As someone who has been in the business of email outreach for about a year now, I would like to talk to you about what it actually means to do email outreach.

For me, it’s been a rocky year, with ups and downs, obstacles and challenges to be overcome. Even though I do think I know have the wisdom to do it, at least once a week I face a new challenge for which it takes me and my whole team a quick get together to solve it. So, the struggle is a constant in the outreach business.

However, overcoming the obstacles on the way to cold emailing success is worth the struggle.

From my experience, cold emailing can make your business, and break it too. Poorly written emails, wrongly selected target audience, follow-up emails that are annoying as your little brother or sister, and all the power is gone.

Envision a running track with hurdles.

The track is your cold emailing campaign. The hurdles are challenges and obstacles you face.

Your obstacles are finding suitable prospects, reaching out to them, following up with them at the exact right time, so that you DO get an answer, be it positive or negative.

Reaching the finish line without knocking over the hurdles brings you the power of cold emailing – the success of your business and the feeling that you are the king of the outreach game!

Let’s run together:

#1 Challenge: Building a Customer Profile and Segmenting

This is the first hurdle on your way to success.

Building a customer profile is essential to creating a good cold emailing campaign.

Why? Because, the customer profile determines how you will personalize your emails: what language you will use and how you will structure the pitch so as to hit the bull’s eye.

Target your audience based on:

  1. Company type – startup with a ready product, up-and-coming SaaS enterprise, mature software developer studio…

  2. Company size – check the number of employees – company’s Linked In profile might be a good source for gathering this information. Crunchbase also contains such information.

  3. Technology – check to see if the company can indeed benefit from your product. For example, if you are offering a software that helps find email addresses you would want to target companies that actually do outbound email marketing and might need a software help them do so. Again, Linked In can help you with this.

  4. Location – knowing business culture helps you approach the prospect correctly

  5. Market (learn about the industry the prospect is engaged in) – for example, if they are offering advertising services for the television, they won’t buy a software that finds email addresses. So make sure you always know what is their market. Linked In can help you with this, as well as the companies’ web pages

Once you’ve built the customer profile in relation to these criteria, choose the exact people you wish to reach out. Your choice will, of course, depend on the goal you have set up for your campaign.

The goals can be various: selling, obtaining a backlink, asking to write a guest post; and for each of these goals you have to choose the right person. Personalization will depend on whether you want to reach out to a CEO, a blogger, a marketing manager or team leader.

Just think of it. You don’t talk to your mom and your friend in the same way. The same goes reaching out to people on different positions.

Then, segment your list.

Segmentation represents a solid basis for writing personalized emails that will seem hand-crafted and will most likely hit the exact point for each and every one your customers. Bluntly put, I will send you to junk if you offer me a software that should help me set up a medical diagnosis and I’m only a poor blogger

Here’s why personalization is so important.

According to a study conducted by Google, CEB’s Marketing Leadership Council and marketing research team Motista, B2B customers are much more emotionally connected to their sellers and service providers than consumers. This makes sense as the buying decision employees make in the name of their company affect not only them personally, but their company as well.

However, buying decisions are not only motivated by the company’s gain. The same study shows that the B2B buyers are around 50% more likely to buy a product if they see personal gain in making such a decision (e.g. career advancement). Just ask yourself, wouldn’t it be nice to get an offer that would help YOU and your company move forward? For example, if you are an advertiser looking for publishers

So take the time to really get to know the potential customers as that’s the first, and crucial step in your cold emailing campaign. Know your prospects!

#2 Challenge: Finding Contact Information

Let’s see how we can jump over the next hurdle.

Naturally, once you found who exactly you want to reach out to, you need to find their contact information. This can be complicated as there are several means which can help you find email addresses you need.

There is a saying that too many cooks spoil the broth which in the process of finding contact information means that having too many methods to choose from can actually do more harm than good . In other words,  deciding  which  method will save you time and give you the most optimal results so as not to damage your outreach can be very complicated.

Usually, this is the most complicated part of the process, as you have to spend hours and hours mixing and matching methods to get the most optimal results. You know how I cope with it? Play some music, sing along and dig in.

1. Web scraping and guessing:

Web scraping and guessing can be time consuming and unreliable. But, there are tools such as VoilaNorbert,  Anymail Finderand Email Generator that help you guess, and tools like that check if the guessed addresses exist.

2. Buying email lists

This is an easy way out but is a big no no in the business world. It likely represents a violation of your email service provider’s  Terms of Service and is a clear violation of  CAN SPAM act. for emails sent in the USA.

