Brennan Dunn: Scaling Relevance – to Infinity and Beyond

“When you speak to everyone, you speak to no one.“

Seth Godin

Sales teams understand the significance of tailoring their communication to the specific individuals they interact with. They adapt their approach based on the person’s behavior, objectives, and other relevant factors. By doing so effectively, they ensure that their offerings resonate with the intended recipient, and any potential objections are addressed proactively.

However, applying this approach becomes challenging when it comes to “broadcast” marketing, such as websites, email campaigns, and social media. In these cases, we often take a broad approach, defining our ideal customer and their needs and motivations. Unfortunately, this strategy not only risks alienating individuals who don’t perfectly fit that profile but also places the burden on potential buyers to figure out how our product or service can benefit them.

In this talk from BoS Europe, Brennan demonstrates how both B2B and B2C companies are dynamically repositioning their offerings and achieving tangible results. They employ behavioural research, customer insights, and data-driven research to deliver the right messages to the right people at precisely the right moments. Through Brennan’s insights, you will discover how to implement these strategies and start achieving similar outcomes, regardless of the size of your company.

Slides

Transcript

Brennan Dunn
Thank you. Good morning. It’s good to be back.

So a few years back in the olden days, I was at another software conference this time it was in Las Vegas, not Cambridge, which, if you’ve ever been is slightly different than Cambridge. And after, after the day, after all the talks, some friends and I were going out in search of food. So we’re walking up the Las Vegas Strip. And, again, I don’t know how many of you have been there, so forgive me if I indulge. But there’s a lot of people hocking for your attention, who want you to do certain things. And I remember I’m walking with these friends to dinner. And somebody says, hey, for people in blue T shirts with tan shorts, half off tonight, admission to our nightclub. And just hazard a guess what I was wearing was a blue t shirt with tan shorts. And yes, that’s gimmicky. That obviously didn’t work, I didn’t end up going to this gentleman’s nightclub. I think it’s, you know, this idea of being able to send more relevant messages that get people’s attention that get them consuming what we have to offer, and ultimately clicking that big Buy Now button is probably what most of us want, yet practically speaking, this thing of send the right message to the right person the right time. Well, what does that actually mean in terms of doing something? So that’s what I’m going to explore today. In, in this talk.

So, it’s hard to give up something that’s working. And in 2017, I had a very nice gig going on; my business, it was called or is called still Double Your Freelancing. And in the previous year, it spun off about 700,000 in revenue, 95% of which was personal profit. I worked part time on this business. And it did really, really well. But like many of us here, I was bit by the software bug, I was kind of tired of peddling PDFs and video courses, and I wanted to sell actual software. So I decided to do the startup thing. I recruited a technical co founder, we raised money, we hired a team. And like many new founders, I did the whole, I’m not going to pay myself much of anything thing, which was, frankly a little difficult. I had a mortgage, I had a lot of expenses, and I had a pretty nice lifestyle that I was coming out of. So the thing that I want to talk about is how I was able to make this transition safely without affecting my personal finances. And the secret/the trick that that allowed me to make this this move was that I had brought on an incredible business partner to run Double Your Freelancing day to day while I went out and did this risky new startup that had no customers and, you know, burn rate that was slowly chipping away at the business bank account.

So this partner that I brought on, was the most incredible hire ever. They worked nonstop, they never called in sick. They handled all the email campaigns and setting up all the stuff for me. They handled all the sales promos, they did market research for me, they did ongoing customer kind of development, and they even proactively followed up with non buyers to find out, you know, what held you back and why you buy and try to rescue the sale. Incredibly, their salary, or what I paid them was very humble $369 a month. And this partner – surprise, surprise – was my email marketing platform. So that’s what I’m going to talk about today is what allowed me to do this was that before I left this very profitable business, I wanted to put into place a system that not only would keep selling and keep the lights on, but also do it in such a way that was highly personal, which involves segmentation data, which involved really prying and trying to figure out what is this unique person wanting and how can we best serve them and that allow helped me to make this transition so that I can go and build this new company called Right Message in a way, that allowed me to, frankly, keep living the way I had, even though I was living off of ramen profitability with this new venture.

Before I get into the details of the system, I want to talk more hypothetically, about the distinction between sales teams and marketing teams. And specifically, what do sales people do that most of us who do marketing, whatever that might mean, aren’t doing. So if you look at kind of the typical thing that a marketer for a traditional SaaS might do, it might look something like this. So you set up a bunch of landing pages, and you have different channels that bring people to these pages. And the goal of these landing pages is to get somebody to give up their name and email address in exchange for some sort of lead magnet. So we did the whole, like, you know, Seth Godin-y, lets build or build an audience. And then over time, we’ll get that audience to buy from us. So we get them in with a lead magnet, maybe it’s a free report, or some sort of, I don’t know, worksheet or white paper or whatever else. And then over time, we deliver welcome emails, we deliver long term nurturing emails, and these emails, bring people piecemeal back to our website, maybe to a case study brings them hopefully, to the pricing page. Hopefully, they go and sign up for a trial. And we build the systems that are designed to capture somebody to turn a drive by visitor to a landing page to a blog article to whatever, and get them into our audience. And then over time, slowly turn them into hopefully, a new customer. So this is the ideal, and I’m sure many of us have done something like this, when it comes to how we go about selling what it is we have to sell.

