My friend Leo is a talented engineer building a software business. He got passionate about a specific area of the user journey and decided to build a product to help other software companies optimize this.
In his product area, there are a few pieces of software that address a similar problem, but they tend to cost $300 to $500 / month and, in his opinion, tend to be complicated and difficult to use. He’s built a product he feels is simpler and priced it at $50-$100 / month.
He’s now starting to do outreach, but is new to this and isn’t quite sure how.
This is a common problem. There are a lot of different solutions, but there’s one that I found that works well for me and others. It requires a few things: you have to be a reasonably good writer, reasonably curious, and reasonably analytical.
But let’s start with Leo. Leo’s biggest problem right now isn’t actually that he doesn’t have any customers. His top problem is that he isn’t currently able to tell an accurate story about the top three situations where someone would use his product.
(This challenge is common at all stages of startups, especially for flexible products like startup and devtools; every year, we’re shocked to discover the new things people are doing with Gatsby.).
That said, the solution to his challenge is the same — he needs to talk to his target demographic. The easiest way to do this is usually targeted cold email. Cold email has low response rates, so he’ll need to email a lot of people.
He will probably need to talk to 20 folks to really understand what’s going on, and hopefully he’s able to convert a couple of them into paying customers. If his emails have a 5% response conversion to video chat, which is optimistic, he’ll need to email 400 people to get there. Oof.
There’s a better way, which we’ll get to. But let’s start with the mechanics.
The Mechanics of A Bulk Email Campaign
Prospecting & bulk emails
You want to start with companies matching your hypothesis, which you can find (as Leo did) from reports from BuiltWith and similar databases like Crunchbase. If you need to filter by number of employees or revenue, you can enrich data with Clearbit; their Google Sheets plugin is great.
To send X emails, you need to find, say, X / 2 relevant companies, find the names of 2 relevant people at each company, and then get their emails. This is called prospecting. BuiltWith and similar databases like Crunchbase are good to get companies fitting a certain profile. You can then use LinkedIn, especially LinkedIn Sales Navigator, to find people with certain titles at these companies; tools like Hunter.io will help you find their email.
(This can be tedious! If you have a bit of a budget, one you have a company list and persona title, you can outsource the person & email finding via services like Fiverr; but carefully monitor data quality as it can vary between contractors.)
Then, you need a tool that lets you “mail-merge” emails — that is, send templated emails from a spreadsheet. I’ve used Mixmax, which is great. It lets you edit individual emails but send them all with a push of a button, which is helpful.
However you’re doing this, it’s important to batch tasks; this increases efficiency by reducing context switching. Especially separate out profile collecting (pulling BuiltWith data, surfing LinkedIn, using Hunter.io or Resource from writing or customizing emails. If you’re doing this work yourself, you need to be able to get into a flow where you’re finding at least a person or two per minute and cutting-and-pasting their details in.
Writing an email template
Now, it’s time to write the emails. Some general principles:
- only one idea per email. Save other ideas for an automated follow-up.
- make it personal
- write simple emails
- make it easy to book a meeting (ie, use a Calendly link)
The Magic of Applied Curiosity
Okay, fine, those are the mechanics. But startups are always a mixture of mechanics and magic. This is the magic.
There’s one principle which I’ve found vastly increases the response rate, if you mean it genuinely: ask for someone to share their experience.
I learned this lesson early this year. I was doing two campaigns reaching out to Gatsby open-source users. Both campaigns were looking for user feedback. But the copy of one led with “we launched X feature”, and the other led with “I’m reaching out to understand what’s working well (or not so well) for you.” The second one was much, much more effective in helping me chat with users.
Don’t ask for time, credibly ask for help
Back to Leo. His challenge in asking for feedback is that he isn’t a co-founder of an open-source project his recipients are already using. He’s just someone emailing them out of the blue. He needs a credible way to ask for feedback.
One way to do this is to write blog posts about common customer pain points, and interview target personas in order to write the blog post.
This kills multiple birds with one stone: it warms up the cold email, and genuinely asks for help while simultaneously tacitly offering meaningful help (writing a blog post to distill their hard-earned knowledge!).
