Make It Happen Mondays Podcast
July 8, 2019
This episode features a conversation with the CEO of Autoklose, a sales automation platform with a built-in B2B database, about the overuse of automation in sales outreach. The discussion covers how to personalize sequences, how many touches a cold versus warm prospect should get, and how persona-based messaging compares to deep personalization. It also touches on the guest's background as a competitive tennis player and how that experience shaped his approach to coaching a sales team.
For a completely cold prospect, roughly eight to twelve touches spread out over about 30 to 45 days is recommended, rather than bunching them close together. Warmer leads who have already engaged with content, such as a newsletter, need fewer touches, closer to four to six.
Relying too heavily on automation platforms can make reps lazy, sending high volumes of generic emails that look identical to marketing blasts and produce weak results. The episode argues that automation should only handle the repetitive sending, while reps still need to do manual work like LinkedIn engagement and follow-up calls to build real connection.
According to a test discussed in the episode, fully personalized emails did not dramatically outperform persona-driven messaging built around common pain points for a buyer type. The response rate gap was small, suggesting scaled persona-based messaging can be nearly as effective as time-intensive personalization for every single prospect.
Rather than sending a connection request before a first meeting, the suggestion is to use LinkedIn as a secondary touchpoint after initial emails go unanswered, such as endorsing a skill or commenting on a post. These small social impressions keep you visible without being pushy and often prompt a reply that a cold email alone would not get.
A conversation between John Barrows and his guest, recorded July 8, 2019. This transcript is machine-generated and will contain errors. Where it disagrees with the audio, the audio is right.
I'm doing something I've never done before, which is the first open Filling the Funnel program. July 19th in San Francisco, in partnership with SalesLoft, LeadIQ, and Costello, I'm going to be hosting a full-day workshop bringing my Filling the Funnel program to you. If you've wanted to attend my program in person, or you have a small three-to-five member sales team, this is a great opportunity to access the same training companies like Salesforce, Slack, Dropbox, and many others have made a part of their coaching. Let's make it happen. Good afternoon, everybody. This is John Barrows. Make it happen Monday. Hopefully, you all had a good weekend and good week. I'm a little frustrated. I'm talking to somebody who right now, we're at odds right now because of our teams right now in the playoffs, Toronto versus the Bruins.
We got smoked last night, so I'm a little bit frustrated with that. But I want to introduce Sean Feiner, the CEO of AutoClose. How's it going, Sean? Good. How are you doing, John? I could be doing better as far as our teams are concerned, but I've got to give you guys credit. You kicked our ass, and we pretty much looked like we were sleeping last night. Yeah. But, Sean, tell the audience that doesn't know you, what are you doing these days? What's AutoClose all about, and what are you guys working on? Perfect. So, yeah, about four and a half years ago, we started our first company called Exchange Leads, which is a data provider of B2B data. And what happened was we had a lot of clients that loved using our data but didn't know where to email it from.
So, one day, instead of paying the Canadian government a hefty tax bill, we said, let's do some R&D and build a second platform, which is AutoClose, which is a sales automation platform with a built-in B2B database. So, unlike your usual sales automation platform by itself, and then you have your Discover Orbs and Zoom Infos, we have it all in one place where you can do your sales follow-ups, but also use our database to prospect to call leads. Nice. Cool. So, you know, it's a timely conversation because I'm starting to, you know, I'm starting to get kind of frustrated with reps and what's happening in the marketplace, right? Because we had, you know, 10 years, we had marketing automation and all that stuff, and it just, okay, flooded the marketplace.
Great. Okay, good. Inbound lead generation, great, you know, scale, everything else. And then, I don't know, five or six years ago, the sales automation or the sales efficiency tools started coming out to give sales reps the tools to really put together contact strategies and all that other stuff and do it at scale. But what's happened is I'm starting to question the difference between a marketing automation and a sales automation, right? They look exactly the same to me, and I can almost pick out who the vendor is, by the way, of what you're using these days based on the sequence or the cadence or the whatever the hell you want to call it is, because it's like, it's almost like they replicate the exact same templates.
