The Startup Founder Guide To Sending Personalised Cold Emails

The Startup Founder Guide To Sending Personalised Cold Emails

Insiders: Peek into our friendly guide on how to send highly personalised cold emails that will help you convert more prospects and retain stronger relations.

While cold mailing may not be the most scalable solution in the long run, it is extremely useful for gaining traction in the early stages of your business. When done correctly, you can gain the trust of notable business partners, recruit early adopters and even gain media attention.

Whether it's a sales pitch, a partnership, a new business venture - the most important factor is to make sure your email is personalised to the recipient. No one wants to receive an email that starts with a 'Hello' without even their name on it 😒

Here we'll discuss what makes a cold email personal and share with you a compilation of powerful, tried and tested examples that you can reference off for your cold outreach.

Let's Get Personal

As a budding business trying to grain traction, you're probably reaching out to a dozen people daily and sending out cold emails with different intentions. They could be sales pitches, partnership requests, or acquiring new customers.

It's even more painful if you're a solo founder and you have to focus on other business goals like building your product, keeping your customers happy...where does it stop?

The truth is, the recipient of your email is likely experiencing the same cognitive load as you are. And they are probably busy with other activities that will benefit their own business or career.

In your cold email, you should be able to capture the prospect's attention in the shortest time possible with an incentive that is unique and personalised to the recipient.

We're going to show you a really good example of what a unique and personalised cold email looks like:

Pay It Forward

One thing we really appreciate but don't see a lot around cold emails is this - someone who knows how to pay it forward. Here's an old email our co-founder Stuart received awhile ago. For context, the sender wanted to feature Stuart in a piece of content they were working on and wanted Stuart to answer some questions.

The sender starts by offering to have one of Stuart's article featured on their website:

Stuart accepts, and the sender responds with a link of where our content is being featured. A couple hours later on the same day, the sender comes back with another request:

The sender got their foot in the door technique right!

Some great points about this email and the particular sender:

  • Paid it forward by doing Stuart a favour beforehand
  • Went straight into their intentions
  • Shared with Stuart that they have followed Gleam since way back
  • Gave praise by saying Stuart pretty much single-handedly grown Gleam
  • Provided sense of exclusivity by name dropping other entrepreneurs in the same sphere

By taking the initiative to offer something first, not only did the sender deliver a highly personalised experience to the cold outreach, they also increased their credibility in the eyes of the recipient.

At this point, the recipient would feel obliged to return the favour and respond to the sender's request. Furthermore, the trustworthiness helped build the foundation of a new business relationship.

Now depending on your own circumstances, here are some things you can offer upfront in your cold outreach:

  • Feature the recipient in your content (as discussed)
  • Offer free trial of your product
  • Invitation for a free coffee
  • Send a physical postcard to the recipient's company

Build Rapport To Build Trust

As the lead becomes warmer and the exchange progresses, there will be more opportunities to build rapport. Pay attention to your recipient and their recent activities, then highlight their strengths or achievements where you see fit.

While you're doing this, make sure to maintain a conversational tone and not be incongruous. Imagine you're having a conversation with someone at a conference, how would you behave? What would your tone be like?

From the same conversation, notice how the sender name drops someone from the same industry to delight the recipient. The association with someone of similar calibre can really make the recipient feel acknowledged for their work:

The sender is also very good at building rapport by leveraging off their geographic proximity. Again, notice that the sender actively shows interest in the recipient's business:

Give Praise

Another way to warm up your prospect is to of course give praise. You can highlight the recipient's achievements or capabilities - be it something they did in the past or present.

From the same example, see how the sender expresses their gratitude by giving praise as well as affirming the recipient that their business will be well-received by both their audiences in the concluding email:

The sender also frequently addresses the recipient by their first name.

If you deliver your part of the deal on time and make the recipient feel good while you're doing it, there's definitely going to be a second or third chance to work together again.


Now that we've shown you some traits of a unique and personalised cold email, we're going to walk through some major pitfalls of cold mailing and offer solutions for each pitfall.

Finally, we'll share some examples of common cold emails you'll send as a startup founder.

Pitfall 1: Email Ends Up In Spam Folder

Whatever you do, you'll want to avoid ending up here - the spam folder:

By default, Gmail doesn't send notifications if an email arrives in your spam folder. That means, not only will your email never reach the recipient's inbox, they won't even get a notification that your email has been sent to them.

If this goes on, your email address's open rate will continue to decline, which makes it more and more difficult for you to send cold emails in the long run.

