The complete guide to cold outbound emails in 2020

Alfie Marsh
Nov 11, 2019 · 15 min read

Below is a guide on how to write cold emails in 2020, I have taken tips & tricks both from my own experience as an SDR and sales manager as well as curating the best bits from top articles, blogs & videos on the internet to build a one-page guide.


Photo by Web Hosting on Unsplash

Key components of a cold email:

  1. Subject line: Get them to open it
  2. Why Me Why Now: Let them know your reason for reaching out and capture their attention enough to keep reading
  3. Value proposition: Clear and concise value proposition that clearly relates to their goals and desired outcomes
  4. CTA (Call-To-Action): What action do you want this prospect to take after reading this email?
  5. Credibility & Legitimacy: Demonstrate why the prospect should trust you
  6. P.S (optional): Throw away comment at the end of the email that can be helpful for ad-hoc information or including things that are less relevant to the body of your email

We’ll look into each one of these in more detail below, but first lets take a look at the key characteristics that render an email A+ player 🚀

Key characteristics of a good cold email:

Becc Holland over at Chorus.ai gave a fantastic webinar with the folks at SalesHacker on ‘how to personalise at scale’, she outlined 7 key pillars of messaging which I go into more detail on below.

The idea is not to give SDRs email’s already pre-written but empower them with the liberty to write in their own creative style whilst offering them a framework to stick to that will help them be successful. Here are the 7 key pillars Becc discusses in her webinar:

  1. Prospect centric
  2. Pain centric
  3. Pride aversive & proactive humility
  4. Fluidity
  5. Relevance
  6. Brevity
  7. Noticeability

Breaking that down into a real-life example looks a little bit like:

1. Prospect centric

We want to put ourselves in the shoes of our prospects, talk about their hopes & dreams and focus on what they want, not what we want. To do that, we need to really understand our buyer persona’s.

Not prospect centric: “ I’d love to schedule a call with you”

The above is self-serving and is talking about what you want, not what the prospect wants.

Prospect centric: “I’d love to understand more about the challenges you face in training your sales team“

Or in a classic follow example:

Not prospect centric:” I’ve sent a few emails over, it would be great to know if we can schedule a discovery call on Thursday for 15 minutes?”

Could be transformed into:

Prospect centric:
Hi XXX,

I understand you may be very busy closing out the quarter. I wouldn’t like to fill up your inbox unnecessarily if you don’t think this could be of value. To save your inbox perhaps you could shoot me back a quick 1,2 or 3 from the below so I know how best to move forward.

1) Not interested

2) Interested, but bad timing

3) Other, look back in X amount of time

Cheers

Being prospect-centric means

  • being respectful of their time
  • not underestimating their intelligence by lying, using manipulative techniques etc
  • talking in terms which the prospect understands and relates to
  • talking in terms of their hopes and dreams
  • not pushing our agenda
  • not being offended if they don’t reply
  • not making the prospect feel guilty for not responding
  • understanding that our prospect is busy or you haven’t done a good enough job to explain why they should respond, its our responsibility to be successful not theirs

2. Pain centric

Pain centric as an extension of being prospect-centric. Instead of talking about our product features, being pain centric means talking about how you can help them achieve their goals by removing a particular pain (clearly through your product).

Prospects often don’t know what your product categories are or even mean (unless you’re lucky enough o be Hubspot where MAS Marketing Automation Software is widely known). Talking about ‘conversational marketing’ or ‘ spend management’ or ‘conversational-intelligence’ is just jargon to prospects.

Prospects do, however, know exactly what their responsibilities and objectives are and what pains are preventing them from getting there. Its therefore much more pertinent to talk to them in that terminology than refer to your product features or product category.

Remember:

  • that the prospect probably doesn’t understand what your product category is
  • not to product / feature dump
  • remove all jargon and speak like you’re talking to your grandma

Example:

Lets take a product called Lemlist that you may already be familiar with and run through emails.

Bad example:

Hi XXX,

I’m reaching out because of XXX.

Lemlist helps you personalise your emails, quickly and efficiently through using the latest technology to embed your customers details onto unique GIFs and photos.

Could this be of interest?

We could transform this into:

Better example:

Hi XXX,

Congrats on your new role as VP Sales at SalesCompanyX. I read on the job description that ensuring consistent pipeline is one of your priorities. We understand this can be pretty challenging when your SDR’s email response rates are low or vary widely.

