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Interview: Creating an Outbound Sales Strategy in 2023

The sales landscape is constantly evolving. So what can sales teams do to evolve their outbound sales strategy in 2023? James Urie, head of partnerships at Close, invited me onto the Close Call podcast to discuss this and more.

Our conversation covers many topics including the overall state of outbound sales in 2023, data quality challenges, email deliverability challenges, relevance challenges, more tips to stand out, and choosing the right outbound tools.

The Intro CRM team does this work every day, on our behalf and on behalf of our clients.  And we're always learning. Let us know what you think and what you're doing differently. For more of Harris' take on these topics, follow Harris Kenny on LinkedIn. And if you don't have time to watch the video below, scroll down for the transcript and chapter markers.

If you want to skip ahead, here are the section markers in the transcript below:



[00:00:00] James Urie: Hey everyone. Um, I'm here with Harris Kenny. He's the founder of Intro CRM. He is a close partner. He's also a good friend and a great dad as well. Um, so Harris, thanks for coming on with us. Um, we, today we are going to talk about. Outbound in 2023. Obviously a hot topic, but a unique topic in 2023 given the economic downturn that's currently taking place.

[00:00:28] James Urie: And so inbound is gonna slow down, outbound is going to go up. Now there's a few problems with that, right? You can, you can do outbound all you want, but today you may never land in an email inbox. You may, any of your efforts may never be seen. And so the reason I brought Harris on is he's an expert. He does this, he lives it, he breathes it.

[00:00:50] James Urie: He does it on behalf of clients and he has come up with a formula that is really helpful, but he's also discovered the problems that come with outbound in 2023. So Harris, um, yeah. Thanks for coming on

[00:01:03] Harris Kenny: with us. Yeah, thanks for having me. It's good to speak with you again and great to have most of the time, I'll say sending a cold email is much easier than getting a two-year-old to, uh, brush their teeth if they don't feel like it.

[00:01:13] James Urie: Oh, god. A hundred percent. A hundred percent.

The State of Outbound Sales in 2023

[00:01:16] Harris Kenny: Sometimes they'll lose my cool, but email's easy. I could talk about email all day. Yeah. And, uh, I think that the, the big picture themes that you're talking about are really good place to start, which is just like what's happening in the landscape first. In general, um, because there are a lot of things going on that are affecting reps that are, that are totally outside of a sales rep's control that will affect their ability to hit their numbers.

[00:01:38] Harris Kenny: Yeah. And that they not, may not be totally aware of. And, and frankly, their manager or the, they're working for a founder or whomever that level may not be aware either. And so, you know, if you're responsible for closing deals, whatever level the org chart you're in, y you now have to take ownership of.

[00:01:58] Harris Kenny: Conversation around, how do I make sure I'm getting in front of the right people with the right messaging? Because just to be honest with you, the people that aren't in it doing it every day, they're just not learning quickly enough. Things are changing so fast unless you're in it every day, you're just, it's impossible to keep up.

[00:02:13] Harris Kenny: I'm doing this every day for a bunch of clients and I'm constantly learning. I'm in WhatsApp groups and I'm learning things on LinkedIn that like short takeaway is like you as an individual, if you're responsible for deals and caring deals, it is your job to understand what's happening. Bigger picture.

[00:02:27] Harris Kenny: If you're not hitting quota or whatever, they're not gonna understand why or care why, and so the better you can speak to that, the more in control you'll be of being able to help your customers and being able to navigate all this. So

[00:02:39] James Urie: sales reps, they, they really need to educate their leadership team or their manager on what's happening in the landscape of 2023 and outbound, and we're gonna tell you what to educate them on.

[00:02:49] James Urie: Right. Um, and so this will be useful for you if you're experiencing that conundrum of, I'm doing this much outbound and I get no responses. This is gonna be useful for you. And where we wanna start is, um, some of the, the problems that Harris, you brought to our attention. We're gonna go through a couple of these points that Harris brought and we started chatting about yesterday and we were like, this is super valuable content for all you, all of the sales reps out there that are hustling.

[00:03:14] James Urie: Um, and so the first one is data quality. So there's a data quality issue. Uh, Harris tell us

Challenge 1: Data Quality

[00:03:20] Harris Kenny: more about that. Yeah, so as people are probably seeing online reading in the news, a lot of people are changing jobs, right? And what that means is that the places that you would normally source data from your data providers, you know, the places you'd normally get data from are increasingly inaccurate.

[00:03:41] Harris Kenny: So if you're relying on list polls, and, and frankly this is even true if you're working leads within your existing C R m, if you say, oh, well I'm just gonna run a sequence to everybody I talked to. Yep. You know, in the last three months of last. There's a decent chance that one, if not multiple of those people have moved on.

