to startup founders, here are some potential ‘buying signals’ we identified:
→ A startup has recently closed a funding round 👇
If they’ve just secured funding, they’re likely eager to learn how to effectively manage their new resources and grow their business, making them ripe for taking your courses.
→ A founder identifies themselves as a first-time entrepreneur on social media 👇
First-time founders often seek out educational resources to help them navigate the uncertainties of launching a startup. They may actively seek courses that help them understand best practices.
→ A company is expanding its team rapidly 👇
When a startup is increasing its headcount, it may indicate growth and the need for training and development resources, which could lead them to your courses.
LinkedIn Sales Navigator offers specialized filters that allow you to find and target these specific accounts effectively.
CrunchBase
I frequently use CrunchBase to effortlessly build targeted prospect lists. With its powerful AI Search Builder, you can simply type a query like, “North American AI companies with recent funding in the last 30 days," and instantly get a curated list of companies that match those exact criteria. It’s an incredibly efficient way to identify potential leads tailored to your specific needs.
Ocean.io
Ocean.io is a prospecting tool that helps businesses find lookalike companies based on their Ideal Customer Profile, enabling you to scale your outreach with precision and efficiency.
If you already have a handful of clients for your business and want to scale further, one of the best strategies is to find similar companies to the ones you’re already working with. Ocean.io is an excellent tool for this purpose, as it specializes in identifying "lookalike" companies that match your Ideal Customer Profile (ICP). With its advanced algorithms, Ocean.io creates a targeted list of companies that closely resemble your existing clients, making it easier to expand and grow your business efficiently.
Once you’ve developed a few hypotheses, it’s time to test them in the market.
For example, it may be true that first-time founders who recently secured funding face challenges in managing their new resources effectively. However, it could also be the case that these founders are more focused on growth strategies than on learning the fundamentals.
The only way to find out is by reaching out to these startups. The first step is gathering the necessary data.
Finding Data on Ideal Accounts
Now that we’ve developed the hypothesis that recently funded SaaS Startups in blockchain are a great fit for our courses, the next question is: how do we compile a list of these companies?
There are several approaches we can take, but the most effective one we found is to target new startups led by first-time founders. We’ll dive deeper into the data sources later, but for this example, we used Apollo. They provide various filters, including signals such as office expansions, cost-cutting measures, new product or service launches, and recent funding.
In addition to Apollo.io, I’m also creating a page of AI Sales Tools that could be beneficial for you.
Identifying Initiatives
Often, there may not be an obvious problem to address, and it can be more effective to focus on the current initiatives of companies.
Apply the same reasoning to identify priorities. Pay attention to what companies are experiencing and develop a hypothesis about their immediate goals.
For instance, if you’re offering an advertising tool that helps businesses optimize their ad spend, keep an eye out for job postings for positions like ‘media buyer,’ ‘paid media specialist,’ or ‘advertising manager.’
Companies hiring for these roles are likely to increase their advertising efforts. If your solution can help them or their new hire achieve better results, it could be the perfect opportunity to reach out.
Here are some tools I recommend for gathering this data:
Apollo.io
Apollo is the most efficient software to build highly targeted list of prospects.
Plan starts from $39/month
Clay
Clay finds data from 50+ data sources and leverages ChatGPT to personalize emails.
Plan starts from $149/month
Ocean.io
Ocean.io helps businesses find and target their ideal customers using an AI lookalike search.
Plan starts from $59/month
Chapter 2 | Targeting the Right Person Within Your Accounts
How to Approach People Targeting
The easiest way to find the right answers is by asking the right questions. As cliché as it sounds, there are a few questions I ask myself repeatedly when deciding on my targeting strategy.
Here are two of my favorites:
“What 3-5 attributes must be true about a lead, similar to those of your last 10 best customers, that made them a great fit?” by Jordan Crawford.
Another, more straightforward way to think about people targeting is to ask, “Who is most likely to be held accountable if the initiative fails?” by Morgan Smith.
Here are some criteria to consider when determining your targeting:
What are the most common job titles among your inbound leads?