If we could help you 2x your sales pipeline by driving up SDR’s conversion rates to 20% consistently on their email campaigns , would that be of interest?

Cheers,

P.S We increase email conversion rates to 25% by using highly target customized GIFs with our technology, here’s some case studies if you’re interested.

3. Pride aversive & proactive humility

Pride aversion means not bragging about how good we are. ‘We’re the fastest growing startup in this space” or “Our products the best on the market”.

Switching from self-promoting to prospect-promoting can have a hugely positive impact. This can take many forms such as;

  • congratulating them on articles they’ve written/ a new job / opening of an office / new partnership etc
  • admiring their quick career progression or transition from one industry to another
  • admiring something they wrote about on their LinkedIn about a project they completed or successful impact they had at a company

The best way to promote ourselves is have other people or companies doing it for you. Think about gathering customer testimonials and videos, even if they’re hand recorded on your iPhone at an event, this can be a great way to get that credibility without bigging yourself up.

Becc talks further about proactive humility (minute 52) as something where you are prepared to admit you are wrong and be humble. This can be helpful if someone doesn’t respond to your outreach, or you messed up a sales call. You could email them back explain what you feel you did wrong and ask for another shot.

4 & 5. Ensure fluidity & relevance

This is crucial. I’ve seen many reps focus so much on personalisation that they completely lose the prospect because their email didn’t make sense. In other times the personalisation had no logical link to the reason for the reach out and is clear its just been done for the sake of it.

  • The subject line must relate to the body of the message
  • The Why Me Why Now must relate to a a pain that you can help them solve
  • The pain must relate to the value proposition you offer
  • Other personalised information must be relevant to the topic of your product / service.

Don’t do this: “I saw on Twitter that you love Justin Bieber, would you like to buy my sales automation tool?”

We often think of personalisation as a way to show the prospect that “this email really is for you” or “i haven’t sent this to hundreds of other people ” but this is dangerous if we forget about the importance of fluidity. If the personalisation does not flow or is not relevant then the message can be lost and actually have a negative affect on the prospect.

“Personalisation requires relevance to work”

If you’re going to personalise based on the prospects personal hobbies or interests, then you must find an innovative way to link the two. If you can’t link them clearly then its best to avoid it.

Justin Bieber reworked:

Subject line: lost deals

Hi XXX,

I saw on LinkedIn that your sales team has doubled in size in the last six months to over 85 people and you’ve got new offices in New York, SF, Texas and London. If ‘all that matters’ at the end of quarter is hitting quota then I’d hate to be a ‘heartbreaker’ and say that reps who don’t share knowledge or follow your company’s sales methodology will often lose deals.

Luckily, you don’t have to travel ‘all around the world’ to find out what’s going wrong because there’s ‘nothing like us’ to help you increase your sales numbers.

If you could walk into a meeting with Dyane, your VP of Revenue, with a plan to increase sales by upping close rates to 80% and reduce SDR ramp time to 4 weeks would that be of interest?

Perhaps ‘I’ll show you’ over a quick call this week.

Would that be interesting?

P.S Excuse my Justin Bieber song quotes there, I saw you were a big fan on twitter and hoped you’d appreciate my terrible jokes!

6. Brevity

The shorter and less sculptured the email feels the more human it will be.

Keep it short…. simple!

This is particularly important as many emails are now read directly on a mobile phone.

This is short enough to be read on one screen on your mobile phone 💪🏻

7. Noticeability

At Spendesk we often use GIFs and other interesting pictures or videos to increase noticeability in emails, but be careful not to make the look like a marketing email. (also, embedding videos or external links can increase your spam score, so be careful to use these for your high priority accounts).

For example, we may include a virtual card with the prospects name on. That’s going to make them stand out! They’ll say

“That card has got my name on it! This email must be meant specifically for me and what on earth is that big purple card for anyway?”

Another example is when Intercom reached out to ourselves at Spendesk to pitch their product, they sent a GIF with our own website embedded (which we recognised straight away and realised they weren’t spamming a large numbers of people with the same email… this message was meant for us). The GIF had their live chat featured on our website to help us visualise what it would look like for Spendesk.

