How are you when it comes to lead generation? Is that something you think should be left to marketers? Are you putting it off because you don’t trust your own writing skills, or is finding suitable content your stumbling block? How to generate leads in sales is an age-old question?

In this episode of INSIDE Inside Sales, Darryl is joined by the respected speaker and President of the KLA Group, Kendra Lee. Darryl and Kendra dig deep into the challenges of lead generation and offer up some terrific tips on writing styles and the many places where you should be leveraging your content. They also go over tactics such as using video to break down walls, ways to measure your results over time, and using content to enhance conversations with your prospects. Everything you wanted to know about lead generation on this episode of INSIDE Inside Sales!






Host: Darryl PraillVanillaSoft

Guest: Kendra Lee, KLA Group


Lead Generation: By Sales Reps, For Sales Reps

Darryl Praill: How you doing, folks? I say that every week. I really probably should come up with a new way of saying hi to you guys. What can I say, I suck, I’m a loser at that. It’s been a good week for me. You know why, ’cause I had all this production work going on a little while ago, and I actually have a couple days to breathe, and do my marketing and sales gig, and I like when I can do that.

Darryl Praill: Don’t get me wrong, I love talking to you guys, but you’re the highlight of my week, I often say, but I get anxious, I get stressed out if I don’t do my CMO type activities, and show ROI for my salary, and ROI for the program I spend, it causes me grief and stress. Now you may not know that if you were to meet me hanging out in the office, ’cause I like to goof around a little bit and have fun, but I’m stressing, I’m stressing doing that daily thing, and I’m sure you can relate, right. I mean, just look at your job.

Darryl Praill: You’ve got to do how many phone calls a day, and emails, and pull up to activities, and if you don’t have enough conversations, you don’t enough demos, you don’t advance the conversation, or at least continue the conversation, whatever it might be, conversion rates, or worry about how are you engaging, and are you’re using the right words, and are you talking too much, you’re listening not enough?

Darryl Praill: Do you have crutch words when you have your conversations? I mean, my gosh you guys, your daily gig, and I’ve done it, it’s stressful. So I feel your pain. I was reflecting actually not too long ago with someone about how I got into marketing, and I think I’ve shared the story before. I began life as a programmer, and one thing led to another, and here I am today. I’ve done sales, I’ve done marketing, etc., but there’s an interesting story that I want to share with you, because I think it applies to what you do, which is, I remember when I came through the ranks, I went from a development role to a sales engineer.

Darryl Praill: That was my first approach to sales, other than my first stint selling copiers door to door for six months, and then I went to back to coding, ’cause I said this part sucks, door to door sales, my gosh. The stamina and the rejection, welcome to life, Darryl. But eventually, after coding for several years, I decided I want to make some changes, and I became a sales engineer, and lo and behold I saw a salesmen, a very different world, a different point of view. It wasn’t door to door, it was very strategic, it was very tailored, very personalized.

Darryl Praill: It was all about what’s in it for them, etc. It was great, Azure’s a great starting ground for someone who wants to get to sales. Then that led me to be, ’cause the sales engineer part of me, that brought me to product management, which then led to product marketing. Then I lived in marketing, and something happened in marketing that I didn’t like doing. I genuinely did not like doing this, and I’ll share it with you shortly, but it seemed no matter where I went and what I did, and who I worked for, I had to do this, and I wasn’t very good at it.

Darryl Praill: I wasn’t comfortable with it. I didn’t have the skills, or the knowledge, or the training. Yet it was a big part of what I was measured on. So, what was it that I didn’t like doing, and I still do today, and now it is like, it’s only gotten bigger and bigger with every job I’ve taken on. The task I didn’t like doing was demand generation. You know, I thought Marketing was about cool advertising, and trade shows, and brand, brand, brand, brand. That’s what you think of, right. Madman brand, but demand gen, especially in B2B is the core of why you exist in this role.

