Closing Time

Close More Deals with These Content Marketing Tips for Salespeople

No one wants to receive a “check-in.”

In fact, it might be the worst follow-up email to send (or receive).

No value. No update. No bueno.

Instead of the same tired cadence, the most effective salespeople leverage content marketing resources – like blogs, articles, press releases, reports, podcasts, videos, and more – throughout the various stages of the sales cycle to provide value, generate interest, and capture demand.

By utilizing content marketing resources effectively, sales reps can differentiate themselves from competitors and maintain meaningful engagement with buyers. Instead of merely reminding the prospect of their existence, they offer valuable information that addresses the prospect’s concerns and helps move the sales process forward.

In this episode of Closing Time, Jay Baer discusses the latest tips and trends in content marketing and shares proven content marketing tips for salespeople so that every email, call, and text you send also makes your prospective customers better, smarter, and more ready to buy.

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Key Moments:
Never just "check-in" in prospects

Buyers don’t want to feel like they’re being pursued solely for a purchase. Instead, they seek value and a seamless acquisition process. Unfortunately, many sellers and go-to-market specialists often fall into the trap of automated communication, where they send generic emails or messages just because the software prompts them to do so.

By “just checking in,” reps may give the impression to the potential customer that they have neglected the salesperson and the ongoing sales process. However, it is improbable that the prospect has actually forgotten. There is always a specific reason why they have not replied, and it is essential for sales representatives to identify and confront that reason.

Rather than resorting to a simple “checking in” message, sales reps should leverage content marketing resources to provide value to the buyers. By understanding the buyer’s needs, challenges, and preferences, sales reps can curate relevant and informative content that resonates with the prospect’s interests. This content could be in the form of educational articles, industry insights, case studies, or success stories.

When sales reps provide valuable content, they demonstrate their expertise and show that they genuinely understand the buyer’s world. This approach helps build trust and positions the sales rep as a trusted advisor rather than a pushy salesperson. The content serves as a touchpoint that keeps the sales process alive without being intrusive or annoying to the prospect.

Bring value to every interaction

The challenge of providing continuous value to prospective buyers becomes even more crucial as we move from sales to marketing to customer success. When reaching out to buyers, it’s essential to demonstrate that effort has been invested in understanding their needs and interests.

Why would anyone send something to a client or prospective client that lacks value? It’s worth pondering the argument behind such a choice. In the postal community, we term such unappealing content as junk mail. When we receive something in our mailbox that holds no value for us, we promptly discard it. However, the digital realm, encompassing emails, LinkedIn messages, or text messages, seems to have lowered the bar for content standards. We mistakenly believe that these digital communications don’t require the same level of value. This perspective is a grave error.

Go-to-market leaders should aspire to establish a program and process where anyone interacting with customers or prospects, be it sales, marketing, or customer support, has access to a repository of value-rich resources. These resources can be drawn upon and shared alongside the message, ensuring that it never becomes a mere “checking in” routine.

Instead, the message should offer something remarkable that the recipient would appreciate. By providing value, the client or prospective client will naturally connect the dots and recognize any pending matters, such as an overdue contract, without explicitly mentioning it. The focus should always be on delivering value and allowing the recipient to make relevant connections.

How salespeople can leverage marketing content

Sales reps must proactively explore and familiarize themselves with the marketing assets at their disposal. On the other hand, marketing teams should also strive to understand the specific format and level of usefulness required by sales. A salesperson, unless deep into the consideration funnel, wouldn’t send a lengthy recorded webinar to a prospect. It’s like asking someone to devour a four-foot sandwich in one sitting – simply too much to handle.

This is where marketing can step in and improve by breaking down their assets into bite-sized chunks that clients or prospects can consume in three minutes or less. Marketers should excel at communication and should be adept at creating content that is easily digestible and impactful. This applies not only to external communication but also to internal alignment. If marketing can’t get the sales team excited and inspired by their content execution, how can customers be enthusiastic about it?

It’s crucial to start from the inside out. Jay recalls when he and Chip worked together at ExactTarget, specifically on the “Subscribers, Fans & Followers” series. One of the valuable lessons they learned was the importance of giving the content to the sales team before sharing it with customers. When the sales team is genuinely excited, the impact on clients is remarkable. Sales gets the first taste, and that initial enthusiasm creates a ripple effect, generating more enthusiasm and adoption among customers.

Do's and don't for email content

When it comes to email optimization, the principles remain the same as in the olden days. An email from a salesperson should be personal, relevant, and anticipated by the recipient. It’s crucial to avoid sending emails that simply say “just checking in” without providing any valuable information. Equally ineffective is sending generic content that you assume applies to all customers. While it’s better than nothing, it still lacks relevance.

The ideal approach is to identify a specific piece of micro-content that is uniquely valuable to a particular prospect. By tailoring the content to their specific needs and interests, you ensure its relevance and increase the chances of engagement. It’s fascinating to see how the marketing landscape has shifted. In Jay’s 30-year career, the goal was always to reach the largest possible audience. However, now we understand that a broad approach is flawed.

