S2E3: How do you create an effective outbound email sequence?

S2E3: How do you create an effective outbound email sequence?


Welcome to the Belkins Growth Podcast, season 2 episode 3!

Today, Michael is joined by Sarah Hicks and Patricia Simms, from Predictable Revenue Inc. Both Sarah and Patricia work closely with SDR teams servicing clients in multiple industries.

Michael is trying to find out the best practices for email sequence creation, tips, and tricks of a good email copy versus a bad one. Sarah and Patricia share ideas with Michael about what makes a good email copy great.

Listen to the audio version of the podcast on Spotify, Apple Podcasts, Simplecast, and Stitcher, or watch a video version on YouTube.

Stay tuned for more great episodes for season #2, as we have gathered experts in sales and sales development revealing all aspects of the appointment setting process in great detail.

Enjoy watching or listening, and subscribe for more episodes directly delivered to your inbox!

Transcript of the Episode

Michael: Great having you on the show. Really appreciate your time. Last time when Sarah was on the show, we discussed the process, the best practices. This time, considering we have you Patricia with us as well, I really wanted to dig deep into an actual outreach sequence creation, the strategy behind it, how to work with ICP, what kind of best practices you guys can share with us as well as sharing some of the things that we worked on and so on and so forth.

Sounds good? And just to give some context here, I'm working on the second season and this season is dedicated to appointment setting, and every episode I'm talking with industry leaders about different parts of the funnel. So we are going to be starting with how to research leads and how to work with spam, and how to manage appointments, and all of that.

I wanted to streamline our discussion around content behind sequences, because as far as I know I mean obviously like 50% of the success is how good you create your sequences and templates. So with that being said, what kind of approach do you guys take in sequence creation?

I mean, do you guys want to personalize it, considering the ICP or you're looking more into a sort of creating an omnichannel approach? Do you have any sort of pattern in terms of, if we take a new project, that's what we're going to go on, or these are the best practices with us that have worked so far?

Patricia: Happy to start, Sarah or you can start if you like. It's either way. From a strategy point of view, given the work that we do at Predictable Revenue, it's very account to account based on how we want to approach strategy. Of course, there are best practices with no matter what, you want to test your subject lines first and foremost. Are your emails and copy getting opened?

You have to run X number of individuals through a sequence to even decide whether the copy is working or not, or you're targeting correctly. So that's sort of best practice to start with subject lines. However, we have about a month for each of our accounts where we really dig deep into the client's ICP and we spend a lot of time building out that ICP.

If you get it right the first time, or at least you have a really good hypothesis the first time, it makes the back end of your engagement and your prospecting that much easier, and then all you're doing is iterating on a copy. Happy to kind of walk you through how we do that, but there is a goal in mind to really get into a customer-focused strategy right out of the gate.

Michael: In other words, this is more like considering your buying personas, who they are, what their pain points are and you create content knowing that, correct?

Patricia: Absolutely.

Michael: Okay, and usually when we think about ICP, I'm not saying anything about actual value proposition that can be tailored, more about the personalization. Whenever you create the database with leads, many people personalize obviously the first name, company, name, title, industry location, are there any specific personalization points that you guys kind of noticed over the years that worked really well besides these points that I just mentioned?

Patricia: For sure. And Sarah can probably speak a lot to the actual copy itself, but for us, of course, account to account, one thing we'll personalize is all of the SDRs are trained on how to do research around the accounts. Are they mapping the organization? Do they understand who's working around the person, the ideal persona that you want to target? Are they asking for referrals? Are they referencing relevant content that they've seen say on LinkedIn that is relevant to this particular company or accounts the way they exist in the world? Are they even in tune with what's happening in the market?

As an example, I've worked on an account with a supply chain and 2020 was a mess for supply chain. Global supply chains were completely thrown out of whack. So are we temperature checking what's happening within the market and sharing even relevant content that might support what these people are going through on a day-to-day basis? Are you speaking to what's happening? And for us, are we listening to our own clients and listening to the feedback they're receiving, especially from inbound leads? You know, outbound and inbound, there's a symmetry that runs, or a synergy if you use the buzzword that works with all of this.

Are you asking your clients okay, so what are your inbound leads telling you about what's going on? Why are they finding you and reaching out to you? And how can you develop that in your outbound copy to say, Hey, I know what you're dealing with and I know what you're up against every single day to get your job done? This is what we do to support that. And if you can bring that relevance and sell your expertise along with your solution, it definitely goes a long way to support personalizing just an account thing.

Michael: Right. And is this the beginning of the email that you were taking, like starting off the bat with a valid proposition or it's more a soft dock? In other words, there was always a debate about whether you should take a softer approach, a more value-based approach, or start right off the bat when you just start, because very often I heard from prospects that they actually don't care what organization you are from, what you want from them, start with a call-to-action and other people say, say differently.

So where is Predictable Revenue right now? Obviously, it depends on the account, but your own preference. Let's say subjectively, where you guys are, what do you like the most more? The soft-touch approach or more aggressive, to the point, short, two-sentence, value, call to action, bam, and then follow-ups? Where are you guys on it?

Patricia: Sarah, feel free to jump in with some context if you are around. A lot of it honestly has to do with your ICP. What's the type of person you're talking to. Are they someone that's going to appreciate sales language? Are they someone that wants to have a conversation? You know, someone in marketing might be more inclined to be conversational and want to be spoken to that way, versus someone in IT probably just wants some really direct messaging that lets you know what you're up to.