Now, in terms of attributes of this system I just outlined, one big attribute is that this is more or less static. Yes, you might stick somebody’s first name at the top of all the emails you’re sending them. But for the most part, if all of us in this room were to go and opt in to say the same lead magnet, we would all probably get the same information and messaging sent to us, we get the same emails, we get the same, you know, case study sent and so on and so forth, regardless of who we are, or what it is we uniquely are looking for, from potentially this company.

Secondly, these tend to be monologues, so it’s me to you or us to them. And while this is okay. The fact of the matter is, it’s not very interactive. So people are on the receiving end of our email communication. They’re consuming our sales pages, they’re looking at our Feature Overviews, and so on and so forth. But it’s not tends to be very read only. And finally, this is baseline, it’s a common denominator. So what we need to do is when we have a wide audience of different types of buyers, maybe across different industries, and so on, we tend to need to cast a pretty wide net, where we want to make sure we’re not excluding anyone. So we kind of dumbed down our language and try to make it as appealing as possible for all the different types of people who might end up buying from us. Now compare this to what might happen with an interaction with a really great salesperson. So let’s say somebody says, you know, I’m curious about what it is you have to offer. good salesperson is going to jump into listening mode and start asking questions about Yeah, so tell me about what you’re looking for. Tell me about who you are. And what they’re going to do is they’re going to piece together contextual clues. So who referred this person? What industry? Are they in? What’s their job role at this company? How technical are they? And all of this is going to get pretty much merged on the fly with the inputs that they’re receiving. So this is what I’m struggling with. I hear you I’m empathising with what you’re going through. Here’s some ways that you can potentially solve this problem or remove the issue. And even when curveballs come like, Oh, I’ve got this really unique issue and I’m not actually sure can be solved or I don’t think you can potentially help you with it. A really great salesperson is going to really demonstrate that they are listening, and that they do understand, you know, the the lived experience of this person, and that they’re going to use that to really take what it is they have to offer and apply it in a way that makes perfect sense.

So really, if you think about it, sales is just alignment: We have something that we’re offering. We have a product, we have a service, this is your unique problems. These This is the world view that you have here sell, but we have matches perfectly with what you need. So this is what’s happening when a one to one kind of sale discussion, if you will, is happening, this is fluid, this is something that is kind of organic, it’s happening in real time. It’s responsive all future, you know, benefits touted or examples given and so on. Always take into account, usually on the fly. I mean, a lot of us when we’re selling are, you know, we have a mental script that we’re working through, but we’re just kind of thinking, Okay, well, this person is really technical. So I’m going to speak about our product maybe differently to them than somebody who might not be technical, or this person is in finance. So I’m going to drop names and stuff of finance companies that we’ve helped in the past, because people ultimately want to see themselves in the product.

And ultimately, this is relevant. So the signal to noise ratio is exceptionally high. You know, I’m not touting benefits that I don’t think this person might care about. I’m not getting into potential objections that I think, don’t really apply her. And so a good salesperson is going to always be thinking, How do I listen and observe the different listen to what somebody’s telling me and observe any behavioural cues that they’re giving me and use this to kind of effect or modify this standard pitch that I have. So this is what happens, you know, day in and day out with a really good sales team.

Now, the big distinction, though, is that can’t really sell scale sales teams that easily, right. You know, while it’s highly personalised, which means it’s highly relevant, tends to be low volume, you know, a salesperson can concurrently do this to 1000 people at any given time. Whereas the marketing team, you know, their whole thing tends to be volume, we’ve got this many people entering the funnel, and, you know, they’re talking in higher volume, but with more static messaging, if that makes sense. So there’s this kind of dichotomy of, on the one end, you have highly personalised, highly relevant messaging being used, that doesn’t really scale. And then on the other end, you have more diluted one size fits all messaging that is intended to, you know, whether it’s being received by one person, or 10,000, doesn’t really matter. And in the world of marketing technology, and just trends around what it is software companies like us are doing, you’re starting to see exploration of this middle ground. So you have companies I mean, how many of us have been to a SaaS website recently, if thing getting to the bottom right corner asking you questions about our pricing? Do you have any, you know, want to learn more, or whatever else, and you see, drift, you see intercom, you see all these different kinds of whether they’re chatbots, or they’re just direct lines to a sales team. You see, this layer of interaction layered on top of static marketing sites.

Now, the big issue that I have with most of these approaches, while they absolutely work, otherwise, people wouldn’t be paying intercoms insane fees, is that these tend to be kind of siloed off to, like I said, at the corner of a website. And what I’m interested in is how do we holistically treat the entire experience somebody has given what queues and what context we have about this person? So how do we affect the emails that they’re getting from us? How do we think about, they’re looking at our pricing page, maybe we want to change the benefits touted or something like that contingent on somebody’s job role. You know, a market as CMO, cares about different things than a CTO would. Same product helps their same organisation. But the things that each of these potential buyers cares about is going to be different, depending on in this case, their job role.

