Despite all the experience and tech, people are still sending out poorly written, bland, impersonal emails that give the discipline of email marketing a bad name. Here’s how to avoid being one of them.
In this episode of INSIDE Inside Sales, Darryl welcomes Tyler Lessard, the verified video visionary VP of Marketing and Chief Video Strategist at Vidyard to discuss the importance of video as a vehicle for building rapport and familiarity with your prospects. The two of them will deconstruct the science behind bonding with prospects we’ve never met, as well as becoming relational with them via the visual and audio cues available only in video.
Darryl Praill: How is everybody doing today? Oh, my friends it's been dynamite just dynamite. Since I've got back from Outbound, I literally have been going nuts. I had been back to back to back to back meetings. A lot of it is playing catch up as you all know, small price to pay when you're down there. Back in the Seattle, talking to real people again on the stage, shaking hands and just meeting the people that you see on social and I could face to a name, all that kind of stuff. It was dynamite. So yeah, I've been busy, busy, busy as hell. And as you might imagine, my team was literally complaining with me yesterday about how horse their voice was, their voices were. Because they'd been on back- to- back demos as result of the Outbound conference sponsorship. So how's that? That's not a bad week for me and the team kind of like it. And of course what I can tell you is that we blew out our numbers last month. It was a very, very good month. So we closed our quarter hard. It's always nice. Isn't it? When you're in the sales game where you can say, I either met my number or I got so close, they're not going to give me grief or I surpassed it. The one... years ago I made a choice way back when... as you all know, I've done sales. I've done marketing. I've done sales. I've done marketing. I had this seesaw back and forth and ultimately I probably went all in on marketing for over a decade because I just got exhausted with that weekly, monthly, quarterly, annual chase, relentless chase for hitting quota. And I always found it so thankless that at the end of the month and the quarter is like, I did it. Can I just... like, yeah, can I celebrate, can I go for a drink? Can I high five? Can I come into the next day and strap my stuff? And I was like, no, no, the next day you're a zero dude. You're nothing now. Yesterday was great. So wait a minute, I busted my behind for 90 calendar days to lead up to a handful of hours where I was able to say, yeah, yeah, and then boom, I'm dirt again. I'm nothing. I'm back at ground zero and that was exhausting. Now here's the funny thing. So it's taken on the role of CRO, doesn't bother me anymore. I don't know why. I don't know if I'm just older, more mature and that's just the routine. I think a lot of it comes back to being confident in myself, confident in what we're doing. Confident having seen enough sales cycles, enough time under my belt so to speak, to know that there's going to be cycles. There's going to be good and there's going to be bad. There's going to be seasonality. And for the most part, people are pretty reasonable with you as long as you're performing your job. So that's been my... so I'm celebrating a good quarter. And by the time you're listening to this, I'm back to zero again, I'm dirt. So brothers and sisters we're dirt together. Anyway, I've had a lot of great conversations. I mentioned all the demos we're doing and so part of that is we're jamming nonstop, as you can imagine about Outbound and our experience with it. I just hung up with a cat, great guy. He was... and I love... he was so blunt, Darryl. Darryl, you know I knew SalesLoft and I knew Lband. I heard a couple of others, but I had never heard of VanillaSoft, and we're making a decision like next week. And, but you were like everywhere. And I was like, who the hell are these people? And you seemed like you know what you're doing. You seemed like a shoot straight with you. So here's what they want and away you go. And then, so it's great. We had a conversation and back and forth. It kept me going back to Outbound. Well, Outbound this, Outbound that. And one of the things that's really cool about Outbound, and I probably sound like I'm advertising Outbound and I guess indirectly I am, that's not my point. My point was, it was so nice to be back with colleagues, peers, people whom you respect and you just rift and you would go from topic, to topic, to topic, to topic. And before you know it, half hour, hour, or two hours has gone by, and it just been deep into it and you've been loving it and you've been feeding off it, and you learn so much. And I said to myself," I got to do this. I've got to recapture that." And I said," Who do I know that's really smart that I can rent with on a variety of topics in a single show." And I couldn't find anybody smart, but I did find Tyler Lessard from Vidyard. Tyler, welcome to the show my friend, how you doing?
Tyler Lessard: That lead in was... I saw that a mile away, Darryl, I knew you were going to get the... I couldn't get the person I wanted, but I found Tyler. It is an absolute pleasure to be here. My fellow Canadian tech leader. I'm super excited to be here and I'm glad to hear you had an amazing Outbound my friend that is exciting.
