DemandJen’s Outreach Tips [+ Video]

You’ve spent nearly two decades closing enterprise deals. What led you to start DemandJen, and how has your frontline experience shaped your approach to sales training?

I spent two decades closing sales deals, but I probably spent more time not closing sales deals, and that’s candidly what caused me to create DemandJen as a business. 

When I was selling, I was working for the company behind the Challenger sale for many years. I was always trying to focus on why our solution was a better way. What I ended up finding was that a lot of times, while the prospect would agree with me that we were the better way, they were actually okay with just good enough. Suddenly, all of these things I learned in sales training around objection handling and showing the value didn’t really work when the customer had decided that good was good enough.

What are the biggest mistakes you see in modern sales outreach, and what specific changes should sales leaders make to move their teams away from these approaches?

It’s a tricky business, which is why I think it’s a great one to be in. It’s a hard job. 

I’ll pick three. 

Number one is the overall intention of the email. There’s an analogy I use a lot: If you ever go to a shopping mall and you see those people who work in the mall kiosks, they’re always selling hair straighteners or something else you never go to the mall to buy.

When you walk by them, the last thing on Earth you want is to make eye contact. Because once you make eye contact, they’re just going to pitch their product, and you don’t need it. So I use that analogy with sellers a lot. Then I ask them to look at their cold email. We are trying to have the exact same conversation that the mall kiosk person is having, just in the inbox. Executives don’t go to inboxes to read a bunch of cold emails, just like we don’t go to the mall to shop at mall kiosks.

The intention of the email matters because if our intention is to tell people how great our solution is, frankly, I don’t think that is a salesperson’s job. I think that is the job of marketing. Do we actually need a ton of humans just saying the same thing marketing is saying, but in an email?

Sellers tend to undervalue what they have to offer, which is what they know about the problem. If you think about it, salespeople sit in on conversations day in and day out. They hear what people are challenged with. They hear the different ways companies are attacking it today. The intention of a cold email should be to spark a conversation about the problem and to share ideas. That’s why executives go to trade shows, why they go to conferences, and why they learn online.

We could include some of that in an email. Before we start pitching the solution, we should probably consider prompting a different view of the problem. 

Number two is easier — it’s the subject line. For years, we’ve been taught to have an eye-catching subject line, which means we tend to do stuff that makes us sound like marketers. We use first names, “game-changing ” and “revolutionary,” and the rocket ship emoji. All that tells the reader is that they don’t even have to open the email; they know what this is.

There are two go-tos that I like here. One of them is internal camo, where you pick the one to two most boring words. The example I give a lot is that if your manager needed you to update your forecast, they would never send you a subject line that says, “Improve your forecast accuracy with Salesforce.com!” They would just say, “Update forecast.” And so part of the idea is looking like we belong in the inbox.

The second subject line framework I like is the CEO comment subject line. Not because the subject line itself is so sexy, it’s just taking the name of the CEO and adding comments, but rather because it forces me, as the writer, to highlight something the CEO said that backs up what I believe is a problem hypothesis. So, I use this example a lot — when Vanta got their last round of funding, in the announcement, they talked about how they would be using some of that funding to intentionally move up the market and invest in more AI tooling. If I were to try to catch the attention of a CRO, one way to do that would be to say, “The CEO spoke about the move up the market.” I don’t have to over-narrate the situation. I can just get to the point.

Number three, I would say, is the hardest one, and the reason why it’s probably one of the most effective is tonality. I read emails all the time. Every workshop I do, I read hundreds of emails, and I read them manually for a reason: because you can start to recognize patterns. I think we’ve been taught as salespeople to come in and show someone where they’re wrong. But if we think about that, as human beings, as we talked about before, it’s very, very undesirable to have someone you don’t know show up and tell you how messy your house is. And so what I strive for is something called unsure tonality. 

Unsure tonality means that anytime I talk about their business, I am an outsider looking in, no matter how much research I’ve done. I’m using intentional phrases like “not sure if,” “seems like maybe,” “correct me if I’m wrong,” and “but” because what I’m trying to do is spark the human desire to correct. If I say, “I like your shirt, it must be from Abercrombie,” and it’s not from Abercrombie, the first thing you’re going to do is be like, “Thanks, but it’s actually from this place.” It’s like an irresistible urge we have as human beings. So we don’t have to be perfect; we just have to be specific and use unsure tonality to open up the desire to be corrected. So I would say those three things, the intention of your email, the subject line, and the tonality of your email, are the three biggest things I would focus on first.

What makes a message genuinely compelling enough to earn a reply in today’s crowded inbox?

There’s been a lot of conversation in the past few years around personalization. And personalization is one of the most confusing terms. It’s confusing in sales because it means something very different to different people. 