So in this talk, my plan is as follows. I’m going to explain a framework that will allow you to do quite a few different things. But most importantly, will allow you to break free of one size fits all blanket messaging, to start moving towards something a bit more responsive, where you’re looking at who is this unique individual and what is it that they want from us, and then that can then be used to deliver messaging that’s more relevant to them. Because the idea is if somebody gets more relevant messages from you, they’re more likely to read what you’re sending them. They’re more likely to get to the end of it. And like I said, click that buy button and pay you money. So what we’re going to be looking at is what are some ways that we can profile and segment based on identity and need, we’re going to look at how we can facilitate ongoing market research. So basically, how are we going to collect and mine voice of customer data automatically? What can we do to better develop trust, brand recognition and problem and product awareness? And then how are we going to use that to then ultimately deliver personalised pitches for your products or services? And then if somebody doesn’t ultimately end up buying from us, how do we uncover and proactively respond to purchase objections that arise? And ultimately, how do we potentially assist in person sales teams, by using all of this to better prime, the leads that they’re going to see that they be speaking with? So how do we help create customers at scale and automatically, in a way that is highly individualised?

Basically, what we’re going to be trying to do is to create an incredible salesperson that doesn’t care about the number of leads you throw at, it doesn’t care about the volume at play. And this is exactly what I created, when I left Double Your Freelancing to start this new company right message. And best of all, they’re not gonna ask for a commission are only going to charge you by contact, which is great, because it’s we’re talking pennies or pence per contact.

So that all sounds good. I want to preface things because I’m sure some of you might be questioning, you know, I’ve talked a bit about email. And those of you who might know me know, I have a bit of a thing for email. And I want to talk about why I think email is such an important medium and why email is not dead, when it comes to what I’m going to be describing.

So first thing is email is relational, it is truly one to one, there is no way for you to tweet something that will have different tweet content, depending on who’s reading it. Tweeting, Facebook posts, LinkedIn posts, whatever. They’re all one size fits all what you tweet is what people get. Not so with email, with email, we can send messages that are effectively stitched together and generated on the fly, where we’re taking in and merging in data. And we’re outputting a message that reflects what it is we think this person needs to hear from us. Email is also lifecycle meaning with a you can’t really do a lifecycle based Twitter campaign where, you know, five days after somebody follows up, let’s send these tweets and then 10 days, let’s send that tweet. With email, you can set up a system that allows us to send automated emails based off activity or key actions. So when somebody buys we want to send them these emails afterward, when somebody is, you know, we think ready to supply a testimonial, this is the campaign that we’re going to be sending them.

Emails also permanent. And what I mean by that is, you know, when I’m at when I’m at an event like this, I tried to stay off my phone as much as possible. But the fact of the matter is, people I follow on Twitter are tweeting right now. And I’m never going to see these tweets. However, anyone who emails me right now, I’m gonna get back to an inbox that is going to be ugly. And I need to either read the emails or archive them. So email needs to be dealt with, whereas social media is ephemeral. You know, if I don’t see it, if I’m off the grid for a week, all that stuff went into the void, and I never will see that not so with email.

Email is universal. For the most part, anyone you’re trying to sell to probably has an email account. It’s decentralised, meaning a the powers that be can’t really shut it down. It’s the with Facebook, they can fine tune their algorithm to affect your distribution of content. With email at the end of the day, it’s new to them. It’s there really no one owns email as a medium. And finally, email systems email platforms these days have really great personalization tools built in that are severely underutilised. So in terms of being able to personalise content sent by email, it’s actually fairly simple to do these days, assuming you know, how to use the personalization tools. And most importantly, assuming that you have the segmentation data that can then drive personalised emails.

Okay, so that was my rant about why emails amazing out of the way. I’m going to now shift gears to explaining what this framework looks like, and most importantly, how to apply it in your own organisation. So the first thing is, before we can really do anything we need to be thinking about if we eventually want to personalise our content, that means we need to have segmentation data assigned to contacts or in our CRM or you know, platform. But to have segmentation data we need to know what segments are available, what are the what are the various segments at play. So to do this, my favourite exercise is to create research, flywheels. So what these are, are basically things that are put in place that are automatic, that a key point in a relationship with somebody, you reach out and try to get in their own words, information about this key event. So for example, in this case, when somebody buys this WordPress plug in called Client Portal, we want to find out hey, in a sentence or two, who are you? What kind of business do you run? And most importantly, since you trusted us with your money, and you will presumably be trusting us with your time in setting up our plugin? What do you need this thing to do? For you? Simple question, you paid us money, something about our marketing site and our marketing won you over? What do you need this to do? It sounds like a silly question. But as I’ll show you in two slides, what you learn from this is pretty remarkable. Because there are a lot of people who want client portal for very different reasons. And so what you see right here, I don’t know how easy it is to see, depending on where you’re sitting content is tricky with slides is that putting them together, when you’re staring at a 27 inch display, you see all the text, but when you’re in the background, and you see little text, I don’t know how easy it is to see. But anyway. So this is an example of an email that’s dispatched immediately after purchase. And the idea here is to collect in their own words, who are you? And why did you buy?

Likewise, one thing that I’ve been doing is when somebody joins my newsletter, I send out a very simple email a day after saying, Welcome. I’d love to know, if I could write next week’s newsletter to you specifically, to tackle whatever it is, you need help with, you know, presumably, you gave me your email address. No one wakes up thinking I’d love to get more email today. Like, you know, if you opt into something, you’re thinking that it’s going to help you in some way, shape or form. What does that look like for you? What can I write about next week for you? And the amount of information I’ve got about who’s on the list not just names, not just volume, not just X many subscribers, but who? What are they struggling with? What kind of business do they run? Why are they here? Why are they trusting me with their attention. This has allowed me to not only come up with really easy content ideas to write about, most importantly, to have a profile of the average types of people who are joining, in this case, my email list, because what you can do over time, is you can put together these brilliant, lovely little spreadsheets where you take this raw voice of customer data. So the raw visceral pain points that people have, the problems they have in the this is the kind of business that I have data that they’re giving you. And you can start messing around with a spreadsheet and putting in into columns that, you know, represent kind of macro trends that you’re seeing.