Darryl Praill: Hey, so true story my friend. Last night, I'm sitting on my couch and I get this DM on Twitter and it's from a colleague of mine and he's like, Hey, Praill. I'm about to talk to Tyler Lessard, and I believe you know him pretty well. So that my call goes well with him. I don't know if it's a call or a video or whatever maybe. I don't know. I don't know what it is. Maybe two of you holding hands, walking naked through the park. I really don't know. And I didn't ask for specifics. He said, can you tell me all about him so that I have better contacts and a better story I can really connect with him. And I just want you to know brother, I lied my off and as far as he's concerned you're a legend. So there you go.
Tyler Lessard: Well, thank you. Flattery will get you everywhere. It's been a lot of fun over the last few years, any much like yourself, I get so passionate about the stuff that we do as like marketing and sales and being in this intersection of creative and tech. It's so much fun and whether or not we're actually legends. I'm a legend in my own mind just because I love what I do. And I put myself out there and I've made it. I have made it to the inside sales show so.
Darryl Praill: So you're there. Actually one of the things I did say to him and for our audience, we don't know Tyler. You genuinely should follow him on LinkedIn as you can tell, we might get along a little bit and I torment the hell out of him. But I told this fellow, I said, listen, Tyler's an interesting cat. I said, because he's taken the company from basically startup mode and he's not only grown it, but he's adapted with it, which is a huge statement because the role you have in startup mode, it's not going to be the role you have as you get bigger and bigger and bigger and more people come in and some people can handle that. And some people can't handle that. And I've... and all the leaders that I respect have all watched their role morph and evolve, and they've just gone with it. In the same breath, I said, he's created a category. He's genuinely created a category that for the most part didn't exist with any notoriety and boom, he's done it. So I said, he's going to be a great conversation for you. So let's segue there. I'm having the conversation first. Screw him. I want to repeat Outbound. Let's hit a whole bunch of topics. You're up for it?
Tyler Lessard: Yep. Let's do it. Let's dive in.
Darryl Praill: Okay. So first up for those who don't know, and hopefully I'm not giving anything away, you had this little thing you did a year, 2, 5, 25 years ago, I think it was called something like Sales Fails, and you can correct me on that exact thing. And it might've got a little bit of traction and I believe you're doing it again. So what's up with that brother. What's happening there?
Tyler Lessard: Well, here's the thing we... this was about actually... it's funny I look back at it. It was four years ago, 2017. Was when we were first launching our video for sales tool, right? So those of you don't know Vidyard. Yep. You got cool tools to record and send videos directly to customers and prospects. And at the time we were launching, we were looking for some fun content that would really bring to life the pain that we were trying to solve, right? So we can go out and say," Hey, video is going to help you, blah, the blah, blah, blah." But we all know we respond more to pains than the game. So we... talking to people, we understood, Hey, what we're really allowing salespeople to do here is deliver a more personal impactful message, right? And getting away from the limitations that text- based emails tend to have with us. And so we started playing with that idea and said, how can we bring that pain of shitty text- based emails to life? And I don't know where it came from. Some of us are Jimmy Kimmel fans and Jimmy Kimmel does this skit called mean tweets where he has celebrities read mean tweets about themselves on camera and react to them. So we played off of that and said, why don't we get real people to read bad sales emails that they've gotten on camera and then react to them and pull together a montage of those sorts of things. And we did about four years ago, like I said, and had a blast with it and at that time, because we were coming from being a marketing tech company, most of the people in it were actually marketing experts and leaders. So fast forward to today and you know what we said? We haven't done enough with Darryl Praill. We need something to do with Darryl in the market. Let's bring Sales Fails back and let's do a 2021 edition, because honestly not that much has really changed in how sales people sell and message and everything we talked about four years ago, still today, right? We're still all getting these impersonal emails with crap in them. AI's just shoving stuff in there to try to be relevant. But we look at them, we laugh and we delete. And so anyway, the new Sales Fail video, which is dropping very soon it is a fun montage of Daryl, of Sam McKenna, of Dale Dupree, of Mary Growth from House of Revenue. Some of our favorite friends in the world of sales, reading their least favorite sales emails on camera and reacting to them. So follow me on LinkedIn, if you haven't seen it yet, I'll be sharing it there. It's going to be great.