So, help me get off my soapbox about, like, the danger of these tools and help me understand what should be automated, how should these reps be using these tools so we can differentiate over the marketing automation tools that are out there right now. Yeah, perfect. It's funny you say that, actually. I received an email this morning, and the subject line was company with an arrow to the other company. I was like, hmm, I've seen that. I've seen that exact template that they have on their website that they recommend for all of their clients. So, right away, I knew the tool was coming from. But I'm going to say that the key is personalization. So, yes, marketing and sales, you can send the same email sequences, but what you want to do is really know more about the person at a personal level.
So, for example, what we recommend in our sales cadences, et cetera, is, for example, if you were, you know, selling roofs, maybe put the dimension of the property that you're trying to sell the roof to. So, try and have, like, almost like a field of really something personal that could be really related to that individual instead of broadcasting on a, you know, a marketing stance where it's going, you know, you're blasting to 10,000 people using a marketing platform and ideally hoping for people to raise their hand. So, I think personalization would be one. One thing we've started doing is actually adding personal video. So, we have a partnership with Vidyard inside, where if you know Vidyard, they actually sometimes will put, like, a little sign up with your name.
So, doing something like that inside your follow-up sequence and editing your sequences throughout is also very important. So, do you, because, I mean, I think that's the thing. It's like, do you recommend almost forcing it so that the rep has to do something before that sequence cadence, whatever goes out, so it's not just a press play? Yeah. So, you know, personally what I, you know, and yourself as well, I mean, we're both very big LinkedIn ad guests. One thing that I also like to do to make the sequences feel a little more personal is I'll actually go and have my team look at anyone that clicked or took any sort of action from that initial email that was personalized and then add that person on LinkedIn or try and go on LinkedIn and see if you can get engaged with them through some social or some blog post they did.
So, it doesn't look like, oh, is he just sending me the, you know, the RE follow-up, follow-up, follow-up, but you've also touched them in more than one place. So, when they actually receive your emails, it's like, oh, yeah, Sean just added me on LinkedIn. Oh, yeah, Sean, we had a conversation on that post that John did on LinkedIn about, you know, sales automation, for example. So, I think that's also important, but not just going in for the sale, but trying to learn more, find out their interests on LinkedIn. Do they like tennis, golf, and try and really get that involved in your content. Yeah. I think, you know, I think we've definitely moved into more of an impression world than a, so I'm sure you follow Gary V, right?
Oh, yeah. He's got that jab, jab, jab, right hook, right? Yeah. How you add value, then ask. And I think that the way I look at it these days is it's a little bit frustrating for reps who are being held to monthly quota stuff, but it's a much more long-term play here, right? And the brand building and the social connecting and the impressions, right? So, quote somebody, if you go on somebody's LinkedIn profile, you type, you know, and you follow up one of their blog posts or something like that, all you got to do is make a comment or, you know, retweet one of their whatever it is. That might not be an act, you know, an, oh, look at Sean just did that, but there's an impression there. I saw your name and I saw your face and it might not have consciously registered, but it might potentially subconsciously registered.
So, the more you do that, the more after that fourth, fifth, seventh, eighth touch, I'm now there's a familiarity with it. And it's like, okay, now let me reach out to this. Now let me respond the way I want to respond. Yeah, exactly. And I think you said it. And I mean, one thing that I love to do is, especially when my team have quotes out, is if I send a quote out, say I send a quote out to you, John, and I don't hear from you for four or five days. Now, as you said, you were just traveling to Dubai and you're always traveling. So, you might not reply within 48 hours or 24 hours. But what you can do is use LinkedIn as that social impression by sometimes just endorsing them for one skill or like something.
Because when you do any of that, it actually shows up on their news feed. Oh, Sean, find your endorsement for this. Oh, I forgot. Five days ago, Sean emailed me about that quote. I never replied. And let me tell you, by using those little impressions, like they're calling them, actually allow you to get, well, get us responses quicker and actually get us more engaged. Because it's not like we're just sending the automation and letting it sit, sitting back with our feet up and hoping a sales, an auto-closure, a sales automation platform do it all for you. So, I definitely agree with the jab, jab, jab, you know, Gary Vee statement. Right? And I think that's why people ask me, you know, like, John, like voicemails, right?
Like, why leave voicemails? Nobody calls me back. Well, the reason I leave voicemails isn't because I get callbacks. The reason I leave voicemails is because my email response rates go up when I leave voicemails. Yep. Right? So, it's like you might, you know, and I just know the way I work, right? So, for instance, if you send me an email, if it's not like super top of mind, something that is a priority for me, but it's something I might be interested, I throw it in my things to, you know, things to read folder, effectively, or like a folder that says tech to evaluate. And then I'll probably forget about it. But then about two or three weeks later, if I get a phone call and a voicemail from somebody, I'll be like, oh, yeah, yeah, I forgot about that.