Which job titles have the highest conversion rates?
What title does the typical buyer hold?
Who is the end user of your solution?
What is the size of their company or department?
In which departments do they operate?
What industry are they in?
Where are they located?
You could also flip the question and ask, “Who would get promoted if the initiative succeeds?”
In our previous example, it’s evident that we should target the founders of these blockchain startups. An effective segmented list would include B2B SaaS blockchain startups that have recently received funding, along with their founders and co-founders. Using a tool like Clay, you can leverage AI to research and analyze their LinkedIn profiles to determine if they are first-time founders. The results can be a straightforward “Yes” or “No,” and ultimately, it’s clear that we should focus on those labeled as “Yes.”
Personas
Personas are built around specific attributes like job titles, industries, and other firmographic data, defining the key groups of people you want to target. They help streamline the process of finding qualified sales leads by minimizing the need for extensive manual filtering. Once you’ve identified your target Personas, you can engage them through tailored sequences that align with your ideal customer profile. Tools like Apollo.io offer the ability to create detailed Personas, streamlining the process of identifying ideal prospects. This not only saves time but also enhances the efficiency of your prospecting and lead-generation efforts by focusing on the most relevant contacts.
Chapter 3 | Build your contact list
Here’s an example of a list of blockchain companies that provided financial services in the United Kingdom that have recently received funding. You can refine this list further by filtering for factors such as the number of employees, founding date, technologies used, revenue, and more.
Example for a list of first-time founders, in recently funded blockchain companies within 500 employees in United Kingdom
Creating a list of people and companies that are hiring for multiple positions is an excellent way to identify organizations that are likely to be interested in recruitment services.
I’ll walk you through the steps to generate such a list. Understanding this approach will enable you to customize it according to your specific needs:
You can target companies hiring for particular roles (e.g., Marketing Manager), which is useful if you specialize in certain positions.
You can choose a different location, industry, or company size.
You can reach out to various contacts within the organization (in this example, we targeted the Head of Talent Acquisition/People/HR, but you might want to connect with the Head of the relevant department for the open positions).
If you need assistance in creating these contact lists or running your prospecting campaigns, feel free to schedule 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 such as Apollo to do the initial filtering.
As you see in the image, we went a bit broad in the targeting. We used the following filters:
- Job Titles: Founders, Co-Founder, Owner
- Location: United Kingdom
- # Employees: Within 500 employees
We also added a condition, inside of Apollo, that the company needs to have recent funding within 3 months.
STEP 2: Export the results to a .csv file and import it into Clay.
After you're finished adjusting the filter settings in Apollo, you can export your list as a .CSV file. When you import it into Google Sheets, it should look like this:
STEP 3: Determine if the contacts are first-time founders
Clay's user interface is similar to other spreadsheet tools. After you import your .csv file into Clay, your initial list will look like this.
Although Clay resembles typical spreadsheet software, it has special features that help us find all the valuable information we need. If you're not familiar with the tool, I recommend checking it out here: https://www.clay.com/
The next step is to check if the contacts are first-time founders. Our initial file contained details like the company name, website, first name, last name, and email. We used Clay to enhance the contact's LinkedIn profile.
As shown below, you can create AI prompts in the Clay table to explore and improve your list. For instance, I wrote a prompt to examine and research the contact's LinkedIn profile to determine if they are indeed a first-time founder, providing a “Yes” or “No” answer.
As you saw in the previous Clay table, we received results labeled “Yes” and “No.” We will filter the contacts marked “Yes” for reaching out. Next, we need to validate the available email addresses. If there are any email addresses missing from Apollo, we can use Clay's built-in waterfall feature to find the missing email addresses.
You have other options too! I recommend checking out tools like Prospeo, FullEnrich, Datagma, Ocean.io, and other popular email finding tools such as Hunter.io and Snov.io.
Chapter 4 | Reaching Out to Prospects on a Large Scale
Contact lists can be quite large, often including thousands of contacts. This means that:
You won't have enough time to reach out to each one manually.
