How to build a cold emailing system that generates hundreds of millions

A walkthrough of exactly how to setup a professional B2B cold emailing system.

Publish Date
Sep 29, 2022
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What does Charles do?

Charles Summers is the founder of Hacking Demand, and has worked on a wide range of growth and demand efforts for various startups. In this growth story, we’ll be focusing on his cold emailing expertise. I’ve been able to see this first-hand by working alongside Charles at SafetyWing.
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📧 What is cold emailing?

Simply put, cold emailing is sending an initial email to a new contact, without prior contact. It typically involves finding (or purchasing, but don’t do that) an email list in a relevant niche, and then reaching out to them via an Email Service Provider (ESP).
The concept is simple, but very difficult to do well. All of us have likely seen what terrible cold email outreach looks like in our own inbox. At best, a bad cold emailing strategy is annoying. But when done well, cold emailing might literally be the key to success for your startup – especially if it’s a B2B product.

💰 How much revenue has Charles generated through cold email?

  • Over the years, Charles has generated hundreds of millions in funnel revenue for various companies

👨‍👨‍👦‍👦 Target Audiences

What kind of companies benefit from Cold Email?

There are a ton of possible niche’s for cold email (we did a previous story where a growth leader cold emailed developers, a notoriously difficult group of people to have success with cold email). Charles focuses on HR people mostly. Founders, C-Level execs and other decision makers are also common targets.
Cold emails work best in smaller orgs and startups – regardless of who the persona is. This is mostly because their filtering isn’t as intense as large enterprise companies. The most difficult persona to go after is anyone in IT, as they’ll likely have their own emails locked down.

📝 How do you set up a cold emailing system from scratch?

1. Build your list

  • Outline who you want to reach out to.
  • Look at your current clients and customers. Try to come up with profile of a customer or person.

2. Find a database that will have contacts in your niche

You need to generate a list of contacts to email from some sort of contact sourcing database. Each platform tends to have different focuses and niches. The costs also differ dramatically, so do your research.Here are some examples.
  • UpLead - Charles buys credits in “chunks”, because he doesn’t like restrictive subscription models with daily limits. Charles is a partner of UpLead, and gets large discounts on packages for his clients. You can also get the discount through this link. The package he will get companies he works with is 120k contact credits (people), which is typically $21k (but $11k with this discount link).
  • Apollo - This is one that I’ve used personally and love. It’s also relatively affordable for smaller projects and smaller companies. They also have packages with no commitment.
  • SeamlessAI - good, but can only pull 1k contacts a day.
Most tools have validity tests as well, which is great because you should only pull contacts that are 100% valid. Stay away from the “accept all” status because a big portion of them are going to be bad.

3. Warm up process

This needs to happen in the first 30 days of entering someone into the system. Your goal is to warm up both the people and the system. There are a few different ways you can do this.
If you have a big sales team, you can start by having the sales reps doing outbound. Put them in sequences (Apollo has sequencer in it, or use Outreach). Create a status that says “this email got through and didn’t bounce”, and then put it into the marketing automation system.
If you don’t have a big sales team, you can do what’s called a “rockstar” warm up nurture campaign. Basically identify the top 4 pieces of content for a client that you have based on past performance (”5 steps to x” types typically perform well), and put them into one single email. You can even lay out the important highlights of the content in the email. Make it text heavy. This is important for spam filters to build reputation with your system and that person. Send them to a landing page where they can fill out a form if they want. Once they get to the thank you page, put a demo or something that takes their interest and moves it forward immediately.
The first emails that goes out needs to be segmented into lists well enough to make the content relevant. This is actually part of doing it legally - you have to be relevant to people.

Email Service Providers (ESPs)

You’ll also need to choose an ESP – basically the program that actually sends emails. This is something you’d need even to email your own audience, so you might have one already.
Charles uses Net-Results, which connects to SendGrid, but he also thinks SendGrid is great by itself.

After the warmup…

You’ll want to make sure you have a system to move contacts into funnels based on their actions and engagements (CTA’s, email activity, etc.). The goal is to have lists that you can segment based on persona and activity. Anything new coming out goes to people who are engaged.
People who are not as engaged will get something like a once a month email or re-engagement campaign. Using a sales teams for re-engagement works well. You can say, “Here’s a list of people who haven’t engaged yet. Let’s send them an outbound sales email to see if they’d convert.” → It works well because it’s personal to THEIR company vs general to industry.
You might also try doing email nurture with un-gated content. But don’t use words like “free”, because it will be caught in spam filters. Use actions that are easy for people to take. Sometimes Charles will take emails of un-engaged people and upload them into a system like Taboola (which can take emails and find alternate contacts and locations to reach them). Then when they come back into Net-Results, they have all that actioned data.
⚠️ Cold Emails MUST do the following 5 things to be considered legal
  1. Opt-Out Method
    1. 1 click
    2. Preference pages
  1. Opt-Outs Must be Honored Within 10 Days
    1. You should automate this and do it immediately
    2. When someone complains that they already opted out and are still getting emails, 99/100 times that person has a different email that is being sent to and forwarding to their inbox and they are just unsubscribing the wrong email. Combat that by looking up others with that email domain and unsubscribing them and communicate that their email is opted out and that if they have forwarding turned on, they need to give you that email to opt out. Ex. Employee leaves and emails forward to their manager.
  1. No Misleading Subject Lines
    1. Be brief and relevant.
    2. Don’t include gimmicks
    3. Ex. URGENT: News about your mother’s health
    4. Don’t ever include the word “free”
    5. Examples of appropriate subjects from Charles:
      1. Humor: “Best of Groupon: The Deals That Make Us Proud (Unlike Our Nephew, Steve)”
      2. Personalization: “Hey Katie – 90.7% of Marketers are Leveraging Data, Are You?”
      3. Sense of urgency: “I called. You didn’t answer.”
      4. Be Yourself
  1. Always accurately represent your company or yourself
    1. From / Reply to
  1. Include your company’s physical address
    1. This is a must
    2. Your email simply wont get through to the masses if this isn’t here because most email providers, like Gmail, will send it straight to spam.
      1. Most email service providers wont even let you send an email
💡 Tips on making sure emails get delivered:
  • Never use “free”
  • First email should be VERY text heavy
  • Use simple subject lines and little HTML design in general (likely to get filtered out or get to promotions tab)
  • Don’t attach documents to initial emails, always send them to a linked landing page. Always link back to the company page
  • Keep an eye on your spam reports, these will start to hurt your email reputation
🛠 Additional Tools - send all your test emails through this tool, if you don’t score a 10 don’t send - send all your tests through this tool, don’t ever use something that’s not a 100

You can follow Charles and his work on LinkedIn

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