This guide is all about helping your early-stage startup write better cold emails that will convert to booked sales calls. You might be sending these emails yourself, or overseeing a new hire / agency kick off your outbound efforts. Either way, the goal is to share some perspective and lessons we’ve learned after running over 100 cold email campaigns.
Here are some of the results you can achieve by following these guidelines:
This is meant to act as a guide - there are real examples included in the final section for each email strategy mentioned here.
A successful outreach campaign requires three things before you can get started.
Without getting too deep into prospect lists, make sure you have all your bases covered. They should:
You want to segment your prospects where possible so you can create more tailored campaigns and evaluate the differences. This could be as simple as splitting your list into two based on company size. Or identifying the three top job titles you want to reach out to and splitting them that way.
When it comes to tools, you are looking for something that will allow you to scale your email campaigns and easily track your performance. There are a number of options here, we have tried several and have categorized the best ones by price:
Streak: Free if you are the only user. This is a decent option if you are sending out just a few messages and doing things completely on your own.
Mailshake: The most intuitive tool at this price point. They carry nearly all of the features of the top tier tools that you would need.
Lemlist: They offer a unique spin on personalizing images and videos in your outreach.
Apollo: A little more expensive, but provides a database of leads as well.
Salesloft and Outreach. Both are great with marginal differences. Don’t use these until you have two or more sales reps already on your team. They may still require a 3-seat license minimum.
Let’s get into the good stuff. What makes a good cold email?
There’s two parts to this. First, you need to meet the minimum bar for your prospect to take you seriously. Once they are taking a look, you need to create enough intrigue, validation and value to take things to the next step.
The bare minimum in a campaign to catch your prospect’s attention comes in three parts: your offer, the contact, and the timing. You need to have a great offer, sent to the right person at the right time. If your campaigns aren’t delivering results, it’s because you are falling short on one of these 3 criteria. You can’t control the timing of your prospect’s buying cycle, which is why it’s important to re-engage your prospects every 3-6 months. But you are fully in control of building a great offer for the right person.
Once your prospect has determined that you are worth looking into, there are three things that exceptional emails always contain:
There is a right and wrong way to do this. Babbling on about how much you’ve raised doesn’t do much for your prospect. The key is to allude to some of the specific results you’ve achieved, and quickly tie it into the issue your prospect is facing. The best way to get a prospect to trust you is to speak their language.
The more specific you can tailor your campaigns, the better. Take the example of a company selling recruiting software. They will see much better results in building a campaign specifically for recruiting coordinators and focusing on the unique issues they face in coordinating interviews than if they sent the same messaging to everyone that fell under the recruiting org.
The second level of achieving this is high-quality research into the specific challenge your unique prospect is facing. What differentiates them from the next prospect on your list? Do they actually need your product, and can you quantify how much they need it? There is a massive difference between promising better software vs. highlighting the pitfalls in the tool they use and why it doesn’t work as well based on their team size and goals.
Assume your prospect will read your email on their phone. Keep your subject line short so they can actually read your opening line. Don’t make them need to scroll to read your entire message, because the odds are that they won’t. Remove all the fluff from your wording.
“The winner in a crowded inbox is the seller who can define the prospect’s problem with the most clarity”
How many times should you email one of your prospects?
Sending a campaign with 3-5 touch points gives you the chance to add more value in your follow up, with examples that are included in the next section. The reality is that most inboxes are extremely crowded and it’s easy for one or more of your emails to go by unnoticed. It’s important to thread your replies when possible so you can provide the full context with why you are reaching out.
Building a campaign with multiple touch points also gives you the chance to test your messaging, timing, tone, and ask. This is where you gather the insights that will allow you to improve your conversion.
It’s important to remember that even within a highly targeted segment, there are a wide range of personalities with different preferences. Some will prefer a direct pitch immediately. Others will prefer to see helpful content before they can trust you.