Let me go check it out. Right? So, I think there's this impression game is an important one. It's the same thing with LinkedIn invitations. Like, I used to use LinkedIn invitations. Like, say you and I were meeting. Before the meeting, I used to actually send you a meeting invitation saying, hey, I'm looking forward to show you that I'm doing it all right? But I actually don't do that anymore. I actually use it to later. So, for instance, you and I talk, right, that type of thing. I send you a follow-up email with some information. I, you know, respond three, four times, and you're not responding to me. Then I'll hit you up with that LinkedIn invitation. And if you accept it, I'm not sitting there doing backflips, but at least it shows you're willing to engage in some way, shape, or form.
Right? Yeah, and I think it's very important, like what you say. It's also, you want to also spread things a little bit. Because, for example, if I email you today and I call you tomorrow, you are gone for the last five days traveling for an event. So, it might not, or you might be away with your family. So, you want to almost keep doing those jab-jab or, you know, or adding on LinkedIn or liking or endorsing, you know, every three, four days. So, when they get back from the vacation or you get back from Dubai, you're like, okay, you know, it's almost like you have to be not annoying, but you have to be persistent. So, you have to almost be in the middle there where they respect you and they want to answer you, but you're not annoying them by just calling them all day trying to follow up.
Yeah, and I think that's also true as far as, like, the right hook. So, you know, I used to be an advocate of every single time you send an email or whatever, you know, be a strong call to action. You know, hey, we want to talk and that type of thing. I actually think we need to back off a little bit. We have to stop asking so much to, I want to talk to you, I want to talk to you, I want to talk to you. And I think we do need to kind of lay it up a little bit more and maybe share a piece of content and those type of things to warm up so that when the ask is real, they pay attention. A hundred percent. I actually had a call with my, we had our sales meeting this morning because I was traveling, I got back this morning.
And we talked about just that. So, we were building out a sequence and my sales had, you know, my calendar, book 15 minutes of my calendar on every email. I'm like, why not do something a little bit different? Maybe the first one might be, you know, what challenges do you currently have? And the second one might be, you know, here's a case study of a success story from somebody. You know, the third one might be, and then on the fourth or fifth, you've earned your way to get 15 minutes with that prospect. Instead of just saying, book 15, book 15, here's what we can do, here's what we can help you. But if you're showing them, here are companies we currently work with, here's the results they got, here's people that are in the same industry as you, here's another IT company and what they did.
They more respect you, they look at your value, they visit your website. So, my first call back sometimes is just come to our website, learn about us. Don't even, I don't want to talk to you. And then go from there and then try and nurture them and then add the, you know, adding on LinkedIn, et cetera. So, I 100% agree with you there. I love it. So, what is the right amount of automation? You know, like when we talk automation, look, I'm all for efficiencies. Yeah. But I also am very, like I said, to kick this thing off, you know, I'm very concerned with over automation and reps just literally going through the motions and being lazy and hoping for the best because, and feeling like they did something because they sent out 50, you know, sequences or whatever today, you know, and they got a couple of clicks and opens and that type of stuff.
So, what do you, from your, you know, what you see using your tool and what you're seeing out there and leveraging, like what is the right amount of automation for a sequence, if you will? Yeah. And then that's a great, actually, another thing we discussed today. And I think a big problem is people turn stuff like auto close or any of our competitors on and they say, oh, I sent 200 emails. No, you didn't. The platform sent it. You pressed one button, start a campaign. So, my whole thing is, you know, there's eight, nine hours in a sale, nine to five, say you're working, eight hours in a day. What else can you be doing? So, stuff like this is automated, but actual LinkedIn engagement and stuff is not automated.
You have to actually go there, read an article, and start commenting. So, what I like to do is a few things. One, in my sequences, at the last email, I want to know A, B, C, or D. I want to know, potentially, A, you know, it's not the right time for you, B, you don't need my product, or C. So, at the end of the day, I want to automate things, but I want to get an answer. So, even if it's something I don't have the money, I'm not interested, I'd rather you say that than just to continue sending emails. So, usually, I would send four to five, but what I'll do is, once somebody replies, they're automatically taken out of the sequence. Within 24 hours, you've got to be on the phone call on them.