There are many potential new clients to connect with!
Before you invest in any sales engagement platform and start automating your outreach on a large scale, there are a few important things to consider:
Your potential new clients receive hundreds of messages every day.
They can easily notice when your approach feels impersonal and automated.
To achieve a good conversion rate, you need to make your messages stand out. We began by targeting companies based on their specific needs and focusing on the right person within the organization (believe it or not, this already puts you ahead of 99% of the outreach out there).
However, we can take this a step further. For instance, by using ChatGPT within Clay, you can personalize your outreach on a larger scale.
The aim is for each of your outreach messages to feel unique. You want your recipient to think, there's no way this message was meant for someone else.
Here’s an easy method to personalize your outreach at scale:
You can do this by leveraging trigger events (like the fact that they're hiring) or using publicly available information (such as their LinkedIn profile or company summary).
One approach I like to use is to take the job description for open positions as an [Input]. By analyzing the text in the job description, you can prompt ChatGPT to identify and summarize the key requirements for the hire. Then you can ask it to complete a sentence like: "I noticed you were hiring a {job title} that specializes in... {AI-personalization}."
I described in a single image here 6 steps you can take to effortlessly launch AI-Personalized sales campaigns targeting companies that are currently hiring.
After following the steps above, we now have:
A list of companies that are potentially interested in our solution
Contact information for the key individuals within those companies
A personalized message snippet tailored to address each company’s specific needs
With this information, we can now reach out on a large scale while ensuring that each interaction feels personal to the recipient.
At Outreach Ark, we utilize:
Instantly to automate our email outreach. We are currently trying out new tools like Smartlead and ReachInbox.
HeyReach or Lemlist for automating our LinkedIn outreach. I've recently started using a tool called Aimfox, which we employ for Outreach Ark and for my clients.
Lemlist has the advantage of enabling multichannel outreach, allowing you to connect with your contacts via both email and LinkedIn. Additionally, it supports sending voice notes at scale.
Lemlist is also highly effective in terms of integrations, making it ideal for sales teams that:
Require a platform with strong integrations for HubSpot or Salesforce
Need a native integration with a phone dialing feature.
We’ve recently started using ReachInbox for some of our campaigns. It offers functionalities similar to tools like Smartlead and Instantly, making it a reliable option for cold email outreach and automation.
Smartlead
Apollo is the most efficient software to build highly targeted list of prospects.
Plan starts from $50/month
Instantly
Clay finds data from 50+ data sources and leverages ChatGPT to personalize emails.
Plan starts from $50/month
HeyReach
Ocean.io helps businesses find and target their ideal customers using an AI lookalike search.
Plan starts from $79/month
You’ve made it this far?
Hey there! If you’re still reading, it looks like you’re really eager to improve your outbound sales system.
I’ve intentionally left out quite a few details in this guide. It’s just that it’s really challenging to explain everything thoroughly without writing a whole book...
In the upcoming sections, I will share best practices for sales copywriting and guidelines to create an email setup that helps your messages avoid the SPAM folder.
That said, if you’d like to talk about how to implement a prospecting system to sell your products or services, I invite you to schedule a time on our calendar right below 👇.
Chapter 5 | Write high-converting messages
How to write a sales cadence that converts
Now that we’ve covered:
How to find companies showing buying intent
How to find contact information for the right people in these companies
How to personalize parts of your messages using AI
Which software to use to automate your outreach
The next question is: How do we write messages that are so compelling that our prospects actually want to meet with us?
Here are a few best practices to make sure your messages get read and don’t end up in the SPAM folder:
Keep your messages as short and concise as possible.
Avoid including links, images, or attachments.
Personalize each message for your recipients.
Use multiple touchpoints and follow up a few times.
Reach out across different platforms and formats (send videos, connect on LinkedIn, follow up via email…).
To make this process easier, you can use tools like:
Lavender, which rates your cold emails in real time to help improve them.
Twain, which provides recommended changes to your emails based on tone, your product, and the specific use case. And if you’re unsure what to write—don’t stress, I’ve got you covered! :)
I’ve compiled a list of some of my favorite email copywriting frameworks, and you can find them in the post below 👇.
