Wednesday, February 4, 2026

DemandJen’s Outreach Suggestions [+ Video]


Most gross sales outreach fails. Not as a result of reps aren’t making an attempt exhausting sufficient, however as a result of they’re saying the unsuitable issues on the unsuitable time.

Consumers immediately are bombarded, burned out, and skeptical. And in case you’re considering of hitting them with one other generic gross sales pitch, don’t even attempt.

We chatted with Jen Allen-Knuth, founding father of DemandJen and a powerful voice for gross sales groups who need to cease pitching and begin making large strikes. On this dialog, Jen breaks down why most outbound falls flat, the best way to reframe your messaging to really earn consideration, and why there aren’t any excuses for lazy pitching within the age of AI.

To look at the complete interview, try the video under:

 

This interview is a part of G2’s Business Insights collection. For extra content material like this, subscribe to G2 Tea, a weekly publication with SaaS-y information and leisure.

Contained in the trade with Jen Allen-Knuth

You’ve spent practically twenty years closing enterprise offers. What led you to start out DemandJen, and the way has your frontline expertise formed your strategy to gross sales coaching?

I spent twenty years closing gross sales offers, however I in all probability spent extra time not closing gross sales offers, and that is candidly what triggered me to create DemandJen as a enterprise. 

Once I was promoting, I used to be working for the corporate behind the Challenger sale for a few years. I used to be at all times making an attempt to deal with why our resolution was a greater method. What I ended up discovering was that a whole lot of occasions, whereas the prospect would agree with me that we had been the higher method, they had been really okay with simply adequate. Abruptly, all of these items I discovered in gross sales coaching round objection dealing with and displaying the worth did not actually work when the shopper had determined that good was adequate.

It pressured me to take a look at all the pieces I used to be saying, doing, writing, sending, and facilitating. Typically, I used to be main prospects proper into that valley of established order, or good is sweet sufficient. I labored with a whole lot of gross sales groups throughout my time at Challenger, and I bought to them. I ended up changing into the Chief Evangelist of Challenger. After which I left to work at a tech startup known as Lavender AI, which was centered on chilly e mail. That taught me quite a bit about the best way to open nice conversations and the best way to write for executives. 

I actually empathize with sellers as a result of in case you spend 5 minutes on LinkedIn, you will get 15 totally different opinions about the precise or unsuitable strategy to do one thing. I used to be actually fortunate as a vendor to have distinctive managers, leaders, coaches, and trainers. I am unable to say I ever noticed myself changing into a gross sales coach, however now, in what I do immediately, I am serving to sellers perceive the competitor of the established order. 

I really like that second when a vendor will get it, as a result of I see myself in these footwear. I did not get it for a very long time. And so I get a whole lot of pleasure out of working with folks and serving to them compete extra successfully.

While you’re coaching groups at totally different expertise ranges — from new gross sales growth representatives (SDR) to seasoned enterprise sellers — how do you tailor your strategy?

There are two large issues that I noticed in myself once I would sit in on gross sales coaching classes. 

One, it is important that you’ve got tenure within the room. You can’t are available off the road and simply begin sharing examples not within the firm language. For instance, once I run a workshop on chilly e mail, I’ve sellers choose a goal account, choose the prospect they’d need to attain out to, and write their topic line and chilly e mail. And the explanation for that’s it offers me, as a facilitator, a very deep understanding of what they’re making an attempt to promote and who they’re making an attempt to promote it to, each from an account and persona perspective. So I can are available and tailor the content material to them. 

Tenured reps will eat you alive in case you are available and simply give examples of salespeople promoting to salespeople. I needed to be very conscious about ensuring I really understood the enterprise and what potential obstacles would possibly make it exhausting to promote that exact product to that exact section.