Darryl Praill: All right, guys, genuinely, you got to do this because the best part about this is you're going to get it. And then you're going to share it with your teams. And you're all going to laugh and you're going to say, is that us? Did we do that? And I guarantee you it will. So true story, on a related note my friend. Mark Hunter issued an email, I get it on this newsletter whatever. It was today or yesterday. And it was, never say these 10 things in email. So you talk about you're doing your Sales Fails, just you were reading bad emails. He says, never ever use these phrases, these 10 phrases in email. And then he had a related blog. You can go to for understanding his reason why, and so I went to my sales channel on Slack and I said, Mark Hunter says, never say these 10 things, are you guys... do you agree do you disagree? And how many of you are guilty of saying any of these 10? And it was hilarious because nobody said... we had a couple of people debate one or two the most, the rest they ignored. But several people say," Well, I do that, but I think it's a good idea and this is why." So we had justification city going on about, that maybe a bad practice. They said, when I do it, it's a good thing because I'm special. No kids, no you're not. So there you go. All right. I want to... I've been meaning to ask you a question for a long time on the video front and kids were talking about lots of things, not just video. But what are you seeing from a sales point of view on innovative uses of video? I'll give you an example. Again on the same sales slack channel we had here internally, my director of sales, Catherine, who everybody can listen to on every weekend, The Drive as my cohost. She shared a post from Andy Paul and Andy Paul said, true stat. We dramatically raised showing percentages. You set an appointment, do they show, are they're not show? We dramatically increased the show ups by the day before sending a 15 or 32nd video saying," Hey, Tyler, really looking forward to our conversation tomorrow at 2: 00 o'clock. I'm going to do this and this, bring yourself a coffee, kick back. It's going to be great, see you then." So it should be sending that reminder that was a video, that was an innovative use and it was all a dramatic use of it. This was also onstage at Outbound. What are you seeing with your clients or even with your community on innovative uses of video that my audience could try and apply?
Tyler Lessard: You see you and I are so instinct. I saw that same post from Andy Paul and it was my friend, Nick Capozzi whose on sport cast talking about that, of doing it right? And it's such a simple idea. So let me spread that out a little bit and give a couple of other thoughts so that one there is a great example, right? Before a meeting, we're all sending that email saying," Hey, can't wait to see you tomorrow." And guess what happens to that email? It gets glanced over. But if you send that email like Nick did with a short video of just your face, talking to him and saying," Hey, can't wait to see you tomorrow." Right? They get to see you again. They get to hear you again. They get to meet you again. And by the way, they feel a lot more guilty about not showing up to your call when they feel and hear a real human, right? And guilt is a powerful motivator. And I hear that one time. And again, the show rates on their meetings, especially early in a sales cycle, go way up when you send a personal video ahead of time to connect with them in that way. And then let's even go to the next step. So you have that meeting, meeting goes great. Guess how many people of the three people that were invited, guess how many of them showed up to that meeting Darryl?
Darryl Praill: Two to three.
Tyler Lessard: Two to three. Absolutely right, ding, ding, ding, ding, ding. Two to three showing up, one of the three did not show up. That's the more important stack. So after you're reading, what are you doing? You're sending an email recap saying here's some great things. Next steps are here. Let's reconnect in two weeks when our calendars align. Instead, what some of the best sellers are doing is recording a short video after that meeting and sending that as part of the followup. Now it's partly to reinforce some of the ideas with those who are on the call, but it's more so for that one person who didn't make the meeting, it's also for the three other people who weren't invited, but at some point may actually play as a stakeholder in the decision that that email is actually getting forwarded to behind the scenes. And now all of a sudden those people that weren't in the meeting, not only are they getting the recap points, but they're seeing and hearing you as a real person, as a real confidence sales rep, deliver that information. You're getting FaceTime with all of these people, whether or not they showed up on the Zoom, right? And then as you move through the sales process, that's the mentality I have with this innovative views. It's actually not innovative at all. It's really simple. It's the simple notion of, as I'm moving through a sales process with a customer, every second they get to see and hear me talk. There are moments of FaceTime. There are moments of rapport building. There are moments of familiarity, they make me more memorable. So when I'm answering a question of theirs, should I have just type back an email or should I hit the record button, show them something on the screen and send it back, right? Might be the very same message. But when you can bring it to life yourself and actually put yourself on camera saying it, it's more FaceTime. It's more familiarity. You become more memorable. You become that most interesting person in their inbox, just by the sheer fact that you're literally showing up there as a real person. So the best sellers that I've seen have made that a habit in saying, I'm going to just continue to communicate through these video messages as a way to stay top of mind state familiar and be memorable and it crushes it. It absolutely crushes it for so many sales reps that I talk to.
