Cold Email Marketing for Startups – What I Learned from Experience

by | Product Marketing

I had written about 2,000 words of BS about email marketing before I just decided to delete it all (maybe not all) and write what I feel is actually applicable. Because, here’s what you should know first, the stats are one-sided. Not everyone receives 80 emails per day. And people (like me) open emails on weekends. In fact, I hate receiving an email on a busy afternoon. But, still, here’s a very important email chart from Hubspot. It shows a decline in email opens on Saturdays and Sundays. The best days for emails are Mondays, Tuesdays and Wednsesdays.

With that said;

I believe there are some things marketers will do well to learn from business emails. But first, let’s examine business emails and what works. Will point out some of the things that marketers can adopt for higher response rates on their pitches.


The business world is a world of information overload and email is a prime culprit. Radicatti says an average office worker receives around 80 emails each day. That’s enough email content to fill up a whole mid-sized book. But with “me and I” salesy pitches. Emails have the tendency to be ignored because they infringe on our attention. But they are a necessary part of business, or even life.


Shoot Up Your Opens and Click Throughs in 7 Steps

1. Make good Use of Subject Lines.

The majority of your email prospects won’t read past your subject line. It’s the vertex of your email. It’s where the decision is made. Your prospect thinks when s/he sees your subject line: Should I open or hit thrash? Think of a newspaper headline. You read the headline and either move on or stay. It either catches your attention and makes you want to read further or it doesn’t.


The email subject line performs the same function. Your subject line should summarize the whole email. For example, if I had to scroll down 80 emails and one or two of them had the subject line “Hi”, I’d probably delete those.


Six things you can do right now to write better marketing emails Click To Tweet

You want to make your subject line a very short summary of your email.

“Meeting with VP of Marketing – 5 p.m”
“Loved your 50th Law Reference”


2. Know your prospect.

The defining point with business email is that the prospect is someone you already know. Probably, a boss, a staff member, a consultant or speaker. You know your prospect, maybe already met them. And that’s why they reply. One of the big mistakes you make with marketing emails is not developing this connection. The real life rules of engagement apply when sending emails. “Don’t talk to strangers”.


So how do you avoid the damning silence? Create Context.


Here is what I mean


I was browsing through my Twitter feed and your quote from “Men In Black 2” popped up. Loved it. (BTW, we follow each other on Twitter). I’m Tobi Olujinmi, COO of  ….




So you see this reason doesn’t make all that much sense, but it creates the context that I need.

Hi name. I’m …, editor of …, found so much value in your “” post. Thanks for being a wellspring of practical … knowledge.


The point is; don’t be perfect with this. Just show them that you recognize what they do and you value it or that you like something they like; introduce yourself and get out, literally.


3. Follow Up with Value

And what if they don’t reply? And even if they do, just wait a few days, go ahead and send a follow up message (follow ups should do one of two things – display value or tackle objections).

“Hi. I sent an earlier message on … So I checked up … and saw that you were looking to hire marketing …. for your (new product). I just compiled an infographic specifically on “product marketing for (niched down industry)”. Made it for you.


Also, here’s the truth I know after much rejection: Emails aren’t about you or your business. They’re about the recipient. This is how your prospects look at you after your big salesy pitch?


  • The crucial question. What’s their need?


Note: Cold email marketing can be a great way to update your buyer personas, making them more potent. This means all the unreplied emails aren’t wasted. They give you more insight into who is not a prospect for your service or product, refining your marketing.


4. Make the ask and make it single.

Now you’ve followed up once or twice already, you’re someone they feel like they know but can’t place a finger on what kick you get from emailing them.

Now you need to make the ask.

Note that this is contrary to the business email reference I used. With business email, you want to go straight to the point in your first email. This might work sometimes with marketing emails but you’ll justifiably have your emails dropped in spam, with probably 0-3% click throughs with this approach unless you have a kickass product.


With that mentioned, jumbling too many CTAs into an email is asking too much of your audience. Business emails go straight to the point. Two CTAs in an email is information overload. Nobody wants to deal with that.

“Click on this link”

Then “like and share this post”.

might work on Youtube. But it definitely does make your email’s call to action less powerful. And your emails unfocused.

The best way to close your email is with a question. See the reason here.


5. Keep it Simple Stupid.

How would it feel to be greeted every morning by a barrage of long emails that drone on and on, once you open your computer. Yet this is what managers and HR folks deal with. Before sending an email, ask yourself “is it necessary to send an email?”. Wouldn’t it be wiser to send a text? This could be more efficient if there would be need for back and forth discussions.