Quantity two is to consider how we behave as people. Anytime somebody involves us and begins telling us all of the issues we’re doing unsuitable and the way ugly our infants are, we get defensive as a result of it feels deeply private. So if I had been to run a coaching workshop, are available and simply tear everyone’s e mail aside, I might in all probability lose the battle of getting them to study as a result of they might be too guarded. As an alternative, I first search to empathize.

For instance, each time I used to jot down a chilly e mail, I might begin it with, “I hope you are properly.” And if I actually thought of why I did that, it is as a result of I felt like I used to be bothering somebody. So I needed to heat them up and add some nicety to start with earlier than I bought to what I needed. It seems a whole lot of sellers suppose like that. So if I are available and I am educating a coaching workshop and I am speaking about that first line of textual content and e mail and I I say, “You are silly for utilizing ‘I hope you are properly’ as a result of everyone does it and also you’re unsuitable,” individuals are gonna defend why it is proper.

As an alternative, I present them screenshots of a purchaser’s inbox and present them what number of of those emails begin with “I hope you are properly.” They’re all chilly emails. Now the query is, do they need to seem like each different chilly e mail within the inbox or not? I am not passing judgment. I am in search of to grasp why a vendor could be doing this within the first place and what new info I may give them that may trigger them to have a unique debate of their thoughts.  

That is an instance of a spot the place we’ve got to be actually conscious that sellers make their cash based mostly on what they are saying, write, and do. We might be guarded if somebody is available in and assaults it.

What are the largest errors you see in trendy gross sales outreach, and what particular modifications ought to gross sales leaders make to maneuver their groups away from these approaches?

It is a tough enterprise, which is why I believe it is an amazing one to be in. It is a exhausting job. 

I will choose three. 

Primary is the general intention of the e-mail. There’s an analogy I exploit quite a bit: When you ever go to a shopping center and also you see these individuals who work within the mall kiosks, they’re at all times promoting hair straighteners or one thing else you by no means go to the mall to purchase.

While you stroll by them, the very last thing on Earth you need is to make eye contact. As a result of when you make eye contact, they’re simply going to pitch their product, and also you don’t want it. So I exploit that analogy with sellers quite a bit. Then I ask them to take a look at their chilly e mail. We are attempting to have the very same dialog that the mall kiosk individual is having, simply within the inbox. Executives do not go to inboxes to learn a bunch of chilly emails, similar to we do not go to the mall to buy at mall kiosks.

The intention of the e-mail issues as a result of if our intention is to inform folks how nice our resolution is, frankly, I do not suppose that could be a salesperson’s job. I believe that’s the job of selling. Will we really need a ton of people simply saying the identical factor advertising and marketing is saying, however in an e mail?

Sellers are inclined to undervalue what they’ve to supply, which is what they learn about the issue. If you consider it, salespeople sit in on conversations day in and day trip. They hear what individuals are challenged with. They hear the other ways corporations are attacking it immediately. The intention of a chilly e mail needs to be to spark a dialog about the issue and to share concepts. That is why executives go to commerce exhibits, why they go to conferences, and why they study on-line.

We may embody a few of that in an e mail. Earlier than we begin pitching the answer, we should always in all probability think about prompting a unique view of the issue. 

Quantity two is less complicated — it is the topic line. For years, we have been taught to have an attention grabbing topic line, which implies we are inclined to do stuff that makes us sound like entrepreneurs. We use first names, “game-changing ” and “revolutionary,” and the rocket ship emoji. All that tells the reader is that they do not even need to open the e-mail; they know what that is.

There are two go-tos that I like right here. One in every of them is inner camo, the place you choose the one to 2 most boring phrases. The instance I give quite a bit is that in case your supervisor wanted you to replace your forecast, they might by no means ship you a topic line that claims, “Enhance your forecast accuracy with Salesforce.com!” They’d simply say, “Replace forecast.” And so a part of the thought is wanting like we belong within the inbox.