Michael: What about the size of the organization? Because I know that many, many companies are really struggling with reaching out to enterprise-grade companies cause obviously the spam filters and obviously because those folks receive a ton of emails.

So with regards to reaching out to decision-makers, maybe VP level, director level, maybe even C level, but not entirely, but anyhow, enterprise-level 5000, 10,000 plus employees. Any recommendation there that you felt like, okay, it worked over the years?

Sarah: Yeah. We rely a lot on organization mapping in that situation where we want to understand who is involved in decision-making and then how do we best target them? Are we asking for referrals because sometimes referrals are just the best way to get a champion, to get you through the front door with someone, or what gatekeepers are you up against, and how do they want to be spoken to?

So the VP might be saying to the director, Hey, source some vendors for me and that's information you have to figure out as you go. So are you giving them a direct call to action? This is exactly what I do and this is exactly what our solution does and this is how we support you. Or are you simply saying, Hey, are you managing a team that's dealing with X, Y, and Z? How can we support the team? Or are you managing individuals who are running up against this? Or a C-level might simply just be hi.

I just don't know who the best person to reach out to is. Can you let me know who in your team is responsible for this? So being mindful of who you're talking to and where in the organization their pain points lie, and especially if they have a team that they're managing. You want to be cognizant of what the manager has to do if they're not necessarily in the weeds with the person or with the problems of the day.

Michael: Do you have any good examples off the top of your head with regards to any recent campaign that you did for this example?

Sarah: So I think something that I've found to be a relatively universal fact is that leading with a value proposition, like what my company does to solve your problem is less important than identifying if that problem exists.

Going with the assumption that they have a problem and then saying like, Hey, I solve your problem by doing X is not useful unless that person has that problem. So rather as Patricia said, figuring out what are the types of day-to-day issues that that role or roles around them are facing, and then rather try to dig into that in your messaging. So an approach that has worked really, really well for me and it is pretty short and snappy and to the point.

It's like four lines, including the greeting and the call to action, but it's one that Becc Holland sort of coined and it's the coming in with the personalization piece. So as Patricia mentioned, something that you found on LinkedIn that's relevant. Relevance doesn't mean we went to the same university or I see that you posted something on LinkedIn today. It means something relevant to the pain that you can solve.

So for instance, if we were speaking as Predictable Revenue and we help people solve their problems with outbound if somebody says like outbound is so hard because of X, Y, Z, that becomes a good post to kind of reference. And you say like, Hey Patricia, I saw you posted that thing about outbound being hard. We do stuff with outbounds. That's like true, true relevance and connection there.

So yeah, personalization in that first little chunk with something truly relevant, and then a what-if question that encapsulates your value proposition. So instead of saying like, I'm going to solve your problem by doing X, Y Z, you say, what if there was a solution to your problem like this, or what if this type of thing could solve this type of problem?

So I'm assuming you might have this problem, what if we could solve it, rather than you have this problem. I'm going to solve it. Give me your money. So yeah, that particular first email template has worked really, really well for me.

Michael: That's perfect. And just to add to this, another example of this kind of personalization is about getting their YES right off the bat, for example, a yes statement. For example, are you looking to acquire more clients or do you have a capacity for new clients? Everyone has the capacity for new clients. Is it yes, I have the capacity, and then what if I can generate those clients without ad spend, would you be interested in discussing this because that's what I've done for your industry?

Let me know. This is to the point, but it tells them that. Yeah, of course. I'm looking for new clients. Oh, I'm not spending the ads. Okay, this is interesting, so I get two pain points at the same time, which is something. And to add to what Patricia was saying, I think that definitely you need to personalize these days because you cannot go to the customer.

You cannot be face-to-face so you have to rely on any digital channel whatsoever and email became very powerful and many organizations are doing it more and more and more. Obviously, it's easy right now to get sign up for a tool like [unclear], pay a few hundred dollars, then get the template, change the first name, change company, and start sending out emails to thousands of people, but it rarely works just because you don't have a strategy behind that.

You don't understand, you didn't analyze your buying persona and you didn't get the right level of personalization, and I always said that you don't need to be too personal because sometimes it just gets crazy. And then you really get those 10 accounts or people in accounts to spend hours researching that and you have a 0% response rate because the product that you were selling wasn't catered to that specific audience.

With regards to personalization, one of the great examples that any person can introduce, and maybe you guys use that as well, but maybe you're not. But when you say in the email, I'm looking for the right person, instead, you can actually use the first name and the last name and the title of the prospect directly.

And you can do that by just simply in your spreadsheet, you can map out the first name of the first lead with the first name, last name, and then put that in one column. And then just with your variable in your outreach tool, you can change that and upload that variable as the colleague’s name and you can use that as a new variable. So then in the email, you can say, John, I was contacting your colleague, your CEO, Michael Maximoff regarding this, but I wasn't sure whether I need to talk to you because you are a VP of marketing about this.

Let me know, so I don't talk to John and spend his time. Thank you. And then if you put your first name or you are John or Michael Maximoff, I'm going to open this because that's my partner's name. The subject line is there, and then when he responds, then someone's going to say, should I be talking to Michael? And then I usually say, yeah, talk to Vlad or talk to me. In this way, that's an automatic email, but not the generic one so it obviously works, even if it's 25% or 35% more effective, that's great.

Michael: So interesting thing about the CDAs and let me know what you guys think of this, but there was a best practice for years now that you don't need to offer a very basic call to action, for example, like let me know if you're interested or tell me what you think, because usually people don't respond that, but you need to be giving you the two options, like let's get a call or let me know your feedback, or let's have a call at that day or something very pushy to the point.