So typically speaking, like in this case, with client portal, she ended up seeing about four or five core business types that kept signing up schools, agencies, law firms, landscapers, and so on that what she would do is as this raw feedback came, and she’d say, Oh, this is from a freelancer, we put it in this column. This is from a financial company, I’m gonna put it in that column. And over time, you start to see that you have not only language that actual customers in this case are using to describe their problems. But this language is now classified or grouped into these big kind of macro segments. And this is going to be really interesting as I’ll be explaining in a bit.

One of my favourite copywriters is Joanna Wiebe of Copy Hackers. And one thing that probably my favourite quote ever by Joanna was this, which is that

“the best copy is curated and not created.”

And I think if you’ve ever written copy, you think, you know, you know, my job is to go and come up with remarkable words that I can then throw in a sales page or something. Joanna would argue that a good copywriter, their job is to listen and to mine, the actual language that the people in the target audience of your product or service are saying, and then basically throw it right back at future people like that. So what you’re ultimately going to want to do is to be thinking, Okay, so I’ve got this feedback loop now in place, the people who are just joining our lists or people who are just, you know, buying our product or whatever else, and I’m finding out in their own words, why they bought or what why they’re here or what, who they are. And I’m now starting to classify this into discrete segments usually vectored, under who somebody is. So their identity, industry, job role, company size, whatever, and, most importantly, their need. So why are they like, what is the reason that they joined your lead magnet? Or opted into your lead magnet? Or what is the reason that they bought your product? And when you start to have this data, then we can switch into the next stage of this framework, which is, how do we actually know now that we have this great database of raw language, raw voice of customer language? How do we start associating this with individuals in our database, because if we can start to associate this with, you know, mark@businessofsoftware.org, or whatever the domain is this, this this, then, when we talk to Mark in the future, through an automated campaign, we can send stuff that Mark probably wants to see.

So, my favourite way of doing this, when it comes to the lead generation side of things, is to not to waste your confirmation page. So, I’m sure you’ve all when opting into a newsletter or downloading lead magnet, the redirect, you do a thank you page that says, check your email, or something useless like that. What I would recommend is to think how can I use this as an opportunity to learn more about the person who just gave me their first name and email address. So I don’t want to just know that this is Mark, and this is his email address, I want to know that he’s struggling with this, that this is what he uses, that this is the kind of company he runs, and so on, and so forth. So that I can then get this data so that when I talk to Mark from here on out, I can drop more relevant messages to him, I can show examples I can show give him testimonials of other people just like him, so that he sees himself ultimately in the product that I want to eventually offer him.

So putting an embedded survey on a confirmation page and basically saying, when you know, all the options for this survey come right out of that voice of customer research that we’ve been doing, where you just lead somebody through and effectively try to get them to tell you who they are. So which of the following best describes what it is, you know, the kind of business you work at? And why are you here? So what are you hoping to get out of this? Pick one, and these aren’t things that were created in a vacuum. These are the macro trends that were established through the exercise of creating these flywheels. And over time, the list you have, your segmentation data will change, because you’ll get more data. And you might have like an other option where people choose other and you ask for clarification, and you find gaps in your segmentation strategy over time, so the version one of any of anything, it’s not going to be perfect.

There’s a company called trugreen. I don’t know how many of you are aware of that they’re big. In the US, they’re massive, kind of lawn care company. And they do everything from overseeing lawns to making your grass greener, to getting rid of mosquitoes to doing tree surgery and everything in between. And one of the things that they’ve done is they make it so when you go to their website, considering they have a kind of a large portfolio of things that they have on offer. They want to find out why are you here? You know, oh, I’m here because my grass is ugly. Okay, tell me more. What’s your biggest concern with it? Well, it’s covered with weeds. Okay. They tell you that you are you tell them that. And then from then on out the messaging and maybe the hero on the homepage, in the emails should you opt in? Surprise, surprise, you’re gonna see a lot of language about weeds. If you talk about animals, and you want to make your grass pet friendly. You probably say that because maybe you don’t have kids and you don’t want to, you know, you’re you. The kid friendly thing isn’t really a factor for you. Well, what you’re gonna see is imagery on the website of dogs running happily on grass. Tell them that you want to make your, your grass kid friendly. You’re gonna see pictures of kids playing on grass. And per this, so HubSpot -Google like ‘HubSpot Personalization research something or other’, you can find the report -but one of the the interesting stats that I found on this report was that based on their surveying, the majority of people are okay with sharing personal info on a website as long as it’s for their benefit. So I don’t know if you can see in this in the microcopy up here, but when we’re asking them to tell us why they’re here and what they’re hoping to get out of the new relationship that they have with us. This will help me send you more personally relevant content. I’m not saying that I’m trying to get this information so I can populate a bar chart on a presentation somewhere. I’m doing this because I want to personally increase the signal to noise ratio of this person.