If you doubtless need to send the email, then keep your message clear and brief with short sentences.


6. Use social proof with numbers.

Ultimately a prospect should know your Unique Value Proposition straight off the bat. And the proof that backs up your unique value proposition. Everybody uses social proof. But what gets people’s attention are the numbers. By this time, you should have gotten some responses. Obviously, you want to chat or call people who have responded to your email at any time. For folks who haven’t responded.


Hi name

I got no response from my last emails. I believe you are busy so I’ll go straight to the point. (plausible deniability of sorts)

(Close competitor) seemed to be having (problem) with (task)/ wanted to solve (goal) (Putting it in form of a story)

We actually did a test last month and so far we have generated 1,000 new leads for them in 3 months. (screenshot attached).

Since you’re in the same industry, I wanted to ask; do you face any challenge with … (or do you have a similar goal of …)?”



6. Yet be personable.
People would ignore you if it doesn’t feel like your email speaks to them alone. Personability is a big deal in 2019. Flip the corporate speak and craft your email as you’d speak to someone face to face if you were a sales person. You know it has to be all about them. So make your email sound like a conversation you’re having with them.


Even if you’re a B2B brand, bring out the human side of your brand and see more people respond to your emails. It’s no more random mail but friendly mail. No more cold emails, but warm emails.


There are other things to talk about like your salutation. Nobody cares about your “yours sincerely”. Nobody cares about “Mr, Ms…”, unless in some settings. In most cases, they make you seem a less confident marketer.


What about your grammar? Bad grammar is unprofessional.

If you can’t compose good English, then try hiring someone who can. You can outsource your email marketing copywriting to Talkbrands.


Note that it takes an average of 5 follow-ups to get through to a prospect. So you should at least follow up five times before you give up and tell them you’re giving up too. It’s crazy how much FOMO (Fear Of Missing Out) compels action


Anyway, it’s binary. A prospect either responds or does not. Then you move to the next. There are more than 7 billion people in the world anyway.

Using Buyer Personas to Form Contexts

Here is a major drawback, the personable outreach is going to take a lot of time. Would it be worth it spending 5 hours searching out Twitter and Facebook for each of my prospects; browsing their websites and looking through their posts, on both social and web? I think it would be worth it in the sense that you can create an email that connects with an audience on a higher level than the average email pitcher.


Yet, this wouldn’t be a wise course to follow if you’d like to reach out to 1,000 prospects. I don’t want to spend all day developing contexts for emails and then having to sort through many personability elements for 1,000 people, if many of the people I’m reaching out to are still going to ignore.


Which brings us to the concept of generalizations in buyer personas. And this is a subtle use case scenario for buyer personas which I am starting to use for real results. I’ve seen some email templates on Hubspot use this too.


A simple case study

Here’s the idea in rough:

Say I have a bachelor night planning service for soon-to-be-wedded bachelors.


My persona is a bachelor who is going to get wedded in a few weeks or months.

He needs a service that handles everything else while he focuses on other aspects of the wedding. He is still probably in the planning stages of the wedding and he’s busy.


How do I create context for my email? How do I start?

Let’s say I did some social listening for soon to be wedded.

Or search out wedding planning websites for names. Or physically visit wedding reception halls

and now I have a list.

I’ll get to work. I’ll draft out a persona;

My persona is (now this is a semi-fictitious representation but it gives me something to work with)

  • Male, probably 25-35
  • Probably has a lot of things going on at the time.
  • Excited to start a new chapter of life.
  • Problem: Doesn’t trust friends to handle the bachelor night planning.
  • Likes: A great time.

Here’s how I’ll use this information:

“Hi name

I hope I’m not reaching out at the wrong time.

I am sending this email because I noticed you have a wedding coming up soon.

I’m happy for you. It must feel exciting starting a new chapter with the girl of your dreams.

But I know how tough it gets having to plan many things and of course, the bachelor night!

We got you covered!

…. “


(Now you’ve gotten their interest).

I could use this format for as many of the people on my list as possible.


Why generalized contextual email marketing matters

1. Find a balance between speed and quality: The reason why generalization matters is that you want to send out emails that are balanced in personality (not too personal sounding or else you’ll put off a lot of people) and that you can replicate. This means your pitching game will be more efficient. And you can quickly sort the yes’es and the no’s.