If you're on the phone call, then you can discuss, you know, oh, why are you interested? What are the challenges? Why are you even interested in sales automation? So, I think automation, people rely on it too heavily right now, and they think that you're doing automation, or you're doing, you know, 20 calls a day, and that's enough. But, you know, there's so much other things you have to be doing within the automation. So, I would say four to six emails, but make sure your last email is getting you a reply. It's either, I know I'm not interested, no, I don't have a budget, it's not the right time, or, you know, give me a few weeks or something like that. But, make sure you get some sort of answer.
So, what are you seeing right now is the optimal amount of, quote-unquote, touches, right? Because if we looked at the amount of touches it takes to get somebody's attention, then we can kind of look at that and say, okay, which ones of those should be, quote-unquote, automated, and which one of those should be personalized. So, what are you seeing right now? What are your statistics showing that it takes to get in touch with somebody or get a response? Yeah. So, if it's a completely cold prospect, for example, you're using our database inside AutoClose, and it's a cold prospect, I would actually do almost eight to 12. Okay. But I'd spread it out. However, if it's somebody that maybe might be going through our MailChimp or our marketing platform, where we're sending out our weekly newsletter, I might only do, like, four to six.
So, depending on if they've raised their hand a little bit or they haven't raised their hand at all, I would do two different. So, I call them cold prospects and, like, your warmer leads. But I would spread the colder over time, even 30, 45 days, eight to 12, but not do them all very so close. So, out of eight to 12, right? So, let's call it 12. 12 touches over 45 days. Yep. What are some of your best contact strategies looking like these days? So, what we've been finding is actually putting video into our campaigns has really helped us. We do one of two videos. One will be a personal video like, you know, we could be doing today just of me. Another one might be maybe they don't want to speak to you for 15, 30 minutes, but if you can show them a three and a half minute video of what AutoClose does, they might click on it.
And then when you click on it, then you get on the phone and you obviously call them. So, I find videos have been really, really good. And also putting success and our customer success website, a link, sorry, for people to go to our website because that just builds trust. And then at least I know, okay, they visit our website. Can we track what link they click? And we've also known they've seen who we're working with. And then that kind of warms them up. And I feel at that point, it's better to go on the call and actually engage with that prospect. So, do you think that just a video, I agree, you know, obviously I'm seeing a huge, you know, videos. Do you think it's persona specific in the sense that you guys sell the VPs of sales, right?
Mark, you know, maybe marketing and CROs and maybe in the areas. And I think we're in that world of, yeah, cool, that's something new, that's something cool. But, you know, for instance, I just got off the phone right before we had this call with a company that does managed service security providers. It's a managed service security provider. And they sell to CISOs, right, the chief information security officers. And my, you know, almost every time when I'm doing a presentation, especially a public one or something like that, somebody will raise their hand about video and they'll say, you know what, John, I'm just not getting good responses on videos. You know, any suggestions? And before I dive into what the message is, my first question is, is what's your, who's your persona?
Who are you reaching out to? And almost always the ones who have challenges say, well, it's a tech, it's a technical buyer, right? Because I look at it and I say, look, if you're a CISO, like you're not going to click on that big fucking thumbnail and be like, oh, what's this? Let me, let me see what's behind that thing. So, so how persona dependent do you think the different mediums are? Yeah. So we actually, we've been actually, it was two weeks ago, we sat down and we actually, the whole morning, we booked it off and we talked about the four different personas within our organization. So, you know, before what we used to do, which didn't work as well, was like kind of like not the spray and pray, but like, you know, we didn't really know who was our buyer.
We'd go after, you know, VPs of sales, but, you know, SDRs are the ones using the platform. So, you know, what we did was we realized, you know, you know, a, you know, do people need data? You know, if they do need data, you know, what are their pains? What are their gains? You know, if they don't need data and they have their own data or they're using just Autoclots for the follow-up, you know, why, why are they using Autoclots? So we've come up with our own personas and I think putting your content towards the challenges and the stuff within those personas will really help you get a higher open and click rate because then you can really relate to them. So at that point, you still have to know who exactly you're dealing with because, you know, for example, with us, we have, we're talking, we have, we have solopreneurs that sign up, but we also have organizations with 25 people.