[00:03:57] Harris Kenny: And so, you know, you need to kind of go in from the get-go and just, and just realize like, is this person who I think I'm talking to, do they even work there at all? Yeah. Is that company still in business? Um, and so there's a couple tools that you can do specifically around email validation, and there's a bunch of email validation tools in the market.

[00:04:15] Harris Kenny: You know, the idea is basically you're testing if an email address is deliverable. Yep. Um, so that's table stakes. Like if you're, and I don't care who you're getting data from, this is all the way up to like the most expensive data providers that charge $20,000 a year in up for access. I'm seeing people reporting like very high error rates and very high bounce rates.

[00:04:34] Harris Kenny: So it's not enough to just check a box. Database tool or whatever. Yeah. Saying give me only verified addresses. Um, you know, ideally you're verifying addresses as close as possible to when you're interacting with those people. Mm-hmm. And if you're gonna be doing some account based research on like an existing lead in your tool, like you're enclosed and you pull up a lead and you dig into the past conversation and you remember what that company does, like, don't just send the one email to the one person you were talking.

[00:05:01] Harris Kenny: Go to LinkedIn, go find a couple more contacts and pop those contacts in there too. Because if you get a bounce, get ready to then contact the second or third person so that you can multi-thread and, and, and try to find the right person. It's not good enough to, to just email the person cuz they're probably there, um, cuz they might not be or, or whatever.

[00:05:20] Harris Kenny: Does that make sense? Oh, absolutely. So

[00:05:22] James Urie: the days of, Hey, I'm gonna go into this expensive data provider, pull this list, blast some emails, that's not necessarily going to give you the quality of data that you need. And it's not that the email address is wrong, it's that there's just so much movement within the industry that the data is not accurate because they simply don't work.

[00:05:44] James Urie: Um, and there's so much Yeah.

[00:05:46] Harris Kenny: Might have jobs. Yeah. Yeah. Who knows, right. A lot of people are moving to, between different departments. Mm-hmm. Like a whole division gets shut down. All of a sudden this person's doing something totally different. Yep. So, yeah, basically the, the way it has worked for, for recent times, um, is changing.

[00:06:01] Harris Kenny: And, and the reality is that the data companies, they can't keep up. You know, they have so many hundreds of millions of records and they oftentimes will update a percentage of that database quarterly. You know, and, and if, and if you're using it all in one tool that says that they'll do all of these things for you, they'll get the contacts, they'll verify the addresses, they'll ai write your email, and they'll send the email for you.

[00:06:24] Harris Kenny: The problem is like, you can't see where your problem lies. All you look is at the end of the day that you're not getting responses and you can't troubleshoot what's going on. And so there's the, your tech stack matters because it's gonna potentially limit your ability to even trouble. Why you're not connecting.

[00:06:40] Harris Kenny: And so you can't say to whoever you're responsible to where there's a problem where your funnel is like locked up.

[00:06:48] James Urie: Oh, that's extremely frustrating. Um, which makes it difficult to educate your leadership team on what is happening and why you're not hitting quota. Um, yeah. So, I mean, just as a solution, that's, that's a problem.

[00:07:01] James Urie: Um, sales reps are gonna be facing it even with the big names and data. Um, they're not able to keep up. They're probably having cuts themselves in some cases where their team is smaller, so handicaps their ability even more to keep up with that data. So like, what would be a viable solution for that problem before we move

[00:07:18] Harris Kenny: on to the.

[00:07:19] Harris Kenny: Yeah. Yeah. And, and they are, I, I just saw yesterday a big, big data provider had let go an entire team exactly what you're talking about. Um, so solution is to be a little bit more dynamic. So there's ways to build lists and gather data in a way that's, um, Where you're tapping multiple sources. Mm-hmm. And so I like to use a tool called Clay, but there's other ways to do this, you know, using web scraping, using other techniques in order to match certain data with other data.

[00:07:51] Harris Kenny: Okay. So like if you can get a list of domains of companies that, where something is true about them, you know, and then you go and you find the LinkedIn company pages, and then you use the LinkedIn company pages to find the contact. It's a different process for getting a lead list rather than before you would maybe just hit in a filter and say, okay, find me anybody who's using Shopify or whatever, um, and say, okay, that's good enough.

[00:08:15] Harris Kenny: Right. Um, so basically my overall recommendation on data is triangulating around like multi-point list building where you're using different data points to try to build a better list rather than just a single thing from a single source. Um, and using heuristics. If I can't find the, the company's LinkedIn page, I'm just gonna scrap it.