Tell me whether you were available Thursday, 2:00 PM. It's still wordy. That's just too wordy because I know that sometimes people feel that approach to be very aggressive in a way so that's why they want to be distant about this approach, saying you wanted to call right now? You didn't give me enough information about your organization and now you're wanting to have a call.

Where are you guys are with? Do you need to be more to the point and offer some exact timing, exact call to action, or first tell me if you want me to send you more information or interested and then get them on the call during follow-ups? Or offer the call or offer that trial or whatever right off the first day? Sarah, what do you think? What worked for you better?

Sarah: Yeah. So this, like so many things in outbound, there is no right or wrong answer. It completely depends again on who you're targeting, what industry you're targeting and how often these people are prospected. If you are one of a hundred people in their inbox saying, talk to me on Thursday, it's not going to go anywhere. But if you're speaking to somebody that's not heavily prospected, it may actually work to say how's your calendar on this day?

I found that with the soft ask, being more around, still looking for some type of concrete answer from them, not necessarily on if they can meet on Thursday, but on if this is a priority for them, or if this is something that makes sense to continue the conversation about, that type of soft call to action has worked really well for me.

So instead of going, let me know what you think because what do you really want from them? Do you want to know what they think about this email? No. You want to talk to them about it? You say like, is this a priority for you? Are you experiencing this that I've mentioned? Does your team use spreadsheets to manage instead of an internal tool if we're trying to sell them something better than spreadsheets? It's a soft ask because you're not asking for their time, but you're asking for a particular reason because you want to gain more context and continue the conversation.

Let me know your thoughts. I don't know if that really continues the conversation. I've heard of using thoughts as a bumper email, so saying like thoughts on my last email but I think thoughts are too soft and there's a kind of happy medium. But then on the other side, I have used a more direct ask actually when using that same Becc Holland’s template where she says to say, so you have your what-if value prop, what if we could solve X problem? And then she says, give me a chance to unpack that on a quick call. How's your calendar this day? And that again, it's not quite hard as in you owe me your time, but it's like I think I have more value for you.

Give me a chance to show it to you. And because you have shown personalization and then how you can solve a particular problem that they care about, they're more likely to give you that hard ask. Whereas if you go fully automated marketing style email that they open and anybody can open these and you look at them and you know it's not for you.

You know that it's been sent to a thousand people and then they say like, let's schedule a time for Thursday. I'm like, I don't know you, you don't know me. Who are you? I don't know what this is. I don't want to give you my time. So if you personalize it really well, hard ask works better. If you're not going to personalize it, maybe a bit of a softer ask, but yeah, it's still a kind of direct soft ask.

Michael: Patricia. What do you think of this, Patricia?

Patricia: Completely agree with Sarah. Across the board, we never have one set way of asking for time. Another thing that oddly enough has worked for a lot of people is asking to put a placeholder in someone's calendar. It gives you an opportunity to continue following up.

Does it always have the best conversion rate? It depends. For one thing it's like, Hey, I'd love to put a placeholder in your calendar for two weeks from now, or if as an example that someone's going through a really busy season. You know that about the market that you're prospecting into, recognizing I know your time right now is incredibly tight. I would love to put a placeholder in your calendar for a month out when you know things are going to slow down. And then that gives you an opportunity to build a conversation leading up to that call so that person does feel more familiarized with you.

One thing we spend a lot of time coaching SDRs on is opening a conversation. So even just in your email copy saying, I would just love to start a conversation about this. It's an ask for involvement without an ask necessarily for someone to write you a novel about their thoughts or stuff like that. So it does give you an opportunity to create dialogue, and then you can start working towards a more hard ask as people kind of work through the cadence. You know, if you're not getting a direct hit from somebody.

And another thing we focus on is getting a NO, making sure if someone isn't giving you a yes, get a firm NO and why, and that still is a response that you can then counter with something. I noticed this person on your team and perhaps it's offering a name, and are they better to reach out to? Is this not relevant? Why? Is it a timing issue? If you can get a no, you can typically get some feedback there as well. So that's another piece too is always trying to look for some response, to get some value from that prospect.

Michael: That's great advice. I know that many SDRs don't pull up on the negative responses. Obviously, if someone's going to say the f-word, you are probably not going to follow up with them, but at once someone says Hey Michael. I'm sorry. I'm not interested, then it's better to follow up and say, John, is it wrong timing or the budget thing? I can follow up with you later on.

And if they tell you what the reason is, and usually give you that, even if it's 3 out of 10 or 4 out of 10, it's still additional value to you and you can still keep them in the book and then follow up later on. Patricia, do you include value proposition in your first email, or is it more like a pain point statement without any elaborative value proposition?

Patricia: We often like to counter a pain point with a value prop because you want to recognize, oh you probably are experiencing this. And to Sarah's point with the Becc Holland method, it's like, can you imagine, think forward-thinking what your life would be like if you weren't experiencing this pain point, and this is how we can offer that solution.

It gives someone the ability to picture their day-to-day without that pain point. So I think it's always important to provide value, but you don't necessarily want to sell someone on the fact that you do something. You want to prove to them the value actually has to do with your day-to-day experience in your role, and we do spend a lot of time when we discuss copy with our clients.