We also have marketing agencies. So each of them have different reasons for using Autoclots, but also different reasons for buying data and different personas in the data. So personas, I think, do play a key part in your content strategy and especially if you're going to do any, any sort of automation with any, with any company. Yeah. Have you started playing around with impact questions like questions based on personas as part of your sequences? So it's funny, we, we just, we just recently started really building our sequence, our personas and we haven't actually started launching our campaign. So I have each of the, each of our reps kind of, well, my VP of sales building their own cadences and then we're going to all discuss them.
But that's the, that's the plan is to go through what are their pains and inside that buyer's persona, put the pains in the sequence. So once they read it, they can say, oh, well, they can solve A, B and C and put A and B under one roof instead of us using two different things and kind of visioning what it could do to help. But definitely a good strategy that we're looking to implement. Yeah. I mean, that's what I'm seeing a lot of luck these days with the volume, right? I mean, I'm always the advocate of, of personalization, like real personalization. Like it was on your website, it was on your LinkedIn page. And there's the reason I'm reaching out is because whatever, right? But again, that's hard to scale, like really scale.
So I always recommend just do that for your logos, right? Like the logos you want, those are the ones you do that for it now. And that's the quality side. Now the quantity side, you got to get volume up, right? So how do we do that? And how do you do that without being a spam engine? And it's, and it's persona driven. And what I'm playing around with right now, because if you think of, uh, how, um, how an email, like, you know, I use kind of old Glenn, Gary, Glenn Ross, AIDA as the format, attention, interest, desire, action to craft my messages. And the subject line gets my attention first sentence gets my interest. Yep. And what am I interested in? I'm interested in me. I'm not interested in you.
Right. So starting off with, Hey, I'd like to, you know, introduce myself to you or any of that bullshit is, is terrible. Um, and so that first sentence kind of has to be about me, but how do you be about me? Without, without, you know, having to go through research. And what I found is that the, the impact question that is very relevant to my persona that gets me to think, then pulls me into the rest of that email. Yeah. Yeah. A hundred percent. One of the questions I actually use that got some good results was when I was reaching out to salespeople, the one thing salespeople want to do is they want to save time and make more money. Right. So in the first, literally I call it three seconds.
Cause especially like you said, if you're on a mobile phone, you're not seeing any more than that first sentence anyway. Right. Of email. So, you know, something like, you know, if I told you as a sales rep, I can save you 5.5 hours per day and, you know, 4X your rep, you know, or your quota six weeks in something like that. You're like, Oh, I'm a sales rep. If you can help me do this, this, and this, I'd be interested. So, um, I definitely agree with that. And I, I can't even tell you how many emails I get saying, hi, I'm this, this, and CEO of this company. And I wanted to do this for you. Like right when I see that, I know they don't know me. Yeah. Well, like we, you know, it's recent surveys say that blah, blah, blah.
And you know, what's funny is because that, that actually aligns with, um, you know, kind of the book of the month club, if you will. Well, it was a little while ago, which is challenger sale, right? Challenger sale talks about lead with insights. Yeah. Well, I think we, what I, it's unfortunately flooded the market with the, the, the, the insight being led with, right? So it starts with recent surveys say, blah, blah, blah. And then it gets to, well, this is why you should pay attention and this is what we can do about it. But you've already lost me at that point. When you say recent surveys, when you say, you know, other VPs of sales, blah, blah, blah, that, that's not about me, you know? So, so start with me.
And I think that's the, you know, something you're seeing all these, um, I don't know if you're paying attention to kind of the artificial intelligence bots, you know, the, the Nova's, the, the, the scale X's and that type of stuff, which I'm still not bought into those. Cause what I'm seeing is that they're personalizing that first 20%, but it's, it's like LinkedIn circa, you know, 2000, which is, it's like, Hey, Sean, I see you're up in Toronto. Do you like the Maple Leafs? And then it comes in with this hardcore, like, like pitch on something else. Yeah. So there's no connection between the, the personalized part and the reason you're out to me. Yeah. I, you know, actually I got a good subject line a few days ago and it actually got my interest because they actually were, I think it was like, can we have a virtual coffee in Toronto?
