If you’ve worked with me before, you know that I’m weirdly into cold outbounding.
I wouldn’t say it’s an obsession, as I reserve that designation for the likes of Survivor and Bruce Springsteen -- but yes, I’m a big fan of cold emails as an outreach strategy.
At the most basic level, I like cold outreach because it needs to be part of your strategy if you're serious about sales. Relying on referrals or hoping for inbounds will not provide the necessary volume for sales momentum.
Beyond this, I love cold outreach because there is zero chance of a false positive. If you email* strangers about your startup and you get more than a 5% conversion to a sales call, that’s real signal that what you are building and how you talk about it is starting to resonate with the customers you’ve targeted. And that is the ticket to finding repeatable sales and product-market fit.
The rub is that cold outbounds are tricky to get right, and easy to get wrong. There is a lot of advice out there that only works for post-PMF companies (if anyone), and all of our digital inboxes are reaching saturation.
Over the past year, I’ve come to stand by five tips for early-stage cold outreach that are a little unconventional. But frankly, following conventional advice about cold outreach will increase the chances that you blend in with other emails, and that’s the opposite of what we’re going for. So let’s get a little weird.
1. Leverage your founder status and story
Cold sales emails need to be clearly sent from a real human in order to get a good response. Milquetoast, impersonal emails are likely to be ignored, so they aren’t worth sending at this stage, period.
But this is good news, in a sense, because one of the greatest advantages an early-stage startup has is that you’re not some big, soulless company. You’re a bold, imaginative founder! That makes you inherently interesting! You’re building something from scratch on a wing and a prayer, dangit!
From sharing why you built the company, to asking for help, to offering free expertise, there are so many ways that you can appeal to your target customer to get them on a call.
So don’t reduce yourself to mimicking bigger companies who send watered-down, rinse-and-repeat emails. They’re at scale, and an early startup isn’t. But, we can leverage your founder status and story to get there.
2. Get inside your buyer's head
We want your personality and story to come through, because emails that are clearly sent by humans get replies. But these emails also need to be acutely aware of your reader's reality.
To write emails that really resonate with your buyer, I recommend reflecting on four planes:
- Demographics: characteristics of your target organization, like industry, number of employees, location, and revenue
- Firmographics: characteristics of your actual buyer, like potential titles, tenure, reporting structure, et cetera
- Psychographics: your buyer’s attitude, behaviors, and beliefs. What gets them promoted or fired? What’s high on their to-do list? What are their desires? How do they speak, and like to be spoken to?
- Their daily lives: What do they do for work? Are they desk-bound or mobile? When do they use screens, and how and when do they use them?
I have a detailed exercise that will facilitate this reflection — just reply if you’d like me to share it.
If you are feeling stressed that you don’t know these answers yet, that's completely normal. At the early stage, NO ONE has a super clear perspective on this. And every company, even the giants, are constantly refining their understanding as markets evolve.
Start with a best guess, send some emails, learn from the responses, and repeat. And if you have any friends who represent your exact buyer type, ask them to provide honest feedback and tough love on a draft.
3. Read it out loud.
By now you get that connecting yourself to your buyer’s desires, actions, and motivations is key. But I’ve seen a strange trend happen with founders: We discuss the importance of standing out by adding relevant personal detail and tailoring to the buyer. The founder is bought in, and starts writing a draft. I open it up and it’s… stuffy!
The passionate and fiery takes that a founder shares with me live about the customer’s problem somehow have become bland when translated into writing. It’s as if there’s a “corporate emailer" inside them that has commandeered the keyboard and stripped away all opinion and color.
You’ll need to fight this urge. These emails have to feel really human, and really stand out amongst the sea of other cold emails they're receiving.
A great way to keep this in check is to read what you’ve written out loud. If it doesn’t sound like something you would actually say if you randomly met a target buyer at a party, it’s not human enough.
4. Human > short.
I used to say that your emails need to be ruthlessly short. I don’t believe that anymore.
If we orient towards short, we may accidentally edit out texture and personality.
I also have a burgeoning theory that if your email is the same length as the average crappy cold email, your reader might assume it is one too. Don’t be afraid to write something longer if it proves you’re a real person worth talking to.
5. Subject lines aren't for selling
The goal of a cold email isn't to make a sale. It's to start a potential sale by getting a positive reply. That's it!
You're not selling a product, you're just starting a conversation so you can explore if there's a fit.
Drilling down further, the goal of your subject line isn't to sell. It has one job, and it's to get that email opened.
If your subject line's subtext is "this is a sales email," the reader won't open it. Instead, we need to pique their curiosity.
It's going to feel a little awkward, but if your subject line is more vague, it will get them to open. Then, they'll find your thoughtful and personal email, and get excited about connecting. Limit to four words or less, and keep it a bit mysterious, and you'll be on the right track.
Final thoughts
Your cold outreach strategy won’t be perfect, especially at the start, but it’s important to not give up so you can keep tweaking and learning.
At the same time, you’re a founder with a one-of-a-kind story and mission. You’ll be surprised by how far your point of view and your humanity can take you.
This is Extra Extra, a newsletter about the tactics and mindsets that drive early sales. I’m Caroline Fay, and I’m an exited social impact founder that’s spent my career launching and selling new products. I help non-traditional tech founders build sustainable, recurring revenue.
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Caroline Fay
*I’m focused on email in this issue, but a broader point here is that when you deeply understand your customer’s mindset and daily actions, you may realize that email isn’t the right channel to reach them. Email and LinkedIn tends to be a reliable way for B2B founders to book multiple sales calls per week if they get the messaging right, but if your customer doesn’t do email, approach them in a channel they prefer.