I also follow and learn from experts like Josh Braun and Jeff Molander. I particularly appreciate their use of 'poke-the-bear' questions in cold emails—strategically crafted to spark curiosity and encourage prospects to take initiative in addressing their business pain points.
3T Approach to Cold Outreach: Tailored, Targeted, and Templated
When it comes to strategic cold emailing, I follow a simple yet effective framework: the 3Ts—Tailored, Targeted, and Templated. Here's what each means and how I apply them:
1️⃣ Templated
Sending the exact same message to everyone on a contact list is something I avoid—and strongly advise others against. In today’s business environment, this approach is outdated and rarely produces good results. Personalization is key to standing out.
2️⃣ Targeted
This approach involves creating personalized emails for a specific group of prospects who share similar pain points or needs. Using tools like Clay or AI solutions such as Apollo Power-Ups, I automate the process of crafting messages that are relevant and engaging while maintaining a degree of personalization. This is perfect for reaching groups of prospects with shared characteristics or challenges.
3️⃣ Tailored
For high-value or enterprise-level clients, I rely on a fully manual approach where I go beyond what AI tools can achieve. While I use AI for summarizing and gathering key insights about individual prospects, elements like analyzing their sign-up flow, understanding their competitive landscape, or uncovering unique challenges require a human touch. This ensures every email is 100% relevant and highly personalized. I follow this method, especially when targeting C-level executives in larger companies, where attention to detail is critical for success.
By applying this 3T approach, I’ve been able to deliver impactful and engaging cold outreach campaigns that resonate with prospects and drive results.
Chapter 6 | Building Your Email Deliverability Infrastructure
How to send 500+ emails a day while maintaining an open rate above 80%.
The final (but critical) step is setting up a robust email infrastructure that allows you to send cold emails at scale—without ending up in the SPAM folder.
Half the battle is avoiding spam filters by steering clear of links, images, and documents in your emails. The other half is ensuring you don’t send too many emails from one inbox, which could flag your account as spammy.
Best practice: Limit your sending to no more than 50 emails per domain per day. Additionally, avoid using your primary domain for outreach. If your emails repeatedly get marked as spam, it can have serious consequences—like damaging your main domain’s reputation. This can result in your critical emails (e.g., customer communications) also ending up in spam folders.
Here’s a quick example of how you can set up an effective infrastructure for sending cold emails:
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Buy secondary domains: We purchase ~10 secondary domains using GoDaddy or NameCheap.
Forward them to your main domain: Each of these new domains is forwarded to your main domain so people can still find your website if they look you up.
Create multiple mailboxes: We set up two email inboxes per domain (to scale outreach even further).
For example:
If our main domain is outreachark.com.com, we’ll create:
useoutreachark.com
tryoutreachark.com
outreachark.io
(...)
Each of these domains redirects to outreachark.com.
Then, for each domain, we create two mailboxes, like this:
deepak@outreachark.io
raj@outreachark.io
Email-sending strategy:
We limit each inbox to sending 30-45 emails per day.
For example, if you want to send 900 emails per day with a high deliverability rate, you’ll need about 20 domains and 40 email inboxes.
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To summarize:
Create multiple secondary domains and email addresses.
Redirect these domains to your main domain (to keep the trust factor intact).
Configure SPF, DKIM, and DMARC records for each new domain.
Limit email sending to under 50 emails per domain per day.
Lastly, use an email warming tool to gradually improve the reputation of these new domains before scaling up.
Pro tip: Email deliverability is a big topic on its own. If you want to dive deeper, check out this excellent article by Woodpecker on how to keep your emails out of the SPAM folder.
Cost-saving tip: If you’re using multiple inboxes, consider using a sending solution that doesn’t charge per email profile. Tools like Instantly or Smartlead allows you to use unlimited email profiles, saving you a lot of money as you scale.
Smartlead
Apollo is the most efficient software to build highly targeted list of prospects.