This was noticeable and really caught our attention. If you can figure out ways to include eye-catching pictures or videos that are relevant then this can help you stand out from the crowd.


Putting it all together: key components of a cold email

1. Subject Line:

The objective of a subject line is simple…get someone to open your email.

Subject line relevance:

Getting someone to open an email can be easy, but you must never use clickbait. The subject line must be relevant and clearly linkable to the content of the message, otherwise its a sure fire way to get sent to the junk folder.

Clickbait is a form of false advertisement …. that is designed to attract attention and entice users…. with a defining characteristic of being deceptive, typically sensationalized or misleading.

Avoiding clickbait means that there needs to be relevance between your subject line and the email itself. That doesn’t mean you can’t get creative but be careful not to use an eye-catching subject line if it has nothing to do with the email.

For example, if you sell an HR solution that can help managers know whether someone has left the company or has been fired (its just a fake example) then you could write a subject line like;

Did Jane get fired?

This is clearly eye catching and you’re going to want to open that email. The body would need to be focused something to do with someone being fired, such as;

“Some managers don’t know whether their team have been fired but can now be automatically notified via the XYZ platform”.

There is clearly a link between the subject line whilst the subject itself is still intriguing.

Research from Salesloft shows the fewer words you have in your subject lines the better. Best keep them between 1–4 words with a big increase in open rate with just 1 word.

  • Research shows that including numbers (like 1,2,3) or percentages (%) can give the impression that its a marketing email. Outbound reps would be better not to include their ‘value propositions’ in their subject lines and rather save it for the body of the email instead
  • Including the recipient’s company name in the subject line can reduce the open rate, better to favour including your own company name
Salesloft
  • Subject lines should be relevant to the body of the email and a clear link should be visible

TIP: think about the content of your email then try and think of a catchy 1–4 word subject line based on this content. Example, if you have a sales solution that helps sales teams attain their sales targets you could have a subject line like “missed sales quota”

2. Why Me Why Now

The ‘why me why now’ is the premise of your outreach. The first sentence should be explicitly clear as to why you are reaching out to this person and why now. This is probably the biggest factor contributing to response rates on your emails.

The reason for your outreach should be as personalised as possible. If you can’t personalise to the individual person then its okay to personalise to a segment. To do this you can find a list of prospects which have some factor in common, you then tailor that messaging to these factors rather than individual people.

For example, as a recruiter I may create a list of all the people who have played football and have lived in London that have relocated to San Francisco. My message could read like:

Hi XXX,

I noticed that you moved from London to San Francisco and are into football. We’re been working with some fast growing startups looking to hire competitive athletes with an international experience and thought your profile could be a great fit.

You can see that this email requires no personalisation and I could send it to a list of 100 profiles that share the same characteristic if i’ve done my segmenting well. However, if I was reading it myself I’d think its definitely meant for me.

The trick here is to spend more time on segmenting your account lists to have similar characteristics so your message needs to be only personalised once for the segment rather than individual people.

Pain centric: the ‘why me why now’ part of your email is a great place to include pain centricity. Helping to show you understand your prospects challenges and if its a pain they’re actually experiencing then they’ll have an emotional response to this phrase.

Why Me Why Now: “I noticed you’ve got offices in Berlin, Oslo and London. As VP of Sales you may find it challenging to ensure your sales reps communicate the same pitch to prospects across different offices, this can lead to lost deals at quarter end.”

3. Value proposition

  • Value propositions should be directly linked to a buyer persona, different people have different needs
  • Value propositions should help the prospect to visualise a better future
  • Value propositions should be clear, factual and completely eradicate the use of jargon

Its important to make sure we have got the right value proposition for the right person. If we sell to different stakeholders or seniority levels in the company, these value propositions may be different. The office manager may have a very different point of view compared to the Head of Operations or the CEO.

Value props for a sales tool:

  • VP of Sales: building a scalable and consistently performing sales team
  • SDR: booking as many qualified meetings as possible with high fit prospects
  • for these two buyer persona’s our messaging would be different, we’d focus on how we can help them achieve their specific goal

The value proposition should also help the prospect visualise a better future.

Be clear and factual, using numbers and statistics can help the prospect visualise success more clearly.