Darryl Praill: So, I avoided it, I dodged it, I kinda skirted it. I did it a little bit, but I tried to do other stuff, and it was only over time that I started to realize through experience and talking to people like yourselves, how important a role it played. You know, if I as a marketer, do my job right, I feed the revenue engine, you, and then that generates money for the company, and then we all get paid, and we grow, and we expand, and we hire more people. We make more money, we get pay raises, rinse and repeat, life is good.

Darryl Praill: And I got it, and and then as I got more comfortable with my craft, with the disciplines, and all the different tactics, ’cause I didn’t have any experience in search engine optimization, which is a channel, or Pay-Per-Click, which is a channel, or email, which is a channel, or content syndication, which is a channel, or content marketing, which is a channel. I had none, no experience in that, yet those are all different levers you can pull to keep the leads flowing in, so that sales keeps on doing their thing.

Darryl Praill: So why do I bring this up? What does it matter? It’s a great story Praill, but hey, how does that apply to me? Well, I’ll connect the dots. The reason it applies to you, is because I like to say in this new millennia that we find ourselves in, this new decade that sales is the new marketing. In other words, you are doing demand generation now. You’re not just working the leads that I’m giving you. You’re doing demand generation to feed yourself. You’re doing email nurtures, you’re doing messaging, you’re optimizing your open rates, and your click through rates, and is your subject line just right? And how’s my social media engagement? How can I schedule my posts?

Darryl Praill: You’re doing everything I used to do, and still do. At least you’re doing that if you’re smart, if you’re wise, if you get you sometimes, you know, you gotta feed yourself. you can’t count on me, or maybe your marketing team isn’t as capable as you wish they were. the lead flow isn’t there, and it’s one thing for you to prospect, something for you to do your own demand generation. Yeah, I firmly believe that is the New World Order of the sales folks. So, like I’ve been thinking, we’ve never ever done a show on how a sales rep can do demand generation, lead generation, as part of their job, and why they should, and what’s involved, what’s not in the job, and how it differs from what marketing does.

Welcome Kendra Lee

Darryl Praill: So, who’s the right person to bring onto the show for that? Well, glad you asked. Let me bring on Kendra Lee. Kendra, welcome to the show.

Kendra Lee: Well hello Darryl, and thanks for having me.

Darryl Praill: I am thrilled to have you. So let me set the stage for your folks who don’t know Kendra. First off, Kendra’s gonna be on stage at the OutBound conference, right. That’s happening at Atlanta in May, and she is the, I love it, she’s the perfect mix of sales and marketing, and yet her background like mine, which was in development, I believe she refers to herself as the accountant turned hunter, and I love her story. She’ll say to you and I’ve read this before that, in spite of starting her career in accounting, failing IBM’s entry level sales, and being given a territory that had never made a sale, being told that she couldn’t sell without an engineering background, she was able to use her knowledge of numbers, to create her own approach to lead generation.

Darryl Praill: And because of that, it took her to the top 1% of sales professionals, and every single company she worked at. Now that’s kinda cool, don’t you think? Accountant turn marketer, or turn sales rockstar, if you will, so I thought she was the right person. You can check her out. She’s part of KLA Group, so, or you can follow her on Twitter. That’s KendraLeeKLA, she’s on LinkedIn as Kendra Lee. So all places you can check her out. Did I get that story right Kendra? Did I tell you that that little abstract of you, or was I mistaken, and I gave you credit for something that’s not true?

Kendra Lee: No, you were absolutely true. I failed IBM’s entry level sales exam. They told me I couldn’t possibly be successful in sales, ’cause I didn’t know anything about engineering. They gave me the worst territory, and they told me to add to that, that I had to make my quota in my first year or I was out. And yet, nobody had sold hardly anything in that territory, in that whole first year, so it was quite daunting, and yet I still.

Darryl Praill: Welcome to sales.

Kendra Lee: Took the job.

