Why quality of your outreach matters

I was going to write something totally different this week but I was emailing with a founder I respect about a new project I’m working on (on which, more below) and he hit on an objection. It has been living rent-free in my head. This objection is so crippling to founders, especially technical ones, that it needs to be killed forever:

It’s a tempting thought because it should be true. Our rational mind thinks that if the problem is urgent, any viable solution should just automatically be accepted. It implies that the problem itself is so urgent and painful that the recipient will overlook any imperfections in how the message is delivered.

The opposite is true: If what you have isn’t solving an important pain, or isn’t perceived as a viable solution to a pain, no amount of execution excellence will matter. Nobody will open your emails, or if they do, nobody will want to meet you or buy your product.

But even if you have something that people want, there are many ways to fail. Let’s put this myth to rest with an example, and then dig into why and what you can do about it.

Changing tactics but keeping the product the same

Like a good social scientist, let’s take a data first approach. To disprove this, all it takes is one example, and I happen to have that handy. The founder/CEO is probably reading this newsletter, and I hope revisiting this doesn’t cause too much agony.

A company we worked with had tried cold emails before we met them. They had an open rate of 8% and had booked zero meetings after sending 3,000 cold emails a month (yes, 100 per day) for several months. Their reasonable conclusion was that cold outreach didn’t work, and they had written it off entirely. In a strategy meeting, I suggested they give it another try, but to let me and my team run it to make sure the experiment was done correctly.

We did two things differently. First, we used different tools specific to the task, and set them up properly. Second, we wrote good emails–focused on customer pain, and short.

Within two months from us taking over outreach, they saw open rates of 65% on average—sometimes as high as 78%—and a response rate ranging from 10-20% (sometimes much higher). They saw 20-30 qualified meetings consistently. The product didn’t change. The market didn’t change. The only difference was execution.

Technical execution matters

There are a large number of factors that result in the major email providers marking emails spam or relegating them to the dustbin of the other tabs. These include domain age, email address age, email provider, list quality, DNS settings, the actual tool you are using to send emails (especially if doing so at scale), and more. The list is long. If you screw any one thing up your emails will never see the inside of an actual inbox. They’ll just disappear into the void.

If you’re sending at any volume it’s critical to get “secondary domains”. These are domains that sound like your domain but are not. I don’t always send cold emails, but when I do, I send them from silverwoodadvisors.co. Depending on sending volume you may want 2 or more secondary domains. This both enables you to send more emails and prevents any blowback from affecting your primary domain (like, your actual emails sent by humans).

Tools like Hubspot and Apollo–even though popular–are some of the worst for delivery. You’ll do better with more modern tools like Lemlist, or AI tools (I’m still curious about your thoughts on AI tools–click here to answer 7 questions).

LinkedIn has made it easier to do automated outreach–you’ve probably noticed. Lemlist also supports LinkedIn (which is key) and you can also use LinkedIn-specific tools like Dripify.

The art of sales

The content matters even more. Just go look at your inbox, and be sad for the people who wrote those lousy subject lines you’ll never open. Maybe open one–is that a service or product something you actually buy or are considering buying? But you’d buy them from someone else, because you were unimpressed by their outreach.

Every prospect, no matter how dire their need, is inundated with messages vying for their attention. Poorly crafted outreach gets lost in the noise. The subject line that doesn’t resonate, the message that lacks clarity, the tone that feels off, the awkward reference to your alma mater’s mascot—all of these mistakes make it easier for the recipient to dismiss your email. Quality cuts through the noise and earns attention.

The way you communicate signals who you are and whether you can be trusted. Sloppy or generic outreach suggests a lack of understanding or care, which undermines your credibility. Even if the recipient acknowledges their problem, they’re less likely to trust you as the person or company to solve it if your initial touchpoint doesn’t inspire confidence.

Worse, your initial outreach often forms the prospect’s first impression of your company. A high-quality message demonstrates professionalism, attention to detail, and respect for the recipient’s time. Conversely, low-quality outreach can damage your reputation before you’ve even had a chance to prove your value. Low quality might mean a very well drafted essay that is simply too long (and thus shows an inherent disrespect for your recipient’s time).

High-quality outreach isn’t just about being polished; it’s about making the recipient’s next step clear and compelling. If your message is confusing, vague, or fails to convey value, you risk leaving even a motivated prospect uncertain about how to proceed.

Rarely are you the only option for solving a prospect’s problem. Even in niche markets, buyers have choices. The quality of your outreach often determines whether you’re seen as the most viable, professional, and effective choice. A competitor with a better message can win even if their solution is technically inferior.

How to do high quality outbound

I’ve worked with a lot of companies on outbound. I have taught a class for a top accelerator for years on how to do quality outbound. I’m always surprised that at least 1/3 of the class continues writing lousy emails after the course. Maybe they don’t want to listen. Maybe I’m a shitty teacher.

Doing outbound well takes specialization–just like running Google ads, live events, or any other sales or marketing channel. You have to be in the weeds on the technical things which change literally week by week. You also have to be great at writing hooks and copy, which is very different than being great at writing. You have to really understand your customers and use their language to communicate with them. You also have to be very very comfortable with failure.

My new project

My new project is running scaled outbound for companies. We’re calling it Skyp (won out over “founder sales” but just barely. One founder I talked with about it called it “rifle shots, not scattershot”. I think there’s a revolution coming in how outreach is done; people are starting to use the term “micro campaigns”. That’s what we are enabling.

If you…

• Want to get more customers

• Want to have more conversations with potential customers of your choosing

• Want to do that at a fraction of the cost of hiring a BDR or getting them through any other channel

• Want to avoid all of the BDR/SDR drama (hiring, firing, management)

• Want to ensure your team and brand comes across as leaders in the field

• Don’t want to learn the minutia of running email and LinkedIn campaigns

Let me know. Just reply, or fill out this 7-question survey. Our goal is to do this at a cost that is a no-brainer, enabling any founder to try it while also enabling them to grow as big as they need.

And if you’re already using something for this, I’d love to hear more about it–just reply.