Timing is important as well. As recently as 5 years ago, you could get away with campaigns that sent an email every 1-2 days. While it’s important to get your touches in, you don’t want to do it at the expense of upsetting prospects. It’s better to space each email out 3-5 days apart. A 5-touch campaign can take up to a month from start to finish, and that’s okay.
You are selling a conversation at first, not your product. Optimize your first email for replies, not sales demos. You’ll end up booking more meetings this way in the long run. You want to get questions that can be funnelled back into your offer.
Put yourself in the prospect’s shoes. People generally dislike being sold to. On the other hand, most people enjoy finding solutions to the problems they face and are happy to learn from those who have solved it before. This is how you have to position yourself during outreach and even your sales calls. You are here to guide and provide solutions, not sell.
The first time your campaign reaches someone, they will have their guard up. Your job is to minimize the friction and their objections as much as possible right away.
This is also the best time to insert the research you have done on your prospect, whether that is about the prospect themselves or the unique pain point the company faces. You can leave the follow up emails to tackle unique points on your value proposition, but the first email your prospect receives is the most important, and often the most viewed.
Bearing in mind the principles of authority, targeting, and brevity, there are four different ways to do this in an initial email:
One of the best ways to display your authority without coming off too strong is through sharing high-quality content that uniquely speaks to the challenges your prospect is facing. This is content that is well-thought out and will genuinely teach the prospect something - this works especially well when you are solving a problem that your prospect may not know they have and requires a more educational angle. The key is to tie this into their current process and where that may be falling short.
Simple formula: identify their challenge, share your solution and why you’re legit. This only works if you can be extremely specific in identifying their pain point, and brief in sharing how you solve it. This requires you to have in-depth knowledge about your market - bonus points if you can point to your own experience with this challenge to make it more relatable.
People respond best to invites and no-brainer offers that cost nothing on their end. The offer can be for a free consultation, a free trial, or an invite to a community you are building around your problem space.
This works best where there are mutual interests/backgrounds shared with the prospect. Options include referencing commonalities, interesting content they share, career path, their ‘About’ section on LinkedIn.
Your second and third messages need to add value to the prospect in some way. Most folks are sending something along the lines of “Just checking in”. Here are ten tactics you can use to follow up and stand out:
This is a solid starting point, but great results come from running lots of testing and quickly iterating on your messaging. Build your hypothesis on what type of messaging could work best and be diligent in testing timing, length, call to action, subject lines, value props, etc.
14 real-life cold emails that booked meetings. Most are emails we have written for our clients, some examples are emails that we came across and really liked. There is an example for every type of email mentioned above in this guide.
Hi Jane,
I’m John, CEO of CompanyX. We enable teams to implement testing best practices to ship high-quality models much faster.
From my experience, using a single metric for testing produces low visibility on model performance. Generic statistics leave huge blind spots, a phenomenon known as hidden stratification.
We’ve written more in this brief post** about the benefits of unit testing models and how ML teams are saving months from their development roadmap.
Would it be worth discussing this and your current approach at [your company]?
** links to an in-depth blog post of the phenomenon they mentioned
Hey Ilana,
I wanted to reach out because I noticed you were hiring multiple backend engineers for your new Android app.
With an abundance of technical engineering jobs available, have you been able to adequately source quality candidates with [current solution] or are you typically finding yourself using recruiting agencies and manually chasing candidates?
With such a competitive job market, we're arming TA professionals with more proactive sourcing strategies and the software necessary to help them crush their hiring goals.
I’d love to have a chat if you’re looking to get more proactive with your hiring strategy in Q2.
Hi Roy,
We’d love to host a few working parents from [your company] to try one of our classes for free this week! This is the best way to experience the magic of [our product] and discover how we could support your team.
Let me know if you are interested and I can walk you through how to unlock your free credits.
Hey Jillian,
First of all, I actually used to work in musical theater up here in Toronto - noticed you also had a similar background. Are you able to find any time to perform in your life as a recruiter? It certainly helps with networking!