It’s also effective. Would you rather talk to a journalist or a salesperson?
Let’s jump to the next step. Leo’s sent these emails, and now he’s got a call scheduled. What should he do?
Most guides to customer interviews you’ll find online are fine, but there’s one thing they’re missing. Yes, come prepared with a few open-ended questions, and generally shut your mouth. But I did journalism for a couple years in college, and learned something there that’s often missing from user interviews: genuine curiosity.
if you aren’t off-script for a significant part of the interview, you probably weren’t curious enough. Notice when you’re surprised, or when you don’t understand, and ask for more details or for them to clarify further. There’s probably something interesting hiding in the creases.
Record each session with Zoom; auto-transcribe with Rev. It’s important to be able to quickly scan each conversation.
Write voluminously about your niche
Once you’ve talked to a few folks, start writing a blog post. This is where you need to not just be a reasonably good writer, you need to be analytical. You need to start coming to a conclusion about why people are answering the same questions in different ways. Why does a workflow work for one company, but not another? Is it size? Org structure? Personality? Job title? Something else?
Don’t wrap it all up in a sermon-y “best-practices” bow, the way you’ll find in some tech publications. Keep asking questions. Keep talking to people. Keep writing. Organize your writing into sections. Eliminate needless words. Distill catchy ledes and descriptive headings. Question sloppy thinking and lazy assumptions. Repeat until you understand what is going on.
Maybe that one blog post becomes two blog posts, or three, or five. Write voluminously. And maybe when it’s all over you’ve talked to not five or seven people, but thirty or fifty.
And then it’s only natural to email them the relevant posts as they come out, and offer to onboard anyone who’d be a good, and of course use all the insights you’ve gained to make your product better, and probably the SEO will help you as well, in addition to the readers who will just feel like you get their problem and try out your product.
Skeptical you have five blog posts in you? I was too, and then I spent so long in 2018 trying to understand what the heck was going on in the website landscape I wrote a five-part series on the content mesh that is still probably the best overview of the space.
Remember Pirsig’s brick
Remember Pirsig’s brick:
He’d been having trouble with students who had nothing to say. At first he thought it was laziness but later it became apparent that it wasn’t. They just couldn’t think of anything to say.
One of them, a girl with strong-lensed glasses, wanted to write a five-hundred-word essay about the United States. He was used to the sinking feeling that comes from statements like this, and suggested without disparagement that she narrow it down to just Bozeman.
When the paper came due she didn’t have it and was quite upset. She had tried and tried but she just couldn’t think of anything to say.
He had already discussed her with her previous instructors and they’d confirmed his impressions of her. She was very serious, disciplined and hardworking, but extremely dull. Not a spark of creativity in her anywhere. Her eyes, behind the thick-lensed glasses, were the eyes of a drudge. She wasn’t bluffing him, she really couldn’t think of anything to say, and was upset by her inability to do as she was told.
It just stumped him. Now he couldn’t think of anything to say. A silence occurred, and then a peculiar answer: “Narrow it down to the main street of Bozeman.” It was a stroke of insight. She nodded dutifully and went out. But just before her next class she came back in real distress, tears this time, distress that had obviously been there for a long time. She still couldn’t think of anything to say, and couldn’t understand why, if she couldn’t think of anything about all of Bozeman, she should be able to think of something about just one street.
He was furious. “You’re not looking!” he said. A memory came back of his own dismissal from the University for having too much to say. For every fact there is an infinity of hypotheses. The more you look the more you see. She really wasn’t looking and yet somehow didn’t understand this.
He told her angrily, “Narrow it down to the front of one building on the main street of Bozeman. The Opera House. Start with the upper left-hand brick.”
Her eyes, behind the thick-lensed glasses, opened wide. She came in the next class with a puzzled look and handed him a five-thousand-word essay on the front of the Opera House on the main street of Bozeman, Montana. “I sat in the hamburger stand across the street,” she said, “and started writing about the first brick, and the second brick, and then by the third brick it all started to come and I couldn’t stop. They thought I was crazy, and they kept kidding me, but here it all is. I don’t understand it.”