We spend a lot of time talking about pain points and what's really grinding someone's gears because if you're able to really attach that and/or attach industry knowledge or expertise, that's another great place to start is if you can offer a little in exchange for someone's time. I'd love to connect you with a specialist on my team that actually works directly with this, or put this solution together from this perspective, which happens to be their perspective.

The value might actually be who on your team can help them. Are you selling the meeting? You know, the person wants to actually connect with the person on the other end. So selling your own expertise as a way to say, Hey, I'm going to give you value on this discovery call, regardless of whether we're a fit, there's still value for you to talk to us. It's not an ego-based thing.

It's simply we want you to know that you're going to get something out of your time spent and being respectful of the fact that you are taking time from someone's day.

Michael: All right. For those who are not familiar with Becc Holland’s' concept, can you elaborate where to find what is it about? Give more information. Sarah, do you want to take this one?

Sarah: Yeah, absolutely. Yeah. You can find it super easily if you just Google Becc Holland's personalization at scale. She's spoken about it in a couple of different settings. There's a couple of different videos. The one that I learned all of this from was her video with Scott Barker of SalesHacker. So if you go Becc Holland/Scott Barker personalization at scale, she breaks it down crystal clear, step-by-step, templates, how to pick what you use for personalization. Yeah, it's great.

Michael: Awesome. We're going to attach that at the bottom of this. So talking about value proposition, you guys onboard clients all the time. Are there any specific sides of the value proposition? What are you specifically looking at when you analyze value proposition? Is it the key studies that they have, and what they do for the customer or it's more about their product? Can you just talk on high level about the process in general, as well as what do you emphasize or what do we specifically focus on when you kind of investigate value proposition? Tricia, do you want to take this one or...?

Patricia: Yeah, for sure. We do spend a lot of time on what we call our market fit or niche workshop. That's where we spend a lot of our time discovering our client's customer. We ask them to take their product or solution hat off, put your customer hat on. And what that does is everyone thinks they have the best solution. You have to, in order to sell your own solution.

You have to think you're the best. And while that might be true, your prospect doesn't know that. And so we actually do spend a lot of time talking about what are key differentiators in your value prop, because we have to prove why especially in a saturated market. That does happen where things are highly saturated, what makes you different and what makes you stand out, and that's a huge piece of where value comes from, which is like we stand firm and we can offer something that someone else might not necessarily excel at.

Is that industry expertise knowledge? Is that a solution that does something that no one else can do, and then selling that to the pain point, which is essentially the value here is we really do want to engage with what you're doing and making your life easier. Everyone can say they have great customer service. You know, that's across the board what everyone says. What does that actually mean? Or my solution alleviates this.

Well, how does it actually do that? And providing people a clear picture of the value that it actually brings to them. So we ask a lot of key questions. We break it down into different verticals around each persona. Why does their job exist? What is the goal of their job even existing? You know, there is an existential piece to all of that. What are they doing on a day-to-day basis to make sure they're achieving that goal? You know, there's integrity in what they want to do, and what are they experiencing that pain.

And then we build the value into all of that. The value proposition is really intricately worked into attacking all of those pieces and then offering something that is really different and unique that if it exists, and if it doesn't, you push people to offer can you get case studies for us? What is your marketing material that we can speak to or share? What are people engaging with on getting your content on your own website?

Asking all those key questions to really pull that knowledge from your own client to really speak to the customer, especially if they have a great inbound funnel. That's a huge bank of resources.

Michael: For those agencies that are in the lead generation business, or just for salespeople that work with clients, what would you recommend guys for those that work with customers who have almost zero content out there, almost no case studies, nothing? They drove their sales through referrals and word of mouth.

They have zero. How do you guys create a value proposition? How do you help them to package their content by creating additional collaterals, or is it more about just getting on the call with them so they can pitch and then working off what you have and that's it, or you don't work with those customers that have very limited resources in terms of their content out there?

Patricia: We definitely work with those clients. There is a piece of investing in building that collateral. If you have a lot of word-of-mouth referrals and that's how you're getting inbound leads, that's a lot of people to talk to. That's a lot of people to interview. Can you build case studies? Can we name drop in our content? You know, we've worked with so-and-so with their permission name drop.

If you're able to give a firm example of someone that you've supported and how even a simple name drop is enough to potentially get your foot in the door while you're working on building that collateral. It's a piece that you do have to put resources in and focus on. and one thing we can do is as we're testing the market, as we're learning about your prospects as we're out bounding - out bounding for lack of a better word - while we're prospecting, we can support that building of material by saying, Hey, this is what your market is telling us.

These are what the prospects are telling us, and there is that relationship around you. Sales has to talk to marketing. Marketing has to talk to sales. Inbound and outbound have to talk to each other. AEs, what are you hearing on the phone when you get people on discovery calls? That all has to speak to each other.

And we focus a lot on the team component around our SDRs speaking to the client, letting them know what objections are we hearing, how are we handling it? All of that can be built into content as you go. And oftentimes what we see happen is those clients that might be sort of newer to their space, they will update websites and update content and build case studies based on our findings.

It might be a slower process than it would be for someone who's very well-established in their market, but the learnings are so powerful, regardless of whether you get a no, it's still learning and you can still work with that.

Michael: Right. Sarah, what is the perfect client set up in terms of their content? What do they need to have when you analyze successful campaigns, opposed to not successful campaigns?

Sarah: That's a good question, and I think content can kind of be indicative of a couple of different things. Like you can have a ton of content and it not be useful, or you can have like one or two great pieces of content that really drive results and it depends on kind of how you look at content.

