Prepping for Outbound Part 2

Megan Killion walks through a cold-email and LinkedIn outreach framework for B2B sales. The sniper approach (highly personalized) beats high-volume shotgun tactics. Key steps: map the prospect's problem to your feature and measurable result, personalize beyond the name, follow up three times with different angles, and on LinkedIn, build rapport before pitching.
Chapters
So knowing the prospect, right? This is mapping their challenge to your feature, to the benefit, and then the relevant result. So this top example. a Cashfly-esque example, right? The website's not loading fast enough in APAC. The feature is premium region CDN. The benefit is that they're caching content closer to the customer, meaning lightning-fast page loads. And the relevant result is that they can get more customers in APAC. Let's do this through one of StreamGuys' products and challenges. So what's a situational challenge that you guys address? Like, what problem are you solving? And you can pick any product, any problem that you guys offer.
Yeah, sorry, I had missed the question. I was fixing something.
You're all good. So like situational challenge would be something like— Monetizing the stream.
Yeah, monetizing the stream.
Yeah, monetization's huge. So right now they're not monetizing the stream. So let's— instead of— that's, that's like a— that's the way we would write it, right? Because we're the salespeople. But let's see, they would think of it as they're not sure how to properly make money off of popular content, right? We'll say it's video. And what's your feature? How do you help them monetize the stream?
Server-side ad insertion would be the broad answer.
Okay. Server-side ad insertion. What's the benefit?
They can directly monetize or programmatically monetize and earn revenue on their digital content.
And the relevant result, presumably ROI. Yeah. ROI without having to charge the end user, right? So this is a really common thing. I'm actually investigating this right now as I'm building out a social media site. Which is better, right? Do I charge end users for something, or do I Ads, use ad insertion to monetize, which do people prefer? No brand really involved, people would actually rather see a 15 to 30 second ad than pay you money each month. Cashfly, do you guys have another one? What's another situational challenge that you guys address? Reach in specific areas.
Of the world.
Okay, so let's say— I would say less audience engagement. Okay, that one's the reach, and then audience not engaging. Okay, so performance as well. Yep, so for this one we'd be looking at premium region CDN again, LATAM. The benefit is Reach into a highly monetizable market, great performance, relevant results. If the audience isn't engaging, It's, it's about, like, global premium CDN because they want whatever's the fastest. The benefit is like faster load times, engage more, and users are staying on the site longer. So spoiler, the more specific you are with this little map right here, which is like what is the challenge they're facing, the feature you offer, the benefit, and the relevant results, the more people are going to respond to you. So there's kind of 2 ways to prospect. They are both effective. One is more scalable than the other. You have a sniper approach And a shotgun approach. Now that shotgun approach is where you're not really taking time to personalize each message to each person. You're just sending it all out as a blast. Maybe you get a 1% response rate, but you're hitting 3,000 people, right? Works great when you're new and you have the whole world to prospect and there's tons of people out there. Doesn't really scale as you grow with an org. The shot— the sniper approach is much more about spending those 5 minutes researching each prospect before you reach out and sending a message that's very specific to them. That scales with you. So the more time you spend doing it, the better you get at it. It takes less time, and you're getting really, really high response rates like In some cases, I've seen 70% response when really personalizing. So we're gonna do a practice cold email here. I'll give you guys like 5 minutes to do it. Here's the structure. You can see it up on my screen, but it's just like, hey, insert the first name, add some personalization. Before we jump into it, I wanna be clear that personalization is not naming their title and the company that they work at. That is the laziest personalization out there. Personalization is bringing up a relevant article that you found, talking about something that you know about them. If you've had a previous conversation with them, the best personalization comes from the things that they've told you. But if you haven't, you know, spent 2 or 3 minutes finding something out about them or about their company that you can speak to, And then you're going to use empathy to address the challenge, frustration, or pain that they have, which is what we did above. So like, if you know that they're not sure how to properly make money off of their popular video content, you're going to talk about what that means for them and how you can solve it. Share any relevant results that you have. If you have something like a case study, that's a good place to insert it. But just sharing stats is fine, like We made 30% more money for X company. Then give them a call, a clear, clear call to action that is concise, and then sign with your name. I will give you guys— is 5 minutes enough for everybody? All right, everybody ready?
Yeah.