Darryl Praill: So let's talk about that for a second, just for context for the audience to really hammer home what matters. The power of Tyler saying, if you're not getting it. Because you keep saying, well, the Lessard, I like him. He's cute. He's Canadian. So we have to like him, but he's a vendor, therefore he's bias and what the hell... whatever. It's like this, so for me it's a personal story, not my personal, your personal. So perhaps there's a television personality who you watch, perhaps there's a YouTube personality that you watch. Perhaps there's a television show that you binge, you watch. And then one day you hear that that person is retiring or that person is leaving the medium, or that show is canceled. And you have this pain inside of like," Oh my gosh, I'm going to miss them. I've grown to like them." We've all been there. We've all seen it. Here's the irony. You've never talked to that person in your life and they've never talked to you. So how could you miss somebody you have no relationship with? Well, the reality is the psychologist is that we bond with people whom we know and like, and trust. And that's developed quickly off of lots of visual and audio cues, and that only comes across in video. So to Mr. Lessard point, when you get in front of these people, maybe they show up to the meeting. Maybe they didn't, but you're still talking to them. They're seeing you over and over and over again. You're becoming more relational with them than the competition is. So when it's time for decision point, if all things are equal, they're going to be biased towards you. And the second thing you can do to his point is you could actually... He talked about, if they share it, anticipating that, why don't you put something provocative in that video? So they will share it without being blatant that," Hey, you should share this." So, you can play off the human behavior. So those are some cool points. The last thing I will continue to say, this came up on Outbound. People continue to be shocked that once you connect with somebody on LinkedIn, you can send them a video message. And again, that was what we talked about at Outbound, just the idea of sending a video message to take an opportunity that's stuck and move it forward is huge.
Tyler Lessard: Hey, Darryl.
Darryl Praill: Yeah, go ahead.
Tyler Lessard: Do you think we could circle back to a couple of quick innovative ideas on the Outbound prospecting side.
Darryl Praill: Yeah let's do it.
Tyler Lessard: inaudible for a moment. All right, cool. Because you sparked an idea there just what you were saying with Outbound is... that's also an area where we've seen a lot of use of these one- to- one videos is when you are prospecting and trying to get their attention in the first place. And there's lots of cool things people are doing out there that may or may not fall into the category, the innovative there. But what they're doing is they're making the video a hundred percent about their prospect and not about themselves. And they're actually doing that not only in their messaging, but in their visuals that they're using to accompany their video and as part of their video. So for example, one of the most successful things that a lot of sellers are doing really simple, but if I were emailing you Darryl as a prospect, and I hadn't heard from you yet, you're still cool. I would make a short video with your LinkedIn profile up on my screen or something about your speaking talk at Outbound. I'd bring up, you're talking Outbound all my screen and I would go," Mr. Praill, you absolutely crushed it at Outbound. I got to watch your recording. I love these two things, but I got a really important question for you about this one other thing that you mentioned, what did you mean by this? And I'd love to hear some more examples, because I've got some things that relate to that that I'd love to think about. Let me know if you've got some feedback on that. I'd love to chat." Something like that, right? And when you see that lend in your inbox, you see a thumbnail image of the video. It's got my face in the corner, but it's got you on the rest of the page. And it creates that... it not only draws your attention in because it's something familiar and relatable for you, but it creates this curiosity gap for you, especially if you make the messaging and the email around it, where you have to fill that gap of like, what is this person talking about with respect to me? And the last thing it does is it shows them literally in a nanosecond, maybe a microsecond that you really did make this video just for them, because that's you on their screen. It's not something generic. And by nature of that, the fact that even their brain immediately they can process that this person made me this video. I'm interested to see what it's about. They obviously did their homework because that's me on their screen, right? All that happens and faster than I can say it. They're more likely to click in and engage because their expectation of value is higher. So that's a really interesting thing that people are doing. And I got to give you this last tip that I borrowed not stole, from crosstalk you know Mr. Dorsey, right?
Darryl Praill: Yes.
Tyler Lessard: Mr. Dorsey, I was chatting with him last week. We had a great session on how his team uses video in their prospecting. And he gave me this brilliant tip, write this one down folks. He said everything about the email that you send is about getting them to click the play button and watch your video. It's not about booking a meeting. It's not about anything else. Everything is about getting them hit the play button, because if they do that's when you got them. Right now, they're going to spend 60 seconds with you. They're going to get to know you, make everything about watching the video, including the call to action at the end of the email, because here's what happens, right? Most people, they send the email and they've got a load of text. And then they've got the video thumbnail image and then after it, nine times out of 10, it says," Can we book 30 minutes to chat?" Right? And I'll tell you what I do as a prospect. And I've learned most other people do this too. When I open up a sales email, I read the first sentence. I read the last sentence and then if it passes the sniff test, I look in the middle and I usually ditch it after I see," Can I book 30 minutes of your time?" I don't care what you said in the middle. I do not have 30 minutes for you at this point, and so what Katie said, he said, try this call to action after your video. Is the problem I showed in the video something you need to fix? Question mark and that's it. That's your CTA. How could you not watch the video then? And your video has those other calls actions in it. I love it.