Bought lists are usually out of date and contain spam traps that can get you blacklisted in no time. Buying email lists will probably do no good to your outreach campaign.

3. Outsourcing

This is also an easy, lazy way out as you delegate finding contact information to freelancers which you can find on platforms such as UpWork and Freelancer.

This method tends to be time consuming as you need to check their work just to make sure they did it right.

4. Tools

Tools are probably  the best method for finding contact information. At least this is the case for me. Different extensions, add-ons and plug-ins save time and energy while producing the most optimal results. Here are some tools that you can use to find email addresses:

Social media based search (LinkedIn, Twitter):

Domain based search:

#3 Challenge: Writing a Good Email Pitch

This is getting tiring, but we need to make it over the hurdle number three.

This is the breaking point in your cold emailing campaign. A good email brings you a step closer to the ultimate goal, the bad one to junk, spam, or oblivion.

This is probably the most challenging obstacle to overcome as it entails creating a connection with a complete stranger.

For me, this is the scariest thing possible! I feel uncomfortable every time I am supposed to meet a new person, even via email. Sometimes, even the barrier that the computer provides is not enough. I know there are more of you who are like this out there!

It’s scary, but you can beat it. To establish a meaningful and possibly fruitful connection with a potential, unknown prospect, your email should be:

  1. Attention-grabbing

  2. Personal and yet professional

  3. Should present value over feature

  4. Short

Let’s discuss each.

1. Be Attention-grabbing


Because, we are curious beings. And if you don’t tackle your prospect’s curiosity, the chances are they won’t bother opening your email.

How #1?

By crafting a thought provoking, interesting and yet curious subject lines. Be creative, use wit and humor, popular culture references, whatever fits the situation. For example, a subject line ‘Should I stay or should I go’ will have me clicking anytime

Here are some examples of good subject lines taken from HubSpot:

  • ‘Question about [goal]?’

  • ‘Do not open this email’

  • ‘Where is the love?’

How #2?

You can also grab the prospect’s attention by writing a good first line of the email, as that is what email apps usually display with the subject line:

So, don’t waste the first line writing about yourself. Would you read that?

Instead, try to make it clear right there in the first sentence why you are writing to them. Or include some flattery. Or praise of the company’s or individual’s achievements.

But make sure you are mentioning something that could be learned from public records, so as not to come across as a stalker  Think of how you would feel if someone says to you: “Hey, congrats on teaching your son how to ride a bike!”

Here are some examples of the first sentences :

  • ‘I love {{}} (been a customer for several months) and I’m also a big fan of your blog. ’

  • ‘I noticed in a recent HR Magazine article that you folks are introducing 2 new health plans this year.’

  • ‘I read your article on volunteering your professional skills in Guatemala – it was really inspiring.’

2. Be Personal and Yet Professional


Email communication in business is our #1 choice. This implies a certain level of detachment and distance. A barrier needs to exist upon the first encounter and an email provides just that. You wouldn’t want anyone hugging you as they try to do business with you for the first time, right?

But you do want to shake hands, be friendly and knowing.

To really get prospects on board, you need to create a connection with them on a more personal, individual level. You need them to trust you, which requires a certain level of personalization.

Balancing the thin line between the two is not easy, but it is possible.


  • Always personalize the greetings. Which means use the first name of the person you are reaching out to.For example: ‘Hello/Hi {{prospect.first_name}}’,

  • Use colloquial expressions. Maybe even include an anecdote. Or be witty. But make sure not to overdo it, so that the professional rapport is still maintained.

  • Include friendly, conversational tone. Sp use ‘you’, ‘your’, ‘yours’, address them directly. They will feel engaged in the conversation.

3. Present Value over Feature


You have to make the email about the potential customer. Nobody wants to read an ode about your-more-than-amazing-self and more-than-the-greatest-product you have.

How would you feel if someone sent you an email where they praise themselves? I would probably be like: “Oh get off your high horse!” and send the email to junk.

The people you are contacting are busy, with particular problems and worries in mind. They want quick, easy, solutions with good price, not your memoir.


Avoid listing features of your product, or writing about yourself. Offer a solution to their problem instead. Bluntly put, tell them: “I can help you with the problem X.”

Then, include a strong, and clear Call-To-Action. By doing this, you are saying: “This is how you can solve your problem.” It is the easiest and the most logical next step to get them onboard.

4. Be Short


Just think of yourself? Would you read a ‘Moby Dick’ in an email? Do you even read loooong emails or just skip them? Is reading and responding to emails your only job, or do you have a lot more on your plate?