EXAMPLE: “If you could walk into a room with ((insert their manager’s name)) with a plan to ((insert value proposition #1)) and ((insert value proposition #2)), would that be interesting?”

becomes:

EXAMPLE: “ If you could walk into a room with your CEO Jonathan, with a plan to increase your rep’s closing rate by 40% and reduce the ramp time of SDRs to just 4 weeks, would that be interesting?

Note the product I’m talking about could be anything (it could be a call recorder like Gong.io or it could be a sales automation tool like Salesloft), but the client doesn’t care about the product they care about the outcome. The product itself is just secondary details. The above example enables the prospect to visualise themselves in a winning situation.

Value proposition structure:

“If I could give you XXX by giving you YYY, could that be of interest?”

“If we could help you ((achieve your important goal #1)) by helping ((value proposition #1), would that be of interest?

How to build your value propositions:

TIP: To understand more about your prospects, find their title such as ‘VP of Sales’ or ‘Head of Finance’ and search for jobs openings on LinkedIn. You will quickly see the sort of key responsibilities they have, learn what terminology to use and also how your product or service will help them achieve their goals.

I just did a quick search for a VP of Sales and saw this job opening.

There’s a lot of juicy information here that can help you write your value propositions:

EXAMPLE: “ If you could walk into a room with your CEO Jonathan, with a plan to build a team of high performing sales reps by improving their closing rate by 40% and reduce the ramp time of SDRs to just 4 week, would that be interesting?

Now that, is relevant 💪🏻

4. CTA or Call-To-Action

Calling someone to act is the end goal of your outreach. What the action is, is up to you.

It can be helpful to think about the techniques from William Ury’s book ‘Getting to Yes’ when writing CTA’s.

‘If you can understand the other person’s point of view, the more likely you are going to succeed in getting them to work with you”

  1. Try on the other person’s shoes: understand their time constraints, their pre-conceptions about cold emails and their goals or desires.
  2. Invent mutually beneficial outcomes: up-front contracts
  3. Insist on objective criteria: be clear and concise about your CTA. Only have one and give a clear success outcome

By showing in the body of the email that you appreciate the person is busy, that you have understood what their role consists of and you understand clearly what their objectives are you are more likely to get someone to commit to a reply because they feel that you have respected them.

Here’s a super useful article on Medium on ‘How to Nail your CTA’s, here’s a quick overview:

  1. Provide a Specific Date and Time
  2. Provide a Calendar Link
  3. Provide a Multiple Choice Option
  4. Reiterate your Value Proposition in the CTA
  5. Request a Connection
  6. Ask a Simple Yes/No Confirmation Question
  7. Ask an Open-Ended Question
  8. Use Humor
  9. Ask Permission to Share Something of Value
  10. Add Some Urgency

5. Credibility & Legitimacy

Prospects often have no idea who we are or what our product does and there is often a lack of trust because of the cold outreach. We need a way to embed credibility & legitimacy into our emails to increase trust.

Saying that “we help companies like ((insert famous company here))” doesn’t work as much as it used to anymore because everyone has logos and more expected that it is impressive.

Remember to be prospective centric. If we’re going to mention a company, we should take the time to tailor it to the right size / industry as the prospect so its relevant to them.

Credibility & legitimacy can come in many other forms however:

  • a news article written about you in the press
  • funds raised from venture capital
  • new partnerships
  • number of customers you work with
  • customer testimonials
  • tweets or messages from your users
  • one of your customers is a mutual connection to the prospect you’re contacting
  • you’ve won awards or a ‘Top XYZ’ list of some sort

6. P.S.

These are useful little throwaway comments we can add at the end of our email. They can be great because the human eye tends to look at the first line and the last line of an email so the P.S section is often going to get read.

It can be used for that extra sprinkle of personalisation

  • a relevant article regarding the pain point you talk about
  • a customer testimonial
  • your fund raise article
  • talking about something you read about them

If there’s anywhere we can get away with not having something relevant in our email it is here, there is almost an expectation that the P.S is going to be slightly non-related to the core body of the email otherwise it wouldn’t be in the P.S section


Hopefully you have everything you need to rock your cold emails. If you’d like to ask me any specific questions please feel free to reach out via linkedin here


Alfie Marsh

Written by

Passionate about SaaS sales & marketing, with experience in building outbound sales teams. Currently at Spendesk, ex-Bloomberg

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