Darryl Praill: Okay. That is gold. Is the problem I talk about in the video, something you need to fix because now I need to see the video, don't know what you're talking about. And it might be. I love, love that. Okay. One more idea through out there. This has happened to me a couple of times, not often, some of it had a bit of a face there. If there's an really important account, you really want to get in front of, what I've seen done successfully is when people go to OnlyFans and say, get some celebrity to film. Hey, Tyler Lessard, a video really wants to talk to you, George. And Tyler says great things about you but he says, you might have this problem. You should talk to Tyler. So that's another stupid example of video that you can do. That is very easy peasy. And there's some money involved in that, of course, but I love Katie's example. I love the idea of making the videos you do shareable. And so you're going to be provocative in the video so they do share it. I love the idea of using video to confirm an appointment. I love the idea of taking stuck opportunities and going on LinkedIn and using video to move it forward again. These are all innovative uses of video and this is an example of what we did at Outbound. We just had this non- stop never ending ramble where we would riff off each other like this. So today was a bit of an uncommon experience, quick and dirty. One thing that you've seen change in the use of video since you started using the tool four years ago versus now, for example, I don't see the white board much anymore. What are you seeing that has changed?
Tyler Lessard: Yeah, I think there's... you're right. There's more use of it now as a connection builder and an explainer tool, right? In a way to explain ideas more so than just trying to get your attention as an attention hack, if you will. Right? That's really what that first phase of using video in sales was, and the idea with the whiteboard and writing their name on it, it was purely an attention hack. There wasn't always a lot of substance behind it, but it was the," What is going to get their attention?" Now, some of that still happens for sure, people are getting creative with their thumbnails when they're prospecting. But most of what I see is, it's now about the authenticity factor especially with the last year, because we've all been disconnected from real life is the videos are just about having your personality, your passion bleeds through, being authentic, making it about connection, not perfection. And I think that's been a really big piece of it in the use over the last little while.
Darryl Praill: So this is an example of what I'm going to be doing on video next, give an example of being innovative and use it for authenticity. I talked about how I had a call with a demo and the prospect from Outbound earlier today. And they were saying, we hadn't heard of you, but we talked to SalesLoft and Outreach and now... and there are clear next steps demos, pricing. He wants pricing in advance and a few of the things and I said, no problem. What I'm going to do is, I'm going to send him a video as we discussed, blah, blah, blah. But then I'm going to do a screen share. And then I'm going to bring up the pricing page. I'm going to show him your SalesLoft site, here's Outreach site. Here's my site. So three browsers on one screen and what you'll notice right away is that we post pricing on our site. With VanillaSoft, there's no surprises. And that's going to be my hook to build authenticity. So I'm always planting a seed. My friend, we have run out of time. I apologize. I wanted to hit you up and just talk about what's going on at Vidyard. Not from the sense for you to do promotion, but I just wanted to learn what sales tips and tricks and evolution has taken place from you and your team as you've grown. And as you evolve and what did you have to overcome? So I have to save that for another day. I apologize, but dude, what's the best way to get ahold of you? Is it LinkedIn? What?
Tyler Lessard: Yeah. I'm on LinkedIn folks hop on there, Tyler Lessard at Vidyard. And of course, if you aren't using Vidyard yet it's free. I don't know what you're waiting for. Just hop over to vidyard. com. You can sign up and start sending your own videos, how about it? And see success with it, and of course you can do that from right inside of VanillaSoft as well. Because there's really nice little integration there, but we'll look forward to coming back and talk a little bit more about where our sales team is at. So thanks again for having me Darryl.
Darryl Praill: Is he a marketer? Is he a sales rep? I don't know, but he kicks ass, I call the actions. I love it. My friend, Tyler Lessard, take care my friend, we shall talk to you soon. Everybody else happy selling. You may be dirt now, but in 30 to 90 days, you're going to be on top of that mountain again, my name is Darryl Praill and this is the Inside, Inside Sales Show. Take care. Bye- bye.