So again, don’t be afraid to think about ways that you can capture this data because you you need to capture this data because without this data, you can’t personalise you can’t personalise content without segmentation data. So you need to be thinking, what are some different ways that I can get this information and start associating it with the actual individuals who are in my audience? Now, this goes without saying, and I think most of us understand intrinsically that we need to be doing this. But we need to be thinking about how we can use our email platform slash CRM as our single source of truth. So what I mean by that is, say you’re using a platform like HubSpot; How do we go beyond just you know, Mark, Mark’s email address, tag of customer or something, and really, fully represent what it is we know about Mark and how we can best serve Him. So we know he’s a customer. But do we know what industry he’s in? Do we know what he’s struggling with at the minute? Do we know how big his team is, because all of that can be used to send better messages to Mark in the future. So I know most of us are probably doing some sort of data warehousing within our email platforms. Even if it’s not your only source of truth, I think it should be something that you try to get as much information about, you know, purchases and this and that even things like NPS score stuff, into the into the individual contact record of each person and your audience, because this is gonna allow you to drive really good campaigns, if somebody has a high NPS score, the likelihood that you then want to put them on some sort of affiliate or referral campaign is significantly higher than somebody who thinks your product is crap, and probably shouldn’t be asked to refer you or anything like that, they should be getting different communication from you.

Okay, so let’s go back to this diagram that I had of the typical marketing flowchart, if you will, there’s a lot of emails that are being used as kind of the backbone of things. And most of us, I think, will try to have some sort of welcome sequence that then maybe leads into like a long term nurturing sequence, like a weekly newsletter, or quarterly news, or some sort of interval, newsletter, whatever that might be. But what I’m going to encourage you to do is, especially in your onboarding emails, and your welcome emails, and the first time that you have to really knock somebody’s socks off, is to think about how you can take that voice of customer language that you’ve already been mining, and associate it really nicely with the discrete segment data that you’ve hopefully now collected about somebody so somebody opts in to your lead magnet, you find out they’re in this industry, you find out that they’re struggling with this problem, how do you then reflect that in the first email that you send them the first bout of communication that you deliver their way?

So here’s an example of a marketer who has not yet full time in their in their freelancing career. They’re just doing it on the side. And they’re struggling with impostor syndrome, they think that they are not good enough. So here’s somebody that you tell me those three things. And I know for a fact what they need to hear from me and how do I know this because of the, the research flywheels that I’ve set up where people who are struggling with impostor syndrome, what if you’re not good enough? It sounds easy as a bit of copy. But this is just pulled right out of a spreadsheet that I have of raw feedback. And if you should charge what if people are saying you’re charging too much everything you see here is actual voice or customer language, that all I did was put a bit of conditional content in my welcome email that said, hey, if they say I’m not good enough for imposter syndrome is there, why segment, spit out this. And this is me just lazily going into a spreadsheet and pulling out key bits that sound good. And what this has done is I’ve gotten so many this is from Double Your Freelancing, which is that company I kind of moved out of to go full time on write message. The amount of replies I’ve gotten in this email saying how excited somebody is. Granted, this is day one, this is minutes after they opt in, is through the roof. Because what you know, instead of just saying, Hey, welcome to Double Your Freelancing, blah, blah, blah, here’s me, me, me, me, me and said, it’s, Hey, you’re not yet all in. You’re a marketer. You’re struggling with this. Here’s how over the next few weeks and months, I’m gonna help you with this. People love this and this wasn’t hard to do this was just me basically taking raw feedback and stitching it together on the fly using off the shelf software.

Another thing is, when you’re thinking about how to bring Somebody’s into the fold. Somebody joins your you know, they they download your free report, they join an email course of yours, they simply join your newsletter. One thing you should be thinking of is how do I make what I’m sending people a bit more interactive, is one of the hallmarks that I talked about of a good salesperson discussion. And one thing that company called ripped body out of Japan, it’s a health and fitness company does is when they get people onto their list, loads of people, I mean, they’re, they’re huge. One thing that they do is when they deliver educational content, they’re not just saying, Here’s some information, in this case about macros. Instead, what they do is when they get to the end, when you get to the end of that email, they ask you to go and do a quiz, where the idea the goal of this quiz is to apply what you just read to your unique circumstances. Because let’s face it, if you can think of how does this what I’ve just heard, translate to me and my needs, it’s gonna be more, it’s gonna be a lot more effective for you.

But what they do, kind of sneakily in this quiz, is they capture where segment data, they find out more about this person and what it is they’re, you know, in this case, what are their – not to get too jargony – but what are their preconceived ideas when it comes to macronutrients and the role of protein versus carbs versus fats and stuff like that. So think about ways that you can make it. So when people are getting communication from you, it’s not just, you know, the only interactivity is not just clicking a link that goes to a sales page. Now consider, especially if you have a sales team, asking people to reply, getting people to reply back with more context, more voice of customer language that your sales team can can jump on. But you can also file away into one of these glorious spreadsheets that will allow you to drive future communication even better.

I don’t know if these were thing in the UK. But as a kid, I used to love these Choose Your Own Adventure books where you get to like, you know, you finish the page. And let’s say to go into the cave, jump to Page 18. To run away, go to page 12. And, you know, the idea was to turn a linear thing like a book into something nonlinear. And personalization done right When it comes to email sequence can can allow you to do that. Because you can be thinking, what does this person need to hear next for me, because ultimately, what we’re trying to do, all we’re trying to do is to say, we’re not trying to waste their time, we don’t want to give them stuff they don’t care about how to. They’re here for a commercial relationship. They didn’t join a SaaS’s email list thinking that they’re not gonna be told about this house. What we need to do is we need to be thinking, given what we know about this person, how do I best prepare them to be our next customer? And that’s all we should be thinking about is what do we do in terms of the messaging that we’re dispatching to make that even clearer?