Solution: Check Your Email Address

For that reason, you will want to take measures before reaching out to prospects. One trick is to use a spam checker tool like Mail Tester to test out your email address's spam score:

If you get a high score for your 'From' email address, then it's more likely your cold email will land in your prospect's inbox.

Pitfall 2: It's About The Recipient, Not You

Cold emails often come across as self-absorbed and focused on the wants and needs of the sender. You are likely to lose the recipient's interest if they haven't warmed up enough to you, and they will put your message in the bin before even considering your offer. In fact, 99% of Staurt's cold mails go straight to the bin.

Even worst than getting your email binned is if you build a poor reputation on professional social platforms.

For example, this cold email looks like a memorandum:

In the example above, this particular sender boasts about the benefits of their offer without first considering if the recipient is even interested, then proceeds to write at length about the offer and worst - ask for money upfront.

If you have also noticed, the email clearly looks canned and Gmail has gotten very good at marking templated emails as spam. That's like shooting yourself in the foot.

For example, Stuart doesn't identify as a 'CEO', he prefers the term 'founder' or 'co-founder', so the sender obviously does not have a good understanding of the recipient's business or preferences.

Solution: Show Them What It Means To Them

When you're asking for something upfront, you have to first entice the recipient by giving them something you think they will need. It could even be something they didn't even know they would need.

To do that, you have to do 'favours' for the recipient by making it easy for them to 'preview' the final product of your potential partnership.

One way we do this at Gleam is by creating mock Competitions for potential customers using their own branding and actions we think would benefit them. We then cold mail potential customers with a link or screenshot attached to the demo we built for them:

Showing potential customers the final product means one step closer to a conversion.

Doing a mini case study and understanding your prospect beforehand can really help build context and give you a better understanding of how you can work with each other.

In our case, that meant studying a prospect's business and getting a rough idea of what could be improved, then reaching out to focus on those improvements and how we can help them achieve it.

If you think your prospect has a problem that they don't know how to solve yet, then this step is even more important because it's your chance to help them tackle a pain point.

Pitfall 3: Not Use Your Own Email and Real Name

Ever received emails from addresses that start with noreply, hello, or sales? How inclined were you to click on them?

While notifications and announcement emails could be automated and sent by bots, you will want to avoid this method when it comes to cold mailing a prospect.

Humans like humans, it's important to make a good impression by introducing yourself as a human being instead of having your message automated by a bot, or using a handle that doesn't represent your real name.

No one likes to feel like they're just a number, especially if it's a prospect that can help you out with your business.

Solution: Keep It Personal

Use your real name in your email address. And aim to use your own company's domain name instead of something generic like @yahoo.com.

For example, stuart@gleam.io is short and concise. It's easy to read that the sender is Stuart from Gleam.io.

So now you have a real name and a respectable email address. As a bonus, you'll also need a notable Internet presence - which is quickly becoming a favourable asset for business owners.

You'll want to build some personal branding for yourself and make it easy for your prospect to get to know you/your business. This could mean having an active Twitter feed, a blog with leadership content...anything that will have you known on the Internet as someone credible and worth working with.

For examples of what are notable or worth mentioning, check out our co-founder Stuart's author page.

While the emphasis of the cold email should always be your recipient, keep in mind to make yourself reachable and discoverable using your email signature. Here's what our co-founder Stuart's signature looks like:

Stuart has his name lettered in bold, followed by his position at his company. Then, his phone number, company website and Twitter handle are available underneath should people want to reach out through other platforms.

Conveniently, Stuart also promotes his top performing post - 50 Growth Hacks Using Gleam in the footer 😎

People are going to Google you before they reply anyway, you might as well make it easier for them. Fashion your email signature in a way that encourages people to reach out to you, as well as provide some links so people know what you're good at/what you can do.

Here are some link examples:

  • Relevant press articles
  • New blog post you wrote
  • Product introduction video
  • Webinar you conducted

Pitfall 4: Targeting The Wrong Person

Not doing your research before you reach out could cost you. Remember, the currency here is attention. If you were speaking to someone that's irrelevant to the offer or task at hand, then they're less inclined to respond or even read the rest of what you have to offer.

To avoid this situation, try your best to find out who's the best person to speak to in the organisation. If that fails, you can at least send the cold email to the right department in hopes that someone would attend to your offer.

Think of what the person needs for their organization right now and how you can provide a solution. Don’t worry about getting it wrong, just give your best guess.

Solution: Find The Right Person To Speak To

We highly recommend using an email search tool like Hunter.io to help you find the right email address.

Hunter basically scrapes the Internet and finds instances of email addresses matching to a certain domain. That means you can easily enter your prospect's domain name and uncover a list of addresses from people or departments under that domain.