Darryl Praill: Yes, either that’s youthful naivety, or just sheer chutzpah and confidence. So, I’m gonna go with the latter. Let’s go with that. Again, one more thing if you’re intrigued all ready, I’ll give you a little tip. Go to Amazon, Kendra’s written a crazy book, called “The Sales Magnet,” and that’s about how to get more customers, without cold calling. How’s that for the teaser, without cold calling. Check that out. All right, so Kendra, I look at this as lead generation for sales reps by sales reps, but I gotta ask you, when you are doing what you’re doing, you’re speaking, you’re training, you’re coaching, and you bring this topic of lead generation, what’s the reaction you get from sales reps? I’m really, really curious.

Kendra Lee: They often just think, well I’m doing prospecting. I have a list of people or I’ve been told, go mine LinkedIn, or go buy a list, and just start calling. That’s one reaction I get. Another, which actually I love is, well why would I do lead generation, why wouldn’t I just pick up the phone, and just try and reach people.

Kendra Lee: So it’s usually one or the other, and they’re often not expecting that this is their job, which baffles me, because we’ve got a quota. We’re the ones that are being held accountable for it, and ultimately, we’re the ones that are going to have to go find the opportunities, if somebody doesn’t feed it to them. So, we’ll find these people who are just expecting that marketing is going to pass them leads.

Kendra Lee: Oh by the way they’re gonna be great qualified leads, and when I call they’re gonna want to take my phone call, but that’s not the situation. So that’s what I’m hearing when I talk about lead generation with salespeople. They don’t think it’s their job, or I should call and not do lead generation, or well marketing is supposed to be passing me leads, but they’re not. So, that’s the message I’m hearing Darryl.

How to Generate Leads in Sales: Lead Generation vs.Prospecting

Darryl Praill: All right, so let’s start with that, ’cause you mentioned they think they should be prospecting. So, let’s just get some clear definitions on the table. How is lead generation in this case, from a sales point of view, how is that different than the prospecting they’re doing today? Because if I’m a sales rep, I might contend, well listen, I’ve already got a list, and I’m already sending out emails, and I’m already calling. I mean, marketing does a lot of it. They may not call, but they send out emails, so I contend I’m already doing that. That’s part of my prospecting, but you’re saying it’s different. So, give me an example, definition, real life scenario, whatever you want to do, so I better understand how it’s different from prospecting.

Kendra Lee: When I look at prospecting, that is where I know what I’m going to say when I call people. I’ve got my list, I know the cadence with which I’m going to call the, how frequently. Am I going to leave a voicemail, am I not? I’m gonna follow-up with email, but it’s really all about the message that I’m delivering to whoever my target market is, and if I’m smart in my prospecting, I’ve actually grouped the lists of people that I am reaching out to so that there’s a similarity.

Kendra Lee: Either their title is the same, the business issue they have is the same, maybe the industry is the same, so that I can get into a groove, when I’m doing my prospecting, and I absolutely have a plan that says, I’m going to call every three days. I’m gonna follow-up with an email every other time that I call, and leave a voicemail. I’m going to send some calendar invitations in between there, if I’m not reaching people. So, I’ve got a whole playbook that I’m going to use in prospecting. That’s how I look at prospecting. How it differs from.

Darryl Praill: No, go ahead. I was just gonna say, and how does it differ, but you beat me to it, you said, this is how it differs, so I’m listening, I’m on the edge of my seat, how it differs, go for it.

Kendra Lee: So it differs from lead generation in that you’re going to start using more resources to try and grab attention. With prospecting we are, let’s say, relying on our brute force, our knowledge of this is what our message is. This is what we have to convey. And in lead generation, we’re using a whole bunch of different activities, not just email, and let’s say we’re adding in social media, but primarily email and phone, not just that.

Kendra Lee: With lead generation, we may be adding in other activities, and we’re going to add in other resources. So, we may use blog posts, we may use videos that our company has created, there may be an event, there may be someone else that we want to reference. There are all these different activities that you can use to try and generate interest in talking with you, not just the message that you’re leaving when you call, or when you send an email, and lead generation also has its own cadence.