If I had to pick one word, it’s relevance. It is showing up, showing that you have a valid reason for contacting them. 

When I used to go through my territory, I would identify the biggest companies with the biggest sales teams and assume they would be the biggest deals with the greatest need. That makes no sense. If they’re number one in their market and they’re outperforming all of their competitors, they probably don’t perceive that they need sales training. When we aim for relevance, we’re trying to show the reader that they are not someone on a list of a thousand names and titles that we’ve given zero thought to. Instead, we are being very respectful of their time by getting to the damn point up front and then bringing to the surface not my solution, but ideas. 

How many of us like watching commercials? How many of us love a sales pitch? Very few of us. It goes back to the intention of the email: to share ideas, help create an awareness of the problem, and identify potential underappreciated root causes. And then in the conversation, if it warrants looking at a solution, to me, that’s the time to talk about a solution. I think we just have to be very real about the fact that buyers are learning on their own. 

If I get an email from G2 and I’m living under a rock and don’t know what G2 does, I can go to G2’s website and figure it out. Now I’m on a learning journey. Now I’m seeing your content. That’s why the standard way of looking at cold email is probably why a lot of people think cold email is dead.

I’m interested in hearing a bit more about the rumor that cold outreach is dead. That gets thrown around a lot. Whether you’re in sales or not, you’ve most likely heard someone claim that cold outreach is dead. Is it really?

Nothing is dead! I think it is wild to have such a finite number of channels that we can use to reach customers and then proclaim that any one of them is dead because we’re not good at it, or it didn’t work for us. 

We can’t write for our own preferences. We have to write recognizing that some people are going to pick up the phone, check their emails, and go on social media, and some aren’t. So we should pay zero attention to any of this clickbait nonsense that something is dead. 

The reason people love to say it’s dead is because there was research Salesloft did a couple of years ago. It reported that 96% of sales emails are automated, and everybody essentially gets the same message. I do think that’s dead. I don’t think anybody likes to be treated as a number, particularly when we live in a day and age where it’s so easy and efficient to research the person you’re reaching out to.

What role should marketing play in shaping outbound messages that build trust? How can marketers and sellers better align?

I have many strong opinions on this one. I think we tend to templatize everything in sales. I’ve worked with many companies where marketing hands over a set of templates to send out. Anytime you use a template where someone just fills in the blank, what you end up with is a watered-down version of something that nobody wants to read. You’re exchanging quality for efficiency. 

Marketing teams are often sitting on all of this customer insight. They’re sitting in and understanding from the product team what problems this solution was built to address. As salespeople, we sit over here on the receiving end, waiting for some good ideas. A lot of sellers are hungry for conversations where we’re not talking so much about the product, but understanding the pros and cons of different alternatives to our solution. Your average performer is not going to take that extra research time; they are going to follow the instructions because following instructions is largely what we message. When it doesn’t work, now where are we?

Marketing, sales, and product should be together in a room, thinking about what customers don’t understand about the problem we solve. What are the different ways that companies solve this problem without us? What are the pros and cons? Then, you can develop more point-of-view content, which is arguably more engaging.

As buyer behavior evolves and tools like AI and automation become the norm, how do you see outbound changing, and what can teams do to ensure their outreach stays human, relevant, and effective?

There’s always been one big excuse as to why people don’t write relevant outbound: it takes too long to do the research. Every seller has said it at some point in their career. I know I’ve said it. The thing that excites me most about AI is that it removes that excuse. 

If I’m working with a team that’s selling into enterprise, you’ll have a really hard time being successful if you’re just spamming your prospects and hoping that volume will hit a number. It’s arguably even more important in that enterprise to make sure you have a relevant message. I can go in now and ask AI to help me make sense of what a business does, which helps me contextualize the problem we can solve for them. So I’m not writing with no clue what’s important to the executives. I can go in and say, “Who is the CEO, and what are their biggest growth priorities for the year?” 

All of these things eliminate the excuse of “I just don’t have time to do the research.” You can get these results in 90 seconds. If you can’t spend 90 seconds on someone you are asking 30 minutes from, I think we’re just in the wrong job. So what excites me about AI is that it allows us to do the right thing.

The second thing that I think is really compelling about it is that it also just makes it easier for us to have a higher level of confidence in what we write. If you feed it examples of what a good email looks like, you can ask it to critique your email draft. Now we’re not waiting on another human being to have that extra layer of confidence. 

There’s a ton of use cases, but the place where we tend to go as humans is to hit the easy button. We did it with sales engagement platforms, we do it with everything. So that’s the danger. Could it write emails for you? Yes. Is it gonna create a great product? Absolutely not. So do the right things, even if they take a little bit longer. You choose your “hard” in sales. Either do the hard work upfront, or pay the hard work in the end.