The second topic line framework I like is the CEO remark topic line. Not as a result of the topic line itself is so horny, it is simply taking the title of the CEO and including feedback, however relatively as a result of it forces me, as the author, to spotlight one thing the CEO stated that backs up what I consider is an issue speculation. So, I exploit this instance quite a bit — when Vanta bought their final spherical of funding, within the announcement, they talked about how they might be utilizing a few of that funding to deliberately transfer up the market and put money into extra AI tooling. If I had been to attempt to be a magnet for a CRO, a method to try this could be to say, “The CEO spoke concerning the transfer up the market.” I haven’t got to over-narrate the scenario. I can simply get to the purpose.

Quantity three, I might say, is the toughest one, and the explanation why it is in all probability one of the vital efficient is tonality. I learn emails on a regular basis. Each workshop I do, I learn tons of of emails, and I learn them manually for a purpose: as a result of you can begin to acknowledge patterns. I believe we have been taught as salespeople to come back in and present somebody the place they’re unsuitable. But when we take into consideration that, as human beings, as we talked about earlier than, it is very, very undesirable to have somebody you do not know present up and let you know how messy your own home is. And so what I try for is one thing known as not sure tonality. 

Not sure tonality signifies that anytime I discuss their enterprise, I’m an outsider wanting in, irrespective of how a lot analysis I’ve completed. I am utilizing intentional phrases like “undecided if,” “looks like perhaps,” “appropriate me if I am unsuitable,” and “however” as a result of what I am making an attempt to do is spark the human want to appropriate. If I say, “I like your shirt, it should be from Abercrombie,” and it isn’t from Abercrombie, the very first thing you are going to do is be like, “Thanks, nevertheless it’s really from this place.” It is like an irresistible urge we’ve got as human beings. So we do not have to be excellent; we simply need to be particular and use not sure tonality to open up the will to be corrected. So I might say these three issues, the intention of your e mail, the topic line, and the tonality of your e mail, are the three greatest issues I might deal with first.

What makes a message genuinely compelling sufficient to earn a reply in immediately’s crowded inbox?

There’s been a whole lot of dialog up to now few years round personalization. And personalization is likely one of the most complicated phrases. It’s complicated in gross sales as a result of it means one thing very totally different to totally different folks. 

If I needed to choose one phrase, it is relevance. It’s displaying up, displaying that you’ve got a legitimate purpose for contacting them. 

Once I used to undergo my territory, I might determine the largest corporations with the largest gross sales groups and assume they might be the largest offers with the best want. That is unnecessary. In the event that they’re primary of their market and so they’re outperforming all of their rivals, they in all probability do not understand that they want gross sales coaching. After we goal for relevance, we’re making an attempt to indicate the reader that they don’t seem to be somebody on an inventory of a thousand names and titles that we’ve given zero thought to. As an alternative, we’re being very respectful of their time by attending to the rattling level up entrance after which bringing to the floor not my resolution, however concepts. 

How many people like watching commercials? How many people love a gross sales pitch? Only a few of us. It goes again to the intention of the e-mail: to share concepts, assist create an consciousness of the issue, and determine potential underappreciated root causes. After which within the dialog, if it warrants taking a look at an answer, to me, that is the time to speak a couple of resolution. I believe we simply need to be very actual about the truth that patrons are studying on their very own. 

If I get an e mail from G2 and I am residing beneath a rock and do not know what G2 does, I can go to G2’s web site and determine it out. Now I am on a studying journey. Now I am seeing your content material. That is why the usual method of taking a look at chilly e mail might be why lots of people suppose chilly e mail is useless.

I am excited about listening to a bit extra concerning the rumor that chilly outreach is useless. That will get thrown round quite a bit. Whether or not you are in gross sales or not, you’ve most certainly heard somebody declare that chilly outreach is useless. Is it actually?

Nothing is useless! I believe it’s wild to have such a finite variety of channels that we are able to use to succeed in clients after which proclaim that anyone of them is useless as a result of we’re not good at it, or it did not work for us. 