Kendra Lee: With prospecting, when we train in prospecting, we have you prospect hard for a month, and if that person doesn’t respond to you, then we say, put them aside, and you’re gonna wait a time period, and you’re gonna come back, and you’re going to repeat. So, there’s the rinse and repeat. With lead generation, you may have identified people that you know you want to gain access to, and so you’re gonna drip on them, and your playbook lasts a much longer period of time than that month. So, that’s how I view lead generation to be different, using lots of resources, drip playbook.

Where the Heck Do I Get Content?

Darryl Praill: I’m also hearing you say lots of resources. I’m hearing you talk about different kinds of content for lack of a better word, right? You mentioned the word video, you mentioned blogs. You didn’t mention this, but I’m assuming you mean, maybe it’s articles, or eBooks, or what have you, that you’re an expert in, that you wouldn’t be doing now, because once you’ve got that, then you can flog it to generate interest, and that is really very much what marketing does a lot of today, so you can see the overlap.

Darryl Praill: I want to know more about the whole content thing. Where do you get it from? How do you write it? Especially if I’m not a marketer, I don’t necessarily have those skills, but I’m not gonna get that answer from Kendra until we get back from this commercial break. We’ll be right back.

Darryl Praill: Okay, so let’s talk about content. Do I get the content from somewhere? Do I rip it off from somebody? I’m sorry, not rip it off. Do I leverage it expeditiously, and maybe give them credit, maybe not, or do I craft it myself? As an adjunct to that question, if I’m crafting it myself, where do I find the time to do that? So content time, over to you.

Kendra Lee: I think one of the reasons that sales people don’t think about doing lead generation, more like marketers do it, is because they don’t know where to get the content, and if you look, almost everybody on their website, has blog posts, they have articles, they have assets, like you mentioned, there could be eBooks, there could be assessments, checklists, all sorts of cool assets that are at your fingertips, if you just look.

Kendra Lee: You know, it’s really interesting to me, when we are working with salespeople, and we’re training them in prospecting, we recommend that they go look at their blogs, and see what do they have, and so many of them aren’t familiar with the own resources that their company has, that they could leverage in their prospecting. So, I would look within your company, and if your company doesn’t have it, then for the industry that you’re targeting, or the size company that you’re targeting.

Kendra Lee: Are there interesting blog posts or resources that you have found, that you think may be of interest, that you could leverage? So, you don’t have to become a writer. You don’t have to write your own blog posts. You could, but that takes away from your sales time. Use what’s already available. If you’ve got a marketing team, go meet with them and find out what they’re doing. If you partner with other vendors, maybe you resell other companies or you align with their software, there’s a lot of that in sales.

Kendra Lee: Maybe they have content. So, really getting out, and planning, and understanding what’s available to you, that you could leverage in your lead generation, you’ll discover that there’s all this information, and it’s really valuable, and it will enhance the conversation that you ultimately can have with your prospect. So that’s where I would go Darryl to get it.

Darryl Praill: So I’m gonna share, your gonna be my therapist for a minute Kendra, but I’m really talking to all the sales professionals who are listening. My biggest beef in my role running marketing of VanillaSoft, and I’m not intentionally throwing my sales reps under the bus, ’cause not everybody’s guilty of this, is that they don’t know the content that we’re cranking out in massive volumes. I cannot tell you how many times, two things, which is gonna blow you away.

Darryl Praill: I see reps making mistakes, like let’s say they’re not doing discovery, right? They’re not having opening questions, or they’re not following a script, and I bang my head against the wall, and I yell at them in a very supportive loving way, and I say, did you not listen to, so and so, whom I had on the podcast, who told you exactly how to do this? Did you not watch the webinar where we had the panel, we covered the do’s and the don’ts of this sales tactic, and you’re doing the don’ts.