So you could have somebody who's building content that is like value first. I would say it is always the most beneficial content that you could use because Patricia mentioned that one of the things that you're selling is your subject matter expertise in the space that you're trying to sell your prospect on. So if you can give them something that doesn't ask them to pay money, but they get some value out of it, it's like a step-by-step on how your company solves this small problem in this space. Or it's like an interview with someone else who is solving the type of problems they're solving.

Stuff like that or stuff like this. If we're selling sales expertise and we're sharing our knowledge. This is great content because it builds trust in your expertise. It builds brand awareness, and it warms prospects to the idea of you because you haven't asked for something in return.

So that type of content, if you can share that those types of collateral throughout the prospecting, throughout the cadence or sequence, that can be really, really useful. And then on the other side, collateral that shows kind of exactly how you did something because I think especially these days with all the access that people have to information on the internet and all of that, people don't necessarily want to have to rely on having so many calls with the salesperson to understand how they're going to help.

They'd rather understand that sooner in the process. So, if you have a case study and you can break down- sure you can't give away your trade secrets or industry secrets - but if you can break down how exactly you helped and then what tangible results you produced for that client, that type of content or that type of collateral is also going to be super vital.

So, if you could only spend a small amount of resources on building collateral, if those are the two you can build, like something super value-based for your clients, that's going to help them achieve something or solve a pain for nothing, that's great for driving inbound and then also driving trust that you need to be able to get that outbound meeting.

And then on the other side, really clear business impacts that you've provided a client like them that they can see themselves in. That would be ideal. If you could only have two things, I'd say that would make those two things be perfect.

Michael: Back in the day, I talked with this agency owner, and we were discussing case studies and we've got to the point where we realized that if you invest in case studies and usually produce a lot of those case studies, it's irrelevant because as long as those case studies are in the same category, they are irrelevant.

So if you create one case study per category or per industry that you can refer to and you can create five different industries, that's enough. You don't need to invest more into multiplying that, creating150 case studies because then you cannot use them. And at the same time, you can create more customer testimonials that show how successful you are.

But the point is that having that value-based industry expertise and the process that you took to get to that point, it's very valuable. And honestly, if you even share one or two trade secrets at the end of the day, it's about the execution.

I mean, every other company would probably have different customer support, different development, different pricing model, so there are so many variables in that process, then if you can share one or two that were there, that really make the difference with the customer, then why not?

Michael: You touched base on using collaterals and using case studies and using additional references through your sequence with follow-up. So when do you start adding those external links? When do you guys think that it's best to start adding either attachments or lanes? What's the best process when you think in terms of email deliverability, in terms of actually creating value?

Patricia, maybe you can speak to this, in terms of when you look at the sequence, when do you guys usually start adding links, right up the second email or below that?

Patricia: I was going to say Sarah is actually probably very good at this.

Michael: Okay, let's make Sarah talk to this. Sarah, can you take this one?

Sarah: The two sides of Predictable Revenue's experience? I'll go quickly and we'll touch on this as well. I find that the one thing I know for certain is that the first email is not the place for collateral. Other than that, none of it is black or white as with everything else in outbound. I think the reason that is is because it does impact your deliverability.

So you want to give yourself the best shot of actually showing up in that inbox, attaching links and PDFs and that kind of stuff is not going to give you that. So, I like to think of it as a continuation of the story or like building color in every additional email. So if that first email is that really short and sweet, if you've got this pain problem, what if we could solve it then the next one is maybe where I elaborate a little more on how we solve it, or the types of clients that we've helped that look like this prospect, and maybe that's the time for a case study, or it's time to say, if you are experiencing this, we built this eBook on solving it.

Maybe you'd find some value within it or whatever. So if you can think of each subsequent email, each follow-up as adding color to that story, making it a more complete story so that by the end of the sequence, they really understand your voice as a company, how you help people, the value that you bring and how. So, however, you can kind of slot in your collateral in those follow-ups, but I would say just not email one and then test it from there.

Michael: Perfect. How many follow-ups per sequence, when we talk about email sequence in general? Three, five, seven, nine? Until they answer? What's the best practice? Patricia, what's your number? What's your best number right now across the board? What's the favorite optimal?

Patricia: Between five and nine, I would say.

Michael: Five and nine. Okay.

Patricia: Between that. You have to include calls and whatnot.

Michael: So without calls, it's five to nine emails basically. Sarah, what's your number?

Sarah: Yeah. So this, again, it's worth really experimenting kind of per industry, because we've done some experimentation that shows that the optimal can be within three and five because people just don't answer after the fifth, but that's like within one industry or one buyer persona.

You might be targeting somebody that is more difficult to get ahold of, in which case don't give up after the third, fourth touch in a sequence, but that's where tracking your data within something like Outreach or something like Salesforce is really important because you can start to see from which step did the meetings come.

And if you never get anything from beyond touch eight, why are you spending the next two weeks continuing on after that? It's not worth it. Kind of condense that sequence and see if you can increase further your conversion in those first eight touches. So, yeah, I'd say that's where it's really important to kind of look at the metrics and understand where in the sequence your meetings are coming from and that'll give you a really strong indication of how many emails you should put in there.

Michael: I agree with you guys, cause it's always better to add one extra email and then cut it short, rather than just get it to three or four, and then maybe you would be more successful with the five. When we looked at some of our numbers, we saw that either it should be under five and that's when we see the best result because then there's a lot of negativity coming to the campaign, or after the ninth or more, because it started getting five.