[00:08:38] Harris Kenny: Like, if, if they don't have a LinkedIn page, they're probably not big enough for what I'm selling. Yep. Um, I'm just gonna, I'm just gonna, and so it's more of like an iterative list building process where you start with a bigger list, you pair it with other tools, and then you filter down, filter down, and then you end up with a, with a better list where, and, and this'll be the thing, something we'll talk about a little bit later is you'll, you'll be able to write more relevant messaging, um, cuz people aren't impressed anymore if you just say, Hey, it looks like you use.

[00:09:03] Harris Kenny: Shopify. Yeah. Yeah. Duh.

[00:09:05] James Urie: Personalization is the name one for sure too. Um, absolutely. In 2023. So, all right, let's, so let's say you've, you've gone through that hoop. You've educated your, your leadership team, Hey, this is a problem. Now you're being more dynamic to get. Better data, which takes more time and effort, human effort, that not a lot of, you know, tech can just solve for you, uh, which makes you a good sales rep.

[00:09:27] James Urie: Sometimes you just do have to do the work, right? Um, and get the data and hit it from several points. So now you have the data. That's great. But the next biggest problem that we're running into in 2023 is deliverability, um, and making sure that you're even landing in their inbox. So you've done all this.

Challenge 2: Email Deliverability

[00:09:46] James Urie: You've put together this amazing personalized email, whatever you've done to personalize it, video messaging, whatever. Now you've sent it off into the ether and that person may not ever even see it. So let's talk about that problem deliverability, um, your perspective on it, and then, you know, how sales reps can, one, educate their, uh, leadership team again on it and a solution for it.

[00:10:10] Harris Kenny: Yeah. So the big picture here is that the, like different tech companies, Really fighting with each other over very basic things. What, what's happening overall, I think in the, and most, you know, I think especially, you know, folks who are listening to this, selling to tech technology companies, excuse me, using technology.

[00:10:31] Harris Kenny: So you, it's not like the old days where you're knocking on doors. So, so it matters what the different platforms are doing. Right. Okay. So like Google and Microsoft and Zoho and these different. Are treating each other's email differently, just like for starters. Okay. So like they're referencing e emails set within their own tool.

[00:10:50] Harris Kenny: So if you send an email from a Google Workspace account to another Google user, it's more likely to land in their inbox, for example, than if you were to send it to an Outlook account. And so like, so all the way down to the tool, the email provider that you're using, uh, and then, so the thing that you can control a little bit more easily is like you're sending.

[00:11:08] Harris Kenny: So, you know, they're watching behaviors on email accounts, and if things are suspicious, if you have too many identical emails going out at too high of volume in too short of time, like they're gonna lock things down. Um, they're gonna lock accounts and, and that's just gonna keep happening. Like, so there, there's, Google is clamping down on, um, different use of their API and things like that.

[00:11:28] Harris Kenny: So there's, there's a lot of different things that people, I think, take for granted today in terms of their ability to like, get in the inbox. And so, mm-hmm. Like the fundamentals of this. Using the right tool for the job. Um, and so first that's gonna start with like setting up a domain if you're doing cold email for deliverability, so all the DNS records.

[00:11:46] Harris Kenny: Um, if you know, if possible, what I strongly recommend is like these days it's multiple domains and multiple different providers and, and then using the right tool for that sending process. So like there's dedicated pure cold outreach tools that are gonna be able to handle. Variable copywriting. Mm-hmm.

[00:12:06] Harris Kenny: Variable sending windows, things like that. Uh, you know, I like Smart Lead. We use smart lead and that job is really to start conversations. Once you have conversations and replies with people, there's still room for a crm. There's still room for the ability to send smaller sequences out. Mm-hmm. And to call down a list and to, to work in a more targeted way.

[00:12:26] Harris Kenny: But if a tool wasn't built to send, Tons of emails through a channel that wants it. Mm-hmm. You know, you're, you're, you're potentially gonna run into some trouble. And so I think thinking about using the right tool for the right job, um, and making sure that you're not using the wrong tools, because otherwise you're just, you're just, emails aren't gonna send Yeah.

[00:12:45] Harris Kenny: You, you're just not gonna get through and, and doing omnichannel using tools that can support, like phone, that can support sms. Mm-hmm. Adding different channels to your mix is also a really good way to get around. The deliverability problem is so that you're not just a one trick pony. And so that if, if you do have an issue with one channel, you, you're not all of a sudden hung up to dry.

[00:13:04] Harris Kenny: Totally.

[00:13:05] James Urie: Um, which then comes back to your point. If you're, you, you're trying to do this all in one solution, you're not gonna be able to identify the problem appropriately if you are using a specific tool for warming up your. Sending those emails at a higher volume using different domains, tracking that you have specific analytics for, that you can identify if the problem's there, right?