When it comes to the offer, so a lot of us think about the offer, being the product, the service, whatever it is that we have to sell. The big eye opener for me kind of over the last few years is I’ve gotten gone down this rabbit hole of personalization and stuff is really realising that an offer is just alignment. It’s saying, here’s what you know, here’s what we have to offer, here’s the thing we’re selling, here’s what you need. Here’s how they fit together.

And when you start to get this data, you can start to be a little more calculated about what the offer you’re presenting actually is. Because why somebody might if somebody wants to, let’s say, to go back to client portals, for example, if somebody buys client portal because they want to look more professional with their clients, and they are a school administrator, they’re going to be wanting to hear different things than an agency owner who wants to just get less email back and forth emails from their customers and clients. So if you can figure out this person is struggling with professionalism, they are a school administrator. You can come in and say we have the ultimate platform that will help your school better communicate with parents and show them about, you know what’s going on in the classroom, upcoming events and so on. So you don’t need to think about building or coming up with some custom thing to do this. Like we do this for you.

That is a very different offer than an agency who wants to cut back on. Hey, can you resend the link to our proposal can you resend the link to the Trello board can you resend this can you resend that these are very different things that the same software equally serves both in the offer is going to be different the offer and what you’re saying the software does is going to be dynamic.

So this kind of extends what I was just saying but the the way that I I try to think about this is that your product, the thing you’re selling is the connection between today and tomorrow, right? So today my problem is professionalism. And then your offer is basically the bridge that connects the two. So great, you want to you want, you want to be more productive, you want to look more professional, your clients, you want to stop playing amateur hour, you want to look like you know what you’re doing when it comes to onboarding, and so on and so forth. If this problem were to go away, what would that look – What would that look like for you, and if you can get this information, and you can just mad libs style slotted in to when you go ahead and pitch your product or service over email, people are gonna see this, and they’re gonna think, oh, you know, they’re listening to me, they know what I need. And obviously, this is what we want. This is exactly what a good salesperson a flesh and blood salesperson would do when talking with an actual potential buyer.

Another thing that to think about too, and I’ve kind of hinted at this is if you can capture identity data, so industry somebody’s in, job role, whatever. You can use this to better to take what it is you have, and show better social proof about others who have forged this path already. So an example of this where I really where this really hit home for me was years ago, I was selling a course on Adobe or freelancing that was on pricing, pricing theory for freelancers. And most of the people who bought it early on, were people that I knew from a website called Hacker News. So they tended to be developers, sometimes designers, but for the most part, they were people like me, coders, designers, whatever. And I remember getting an email from a copywriter who said that she had heard great things about my course. But she’s looking at the sales page. And it seems like it’s targeting developers and designers, and she wanted to ask me point blank, could this help her?

Now I was able to rescue the sale, because frankly, the course was non technical. It’s not specific to any industry or whatever else, it’s just a course on how you get a lead. Here’s how you write a proposal. Here’s how you think about the value you’re offering, and so on. But it got me thinking how many other people like her had that same thought, but closed the tab. And thought now, I don’t see myself in any of these testimonials, I don’t see myself described in the product, they’re not using the language that I use. So you want to be thinking when you go about pitching, if you know they’re in a certain industry, people want to see themselves in and the product you’re selling, they don’t, frankly, the agency, if they see a bunch of freelancers, they’re gonna think they’re the wrong place, let’s say to go back to let’s pick on freeagent for a second.

If you are an agency in US region, do you really care what a bunch of lowly freelancers are done with the software? No you want to see, you want to see other agencies who are kicking ass with freeagent, right. And so if you can be getting this data, and ideally, also segmenting your testimonials, and your case studies so that you can say, hey, when somebody’s in this industry, this is the future case study, we want to show that’s gonna go a long way to showing people that they belong.

The offer is really just the alignment of what you have to sell. It’s all it is, it’s all the offer needs to be internalised as is just, here’s what you’ve got, or here’s what I’ve got, here’s what you need. And this is my way of packaging up what we have to fit what you need.

Another thing to think about, too, if you’re using email to pitch, I’m talking about urgency. This is always a fun thing about that I think a lot of us in the software world could learn from the internet marketing world about how to do this better. So if you’ve got somebody who joins your list, and they’re getting great information from you, and they’re learning about what it is you have to offer there, see how it can be used for them. You don’t want them thinking this sounds great. I’ll come back to it when I have time. You want to have some sort of incentive for them to actually take action and fix the problem that you now know that they have. So if they told you they’re struggling with professionalism, you give them some ideas, you show them how professionalism can be increased in their business by doing XY and Z. And then finally, you want to offer them a way to fix it in that way is your product but how do you get them to actually take action today? Well, in terms of urgency, the big one, the one that frankly works best typically but can also be most catastrophic is through discounting. So usually our plans are $50 month, you sign up this week. You can get a your account will be $40 a month or something like that. But there’s also other things that you can do that I’ve seen other software companies use, including my own my own my software company, that tend to work pretty well. Things like bundling. And so if you have, let’s say you have a course a paid course that accompanies your, your software, maybe somebody has written like a fret, the guy who wrote it for Infusionsoft. But he basically wrote the Infusionsoft Bible. If you could say, hey, well, we’ll throw in a copy of this course, this book, this whatever, if you sign up this week, that’s a really nice incentive.