Today, the focus is on reaching as few people as possible with the perfect message. With the rise of account-based marketing and one-to-one B2B strategies, we have the tools and capabilities to treat each prospective customer as an audience of one. This shift in attitude is crucial, and it’s essential for go-to-market teams to understand the importance of delivering useful, personalized content to each individual prospect.

Mapping content to the customer joruney

Research has shown that different individuals prefer different content formats at different points in the journey. This is especially relevant in today’s multi-generational market, where sales teams interact with boomers, Gen X, millennials, and even Gen Z. Understanding the content format preferences of these different generations is crucial for effective communication.

For instance, there is a need to reconsider the overreliance on email, especially considering that younger generations may perceive it as overwhelming or burdensome. The New York Times conducted research where college students expressed feeling overwhelmed by emails, likening them to being stabbed.

By diversifying the content formats and utilizing mediums such as video, sales teams can tailor their approach to specific generational preferences or early funnel stages. It’s not solely about generating content; it’s about choosing the appropriate medium to effectively connect with the audience.

Implementing a CRM system, like Insightly, can help track prospect preferences from the early stages of the relationship. By providing content in different formats and observing prospect interactions, such as which format they engage with the most, sales reps can gain insights into their content preferences. These preferences can then be logged in the CRM, allowing for personalized future interactions based on their preferred format.