[00:13:26] James Urie: Um, versus if it's just you're blasting it out in a different tool and you have no awareness, you just don't know what the problem is. You could be writing the best copy ever, but you have no clue if, uh, that that copy's actually delivered.

[00:13:39] Harris Kenny: Um, exactly. Exactly. And, and like, just to be honest with you, it is a numbers game.

[00:13:43] Harris Kenny: Like you need to be able to build a system that allows you to hit some level of volume. Yeah. I'm not saying go out and email 10,000 people a day, but if you're writing personally two to five emails a day, like it's just not gonna cut it. Like it's not enough activity. You, your service area for, for opportunity is too small.

[00:14:01] Harris Kenny: Yeah. So you need to have tools that are gonna allow you to operate at, at a little bit of a higher volume.

Challenge 3: Relevance

[00:14:06] James Urie: Got it. Got it. Um, and now let's say you overcome those first two hoops. You got decent data, uh, you've got a warmed up domain, you're following what Harris said. Maybe you're using multiple providers like you're, you're doing it the right way in order to give you the best chance to land in the inbox.

[00:14:24] James Urie: Now, once you're in the right place and you've made it to their inbox, now how are you?

[00:14:32] Harris Kenny: Yeah. So, you know, my bias is towards relevance here, where it's like, how do we think about messaging that's gonna be broadly interesting to folks? Um, rather than being like, Hey, I saw, you know, on LinkedIn that your cat's name is Fluffy or whatever, you know, if you can speak to like, what's happening within an industry, what's happening within their job function.

[00:14:52] Harris Kenny: If in, in a way that's very simple, very to the point, like is a really good tool to help you with your copy. You want your emails to be a couple sentence. Ending with very close-ended questions that speak to where they're at and, and that, in my experience, outperforms personalization at lower volume.

[00:15:11] Harris Kenny: Mm-hmm. So somewhat higher volume with more relevance where you're doing a little bit more research ahead of time, which you can do programmatically. I'm seeing better results. I'm seeing folks are getting better results that way. And, you know, relevance means just like understanding what is it like to be them?

[00:15:26] Harris Kenny: What is the challenges that they're facing? What are the challenges that people like them are facing? Yeah. Um, and you know, not writing complicated emails, not having attachments, not having a bunch of links to other things. Like you just need to say, you know, what can I do to get their attention in a couple sentences with text to start a conversation.

[00:15:46] Harris Kenny: Mm-hmm. And that, that needs to be the bar that you need to clear. Okay. It, it doesn't matter if marketing made some incredible. You know, five minute case study video. Like they don't know who you are or care enough to watch that yet. And so if you can't speak to them in a relevant way, in a couple sentences or text, keep workshopping it until you can.

[00:16:04] Harris Kenny: Okay?

More Tips to Stand Out

[00:16:06] James Urie: Now, if to give, uh, you know, sales reps who might be listening to this or reading this some, some perspective, let's say, let's say there's one prospect that 10 sales reps are going. And how many of those sales reps, one, do you think land in the inbox to actually push their relevant messaging? Hmm.

[00:16:32] James Urie: Like today, if you just ballpark it, this is just like gut

[00:16:35] Harris Kenny: check. Uh, that's a great question. I, what, what I would say that people don't realize is, It depends on when they started their job and when they started sending these emails. The longer someone's been in a job, the, the typically the more things will dovetail.

[00:16:53] Harris Kenny: So, okay. It's, it's really hard for me to say, but, but I would say, man, um, I, I would say a majority of those emails that are getting sent are probably not landing in the inbox. So I would, I would say probably more than half aren't getting there. Like you can, you can distinguish. Quickly by doing these things.

[00:17:16] Harris Kenny: Um, and then doing some extra stuff like setting up your LinkedIn profile and doing social selling and being active there. You know, you mentioned video getting comfortable with if you can get that person's attention and then they're in your pipeline sending a personal 30 to 62nd, you know, vi yard type video.

[00:17:31] Harris Kenny: Yep. Um, you know, there's things you can do to be really exceptional. Um, and if you can even just get in the inbox, I think you're ahead of a lot of reps, I think, I think a lot of people who are sending it volume. Most of their emails are probably landing in spam. Okay.

[00:17:46] James Urie: So you have the good data, you land in the inbox, you have good messaging.

[00:17:50] James Urie: You might be one of the only ones that are actually competing at that point, even if in a pool of 10. Yeah, yeah. Competing at the same exact time for

[00:17:59] the

[00:17:59] Harris Kenny: same prospect. Yeah. Yeah. And, and then, and then the last thing to think about is like if you know your prospect, then, and this is something where I've seen like a lot of lift on our.