Darryl Praill: We’ve got all this experience and advice just in-house, let alone sharing it with our prospects, right. Then I see them do emails, and I occasionally get copied, and I’m like, who wrote that for you, and why the hell did you not include this blog post, or this eBook, or this listicle, or this infographic, ’cause it speaks right to it, and it’s right there. I’ve got a product marketing person whose whole job is to bring all this content to them. We have sales enablement tools, and everything else.

Darryl Praill: So, my goodness, kids, go to your marketing team and steal all this stuff, buy them a coffee, and say, educate me in what you’ve got. So that’s the first part, I agree with you that. But you made a comment though, you talked about writing, and about you don’t have to be a marketer, but there is writing involved.

How Do I Generate My Own Leads?

Darryl Praill: Let’s say I was to do lead generation drips, you mentioned drips. You know, I’m not a marketer if I’m a sales rep. I don’t know how to write like a marketer. Do I have to learn how to write like a marker to do my own sales lead generation? Talk to me.

Kendra Lee: Absolutely not, and what’s interesting is, when we see salespeople start to do lead generation, suddenly they begin to think they have to write like marketers. You’ll get all the weird headlines. They’ll think up all these creative things that you would expect to see from a marketer. My favorite one, this is using direct mail as part of your drip. You know, you send someone a shoe, and then you follow-up and you say, I just wanted to get a foot in the door. Okay, marketers do that. Salespeople have genuine conversations with people about their business issues, and you’re trying to get in the door, to have that conversation.

Kendra Lee: Yes we could send the cool shoe, we can send the Lamborghini model, and it’s missing all the wheels, and if they want the wheels, they have to set an appointment with you. Let marketing do that stuff. What you’re doing instead, is you’re writing a genuine email, as if you were going to have a conversation with them, but you’re not writing it too long, because the mistake salespeople do make when they’re writing their emails, is that they try to say everything in the email, instead of realizing that there’s a bit of mystery. All we want to do is get the appointment.

Kendra Lee: All we want to do is share a piece of content. We want to give them a blog post that we think is interesting. So, don’t try and write like the marketers, it will actually work against you. Be your genuine self as you’re writing, and then keep your emails brief. Don’t write too long. Can I give a plug Darryl, for our Email Power Prospecting eBook.

Darryl Praill: I would wish you would do that, go for it.

Kendra Lee: So, if writing emails is something you really want to perfect, our most downloaded, most popular resource on our website, is our “Email Power Prospecting” eBook, because it tells you how to write your emails, and that’s the approach you want to use for the lead generation emails that you are writing, and it works within LinkedIn as well, because you’re gonna write similarly for LinkedIn, only keep it shorter. So go get that if you’re focused on how you can write more effective emails.

Does Video Work for Lead Generation?

Darryl Praill: Would it be fair of me to say, when we’re talking about lead generation, and comparing marketing to sales, you know, there’s a lot of channels that marketers use that sales wouldn’t use. A sales rep isn’t gonna use Pay-Per-Click, a sales rep isn’t gonna focus on optimizing their website to get more organic traffic, you know, etc., but you do talk about activities, you do mention blog, you mention videos. Talk to me about video as a tactic for our sales rep to use in lead generation. Give me an example of that.

Kendra Lee: Oh, video is fabulous. We have one salesperson, I just love what he does. He will actually create a personal video to a contact he’s trying to reach, and he doesn’t send it in the first or the second email, or the first or second communication, because you want them to know that it’s genuine. This isn’t a phishing type of email, it’s safe, but by the third one, he’ll send a video that talks about a business issue that he has seen someone like this contact experiencing, and say this is what he wants to talk about in their conversation, or he’ll pick a piece of content that he read, that his marketing team put together, and he’ll include a tip and say, this is what I wanted to talk with you about.