Just say no to the no content check in. We’re exploring adding value in your sales touch points on this episode of Closing Time. Hey everyone, and welcome to this episode of Closing Time. My name is Chip House CMO at Insightly. This is Closing Time, the show for go-to-market leaders. And I’m joined today by Jay Baer. Jay’s been called the world’s most inspirational customer experience and marketing keynote speaker. He’s the author of six bestselling books, a seventh generation entrepreneur and the founder of five multimillion dollar companies. Plus, he’s a certified Tequila sommalier and a lover of all things plaid. Welcome, Jay. Thank you, Chip. Fantastic to be on Closing Time. So, Jay, like many things in go-to-market, nobody wants to be a buyer when the salesperson is just emailing or calling for a check in. Right. So what’s your perspective? Yeah, I mean, nobody wants to buy. People want to have. Right. They prefer to skip the buying process entirely and just have the thing that they are trying to acquire. And the challenge is so often sellers and go-to-market specialists are almost on autopilot or frankly are on autopilot because the software says it’s time to send a note to the prospect. and so they send it out in the email and many times it’s an email or it might be a LinkedIn message or some such, but it essentially says, hey, knock, knock, knock. Do you remember that. I’m trying to get ahold of you? The ramifications of that are what you’re essentially saying to the prospect is, “Prospect, you’ve probably forgotten that I’m trying to sell to you.” And there is no way that’s true. And it’s not possible. They have not forgotten that you exist. They have not forgotten the deal. They have not. Like, I don’t know what happened.. I went on vacation. I forgot we were in the middle of this contract negotiation. It has nothing to do with their memory of your existence. There is some other reason they have put you on pause in sending an email or any other kind of touchpoint which just says checking in does nothing to solve that problem. All it does is annoy them. And the problem probably even gets more heightened downstream, doesn’t it, Jay? Right. When you’re moving from sales to marketing to customer success, when the outreach happens, right? There has to be some value or making it at least appear like you’ve done some work for the buyer. Yeah. I mean, look what is the argument that you should ever send something to a client or a prospective client that doesn’t contain value? I would love to know what the argument is. That that’s a good idea, right? We call that in the postal community, we call that junk mail, do we not? If you get something in your mailbox that doesn’t have value to you, you call it junk mail. And what do you do with it? You throw it away. You throw it away. Right. You throw it away. Right. And so but yet because it’s digital, because it’s an email message, or a LinkedIn message or a text message or whatever message, we don’t feel like it has to meet that same standard. And I think that’s a huge mistake. So what all go-to-market leaders should be striving for is a program and a process by which whomever it is that’s interacting with the customer or prospect, sales, marketing, customer support doesn’t matter. Any time anybody in your organization is interacting with a customer prospect, they should have a repository of value that they can draw from and send with that message. So the message is never just checking in. It’s, Hey, here’s an awesome thing I think you’d like. The client or prospective client will figure out, Oh yeah, we are overdue on that contract. You don’t need to tell them that. Just give them value and then let them connect the dots. Yeah. Makes good sense. And so what’s the solution there, Jay? Is it just engaging with the content that the marketing team has sent your way? Yes. Partially, Chip. I mean, it is disheartening to me how often salespersons are frankly not aware of what marketing has made. Right. And they say to marketing, hey, do we have something that I can send this prospect about topic X and marketing is like,. Yeah, bro, we’ve got like 14 white papers and three webinars and six podcasts on that topic and salesperson’s like, oh,. I had no idea. That drives me crazy. Right. To some degree,. I think sales does not work hard enough to really roll around in the marketing assets that exist by the same token, however, marketing is not very good in many cases at understanding the format of, of helpfulness and usefulness that sales actually needs a salesperson is not, unless it’s really, really deep in the consideration funnel, is not going to send a full length recorded webinar to a prospect. It’s like, hey, eat a four foot sandwich today, right? You’re like, what? Too much, right? So marketing’s got to get a lot better at taking their assets and breaking them down into small chunks that the client or prospect can consume in 3 minutes or less. This is what marketers are supposed to be good at. Right, Jay? I mean, we’re supposed to be good at communication. And the communication is not just to customers and potential customers. It’s also internally, frankly. Right. First, right. If you can’t get your own sales team locked and loaded and fired up and inspired by your content execution, why would customers be excited about it? Right. It starts at the inside out. In fact, when you and I work together at ExactTarget years and years and years ago, on Subscribers, Fans, & Followers series, that’s one of the things I think we really, really learned in that program was before you ever give it to a customer, make sure you give it to the sales team first. Get them super excited about it, and then once they’re excited, it’s amazing, then how much more lift it gets from the sales team when they take it to clients. Because sales got the first sort of bite of the apple. Jay, I’m glad that you brought up email in the olden days because to optimize an email, we used to talk about having to send an email that’s personal, it’s relevant, and it’s anticipated by the recipient. And so it’s no different for a salesperson, right? Yeah. I mean, look the worst thing to do is send an email that doesn’t say anything other than just checking it. Second worst thing to do is to send an email with some “content” that you think applies to all customers. Right? This is a thing that exists. That’s better than nothing, but it’s still not relevant. Obviously, the best approach is to say this particular piece of information or content, kind of micro content is really only of interest to this particular prospect. So I want to make sure that they get it. We’re at a place in marketing where Broad is flawed, and I find that fascinating because I’ve been doing this for 30 years and for almost the entirety of my career, it was the exact opposite. The goal of marketing was to reach as large of a potential addressable audience as possible. How many people can we reach? And now that is the wrong question to ask it. It’s how few people can we reach with the perfect message and all of the account based marketing trends and all of those kind of true one to one B2B marketing, it’s all possible now. But a lot of it is attitudinal, is making sure your go-to-market teams understand we have to treat each prospective customer as an audience of one and give them useful content accordingly. So one of the things that we didn’t think about, frankly, I don’t think in the olden days was the relevance around where the customer is in their journey with our organization. Right. And I mean, what’s your perspective on that and what the content marketing folks can do about that to help their sales team do a better job? Yeah, it’s one of the things that my consulting firm. Convince & Convert does with enterprise brands a lot, mostly in B2B, is to say, let’s map not just topics to funnel stage and sort of customer journey, but also modality to customer journey. So if you’re early in your consideration process, you’re going to prefer your content assets to be things like videos or articles or maybe even checklists as you get further down, you’re more interested in things like case studies and reports and configurators. And so you have to to tweak the format of what you’re giving your go-to-market team based on where that particular customer is and how close they are to actually making a purchase. There’s a lot of interesting research on this as well that illustrates how different people prefer different content at a different point of the journey. Furthermore, Chip, as we’re now in a really, truly a multi-generational go-to-market environment where you’re selling to boomers, you’re selling to Gen X, you’re selling to millennials, and in some cases you’re selling to Gen Z. They have very different preferences for content format. We’re talking about email, the New York. Times, did this amazing research last year where they interviewed college students about email marketing and sort of email in general. And I remember it vividly. One of the quotes from a college student was, “every time I receive an email, it feels like I’m being stabbed, it’s just another thing to do.” And that’s amazing, right? But we are so reliant on email in a lot of B2B go-to-market environments and maybe we should rethink that at least at some level. Right? So it’s not just about generating content, it’s about picking the right medium as a go-to-market team to really engage the people you’re trying to sell. And if it’s Gen Z, maybe you need more video. Precisely or even earlier in the funnel stage, more video, even if it’s not Gen Z, one of the things that I would want to use Insightly for is, to track that as early in the relationship as possible. You can give a prospect content in different formats. Here’s the article, here’s the video, here’s the puppet show of the same thing, and then you see which one they actually interact with. And you log in the CRM. This person is pro puppet show and then every time that you interact with them thereafter, it’s a puppet show because they’ve basically told you with their behavior, what content format you like. That’s not that hard. But yet very few people do it. You know, I have to say, Jay, as you know, we’re doing video. It’s kind of meta. We’re doing it right now, but we are not doing any puppet shows at the time. That’ll be Closing Time 2.0. Will be a series of puppet shows about go-to-market excellence. I can’t wait. Exactly. Well, Jay, do you have any final thoughts on how sales people can make the most out of the content? Yeah, I mean, two things. One, be really good about interacting with marketing and saying we love that you did this 37 page report, but can I have that in ten two paragraph chunks, right? Taking your big assets and atomizing them into small assets. That’s really the key here. And then making sure that you’re being as relevant, personalized and customized as possible when you’re associating those content snacks with the outreach. Snackable content. You heard it from Jay Baer. Thanks again, Jay. My pleasure. Great to see you. Yeah, and thanks to all of you for watching today’s episode of Closing Time, the show for go-to-market leaders. Just tick the subscribe button, then click the bell so you don’t miss any episodes and we’ll see you next time.

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