[00:18:08] Harris Kenny: Think about their day. Yeah, right. So like when do they check email? Mm-hmm. And if you're sending, if you're loading up sending tool and you're saying, okay, send these emails between nine and 5:00 PM you know, Eastern time, it's like maybe they're in meetings, maybe they're getting slammed with stuff, play around with some weird sending windows.

[00:18:26] Harris Kenny: I've actually seen some pretty good traction sending campaigns on Sundays. Seen some pretty good traction sending campaigns in the evenings between. Four to 8:00 PM when maybe someone's checking a couple emails before bed. Sure. Um, so I think the way you're thinking about it is exactly right. Like, what is it like to be the prospect?

[00:18:40] Harris Kenny: Mm-hmm. What is it like to be in their inbox thinking about their day? They've got their to-dos, they've got phone calls, whatever they've got all these meetings and stuff going on. What is it like to literally be them? Yep. And how can you stand out relative to all the other people that are fighting for their attention?

[00:18:53] Harris Kenny: I think like if I had to end this with one thing, I think that is like the most important thing is what is what you're emphasizing here, which is, Put yourself in their shoes and, and what is it like to receive via email? You know, would you want that? Yep. Is that when you would check it? Is this something that you would easily reply to, or would you have to think about how to reply, stuff like that?

[00:19:13] James Urie: Absolutely. So I, what I, what I love about this, uh, conversation in general is I think in 2023, there's gonna be a, a major marriage. Yes, good quality tech that allows you to land in the inbox. But once you're able to land in that inbox, the sales rep's job is to be human and build that relationship. Mm-hmm.

Choosing the Right Outbound Tools

[00:19:34] James Urie: And solve a problem for somebody and understand the other person. Right. That's what salespeople are. Paid the bid bucks to do really, really well. So if you're a sales rep and you're listening to this, like this is your opportunity to compete. If you can do, take Harris's advice and get in their inbox with really relevant high quality messaging, um, you, you can go and win the world this year.

[00:19:55] James Urie: Um, but with your sales, accompanied with that tech to land in the

[00:20:00] Harris Kenny: in. Yeah, yeah, yeah. I mean, what all we're tight is just like the pregame, right? It's like pregame, okay. Now they, they replied, they're interested. Now is where the real sales begin. Mm-hmm. Yeah. You know, where I gonna listen to them in their conversation, you know, if I have a cool tool that can record my calls and, and makes it easy for me to keep up with my tasks instead of having like a mountain of overdue tasks that I never check or care about.

[00:20:27] Harris Kenny: You know, smart views are great for this. Being able to cut through and be like, these are the things I need to focus on. Yep. You know, and, you know, Smartview is unique to close. This is all table stakes. This is like literally just to like, get there, get to the party, and then this, this is where you as a salesperson really prove your worth, do your job, and have the right, uh, you know, set of tools and process and approach to, to actually help solve those customers problems.

[00:20:51] Harris Kenny: Tools are secondary, but I do think it's like finding the best one for the job, um, can allow you to stand out because frankly, like, you know, a lot of close customers, Uh, scrappy. You know, they're not these huge, heavy companies with 500 person sales teams, and like that can be an advantage. Yes. Like you can't afford the tools that those big teams pay for.

[00:21:11] Harris Kenny: But those big tools also, like they have bloated product management pipelines with features that never ship. And it's like, if you can find the right set of tools with smaller teams, with more responsive engineering groups that are shipping features faster, that can be your advantage. So like you can't beat a big company by trying to use their same tools and trying to B like them, because A, they can afford it and they can afford the support and they afford the implementation and all that stuff.

[00:21:36] Harris Kenny: But B, like why would you accept the handicaps and constraints that come with those tools? Why not pick tools that give you an edge, you know?

[00:21:45] James Urie: Agreed. Agreed. Um, well, cool. We will, in this, in this post, we will put the, the links to the tools that Harris recommends. Um, Harris consults on this stuff too, so he's an expert in this.

[00:21:56] James Urie: If you are really struggling with this, you can contact Harris. Um, Harris, do you have a preferred way of, of being contacted LinkedIn Email,

[00:22:04] Harris Kenny: website? Yeah. Um, sorry. Sites interest You can email me harris interest, uh, or find me on LinkedIn. Yeah. Cool. I'm, I'm active in those spots and uh, would love to.

[00:22:15] Harris Kenny: Awesome. Cool.

[00:22:16] James Urie: Well, thanks Harris. Appreciate it. Yeah, thanks James. See you.