Who is brave enough to send their message in the chat and let me dissect it? All right. Tyler is brave.
Yeah, I left it pretty broad just because I don't have actual relevant data here. But typically, like, if I do have the time and I'm using the, I suppose, the sniper approach, I try to at least look up an article about them. I just go to the news section of Google.
Google News is a great resource.
Yeah, I typically will just try to post something along those lines. Try to make a quick anecdote about the article and then get into the topic that we think is relevant to them.
Okay. So let's create a hypothetical here. What company are we reaching out to?
I would say maybe something in sports betting universe would be good or an actual athletic team.
All right. Let's see who we have in sports betting. Sportsbetting.ag. DraftKings, maybe?
Yeah, sure.
All right, we're gonna say we're targeting DraftKings and we're gonna do a quick LinkedIn search to see who we're talking to. Do you guys use Sales Navigator?
I don't.
All right.
Is it just through LinkedIn and the premium account?
Yeah. So I honestly, like, I have Sales Navigator and more often than not, I end up just using regular old-fashioned LinkedIn.
Yeah. That's typically the workflow I go through is going through the org, going through the page and then looking for mutual connections. However, in the past, I think we've taken leads from LinkedIn and then reached out to them via email rather than reaching out to them directly via LinkedIn, which I think we should likely kind of switch that.
So probably any of these people could be your target. We'll just talk about this SVP of international strategy to make things short. So we're going to say hello. To Jeffrey, and he's the SVP of International Strategy, technologist, entrepreneur. He got his education in economics and journalism, digital and retail gaming business for DraftKings. He was the Chief International Officer at one point. He's a Canadian and UK citizen. Okay, so he's— this is, this is my favorite type of LinkedIn profile. It is a wealth of information for us, right? Like, he has told us so many things about himself before I even start looking at his posts, which is my like second piece is going in and looking at what they've posted. We're not connected, so I can't do that. Easy enough to send a connection request though. So we're talking to Jeffrey. We recently saw an article posted about DraftKings.
That shouldn't be a hard one to get news for.
Nope. Oh, they bought Golden Nugget Online. A lot of it. Oh, but they're under federal investigation from the SEC. So if you want to talk about security, now's a good time. They just— they're spending $1.56 billion. Oof. Sportsbook promo. Okay, there's a lot here. It looks like they have a lot of interest in data. They're clearly building their revenue and they're investing in things. These guys are in major growth mode, so I would definitely talk about that. Sure, that makes sense. It's great to see that DraftKings has been focusing on growth recently, right? I would not put this top. So one thing, especially this is your first message to this person, right?
Yeah.
I really like a form of messaging and it's not for everybody. I like consent messaging. Which means in my first message, I do not pitch.
Okay.
I ask them to opt in to letting me pitch. So I say something like, since DraftKings is so focused on growth and security, I thought now might be a good time to discuss whatever product/service. Then stream guys, I'd love to share our case study, and then this part works. Insert your information from above about how company got results from product. Okay, if I Send that over, or would you rather connect on a Zoom? Right? Yeah. So my big things twofold, right? One is getting the prospect's consent to the continued conversation. And then the second one is giving people options in how they want to engage, Especially right now. I wasn't super focused on engagement options 2 years ago, but with COVID everyone is under so much stress in their roles. You want to give people the option to tell you, I'd rather read something, or I'd rather talk to you, because people are different. Some people have so much Zoom fatigue. Like, if I get an email and someone asks me to jump on a Zoom with them, Like anything else, ask me anything else in the world. Please don't make me sit through another meeting. I'd rather die. If someone there's other people who are like, goddamn! I don't want to read another white paper. It's just going in my junk email folder. I'm never going to open it. I'm never going to look at it. Right? The only other thing I might add here is something specific to his role. So like. Given your role, are you experiencing this problem, right? You can ask, are you experiencing the problem you're about to pitch? I also— that also does something called layering the question, which causes people to think more in the message that they're reading. So if here we added something like specific Regarding this case study. So if you said, and keep in mind, social proof either connects or it doesn't. So you'd wanna like mention somebody similar to DraftKings that they're gonna recognize.
Oh yeah. So like, um, we work with one of the, the companies they just purchased. So we would say like VSIN.
Yep. So the S-I-N that they were struggling with problem—is that something DraftKings is experiencing? And then you get down to the case study, right?