So they, so right away I knew you, if you know, you're from Toronto, you must know me. Right, right. And in the email, they were actually a company out of Montreal about four and a half hours from Toronto, but what they were doing is they were probably blasting it to a lot of people in Toronto and anyone that would say they book a day full of meetings, drive out to Toronto and do it. And to be honest, it actually got my attention because it was like coffee, everyone likes coffee. Well, most, you know, most people like coffee and then they knew I was from Toronto. So I felt like even though it was a cold email, it actually got me to click because I thought maybe the person knew me. So I thought that was pretty clever of a company out of Montreal that did that recently.
Yeah. I mean, I think it's even, you know, I got hooked on, I wrote a blog post a little while ago called like finally a contact strategy I can appreciate. And it was one of those kind of, you can tell the kid didn't do a ton of research on me, but he profiled me really well. And even to the subject line, it said like, these apps can add, these apps can add value to your training services. Yep. So I was like, well, I mean, at least the kid knows I'm a trainer, you know what I mean? So what, you know, what is this? So it wasn't just your typical thing. So at least it kind of was that next level down of, at least I know your persona, you know what I mean? At least I'm kind of, and we're finding that the persona driven messaging is actually getting as good, if not a little bit better response rates from the pure personalization at this point.
Really? Yeah. I mean, we did the test, so I don't know. Have you, you know, the company Shakespeare, have you heard of them? Shakespeare? I've not. Yeah. So Shakespeare AI, this was, these were a couple of kids that came out of Salesforce a couple of years ago. And they use my email approach, the why you, why you, well, the Jeff Hoffman email approach called the why you, why you now, which is effectively, Hey, I was on your website and you find it, you open up a new office. The reason that probably need to read out your value statement, right? Whatever. And they said, Hey, we created this artificial intelligence bot that produces super highly personalized emails at a fraction of the time. And, and it was like, Whoa, okay.
So, and I, I, first of all, I called bullshit, but then they sent me an email and I was like, Oh my God, like, this is better than I've ever, this is almost better than I can write. Okay. Yeah. And, and it took, it only took the, the, the bot 70 seconds to write it. Okay. So I was like, Holy shit. But what we did was, um, I had a, I had another company that did, we did under, we did a outsource lead gen for under service markets. So tool like yours to, to go after, you know, lighting and facilities and all this other stuff. And we did persona driven messaging. So it was very short, sweet to the point messaging, very specific to personas and did it at scale. And we, we used our database and their database and we compared and the, and the theory on their end was they're going to get like a 20% response rate and we're going to get like a 5%.
So that Delta is going to, you know, prompt them to really go all in on building this tool out. We ran the numbers, man. And it wasn't that much different. I mean that we got like a five and a half, 6% response rate. They got like a seven, 8% response rate, but it wasn't, it wasn't the Delta. So they were looking for, we're just like, shit. Okay. They shut it down because of that data. Yeah. Interesting. So I think we're getting to a point where, you know, like there's that 20% personalization that I think needs to be there to show you're not a robot, but it doesn't have to be the hyper personalized anymore, which is a little bit disconcerting for me, but, but I get it. You know what I mean?
You know, I think a lot of times when people try to over, I think when they try to personalize a hundred percent, they almost try to over-personalize it, right? Kind of wordsmith something perfect before sending it out there. And obviously there's nothing perfect. So yeah, I think you just need to like, you need a few touches in that, in that, in that message that personalize it. So they know, or at least they, they don't have to know, they might know it's an automated email, but at least they know that you've done some sort of research, some sort of due diligence on that person before you just, you know, started emailing, especially with all the tools out there now that are automating everything, even on LinkedIn and et cetera.
It's very important. Love it. Cool, man. Well, I got a kind of a, a, a, a separate but related question for you. It's a little bit off topic, but it's based on some of the notes you sent over here. Number three, tennis player in Canada. Yeah, I was a, I was actually a, a semi-professional tennis player when I was younger. I was a three, three in Canada, my highest world rank was like 190 in the world at one point. That's pretty badass. So let me ask you, what, what about tennis did, did, were there any learning lessons that you took, uh, from your days as being that high level in tennis to being a leader right now, uh, from an organization or from a sales standpoint? I will swear by this sports is probably the best thing for any young millennial before that we get to want to become an entrepreneur or even a business or work for a company.