People are starting to think that this is just a kind of funny campaign, so they start just responding because they start enjoying this if you are not reported and if you can get some jokes or whatever at the end. By the way, in terms of the sequence writing, again, that might be different, but while I'm on the point, which language to use - direct, indirect, more kind of storytelling.

I very often receive a bunch of emails when people start making jokes right off the bat and I don't usually like that. Is it just me personally, or typically if people start receiving too many jokes, they don't like that? Honestly, depending on the audience. You're not going to target VP of marketing or VP of sales of an enterprise organization with some jokes. Patricia, can you speak to this?

Patricia: We normally save the jovial speak if you will sort of the end, which is kind of like throw me a bone or add something funny. It's me again. Here I am, keeping in mind also who you are prospecting, but usually, at that point, the prospect, if they've received enough material, they're not surprised for you to be like it's me knocking on your door again. Hi, here I am.

They're more receptive usually at that point to a joke. And if you can say, hey just tell me to bugger off. Oftentimes that's where we see a lot of responses in a bumper email, which is, is this relevant to you or down the line, which is like, Hey, just let me know if you want me to bugger off. And oftentimes a lot of times people are sorry.

People apologize, like, sorry, I didn't see your email or so sorry, it's been so busy. And it's amazing how polite people can be when you feel like they are going, oh man, I should have replied when they realize it is a human on the other end. You know you do want people to understand that you are there to speak to them if you've built your copy in a good way.

So, I find closer to the end if you can make a joke, a lot of people will come around with an apology and Hey, sorry. You know, I was busy. We'd love to chat or not relevant.

Michael: Sarah, do you take the same approach?

Sarah: Yeah, I definitely wouldn't be throwing in my memes in my first couple of emails. We did actually have... It's funny that you brought this up cause we had an SDR who used to work for us who gave it a go and he was adamant. He was like, it's going to work because the memes are funny. You wait and you see how well this campaign goes.

And I think it was honestly days after that, that Jeremy Donovan of Salesforce put one of his statistics that have 5 million emails surveyed so it's ultimate facts that were SDRs, if you put a meme in your email, it's 76% lower response rate or something and it was pretty funny. So, I'm definitely not saying anything too witty in my first couple of emails. I think also because I don't want to waste the space.

I'm aware of the fact that the longer the email, the less likely people are to get to the bottom. There are all sorts of little kinds of psychological stuff about the way people read emails and specifically sales emails, where they look at. If you have your phone open. Your email opens before you click into the email, you can see the subject line and then a portion of the first line. So that is really important because if they can tell it's salesy, they won't even open it, but that's really important.

And then once they open the email, they read the first line to try to get a sense of what you are reaching out to them for, and then they jump to the end to see what you're asking.

So if your first line is not compelling, and then they jump to the bottom and see you say can we meet on Thursday? They are not reading it all. So for me, I would be afraid that I would waste some of that precious word space with a joke. Whereas if I can get them in with that personalization piece, like just facts, just really clear and direct, then maybe they'll look at that CTA and be like, Oh, she did know exactly who I am and what I need.

Maybe I'll go back and read the middle. But absolutely, I definitely at the end of all my sequences, I've got a last one email or a breakup email as we can call it and you can honestly throw anything in there and tons of people respond. They're like, haha. This one works.

Michael: Or T-Rex, right? I always hated the T-Rex. Do you know the T-Rex joke? It's like Hey, I haven't heard from you. Are you interested or not interested, or is T-Rex chasing you? Let me know because we're getting worried or something. And people are like ha, ha, ha. T-Rex caught me off.

Sarah: I think that very narrow window, someone posted something about that on LinkedIn recently being like, remember when this was all the rage where people would go like, let me know. Is it A, B, C, or D? And yeah, you're right. One of them is, I've fallen in a hole and need help getting pulled out of the hole. Ha, haha.

I think all of these sorts of fad, trendy things have a very short shelf life, but that being said, humor - don't go for that, cause the fact that you and I both know this T-Rex joke and what that looks like means that if anybody listening right now sends that to anybody, they probably already have gotten an email like that, and it's not new. It's not fresh. It's not cute, but something funny can help.

Michael: You talked about personalization. What I hate receiving the most right now on LinkedIn is the photo of the guy with a piece of paper with this red table or pad, and there was a company name or something. I hate that because I receive thousands of those from different companies and every next one is the same.

And I was like, Oh man, guys, it's bad personalization. It should be either like a rephase or whatever when they add a lot of filters in real-time so that every new filter is in use, and they can use that for a campaign, then use a new one and a new one, but if you go back and use the same photo, it sucks. So I understand using the content, working with a value proposition, feeling creative, and that's fair enough for the companies that have a product or the companies that have a very nice, unique value proposition.

What if I am an MSP? What if I am a software developer? What if I'm an IT consulting company? Talk to me about this. I mean, you guys probably had several campaigns with these types of organizations when you have an exaggerated market, everyone had the same value proposition. What do I do? Let's kind of brainstorm.

What is the best strategy that I can take? Should I be funny? Because people already receive thousands of people like this, or should I be explaining the case studies? Is there any campaign that you guys did in the past for any of these industries that actually work? Can you talk to this, Sarah? Patricia? Who will take the lead in this? Patricia's going to take the lead. Okay. That's the hard one.

Patricia: You know what? And it's just full honesty - it's harder. It's just harder. Be prepared that it's a harder space. If your space is saturated, you have an uphill battle. However, being creative help and sell the meeting. Sell the time that that person and the value that person is going to get out of talking with you because oftentimes it's great to just throw solutions at somebody or throw this is relevant because you do this.