Kendra Lee: It’s really short, you know, 20, 30 second video, tops, and he actually embeds it into his email that he sends. And what’s cool about that is, just like on this, you feel like you know that person, and you’ve heard them actually talk to you. If you’ve got the time, you actually use that person’s name in the video. The other option is you create a video for a group of people. Remember I said at the beginning, similar industry, similar title, and you could send that same video to all of them, just not using their name in it, but that’s one way that you can work in video as a salesperson, and, ’cause I know you’re gonna ask Darryl. There are so many ways you can do video today. There’s so many resources, from your iPhone, to if you use Microsoft Teams, to if you’ve got Zoom. There’s just so many resources, and all you need is your W-4 file.

Darryl Praill: Yeah, I mean there is no lack of hardware. You mentioned the phone, and we use the phone all the time, but there’s also, your webcam is a wonderful device. By the way, get a good webcam, as opposed to using a little built in one. You know, pro tip there, but tools like Vidyard, or Wistia, or BombBomb, or others, are all cool, so check those out. Okay quick question, we talked about lead gen, we talked about prospecting, when would I use one versus the other?

Kendra Lee: Prospecting to me is when you’ve got to fill your pipeline quickly. You’re gonna use that, because it will always be fastest to find your opportunities by doing your calling, doing your prospecting activities. Lead generation to me is when you’ve got that list of people that you really want to gain access to. You may have done the prospecting, and you’ve not been successful getting in the door.

Kendra Lee: Now we’re going to drip on that. Remember I said our prospecting goes usually for a month, our lead generation, the playbook can be much, much longer, and so as a result, I might prospect, and then put someone into my lead generation, or I may have a group of people I want to gain access to, and I’m going to start with lead generation, and then I’m going to end with my prospecting to really hit home and try and gain access to them. So those are two different scenarios that you could apply lead generation to.

Darryl Praill: And both of those cases, it’s really about playing the long game, right? Your example, maybe I’ll do lead gen first, followed by prospecting, is I’m really, I’m softening them up. I’m building my brand, creating awareness, not really pitching, not doing a hard ass, just sharing, then boom, now I’m into prospecting, now I’m going for the ask. Now I’m in pursuit, and the flip of that is, I do prospecting first, ’cause they’re on my list, I’m chasing ’em, and they’re not ready.

Darryl Praill: Whatever it might be, they’re not ready, budget, time, whatever it might be, it’s not right. Okay, I can go into lead gen now, and stay top of mind and current, and relevant, without the pitch, and I might circle back in six months time, and try to pitch ’em again. So, it’s just time and purpose.

Should I Track My Activities?

Darryl Praill: Finally, very quickly, because we’re out of time here, tracking activities, is that important? You know, measuring results, all that kind of stuff.

Kendra Lee: Oh, without a doubt, and especially when you start doing lead generation. It’s hard enough when you’re doing prospecting, and you’re doing it over a month, and you want to space your cadence and have your whole playbook, you absolutely want to have some type of resource, that you are using, that allows you to put your whole playbook, your whole plan for what your lead generation is, into one place, and know where each person is in it, because ideally, you’re gonna have it all laid out, and then you can add contacts to it, as you learn who they are.

Kendra Lee: And now you know exactly what your plan is going to be, so definitely you want it laid out. You want to be tracking your activities. Know when the next time is that you are supposed to do something, and then monitor your metrics. Maybe you’ll find one article has a lot of people responding to it. Maybe you’ll feel like you hit on completely dead air when you send something else. So, paying attention to the results that you’re getting will help you to fine tune your campaign as well.

Darryl Praill: Okay, there you have it folks. You can go see here at for her blog. You can check her out at You can actually go watch her, she’s part of the crew at The Sales Experts Channel, on BrightTALK, along with me, I might add. You can just go see her live at the OutBound Conference. Either way, you need to bring some of that lead generation, some those marketing tactics, if you will, into your sales efforts. That’s Kendra Lee, I’m Darryl Praill, I’m with VanillaSoft, you are listening to INSIDE Inside Sales. We are done for this week, but we should talk again soon. Maybe I don’t know, seven days. What do you say? See you then, bye bye!