I wanted to reach out because I noticed you're all about forming lasting bonds with candidates. It really resonated because that's the exact reason [our product] exists.
With such a competitive job market, we created [our product] to be candidate-centric. Essentially, we focus more on the candidate relationship and less on the singular requisition.
I know you're already in a contract with [competitor], but I thought there might be some philosophical alignment between us and wanted to reach out. I’d love to discuss your current hiring strategy when you have a few minutes next week.
Hi Mark,
In recent months, [competitor 1] and [competitor 2] have launched referral programs to great effect. It can take a lot of work upfront, but enables you to turn your customers into your strongest sales channel.
We’re making this easier for companies to achieve at scale. I’d love to discuss what a referral strategy can do for [your company] and how it might look. Would it be worth discussing sometime this week?
Hi Susan,
I noticed that the designers you are currently hiring are tasked with improving [company]’s engagement and user stickiness. [Company X] saw a 43% increase in user sessions and a 31% increase in returning users after using [our product].
They were able to do so because of:
I would love the opportunity to share more details and see if we can be of any help!
Martin,
Our data platform is built specifically for MarTech companies looking to ramp up outbound prospecting with high volume and accurate prospect data. Our customers include companies like ExpertFile, Zodiac Metrics, and StellaService.
As part of our introduction we're offering a free trial, giving you unlimited access to millions of prospects with full contact info. Would you like to start a trial of our platform this week?
Examples:
Hi Danielle,
I looked through the new benefits [your company] is offering and thought this would be relevant to you as HR Manager.
Working parents in the US are losing 720 million hours each week to stress and caregiving.
[Our company} is partnering with employers to give working parents time back in their day to focus on other priorities - we offer 100,000 live, interactive classes for children of all ages.
I’d be happy to share more about our program and how we can reduce the stress levels parents at [Company] are currently feeling.
Aaron,
Having looked through your unique computer vision challenges again, I'd like to invite you to a webinar I'm hosting next week on how to run unit tests on your model. You can register here and are welcome to invite any of your colleagues as well!
If none of the times linked work, let me know and I will be happy to send you a recording or set up a time to chat 1:1.
Leslie,
I’ve spoken with over a hundred building operators about their unique energy challenges over the past year. We’ve helped many of their portfolio companies in three ways:
We’re helping buildings across Ontario achieve this, and I know that [company] has already done most of the work around GA to set you up for the new grid initiative.
Would you be interested in seeing what this could look like for the [company] portfolio?
Hi Aparna,
Following up - for your convenience, just select a number below and I will handle the rest:
1) I am super interested but would like to know more.
2) I am interested but have been busy recently
3) I have no idea what [your product] is.
4) Not interested, but thanks!
Hi Eman,
Most SEO agency founders I speak with want to implement a VA strategy but haven’t made the time for it or are unsure where to start. I saw that you have been running things at [company] for the past two years without much admin support.
Is this something you’ve been looking to implement as well?
Typically when I haven’t heard back from someone it means they’re either really busy or aren’t interested. If you aren’t interested, this will be my last email to you.
If you’re still on the fence, I’ll summarize why I reached out:
I’m happy to chat even if you’re just curious. Let me know!
Merchants that transition from Clio to Filevine aren’t just building a better experience for clients - they are doing so while saving time and money spent on communication errors.
Alto LLC were bogged down for weeks with support requests when they launched their new communication portal. Since switching to Filevine, they have cut their support tickets by over 50% and reduced their communications spend by another 30%.
We know that time is money to you, so all that we do focuses on giving you back your valuable time so you can do what matters most for your business: grow.
A few more bonus tips:
We’ve seen founders waste months figuring this out on their own, working leaky sales funnels and spending hours on spreadsheets and new sales tools. When we work with early-stage startups, our goal is to:
Our process is simple - we understand your product and target market. We set up the tools you need to scale your campaigns quickly. Then we gather detailed research, create the messaging, launch campaigns and share the changes we make each week with you along the way as we set sales calls for you.
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