That's great. But like you say, they hear it all the time, but be inquisitive and investigate. And even if it's as simple as I would just love to talk to you to understand your thoughts on - not the use of the thoughts - but understand your experience of X, Y, and Z. Whether it's asking for time to ask them questions or investigate, you have time to let me interview you.

If nothing else, you're just bringing something new to the conversation, but it's not a bait and switch. It's general curiosity. It's genuine curiosity. It's going, Hey I recognize you probably hear from a lot of people in this space. What I would like to do is actually better understand what you're experiencing and it gives the person a place to go have a conversation. And maybe you really just have to sell the time and the meeting and sell your industry knowledge and experience.

I would suggest starting with that. Start with this is what we actually have to offer you when it comes to what you'll learn and what we want to learn from you and have a genuine conversation because I feel like that's the piece that is often missed in a lot of these saturated markets. I actually just want to learn from you and you have experience and you have expertise in your own field. What can I learn from you? And a lot of people really are genuinely interested in sharing.

So it's worth actually wanting to ask for someone's conversation and time. And if that converts your pipeline, it might take a little bit more time. Your sales cycle might be longer, but if nothing else, it builds trust, it builds clout and it might open the door for you down the road when you're networking in that industry where someone said, Hey, I actually had a really great conversation with this person from this company. It didn't feel like a sales pitch. That's an approach I would start with.

Michael: Would adding a free perk for example, like a free consultation or a trial or an assessment, is it still working, or are too many people giving away some of the free complimentary stuff let's say? Sarah, did adding any sort of complementary assessment or consultation work for you for any of the campaigns that you had in the past?

Patricia: We have had it work. However, and I know Sarah, probably you have some thoughts on this too. The time when it did work is when we weren't asking for someone to say do a survey because they would have to go out of their way, they would have to click stuff. It's time out of their day. What am I getting out of this? What actually worked for us was asking for a conversation where we could uncover these things on a call.

It wasn't like, I don't need you to click through seven hyperlinks to get to a Survey Monkey survey and fill it in. The other thing we have worked with for clients is if you have an assessment on your website that inbound leads are coming in through, taking those warmer leads and using them in outbound campaigns and acknowledging that they have worked with your content. But I do want to hear Sarah's thoughts on this because I feel like they are important.

Sarah: Yeah. I have a couple of thoughts on the really saturated market type or those industries where you are the same as all of your competitors, and I think there's a couple of things you have to think about if you want to try outbound if you're one of those companies. There's a couple of reasons that it's difficult.

One is that you have thousands of competitors and all of you do the same thing. The other reason is that if you are one of these types of companies in that type of space, what you offer is really broad because you are trying to cover all your bases and offer more than the next guy, and what that means is that you can do a hundred things.

If we're thinking of a dev-ops company, most of them can you an app, but they can do like the internet of things and analytics and all these different things where there's no way that you can say all of the things that they do in that first email without it being clearly just a mass email. So one of the ways to potentially try to mitigate some of that is to get really, really specific. So forget all of the thousands of things that you do.

Just that one thing, the analytics part. say if we're one of these data type companies, the analytics. Analytics - every department wants analytics, but what type of analytics we're really good at, and who would really like that kind? I don't know. The tech persona at a small company that doesn't have their own internal way of looking at these things.

So now all of a sudden, we're really niche and we help small companies that are growing before they can hire their own CTO with their analytics, something like that. So basically, what you've got to do is find a way to find a niche, or if you are building apps, you can build an app for literally anybody in the whole world. They just need a pulse. But if you can say who doesn't have dev-ops people honing in on them all the time but need apps.

Who are the newly digitizing industries that potentially are going to need an app built for them? I don't know. Let's find that type of company. Say it's a small dentist chain that's looking to grow. Now I'm the DevOps guy for a dentist and that's a whole narrower space than if you are the dev-ops guy for the world.

Patricia: Find the need.

Michael: Absolutely.

Patricia: Who needs you? Find the need.

Michael: Excellent. Being the main expert, that's huge in this company. For example, researching a technology that you use. For example, my technology was built on PHP. Say we developed dentists' software in PHP and that's super relevant and you're not just another broad dev-ops company. You are very specific.

Sarah: And even beyond that, I don't think you could even say to the dentist, we developed dental software because that dentist has been doing his job with no software for the past 50 years. So you need to get even narrower and say like, Hey, doesn't it suck when your assistant goes on maternity leave and no one can organize your appointments or whatever.

Why don't you get off of that and onto this? So not only what do we do and what pain does that solve. But he's already got a solution for that pain because he's been doing it for 30 years, so how is this solution going to make his day to day better in a really tangible way?

Michael: I have a few minutes. I want to play roulette with you. Common mistakes of poorly written email copy, and we go one by one. I start with a huge email copy, a massive email. Massive email no one reads, no one wants. Sarah, you're next. Let's go, Sarah, Patricia, and then me again. Let's do a few rounds. Who's going to lose? Sarah, your turn.

Sarah: I'm going to say when they're really assumptive about giving me going to give them the time, basically. They're like, cool. We're going to talk this day and I'm like, slow down.

Michael: Yeah. Patricia?

Patricia: Not including the pain points. Just like, I'm amazing and this is why I'm amazing.