2. Create Converting Email Campaigns: Personas would be greatly beneficial when you’re composing drip email marketing campaigns. The goal of the email campaign is to build trust and awareness. The best way to do this is by delivering targeted value. By segmenting and sending relevant information to different personas via email, Hubspot gained an increase of 16% uplift in clickthrough’s.


3. Follow the Rule of 1: Instead of droning on and on with irrelevancies, you can outline a single most important benefit, need or goal and make this the focus of your message. Dispense of benefits that are not prominent or very important and focus on that one and most important value prop. That’s the rule of 1 from AWAI. It makes your email more powerful.


4. Create An Irresistible Offer: Now that you know your persona, you can align your CTA in a way that appeals with their likes. My persona wants a great time. I could add


“If you order by …, you get a chance to win a FREE trip to the Bahamas for your honeymoon. This is available for only three couples.”


See what I did here. I’ve created a win-win which is a more powerful way of beating procrastination than leveraging fear. Now that’s an extravagant offer. But you get the idea. You don’t always need an offer. But when you do, it’s worth it to go all the way. If I don’t have an offer, I could have a CTA that will appeal to my prospect. Something like “Schedule a time to talk” instead of a generic CTA like “Click here”.


5. Follow up with Impact. And then, you have to think about following up. The reason why you should follow up is again because people procrastinate. We might love something but we wouldn’t go for it at least not now until interest starts to wane. I bet you can relate. So no matter how tasty your offer, most people would not take action. That’s just human nature. With a well defined persona, you understand objections, you can dig out valuable content to use for your follow ups.


I bet you just thought buyer personas were just for content or devising marketing strategies. Now you know better. Send out more contextual emails without having to spend hours browsing people’s feeds and looking like a junkie.


Automate your Cold Email Marketing With these Tools

Automating cold email marketing is a big deal in this time and age. You can find tools to handle every aspect – from researching prospects to sending out emails in mass. And the good news is that most of these tools are free or at least free to try for 14 days and they are pretty much startup friendly too.

Here are some great ones:

1. GMass+Gsuite. While there are some free tools for automating bulk outreaches from your Gmail account, the problem is sending emails from your Gmail looks unprofessional. At just $16 per month for basic plans, Gsuite integrates with Gmass, allowing you to send 1,000-2,000 emails per day. And the best thing is this, you’ll be sending emails from your own domain. That’s just one of the benefits though. With Gsuite, you can replace team chat apps like slack, with Google’s own video conferencing and document sharing apps. Gsuite comes with a 14 day free trial and Gmass allows you to send up to 50 emails per day as a free user. That should give you the hang of it.

2. I have tried a lot of prospecting tools. Hunter makes prospecting very easy. With just a search, you’ll see a list of verified emails from a domain. You can select the ones you need and export it into CSV easily or into a CRM like Zapier. You can even send bulk emails from the platform for free by integrating with your Gmail account.  They give you at least 50 search credits every month. The starter price is $49. With this, comes more functionality like bulk domain search, CRM integrations…


3. If you want to get more efficient with your cold email outreaches, you need a tool like this. You schedule   outreaches in drips for specific dates. You can schedule and forget about it, then come back to see results. It costs about $49 to get on the basic plan. Their free trial is pretty much useless.

4. Zapier. Zapier is an API tool, connecting about 1000 apps. It’s a must have for startups on a budget. This means you can automate transferring contacts from prospecting tools like Hunter into Gsuite. Zapier offers a free level of service, albeit with some limitations. With the free account, you can perform up to 100 tasks per month, but you can only have five Zaps active at any given time. To clarify, a task is a completed action within a Zap i.e a zap is a combination of tasks. You can get started with the paid plan at $50 (3000 tasks across 50 zaps).

5. is a sales CRM, not just for emails but making calls. You can also schedule emails for specific periods. The con is that the starter and basic plans do not offer automation. Apart from this, it’s very intuitive.

Once you start with the professional plan for $95, you get much more functionality and automation access. Anyway, they offer a 14 day free trial of their business plan (which is great).

Note, the goal is not to send 1,000 emails per day. Your domain could be flagged and end up in spam more often. On Gmail, if you send more than 50 emails per day, your account would be flagged. Hence, a word of caution, 50-100 emails should be your target. There are many other free/affordable cold email marketing automation tools. All it takes is a quick Google search. And if you have any tool I should review in a future post, send me a message

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