Valuable Lessons Learned After Sending 1,000+ Cold Emails

We’ve always been skeptical of cold email.

It seems spammy, unreliable, and depressing at times.

And let’s be honest—nobody loves doing startup outbound sales. The difficult truth is that it sucks a lot of the time, and when it doesn’t you still have to grind away.

Jake and I have always tried to make the best of cold email outreach. We’ve put in a ton of hours of research, tweaking, and targeting to increase the open rates and decrease how spammy it looks.

We want to keep a good brand image whilst making more companies aware we exist and that we’re a good alternative knowledge base.

All this effort paid off for us. With B2B SaaS cold email you’re looking for a 15–30% open rate. We managed to hit 60% with a 5% click rate on my signature.

Cold email needs to land at the right time

When you get hundreds of replies streaming into your inbox “Unsubscribe”, “not interested”, and “don’t contact me again” are a common occurrence.

It’s brutal.

Despite replies like these, it puts a smile on my face when my offer of a 15 minute call gets accepted. I forget about all of the no’s I got before when I get one yes.

Even so, it makes me wonder whether all the stress and time is worth it. Whilst I’ve enjoyed talking to people on Google Hangouts, the lead times on switching knowledge bases is long.

There’s a lot to think about and I totally respect that. This is something that hadn’t occurred to me before, but probably should’ve.

You need to catch the prospect at exactly the right time.

They have to be in a position to improve their customer support workflow or at least be thinking about doing so. This is unlikely and I’ve been pretty lucky with my outreach.

Inbound leads are far easier to convert

I may be a little bit bias but I think our knowledge bases are beautiful, functional, and help you keep customer support costs down.

It’s difficult to get that across in a cold email, particularly when you’re trying to keep the length to a minimum (more on that in a minute).

When someone visits our website it’s so much easier to explain. We’ve got copy to explain the benefits, we’ve got links to example knowledge bases, and we’ve got the evidence to back it up in the form of testimonials.

We use Drift which helps us chat 1-on-1 with potential customers and the bot directs leads to relevant articles to help them out before we reply.

Basically, everything is set up to help people answer the question—is this product right for my team or not?

Unfortunately, you’d need to send prospects a 1,000 word cold email to cram everything in there. I don’t know about you, but I’d press archive on that monstrosity.

Our cold email strategy

Ok, so onto the useful actionable stuff. Just how did we get a 60% open rate in the B2B SaaS space?

It’s all in the subject line.

Jake loves making introductions. Being able to introduce two people having never met is one of their favorite bits about being a startup CEO.

When making an intro over email, Jake uses the subject line “NAME <> NAME”. So, if I were to be introduced to someone named Mark, it’d be “Mark <> Jarratt”. We applied this technique to our cold email outreach efforts. Instead of using personal names we used company names. An email to Acme corp would be filled in as “Acme <> HelpDocs”.

I’d fill in the subject line one by one to make sure it was looking good. Nobody wants to open a subject line like “Acme Corporation Inc Ltd. <> HelpDocs”, right? That just screams careless.

Once open, lead with a useful summary sentence

The first question someone is gonna ask themselves when they open your email is “Who is this person?!”. That’s what we wanted to answer right away.

So the first sentence is mega important. It’s a tough balance because you don’t want to bore the person, but they need to know a little bit about you and your company. Why should they care?

Here’s what I used after 3 attempts at making the first sentence awesome:

I'm the cofounder over at HelpDocs. We make hosted product documentation software to help companies like COMPANY NAME drive down customer support ticket volume & keep product docs from aging.

Let’s break it down.

• The first sentence explains my position at the company.

• The first part of the second sentence explains what HelpDocs does. We make help documentation software. Because we were targeting software companies, I made it clear we host product documentation.

• Finally, I told them the benefit. Why they should care and what it’ll help them achieve. There’s no point in getting in touch if they don’t know how it could help them out.

Show them you’ve looked at their website

Y’know what grinds my gears? When someone reaches out and it’s clear they have no clue what we do. They haven’t bothered looking at our site.

We wanted to avoid this, and doing so meant looking through each and every prospects’ website. Yes—every single one of them.

Not only did this help with personalizing the cold email, but it gave me a good honest look at the knowledge base competitive landscape. Who is the clear winner? Who is catching up?

There were 3 scenarios I found:

1. They didn’t have a support site at all. Either they were too early, were a bad fit, or hadn’t had time to set one up yet.

2. They made the product documentation themselves. Either using a Wordpress documentation theme or building out a custom FAQ page. We found these to be our best leads.

3. They were using a competitor of ours already.

When they were using a competitor, it made it difficult to approach. I had to think carefully about how to work with that information.

I didn’t want to say the competitor was a bad choice because we think our competitors do a pretty darn good job. I didn’t want to try and snatch them away either.

If they were happy, there was no reason we should get in the way.

In the end, we decided it was best to try and get on a call to discuss what they think of their current software and how it fits into their customer support workflow:

I know you guys use SOFTWARE at the moment for your product docs. I'd love to learn a little more about how you guys find it and how you handle your customer support.

Sure enough, we did get some calls from support teams already using a competitor. We found it useful for collecting feedback and better understanding the problem.

Finish with a clear call-to-action

With cold email outreach, you have to have a clear call-to-action. Without one you’ll get a dismal reply rate because there’s nothing to reply to.

So to finish off, try to ask the prospect something quick. Just one question, not two, not three. Just one.

I finished mine off with an ask for 15 minutes on the phone. I didn’t say “just 15 minutes” or “only 15 minutes”. It’s kinda offensive because it implies you don’t value their time.

Do you or someone on your team have time for a 15 minute chat? :)

They may be the wrong person to ask, so “or someone on your team” helps me get redirected to the right contact. The smiley face is added for extra friendliness because why not, eh?

Paused for now. Revisit in the future

This is the first time I’ve done cold email and it’s been a pretty great experience overall.

Whilst scary for an introvert like me, I found it exciting to chat to people about their businesses, their customer support processes, and their opinion on help documentation.

If you’re worried about cold email and the responses you’ll get, try not to think about it too much. Just make sure you craft a good email to the right kinda people. Do that, and you’ll be alright.

We’re going to give retargeting a go and see how it performs versus outbound. We’ve learned inbound customers are at a far better stage to convert than cold outreach, and perhaps we need to grow a little more before trying again.

P.S. How’d it perform for you?

I’d love to know how/if cold email outreach worked for you.

Have any techniques or tips to help other B2B SaaS startups? Let us know in the comments below! 👌