Sports helped me become everything I am today. And I'll tell you why, um, at age, after I stopped playing pro or semi pro, I taught the national team for eight years. Not only that, but I taught people when I was 19, I was teaching people in their thirties, forties, fifties, and sixties. And at that age, when I'm really young and people are, you know, going to malls and doing their thing, I'm talking to people 25 years older and I had to learn to be, to grow up very quick. Um, so speaking to those people and I'm talking, you know, CEOs of big banks and, you know, Toronto Maple Leaf hockey players, kids like Max Domi, I taught tennis to, um, and other, and other kids. Um, so that was one thing.
The second thing was competitiveness. Um, I bring the same thing, you know, people now ask me, do you still play? And to be honest, I don't, because there's only one way I know how to play. I know how to play to go on a court and either win or lose. And I don't like to just rally. So how'd that help me now is, you know, for example, you know, as you know, there, there's, there's more than what, you know, articles of sales are mentioned, but there's outreach sale. There's a ton of people. What it, what drives me every day is the competitiveness of saying, okay, I'm the underdog. Okay. You know, they've been in the industry for a few years. I'm going to come in, um, and, and do, try and do things better and grow, um, organically.
Um, so competitiveness is one thing, even on sales call and they say, oh, I'm using this, this company. Uh, they do the same thing. I'm using HubSpot. I'm using this. Well, for me, it's a game almost. So, um, I would say tennis made me a competitive person, um, taught me and actually got me my first two jobs as well before I even became an entrepreneur. So I definitely think, um, playing sports, it could be tennis, could be golf, could be anything is very important, um, to move your way up in the business world for sure. Okay. And what about coaching? So you said you coached, uh, you know, the, like what lessons, what are some similarities of coaching tennis players to get great and coaching sales reps to be great?
Yep. So, uh, when I was a coach, actually, uh, the one thing I really loved was I ran a team. We had about six people at my, at my tennis academy and working with them is like working with, as I guess you said, salespeople at my company. So you gotta, you know, you gotta be able to listen to them and each person has their own personality. So for example, in the sales team, you know, we're trying to see, okay, you're a good cold caller, you're really good at social selling and you're really good at email. You can't just go in and say, okay, well, this is the process we're going to have because you got to know, just like you have to know your tennis coaches, you have to know your sales reps. So, you know, if somebody is a good cold caller, put them on the phones, don't put them on social selling.
If somebody is scared to behind the personal video, don't ask them to go on LinkedIn and do a video like, you know, some of the great stuff Drift and other companies are doing because they just don't know how to do it. Um, so I think that was one thing with coaching. Um, but the competitiveness in me and the, the, uh, the hate losing, um, my sales team will tell you if, if we lose a deal, I'm not a happy camper. So that, that, that's actually a question I like asking a lot of leaders is do you, uh, which one do you like more? Which one is more for you? Uh, do you love to win or do you hate to lose? It's a good question. I would say I love to win. Yeah. See, I hate to lose. I fucking hate to lose.
Like winning to me, like I love, and I think it's maybe a little bit of an experience thing in the, in the sense that early on, I want to win. I want to win. But then once I kind of arrive, if you will, uh, and I, and I'm used to winning, like then it actually flips over and I fucking hate to lose. Like, like I get so annoyed when I lose compared to, you know, winning a huge deal. Like, good job. Like that's what I'm expecting myself to do. But when I lose, Ooh, does it bug me? Right. So like, you know, it's funny how, you know, what drives people, but I think it's an interesting thing. I love to win. And the reason, so what I do strategically when I hate to lose is I try and put not for myself in situations where I can lose.
There you go. So for example, I was away, uh, six weeks ago with my wife and she's, you know, she, she loves going on those paddle boards in the ocean. And I know she would, she would kick my ass. She's like, let's go into a competition. Who could stand up like, I'm like, no, no, it's something you know I was going to lose. So I'm just like, no, I'm just going to tan and read my book by the pool. So I strategically know when I'm, when I'm not too good at something, um, I try and just, you know, whizzle off. But if I'm good at it, then obviously I, uh, yeah, I love to win. And, and, and actually going back to the coaching thing, do you coach towards, so you, I think, I think I know your answer, but cause you said it, but, but with, um, when you're coaching people, there's a whole philosophy of, of playing towards your strengths or improving your weaknesses, um, do you tend to, which, which one do you tend to focus on with your reps?