Likewise, maybe some sort of a limited time doesn’t really apply since most of us are probably selling all the time. But for information products, a common way of doing this is to say you can only buy it this week, I don’t know when we’ll sell this again. But that probably doesn’t apply in this case. But you could also think about extending a trial. And you can think about concierge onboarding. So if you sign up this week, we somebody from our team will help you get set up individually, we’ll jump on a zoom call, and we will walk you through getting set up with our product, we usually price this at x many $100. And we’ll give it to you free.

Strategy call, same kind of deal but rephrased a bit differently, bumped up to a higher tier sign up for the silver tier, this week, we’ll give you the gold tier. Maybe throwing a quarterly review is another incentive you sign up this week. And once a quarter, we’ll come in and we’ll assess your account and tell you what you could be doing better. Or just send them a t shirt. That works too.

If there’s one thing that the final components, so we’ve talked about collective voice, customer data, extracting segmentation, discrete segmentation from that, and then using that to personalise specifically, in this case, the easy thing, which is emails, we then moved into pitching. So how do you then, you know, effectively pitch this personalised offer to somebody? If there’s one thing I hope that everyone here can take away from, it’s this next strategy, which is something that very few people do. And that is to basically ask people point blank, why they didn’t buy, and then re pitch them, given that objection. So there’s typically three reasons why somebody will ignore an offer made to them. So either the price that’s too expensive, you know, just that they don’t see the value in what you’re offering. They don’t have the time. So they’re overwhelmed. There’s so many other things that are vying for their attention, they don’t have the time to sign up for this new product. That is more than just the money. It’s also the time and getting it set up. Or there’s a dubious ri personalization sounds cool. But will it actually be worth it in the end. And then finally, there’s also if you do any sort of urgency, backed, pitching, there’s also Oh, I was on a Caribbean cruise and missed your offer. They missed the deadline.

A company called spreadsheetUp one thing that they did, which I thought was incredibly interesting, was when they pitch their product over email, the following week, they sent out a very simple email that says, hey, you know, we’re very passionate about what it is we’re doing. And it’s totally fine that you didn’t buy, but I’d love to know, just for my own sake, so I can do better in the future. Or we can do better in the future. What held you back? Was it you know, you missed the deadline, you don’t have the time to do the work, you think it’s too expensive? You don’t know if it’ll help me learn Excel? So some Excel training course? Or you don’t want to advance your career, which, you know, stupid question. But what’s interesting is just the breakdown of how people respond to that. And what they were able to do is, if somebody says it’s too expensive, they basically queue up an automated secondary pitch that focuses on the money back guarantee. It focuses on the ROI, the investment angle, rather than it being an expense. This is an investment if you can learn how to do Excel better. This isn’t this will occur as a result. And they just focus that the brunt of their next pitch to be exactly what objection held somebody back. And for them, they’ve been able to increase the overall effectiveness of their email sales pitches by more than 10% Just through this one single email that then leads to a secondary pitch a bit further down the line.

Okay, so in closing, I want to just wrap up with a few different kind of big picture, things to think about. So the first thing is that segmentation is ongoing. So segmentation should not be a one off event that you do when somebody you say first joins your list or becomes customer. It should be something that you’re proactively doing, especially considering segment data changes, somebody’s need might change six months in, they might be thinking about starting a company now but a few months down the line, maybe they’ve started that company.

Present messaging should always be looking to the past. So as you collect more information, you want to use that information to refine future messages that you’re sending to your audience.

Personalization is just simply a reaction to segmentation. We all want to personalise and I think a lot of it Think of personalization as sticking known data in an email, let’s say like, Hi, Mark, hi, Brennan. Hi, Bob, whatever. That’s okay, sure. But you want personalization to be more meaningful, you want us to be thinking, given the fact that this is the problem they’re struggling with. And this is their identity, how do we give them a better message. So it’s always reaction to the segmentation data that we have. And if you don’t have a segmentation data, you can’t do anything. My motto, whenever I think about, Okay, it’s time to put into place a proper personalization strategy is to always be thinking, I have a list. And it looks like yes, I talked about numbers, x, many 1000 people are on this list. But ultimately, every single person on that list is unique. I respect your time, and I want to give you exactly what you need, and nothing more. And that drives every single personalization campaign that I’ve ever created.

So just quickly, in summary, I know we’re getting to the end of my allotted time. But basically, what we’re trying to do is we’re trying to create systems that uncover segmentation opportunities and extract voice and customer language. We’re going to go beyond just first names and email addresses by finding out who’s in our audience and why are they here. We want to deliver bespoke experiences that react to segmentation data, we want to dial in on someone’s specific problem, and then pitch your product as the best way to solve said problem. And then finally, we want to uncover sales objections that you can use to then re individually or individually re pitch and reevaluate your messaging in the future. That’s what I’ve got. Hopefully, it was helpful. I know, it’s hard to think about turning this into something a bit more technical at this point. But considering most of you probably pay for email software, I’m sure it has everything included in it that you need to implement what I just covered, so thank you.