Plan starts from $39/month
Instantly
Clay finds data from 50+ data sources and leverages ChatGPT to personalize emails.
Plan starts from $149/month
Salesforge
Ocean.io helps businesses find and target their ideal customers using an AI lookalike search.
Plan starts from $59/month
Chapter 7 | Building Your Sales Stack for Prospecting Campaigns
How to create a sales stack from scratch with the most advanced outbound tools available.
A strong sales stack is essential for running successful prospecting campaigns. Here’s how you can build your sales stack step-by-step:
1️⃣ Start with a reliable data source
Your sales campaigns begin with good-quality data. Here are some recommendations for sourcing it:
LinkedIn Sales Navigator: A great starting place as most B2B data providers pull their data from LinkedIn. You can leverage Sales Navigator to find prospects directly.
Apollo.io: Cost-effective and reliable for pulling large amounts of data quickly. It works well for those on a budget while maintaining decent data quality.
Ocean.io: Great for niche targeting due to its advanced filtering options. It also has a “lookalike tool” that allows you to find companies similar to your ideal prospects.
2️⃣ Scrape custom data when necessary
If your target data isn’t available in standard databases, custom scraping may be the way to go.
Instant Data Scraper: A free tool that extracts data directly from websites easily.
Clay: Known for its built-in scrapers, it helps extract data from various websites at scale.
3️⃣ Enrich your contact lists
Once you’ve collected prospect information, you’ll need to enrich it to get actionable details.
Prospeo: Reliable for finding email addresses from LinkedIn filters and other sources.
FullEnrich: Excellent for aggregating contact details like phone numbers and email addresses using Waterfall Enrichment for accuracy.
4️⃣ Identify buying signals and trigger events
Identify prospects at the right time by monitoring buying intent and meaningful activities.
RB2B: Identifies visitors on your website (primarily from US traffic) and provides their LinkedIn profiles and contact information. You can gauge their interest based on the specific pages they’ve browsed.
Humanlinker: Tracks account activity in your CRM, notifying you about key events such as funding rounds, leadership changes, acquisitions, or other major developments. These triggers are great for re-engaging accounts with relevant messaging.
5️⃣ Craft engaging sales messages
Having the right message can make or break your outreach efforts.
Twain: An AI-powered writing assistant that provides real-time feedback to improve your sales copy. It gives recommendations based on tone, use case, and product relevance, helping you craft impactful messages.
6️⃣ Scale outreach while staying out of SPAM
When engaging leads, ensure deliverability and scalability with the proper tools for LinkedIn and email outreach.
For LinkedIn outreach:
Tools like HeyReach allow automation across multiple LinkedIn accounts, enabling you to scale your campaigns while staying efficient.
For Email outreach:
Smartlead supports unlimited mailboxes and includes built-in email warm-up features to improve your email reputation. It also allows you to create master inboxes and automated subsequences for more effective follow-ups.
7️⃣ Manage your pipeline effectively
Managing your pipeline is critical for tracking leads and closing deals efficiently.
HubSpot: An industry-leading CRM that integrates well with a wide range of tools, making it easy to slot into your existing workflows.
Breakcold: Perfect for businesses focused on social selling, offering features tailored to engage leads on social channels.
Attention: An AI-powered note-taking tool that captures and organizes call conversations, making it a lifesaver during busy workflows.
With this sales stack in place, you’ll have all the tools necessary to source leads, engage them effectively, and manage your pipeline like a pro. This setup ensures you can successfully run prospecting campaigns at scale while maintaining excellent deliverability and personalization.
Wrapping it up...
That’s all for now! I hope this guide helped you learn a thing or two.
If you found this information useful, feel free to share it with others who might benefit from it.
And if you’d like to connect, don’t hesitate to send me a LinkedIn invite:
Deepak Amirtha Raj (Founder & CEO) -> LinkedIn Profile.
I'm always happy to support you in achieving success for your business. If you'd like, we can set up a free consultation to discuss your goals, learn more about your business, and share some ideas and insights on how to start driving qualified leads.