In some cases it's so smart that it has managed to label email addresses based on its relevance, such as sales, support, and so on.

Did we also mention that you get up to 50 free searches per month? That means it's bootstrap friendly and you can cold mail up to 50 prospects per month for free 😎

Pitfall 5: Following Up Too Much

Another common pitfall is when you deal with the breakup badly - and by that we mean following up extensively even when the recipient doesn't respond.

How many scrolls was that? Yes, we intentionally showed you the whole thread to show you how painful it is.

Solution: Follow Up, But Don't Overdo It

In this case, sending a handful of follow up emails over the next few days is a sensible thing to do, but don't overdo it. If the person doesn't reply on your second follow-up, then walk away with dignity and drop the prospect.

Tip: If you're seeing a low open rate, it's time to revise your subject lines.

Pitfall 6: Not Reaching Out To Enough People

There's plenty of fish in the pond!

A common saying we hear after someone goes through a bad breakup, but in the world of cold emails the case holds true. While manually qualifying leads is not a sustainable business activity, the cold outreach is certainly still a numbers game.

Don't believe us? Ramp crafted a hyper-personalised cold mail and reached out to 50,000 companies in search of more customers and they truly outdid themselves with an amazing >50% open rate.

Let me do the math for you, that means >25,000 companies are now aware of what Ramp is doing, and spoiler alert if you don't read their blog post: 'Some campaigns/sectors have received a whopping 25%+ CTR' (click through rate).

They also made '...tens of thousands of pounds, dollars and euros! 😉'

Solution: Give Yourself A Challenge

In the early days of Gleam, our co-founder Stuart set the north star goal to be our monthly recurring revenue (MRR). Having that thought in mind, he challenged himself by sending out 10 cold emails a day in order to increase Gleam's MRR. He did that in the first 2 months of working on Gleam full-time.

By tying the act of sending out cold emails to the goal of increasing MRR, it forced Stuart to work harder in finding the best prospects and discover the best way to send a cold email. We're talking about lots and lots of experimentation. Again, a numbers game.

Here are some stats from Stuart's challenge:

  • Emailing founders: 90% response rate
  • Emailing marketing team: 50% response rate
  • Using contact us/feedback forms: 10% response rate

A caveat here is that you should not limit yourself to sending only cold emails. In some circumstances, a direct message on Twitter or LinkedIn may work even better. Stuart has tried Tweeting to potential customers:

And here's a cold InMail I recently received on LinkedIn:

I'll spare you the details, but this outreach turned out to be a great conversation opener. The person had naturally directed the conversation into an invitation for closed-beta access to their new product. Smart, right? 😉

Pitfall 7: Not Directing The Recipient To What's Next

Once the prospect is convinced that you're worthy of their attention, the next step is to direct them to a very clear goal. Remember, the goal of your cold email is to get your prospect to take action, but don't give them so many options that they fall into analysis paralysis.

The last thing you want to do is lay out a bunch of options and say to them...'the ball is in your court', which shows you clearly don't know what you want out of the relationship.

Solution: Provide A Clear CTA

Whether it's scheduling a call with you, or signing up for a trial, make this very clear to the recipient on what you would like to achieve.

That means the recipient only has to answer yes or no to one question, be it an interest in partnering with you, trying out your product, or scheduling a phone call.

For example, Are you interested to discuss more about this? gives you a yes or no answer, whereas What's a good time for you? will require the recipient to search frantically over their calendar while also wondering which time zone you are situated in.

Remember, the relationship gets warmer and warmer by each exchange, so try to keep things as simple as possible on the first email. Imagine the relationship like you would a marketing funnel - for each response you get, the hotter the lead becomes.

If they are indeed interested in your offer, they will reply and you will be able to smoothen out the finer details in the next exchange.

Tip: You can also let the prospect know that they can ignore your email and take it as a 'no' after a week or so. This gives the recipient room to breathe without feeling the obligation to respond.

Pitfall 8: Not Measuring What Works

Insanity is repeating the same mistakes and expecting different results.

If you're sending out lots and lots of cold emails, then it's wise to measure what is effective and what isn't. Not adopting a data-driven approach is detrimental and would cost you your open rates.

Imagine, if you're sending out the same cold mail to a thousand people in one go, how would you ever know if a variant would perform better? Or if the open rates would improve if you iterate on your cold mail?