Michael: Yeah. Yeah. That's a good one. Obviously, I'm concerned with some basic wants. Just some basic fundamentals like children's wants. For example, introducing yourself at the very beginning of the email, like Hey, I'm Michael. I'm with this organization. No one cares. So we are probably not going to introduce ourselves.

Patricia: Nice.

Michael: Sarah?

Sarah: Oh, I just had one. What was it? Oh no. Oh, I was just thinking of it and that was a really good one. Somebody just did it to me recently and it was really, really bad, but ... Oh yes. Well, that's the point. They did it to me. Reaching out to an SDR to prospect them as if that poor SDR can even touch the budget with a 10-foot barge pole. Who are you reaching out to? Are they the decision-maker?

If you're not reaching the decision-maker, it better be a referral because I don't know where you think I'm going to get the money from to buy your product. So yeah, reaching out to the wrong person, not knowing what their role is.

Michael: That's a good one. Patricia?

Patricia: I would say not spacing their emails enough.

Michael: Oh my God. Spacing, yeah.

Patricia: If you are hitting someone with five emails in one week.

Michael: Yeah. I mean, you are spacing the emails in terms of their schedule.

Patricia: But also, who you are sending them to. Time and distance.

Michael: Literally spacing the emails. Did you receive emails that every sentence is space and then it's like space, space, space, space? I can't read this. I literally wanted to close it.

Patricia: Or there's like an asterisk and then a bullet point and then a smiley face and then an arrow.

Michael: I am going to tell you right now; I'm going to mention it. A very terrible one. A very terrible one that probably every junior SDR did in the past. I did that, probably you guys did it as well. Missing variables! When you miss a variable, so instead of the first name, you're going to write the first name, like Hi <first name> without actually a first name. When you set up software, you are just new on the job and you started this campaign and you have multiple campaigns, you are probably going to miss one, either the industry name.

Sarah: We've all done it.

Michael: We've all done that, but that's so terrible. Or if your variable was changed and then the first names or the company names are replaced. That's just bad, but that happens, right?

Patricia: Oh yeah. All the time.

Michael: Okay guys, let's do another one. Sarah, anything else?

Sarah: Okay. There was one that came to mind and it's where people try to appeal to your hubris or something. I've had people who will reach out to me and they were like, I know that you really care about making lots of sales because you're a really good salesperson and you want to be good at your job, and it's a little bit hurtful or something, I don’t know. It's a strange approach where they're guilting me into saying yes, because I'm like, well, yeah, I do care about my job and I am a good salesperson, but it's so weird.

Michael: That's a good one. All right, Patricia., Your last one. Anything?

Patricia: I don't know if this is something that is necessarily a sales thing, but when someone in their subject line will add Re: as if they've already written to you and you have replied.

Michael: You don't approve of this?

Patricia: I don't know. It bugs me when I receive it. When I see that in the subject line, it's as if, Oh, did I actually reply to them? And I open it and I'm like, no, man, I opened it, and that frustrates me. And I'm like, no, I'm not replying to you because you assumed I replied. It really grinds my gears.

Sarah: That's like a real bait and switch for me. Yeah.

Patricia: It's a bait and switch. It feels dishonest.

Sarah: Yeah, it does. And you can't start a business interaction like that. If that's you putting your best foot forward, not good...

Patricia: It doesn't bode well for the rest of the engagement.

Michael: And is it for follow-up as well, or just for the intro email or for the entire sequence they can't use the Re?

Patricia: I'm okay if they reply to their own email. That's fine. That's normal. If they send me an email with a subject line saying like, Hey Patricia, and then the next time I reply to my own email, it's going to say Re: Hey Patricia. But if you start the first email with an RE: so that they think maybe they emailed you or they responded at some point, the fake RE: It really bugs me.

Michael: Are there many sequences or emails that you guys receive or saw that have that fake component in them? Are there any examples besides the RE? What else you people usually do with those?

Sarah: It's like a fake referral for sure, where I know for a fact that you were not referred because I'm at a startup and I sit across this room and he would have just told me with his mouth, but yeah, the fake referral is the only other thing I think I've experienced, but Patricia, you're going to say something.

Patricia: Oh no, no, no. I'm just going to say sometimes people refer to a physical quantity of something like, Oh I saw you had the sales quota of whatever, and there's no way you would know this so I know you're just shooting in the dark here.

It's the assumption, especially if it's quantitative, like an actual number. That really, really bothers me. I'm realizing I have all of these little idiosyncrasies I never really thought. I have to evaluate, spend some time reflecting on it. This is a great game. We should play this sometimes.

Sarah: This is a good game. I like it.

Patricia: We'll bring this to what's working and what's not.

Michael: Well, that's another one. I hate when people say I checked your website or you have an impressive LinkedIn profile or something like that. It's so generic.

Sarah: Sometimes it's not even relevant. I looked at your LinkedIn and I see you are a salesperson.

Michael: You are a very successful person. All right guys, listen. I appreciate you taking the time. We should definitely start with the game, finish with the game, or basically have another session. Just several games and just go one by one. That's funny. We are going to need a prize for the next time.

So I'm probably going to get a phone call at some point from Collin so I can negotiate with Collin a surprise for you guys. Who wins gets an additional extra day off or something. Awesome. It's been great having you on the show. It's been a blast. I really appreciate you sharing all of this and spending your time with me, and I'm looking forward to having you guys on Season 3 next season or next year, but I'm going to definitely shoot an email for the next session.

Sarah: Awesome. Thank you, Michael.

Patricia: Thanks for having us

Michael: All right. Take care now. Cheers.

Both: Bye