We will not write for our personal preferences. We’ve got to jot down recognizing that some individuals are going to select up the telephone, verify their emails, and go on social media, and a few aren’t. So we should always pay zero consideration to any of this clickbait nonsense that one thing is useless. 

The rationale folks like to say it is useless is as a result of there was analysis Salesloft did a few years in the past. It reported that 96% of gross sales emails are automated, and everyone primarily will get the identical message. I do suppose that is useless. I do not suppose anyone likes to be handled as a quantity, notably once we reside in a day and age the place it is really easy and environment friendly to analysis the individual you are reaching out to.

What function ought to advertising and marketing play in shaping outbound messages that construct belief? How can entrepreneurs and sellers higher align?

I’ve many sturdy opinions on this one. I believe we are inclined to templatize all the pieces in gross sales. I’ve labored with many corporations the place advertising and marketing palms over a set of templates to ship out. Anytime you employ a template the place somebody simply fills within the clean, what you find yourself with is a watered-down model of one thing that no person desires to learn. You are exchanging high quality for effectivity. 

Advertising groups are sometimes sitting on all of this buyer perception. They’re sitting in and understanding from the product staff what issues this resolution was constructed to deal with. As salespeople, we sit over right here on the receiving finish, ready for some good concepts. A whole lot of sellers are hungry for conversations the place we’re not speaking a lot concerning the product, however understanding the professionals and cons of various options to our resolution. Your common performer isn’t going to take that additional analysis time; they’ll observe the directions as a result of following directions is basically what we message. When it would not work, now the place are we?

Advertising, gross sales, and product needs to be collectively in a room, eager about what clients do not perceive about the issue we resolve. What are the totally different ways in which corporations resolve this drawback with out us? What are the professionals and cons? Then, you’ll be able to develop extra point-of-view content material, which is arguably extra partaking.

As purchaser conduct evolves and instruments like AI and automation turn out to be the norm, how do you see outbound altering, and what can groups do to make sure their outreach stays human, related, and efficient?

There’s at all times been one large excuse as to why folks do not write related outbound: it takes too lengthy to do the analysis. Each vendor has stated it in some unspecified time in the future of their profession. I do know I’ve stated it. The factor that excites me most about AI is that it removes that excuse. 

If I am working with a staff that is promoting into enterprise, you will have a very exhausting time being profitable in case you’re simply spamming your prospects and hoping that quantity will hit a quantity. It is arguably much more essential in that enterprise to be sure to have a related message. I can go in now and ask AI to assist me make sense of what a enterprise does, which helps me contextualize the issue we are able to resolve for them. So I am not writing with no clue what’s essential to the executives. I can go in and say, “Who’s the CEO, and what are their greatest progress priorities for the yr?” 

All of these items eradicate the excuse of “I simply do not have time to do the analysis.” You may get these leads to 90 seconds. If you cannot spend 90 seconds on somebody you’re asking half-hour from, I believe we’re simply within the unsuitable job. So what excites me about AI is that it permits us to do the precise factor.

The second factor that I believe is actually compelling about it’s that it additionally simply makes it simpler for us to have the next degree of confidence in what we write. When you feed it examples of what a great e mail seems like, you’ll be able to ask it to critique your e mail draft. Now we’re not ready on one other human being to have that additional layer of confidence. 

There is a ton of use circumstances, however the place the place we are inclined to go as people is to hit the straightforward button. We did it with gross sales engagement platforms, we do it with all the pieces. So that is the hazard. Might it write emails for you? Sure. Is it gonna create an amazing product? Completely not. So do the precise issues, even when they take just a little bit longer. You select your “exhausting” in gross sales. Both do the exhausting work upfront, or pay the exhausting work ultimately.

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Comply with Jen Allen-Knuth on LinkedIn to study extra about DemandJen’s gross sales coaching workshops and her ideas for defeating purchaser established order.

Edited by Supanna Das



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