Like, out of curiosity for you, I've found different success on like email links. Is your goal usually to try to keep the first email succinct and short or try to actually get the information that you want? Because typically I, I find I leave out a lot of info just because I want to keep it succinct.
Short. Yes. The first one, definitely, definitely short. So I like to go with like worst case scenario whenever I'm sending messaging. Like what's the worst thing that can happen? They tell me to fuck off or they block me like that. Those are the worst things that can happen when you send somebody an email. Unless you're breaking the law and they report you for non-compliance, so don't do that. But, um, the worst thing that happens is like they block your email from sending them another email, or they tell you to screw off. When you send short, concise emails, that almost never happens. When you ask people to consent to a continued conversation, it almost never happens. So keep it short, and then your next email You can send follow-up information.
Yeah.
The next email would be something like, hey, I didn't hear back from you next week. I know email gets buried. I just wanted to share the results that we helped the company get. And then you just send that over as more info. And then my third email, I usually do something weird, right? So I'll send a GIF that I recorded of myself or a video or just something out of the box that causes them to— it disrupts their thought pattern about what they expected to get next. Another one that works really well is just the, any thoughts?
Yeah.
Don't say anything. Just ask them if they're going to respond to you.
I get those quite a bit. The other question I was going to have is, and maybe it's something we'll review at another time. I know we're coming up close to the top of the hour. Your thoughts on LinkedIn messaging and how concise that should typically be. When I receive LinkedIn messaging for prospects, it's usually like, you know, like 20 words or less, it feels like.
Yeah, so I've got kind of a— out of, out of what normal, normal advice you'll get about LinkedIn, don't pitch people in your first message.
Yeah.
At all. Like, don't even, don't even bring up StreamGuys. Don't bring up your role. Just message them about something that they posted recently or something that's part of their job and ask a question. So if someone posts regularly, like I post on LinkedIn about sales and marketing, so if you were messaging me and you were trying To get me to talk to you, bring up like a copy of one of my posts and be like, hey, I found this really interesting. Add your insight and ask a question. Then I think you care about me genuinely. Like you care about me and my business and what I'm focused on.
Yeah.
And then when they respond to you, which they will do because you sent a message that wasn't crazy, then you can bring it back around to StreamYard. And this is harder. It's more work than just sending like, pitches to everybody. But at the end of the day, you'll see more and more people hate being cold pitched right after they accepted your request. They're like, man, I accepted this guy's request because I thought he was going to be cool. And I ended up with a pitch in my inbox. Yep. Before we ever had a conversation or interacted. Yep. LinkedIn, especially like it's social media. So don't treat it any differently than you would any other social situation. Like if you're at the bar and you're at like a networking event after a conference, You're not going to walk up to somebody and be like, hi, my name's Tyler from StreamGuys and this is what we do.
Mm-hmm.
You're going to say like, hey, I'm Tyler, what's your name? Oh yeah, I saw your speech, like you gave a talk about, um, like audio engineering. I thought it was really interesting. I really found what you said about leveling the playing field in multiple regions super interesting. Could you tell me a little bit more about how your company solved for the problem he was talking about, right? You're building rapport and relationship. And even in B2B technology, relationship is more important than you think.
Yep.
We are coming up on the end of the hour. If you guys want to email me your pitches, I will go through them and give you feedback. And there is a little bit more To the prepping for outbound, but it's really a walk through a really common outbound strategy. I call it after; some people call it the reply method. There's a million different names for this, but it's basically just give get the prospect's attention, empathize with them, connect with their feelings and their emotions, not just your product. Target their type, which means like build out their persona and personalize your message. Be extremely focused and get to the point. Don't waste their time with a super long email that they're never going to read. And then respect the person, make them the hero, tell them how you can benefit them, not how they can benefit you. All right, guys, is this helpful?
Yeah, absolutely. Well, thank you so much for having us on. It's definitely Some good strategies we can likely implement pretty soon.
Absolutely. It was good to get to know all of you and feel free to email me with any questions that you have. Send me your pitches. I'll give you feedback. If you have any questions whatsoever about your outbound strategy, let me know. I'd also like to focus on building the list, which I think is heavily important as part of this strategy. So it was good to see all of you and I hope that I'll see you next week.
Good to see you, Megan.
Thank you. Thank you, Megan. Cheers.