Your leads are also busy, with loads of emails to go through and loads of business to do. So try to be as short and concise as possible.


Determine a clear goal before you start crafting your email. Ask yourself: Do I want to offer them a demo class? Do I want them to publish my blog post? Do I want to make a sale?

With a clear goal in mind, write, and edit rigorously. Test and edit again. Finally, your email shouldn’t exceed the limit of 10 sentences in any case, the most optimal number of sentences being 5-6.

#4 Challenge: Timing

Come on guys, the finish line is just around the corner, don’t give up now

Timing represents another obstacle on your way to the stars.

You have to have in mind that your leads probably get loads of emails every day. Just like yourself. I know I do. Sometimes it makes me sick to my stomach when I get into the office, log in to my email account and see 54 new emails regarding the array of vastly different topics from task reminders and office issues  to ‘I wanna sell you a vacuum cleaner.’ To beat that white noise can be a real challenge.

How you can overcome it?

  • A/B test them to see what works best for your prospects

The best time to send emails can be determined with the help of A/B testing. You goal should be to appear near the top of the lead’s inbox. So experiment to see what works best.

P.S. A/B testing can be used not only for choosing the good time, but for other variables as well, such as subject lines, content…

#5 Challenge: Proper Follow Up

Phew, just one more…

My mom always insists that I don’t give up easily, that I keep trying until I either succeed or fail miserably. Because no failure is as damaging as the failure of not trying at all.

And, oh, how she is right. I still regret not completing the history course at the science center. That was the first, and the last time so far I ever gave up without properly trying.

The same is valid for following up. It usually doesn’t happen that the lead will become a customer after the initial contact. It takes time and persistence, and a proper follow-up. How do I know this? Personal experience.

In the majority of cases, I get a response from the lead after the second or third follow up.

When I started doing outreach, I thought follow ups are going to be intrusive. It mortified me to send follow up emails as I thought I am only going to bother people with them. I thought, if they haven’t responded in the first place, they are surely not interested.

But, I was wrong. From my experience, the second and third follow up usually do the trick.

However,  the not giving up part has to be done properly to provide optimal results. You want to avoid being annoying or irrelevant because people will simply not bother with you. How can you achieve this?

1.    Craft relevant follow-up emails

Never send emails just for the sake of emails. Make sure that your follow up emails follow a well thought out plan where each email has a specific purpose. Feel free to remind the prospects about your offer.  For example, my outreach email for Etools, in which I ask the company to take a look at it, is always followed up by two emails in which I simply ask if they have read my email. Because, my initial goal is to get them to read my email and tell me if they are interested.

2.    Avoid massive blasts over long periods of time

Massive blasts will usually seem spammy. And if you send them over long periods of time, the chances are the prospects have already forgotten about you. Space the follow up emails evenly – send one after three days, then after seven more days, then after two weeks, and so on. This is the pattern I follow, and so far it has yielded okay results. Of course, A/B testing might once again be the best way to determine what works for your target audience.

3.    Automate the process

When I started doing the outreach, I wanted to take the personalization to the next level – I wanted to hand-craft each email to make it special, different and unique. Well, that took too much time. When you have to find the leads, their contacts and then craft each email off the top of your head following certain guidelines made my boss scold me because I managed to send out only 10 emails for the 8 working hours. And the goal was 30.

Yep, it was a no go.

If you are sending more than a 100 emails a week, and you probably are, automate the process. It will save you time and provide the most optimal results.

4.    NEVER give up

By never I mean until a ‘yes’ or a ‘no’. You might get some answers in the form of ‘I’m not sure this is the right thing for us’ or ‘This is not the right time’ which resemble a ‘no’. But the point is to continue until you get a definite, absolute rejection. It will come across as ‘I’m not interested in this, stop emailing me’. If you do get such a turndown, respect it. Stop sending them emails and focus on those who do wish to work with you.

Here’s an email I got after the third follow up email, just as I was about to give up:


Congratulations, we’ve successfully made it to the finish line. Doesn’t it feel great? For me, it does, every time an email of mine achieves just what I wanted

As runners in this race, we have to pay special attention to:

  1. Taking the extra care to build customer profiles and to segment

  2. Which tools to choose for the most optimal results

  3. Crafting emails that are interesting, personal and professional, short

  4. What is the best time to send them

  5. Following up properly

And we’ll become the Usain Bolts of the outreach race

I would like to hear more about the challenges you face in the outreach process. Feel free to comment!

About the Author: Jovana Petrovic

Jovana is a writer and outreacher at Etools – a toolkit that lets you find the exact contact details of any business.

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