Q&A

Audience Member
Well, I love the idea of capturing more data, there’s always a bit of a trade off between, is someone gonna sign up if you ask them too many questions? Do you still kind of, do you still have a lot of data that you can’t segment because people aren’t willing to give you information? And is that fine? Or do you kind of err towards you know, well, if you’re not willing to give me the information, I need to do this? Well, then I’m going to let that go. And be like, That’s not great quality data.

Brennan Dunn
Yeah. So about the first point, I typically don’t encourage to include this in the upfront form. Because it just makes like you said it at the every additional question decreases conversion rates. But from our own data, and having done I’ve helped a number of companies get set up with kind of a post opt in segmentation survey funnel. And usually the response rate is about 80 ish percent, so tends to be fairly high. And obviously, there is drop off where you want to, ideally put your most important questions first. But as long as you’re making it, so it’s obvious why you’re asking the questions where you’re asking this so that you can give them better, more curated information that applies directly to them. That’s, you know, obviously, if you ask about credit scoring stuff, that might be a bit, you know, over the line, but typically, if you’re saying, I want to just make sure you get exactly what you need, and nothing more tends to go over well, and again, it’s 80 plus percent, or four and five tend to tend to give up that information which is useful and good. Yeah, sure. Ferris costume, just love to the girls, come on.

Audience Member
Thank you. So I’m curious about your process to get to the segments. And the spreadsheets, for example, for instance, they were, you know, they defined problems. So the reasons why they you know, the buy didn’t buy or whatever it might be in the ROI and those kinds of things, right. And similar your own example that you gave of like those segments that that you were putting into the question. So how did you get to those segments? What was your process?

Brennan Dunn
The easiest thing to do? So to go to the spreadsheet, for example, what they did before they had the click one was to ask people point blank, I’d love to know, in your own words, what held you back, and over time, they were able to kind of dial it down into a set list. And likewise for you know, somebody early in the relationship so let’s say they just joined your email list. It could be as simple as reply and share a bit about it’s kind of like what I think I showed in one of the slides of love to know in your own words who You are and what you want the next edition of the newsletter to be about. And over time, you can extrapolate themes from that. I actually had a friend who sizeable list about half a million people. And he did this reply campaign to his entire list and got a lot of his inbox was a train wreck for a few weeks. But it allowed him to really narrow in surprisingly on about four key things that kept coming up again and again. And you get outliers. Of course, you get people who are just, you know, the extremes. Factor matters, you just tend to ignore that and just focus on the majority of cases that you know, the four common things that keep coming up again and again, and then incorporate that into your more more quantitative approaches of like, click one, which one are you rather than the open ended? It’d be great if machine learning was such that we could somehow turn raw feedback like that into discrete segments, but I don’t think we’re there yet.

Audience Member
So thinking back to the example of the lawn care company, and it was the majority of folks there would give up some personal information for better content. That percentage was very Brexit-y. It was just over the line, right? 50 to 54% 57%. Okay. sorry, politics! What’s the potential damage of the other side of that equation? So is it just a turn off? And they just choose not to? Or is there a consequence to that which is bounce?

Brennan Dunn
I mean, for him that TrueGreen example, I don’t remember the exact percentage, but I think it was something around 20% of people only about 20% engage with that. So if you don’t want to do it, you just see the default messaging, right. But what I think what’s more interesting is that a lot of people – 80% – don’t give up that information that was pre opt in, that’s just on the marketing site, in general. But I think it becomes indicative it helped them see who is the average visitor on this website, because if the 20%, who do engage, tell you, like, you know, X percent are struggling with weeds, and y percent are struggling with mosquitoes. You just look at the numbers as they pan out. And you can kind of extrapolate that to come up with a default messaging, if you will, for the 80%, who don’t share anything with you. So I think there’s still uses for getting this on an aggregate level. It’s just typical, like hot jar style serving. But the difference is unlike with hot jar where you get survey data that is kind of aggregate and anonymized, this survey data that they give up can also be used to individually effect that future session on the website, if that makes sense. So yeah, I mean, I’m not sure in terms of overall brand impact or whatnot. I would think it’s like with anything like I find intercom pop ups annoying. I don’t blame them for using them. I just dismiss the problem and go from there.

Brennan Dunn

CEO & Co-Founder, RightMessage

Brennan Dunn is an email and personalisation geek. For the last few years he’s focused on delivering on the promise that just about every marketing company makes: sending the right message, to the right people, at exactly the right time.

He’s the co-founder of RightMessage, a software company that helps creators better grow and learn about their audience, and recently founded Create & Sell, where he provides weekly intermediate/advanced growth ideas to creators. He started and exited successfully from We Are Titans – web agency, Planscope – SaaS, and DoubleYourFreelancing – a community for freelancers and agencies.

Born in the US, he moved to the UK in 2020 where he likes to ride bikes and attempt to create things with wood, but what he really excels at is delivering actionable, fluff-free ideas that you can quickly and profitably put into action.

Find out more about Brennan

Next Events

BoS Europe 2025 🇬🇧

🗓️ 31 March – 1 April 2025
📍 Cambridge, UK

Spend time with other smart people in a supportive community of SaaS & software entrepreneurs who want to build great products and companies.

Save your Spot

BoS USA 2025 🇺🇸

🗓️ To be announced soon
📍 Raleigh, NC

Learn how great software companies are built at an extraordinary conference run since 2007 to help you build long term, profitable, sustainable businesses.

More Details