Solution: Define Clear Measures And A/B Test Them

You don't need a fancy automation tool to send cold mails, but having a nifty plugin could certainly help with measuring the metrics that matter. We recommend a Gmail extension called Yesware that will help you track the following:

  • Open Rates: Which types of subject lines get the best open rates? Knowing this information will allow you to test ideas & see what works for your product. Use CoSchedule’s Headline Analyzer to test out your best subject lines.
  • Clickthroughs: Do people click on your call-to-action once they read your mail? This metric will help you understand if your message is compelling enough to the reader.
  • Responses: What percentage of people actually respond? Getting someone engaged enough to reply to you will greatly increase your chances of conversion.
  • Closes: Which email types actually help you close a sale?

Real Examples Of Cold Emails

We're here at the holy grail - tried and tested examples that we've used in the past which helped build our business and gain traction.

Have a look at some of these examples for different scenarios, and see if you can incorporate them into your business:

Reaching Out To Find A Co-Founder

Reaching out to partner up with another founder can be a difficult decision, and it's even more difficult to reach out to the right person and get a response from them.

Over a decade ago, Stuart and John, our co-founders of Gleam met at a Ruby on Rails meetup group in Melbourne.

Stuart then filtered through the list of attendees and cold mailed them:

Trying Out Your Product

Once your product is at the beta stage, it's important to provide closed access to people who may have interest in your product. Early adopters are essential for advocating your product and they could help you make word-of-mouth recommendations if you provide a stellar customer experience.

When Gleam was at its infancy, we reached out to folks who were running giveaways on Twitter and sent them a cold mail offering to try out our platform:

In the email, Stuart already knew the limitations or pain points of running a giveaway on Twitter, so he highlighted the features that Gleam had that Twitter didn't in order to entice the recipient.

He then invited the recipient to participate in the beta test and provided some statistics so the recipient can get a rough idea of what they can achieve with Gleam.

Finally, he attached a working demo and a case study for the recipient to explore for themselves. And in the final line, he offers to run the first campaign for free 😉

Here's another example with a more personalised touch:

New Partner Campaign

If you would like to partner up with a complementing brand to run a joint campaign, then you should really check out our customer Greenbelly's campaign. This is the simple email script they used to send to a list of pre-qualified brands:

Hey XXX,

We have a big Backpacking giveaway lined up for early next month with insert company A and insert company B. These usually result in several thousand social shares. It will look similar to this insert link to last giveaway.

We'll handle all of the setup. Just looking for a product contribution and a push on your end.

Please let me know if you want the insert category slot asap!

Cheers,

Chris, Founder greenbelly.co

In his cold mail to reach out to potential giveaway partners, Chris name drops a few other companies to let the prospect get an idea of who Chris wants to work with, as well as provide extra incentive to get the prospect interested in his campaign.

He then sends the prospect a link to an old campaign that worked well to show that there will be tangible results should they decide to partner up.

Learn How to Run a Partner Campaign

Find out everything you need to know about using Gleam to partner up with other brands and run powerful giveaways.

Check It Out

Reaching Out To Influencers

Reaching out to influencers as a budding business is another fantastic choice in order to get some word-of-mouth marketing going. In the very early days of Gleam, we identified bloggers as our target niche and set out to look for the best bloggers to partner up with.

We talk often about doing things that don't scale in the early stages of our SaaS business, but this is especially true when it comes to working with influencers. From scouting bloggers to offering free lifetime accounts, you'll have to be prepared to give a lot if you want to receive in return.

Stuart built a landing page to introduce our product, so most of our product features and other important details were on the page. This helped reduce the length of our email and allowed the recipient the choice to find out more should they want to.

Stuart also used the word hand picked to let the recipient know they were specially invited to run campaigns with us.

Eventually, we started gaining traction and was able to offer an annual account instead of a lifetime account to our first 100 customers. Again, the format is more or less the same:

Reach Out To Influencers For Gleam Campaigns

Another template we'd like to share with you is for our Gleam family.

If you're already a Gleam Competitions user and would like to partner up with influencers on social media to co-host a giveaway, then you can use the template below to reach out:

Hey XXX,

We're working on a new campaign for our new initiative and we'd like to explore opportunities to partner up with you for a giveaway/discount campaign.

We'll be using Gleam to host our campaign, you will be able to get more followers on platform or grow your mailing list alongside us.

We'd like to state offer. Are you interested?

Cheers,

Name, Position at Company

Run A Gleam Campaign With Influencers

Learn more about finding the right influencer and how you can setup a partnered Gleam campaign to expand your audience.

Learn More

So there you go, Insiders! Thank you for following us along our Growth Journey, and we welcome you into the new phase of our business. We hope you enjoyed this compilation of tips and examples for crafting personalised cold emails. If you're looking for more startup founder content, just check out the links below 👇

More Resources For Startup Founders

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