Do you, do you tend to like mag, try to magnify their strengths or try to improve their weaknesses? So I've tried both. And I find that the, the, especially for, for our company, um, where it's, you know, smaller than, you know, the outreach and the sales lofts, I have to go on people's strengths. I can try and spend, or, you know, uh, you know what we did, for example, two weeks ago, I wanted to, you know, I'm very, I'm always on LinkedIn and I walk down and I go meet my friends. Like you're always on my newsfeed. You're always at the top shot. And I'm trying to teach myself, people that listen, your personal brand, five years from now, personal brand is going to be everything starting now.
And you're not starting to do videos and you're not starting to be on LinkedIn. It personally, your personal brand is going to be your resume. So people can look and see how engaged you are with people. So I tried to actually, before working hours, I did a five day where I tried to have everybody come in here and learn how to work on their weaknesses. But during the day nine to five, when we're really, you know, hustle, hustle, you're trying to sell as much and end of quarter, two weeks ago, uh, we work on the strengths, but yeah, you know, for example, LinkedIn, I'm really trying to get my team on LinkedIn. And some people like, what video do I post? Or, you know, you know, just whatever comes to mind, you just gotta, you just gotta go on there and, you know, talk about, you know, it doesn't have about sales, like put whatever's on your mind that could bring value and engage people and just post it.
So I would say, um, strengths right now, weaknesses, I'm trying to get them more involved than, yeah, I mean, I think my, my philosophy on that is I try to magnify strengths and minimize weaknesses. Yeah. So it's like, you, you just want, you just don't want your weaknesses to hurt you. And if you, you know, for instance, if you suck on video, that's eventually going to hurt you because if you don't get like, you could be the best writer in the world, but I don't see what you look like when you write and we're in a visual world. So I want to see, um, you know, I, you, we have to figure out a way to get you comfortable and maybe that starts with, so instead of LinkedIn, because that's a, such a massive audience, maybe it's starting with Snapchat.
You know what I mean? Maybe it's like, why don't you throw a few things up there on Snapchat just to kind of get comfortable looking at yourself on your phone and trying to add value and who gives a shit, right? It's going to be gone in 24 hours anyways. Right. And then moving to Instagram stories where it's a little bit more, you know, saw and then graduating to LinkedIn, that type of thing. If you're trying, if you're trying to do the video side. Yeah. And so what I did for that was actually, I started in the first thing I asked each of them to do is do a video and actually post it internally in our Slack group for my entire company that's remote to see you. So I had them do two videos in the first week and say, okay, start with Slack.
Nobody else between, you know, the 40 people in our company are going to see it. Everyone on our data team, our developer, our support will see it. You know, it could be talk about, you know, the end of quarter, you know, how the end of quarter went for your sales, how the last day of sales was anything you have in the pipeline, give an update on your sales pipeline. And I did out Slack and it was kind of like the first step. And then I'm just slowly, but actually Snapchat and Instagram and stuff like that might be actually better before I post. Cause they keep being, they're starting to do their emails now, but they're, they haven't graduated to LinkedIn yet. Let's just say that. Yeah. Cool, man.
Awesome. Well, look, I appreciate the time here. We always like to keep these in around 30 minutes. So I appreciate the time here. I think there's a lot of tactical stuff that people could take away from today. What's, um, uh, tell people where they can find you, what you're up to these days and, and, uh, how do you want them to engage at this point? Perfect. Uh, you can find me what first place is probably LinkedIn. I'm always on LinkedIn. I always have a tab open. So add me on LinkedIn, Sean finder. Um, if you want to email me, if you have any questions about anything we talked about today, uh, you can find me at Sean, S H a W N at auto close.com. If you have any questions about our platform, you can go to our website, www.autoclose.com.
Um, but yeah, if you just have questions and stuff, uh, LinkedIn is, uh, is where I spend, uh, most of my day. Awesome, man. Well, I really appreciate it. And, um, so everybody out there, thanks for listening. Hopefully you got some value out of this as usual. And like I always say, if you do anything else today, just make somebody smile. There's too much negativity out there. And if you make somebody smile today, it was a worthwhile day. So make it a great one, make it happen. And, uh, I'll see you on the flip side. Thanks, Sean. Thanks, John. Cheers. Cheers. Cheers. Cheers. Cheers. Cheers. Cheers. Cheers. Cheers. Cheers. Cheers.
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