Episode 8: Intelligent Outreach Automation Processes – Mark Kosoglow

Predictable Prospecting
Intelligent Outreach Automation Processes - Mark Kosoglow
00:00 / 00:00

If a sale requires risking political capital, how do you establish trust? Our guest Mark Kosoglow is an expert in outreach and here to share his success tips. Mark believes that effective outreach requires multiple contacts. These contacts are done through a variety of channels and ultimately lead to a sales pipeline. Today we discuss how to provide high value content during outreach while balancing efficient automation and personalization. Mark Kosoglow is the VP of Sales at Outreach.io a SaaS tool that empowers sales teams through intelligent automation of outreach processes. Mark believes that it’s important to communicate with contacts where they live. Effective contact cannot be limited to one channel or a fully automated sequence. Personalizing content and bumping emails dramatically raises the success rate of outreach. Every line read is a step closer to qualifying a sale.
mark-kosoglowEpisode Highlights:

  • Testing to find the right process
  • Tiering to determine who is in buying motion
  • Using a “bump” to increase replies
  • Communicating where they live
  • Varying call times to connect via telephone
  • Personalizing the sales conversation email
  • Using time blocks for efficient calling

Resources: Connect on LinkedIn Email Mark at: mark.kosoglow@outreach.io

Episode Transcript

Marylou:    What I’d like you to do is for our listeners. For our listeners on the show, you know this process, you know the foundational elements. What do you think you took away from that and how did you make it better?Mark:    I don’t know if I made it better. The main thing for me is I think something that I’ve always believed in which is if you talk to a person rather than a prospect, you get a lot further, right? The only way to do that is to write an email, or to make a phone call, or if you’re doing old school snail mail, or co-cowrie stuff by the office is understand the person well enough to know how to talk to ‘em. Why should I talk about a stuff a lot? Sometimes when we’re talking about a certain person or a certain group of people, it’s like one group is speaking Chinese but they’re living in America. They’re always trying to talk to you but it’s in a different language. Their verbiage is just different. While you might get the most of it, you don’t get that intimate connection that makes them a really close friend. If you’re going to live in America, learn English, right? Marylou:    Right. Mark:    Speak English. I think that’s the point of these emails and stuff like that. You got to learn how to speak the native language of the person you’re talking to. When you figure out how to do that, I think you make a lot more connections. Marylou:    You’ve mentioned the phone and you mentioned email. What is work for you? Why don’t you tell us a little bit of what you’re doing first too. Mark:    You mean doing as far as job or overall? Marylou:    Just whatever you want to tell us. I’m sure they’d like to hear about outreach. Mark:    Outreach is a platform for exactly what we’re talking about. You know that. We help empower sales teams to make sure that their sales communication is tight, and predictable, and unified. I like to tell people I think you can test your way to the perfect sales process if you had the right kind of visibility and the right kind of tools. That’s what our tool does is let people continually test their way to the right process, right? Marylou:    Right. Mark:    What we do is we use a combination of three channels. We use email, phone calls and then social stuff. 99% LinkedIn, maybe 100% LinkedIn. Marylou:    Right. Mark:    That’s what we do. Our tool allows you to build a multi channel, multi step process. For example, first of all we tier our account. We tier them based on importance, based on some markers that we found that tell us the potential of a deal. Tier one, obviously most important. Tier two, nice good accounts take ‘em. Tier three, we want the low hanging fruit and we’ll work with it if they’re quick design and not much trouble. The tiering then determines the level of personalization and automation that we put into the messaging for that. Tier three, fully automated. We have some good emails but we don’t spend time on them because again we just want the people that are already in the buying motion, people that are already thinking in this direction. We don’t want to educate them, we don’t want to take ‘em through a three months sales process because the revenue just doesn’t want that level of resource dedication. But tier one, we’ll do anything for tier one. On the first day that we prospect the person in the account, we’ll do three touches. We’ll do a phone call, we’ll do an email and we’ll do a LinkedIn connect.  We’ll wait a couple of days and bump that personalized email that we sent in the first day with an automated message. I can tell you about some of the stuff we’ve found through doing that. Marylou:    Yeah. Mark:    Then another phone call. Basically we touch them 18 times over 21 days to those three channels. Depending on what happens in the response that we get, then we kind of branch to another directions. We want to communicate with somebody where they live. If they live on the phone, we’ll talk to them on the phone. If they live on email, we’ll do it there. If they live in LinkedIn, we’ll do it there. We’re just trying to find where they live so we can talk to them where they live. Marylou:    It’s funny you say 18 times. I can just feel people cringing. Especially B2B. Tell us about that. What did you discover? Mark:    First of all if you have a crappy approach and crappy messaging, you better not be touching people 18 times. Marylou:    There you go. Mark:    If you’re delivering value and trying to educate someone and have a conversation, that’s a much different scenario. A lot of the touches that we do are un-trackable. We might call somebody six or seven times of those 18 touches but we’ll only leave two voice mails. Marylou:    Okay. Mark:    A lot about it is just trying to get in front of the person at the right time and not always leaving bread crumbs that you’ve been there. Marylou:    That’s good because I think one of concepts of the telephone is this best time to call. It’s not an exact science but you have to make those dials in order to figure out on average when your people, your persona is going to actually answer the phone. It’s different per industry. We had an example, I think it was about a year ago. We did a test where we came in the normal 9:00AM and did what I call block time which is you sit down, you put your do not disturb sign on your door and you start making phone calls. In the telephone world, you get better as you go in terms of conversation. We did a 9:00AM to 10:00AM and we got three connects, maybe on average. We bumped that down to 7:00AM and we were done in half an hour. We got connects. I want our audience to remember that you got to try different times to connect with people but that explains the 18 touches. What else have you found out by doing it that way? Mark:    I think that we found out that—my one boss used to tell me persistence beats resistance. You can beat somebody down or bang down the walls that they’ve erected. Basically our CEOs says it’s mail time. Companies are a political organization that’s bent to not purchasing. Everything inside the organization is meant to not buy something. Somebody has to put their political capital on the line when they decided they’re gonna purchase something and that’s putting their necks out. Sometimes in order to build up enough trust with someone for them to risk their political capital in a company, you have to really do a lot of touches. I use something called the momentum of touches. I think that what we found mainly is there’s not one specific thing that works, it’s the momentum of touches, it’s a LinkedIn connect here, a phone call there, an email a few days from now that are all really built to have value. A couple things about value is if you’re always hitting them with an email that takes three or four minutes to read, they’re not going to do it. Hitting them with a nicely crafted shorter email that has real value and then bumping it a couple of times with small two sentences, “Hey, I don’t know if you got this yet but I just want to get your reactions on it.” Bumping it two times like that within a week will typically get you the same or better reply rate on the bumps than the actual first manually written email. We call that three for one. You can write one manual email, bump it twice with automated email. You get three touches when you’ve written one email and each of those touches will have basically the same reply rate maybe a little bit better on steps two and three. Marylou:    We discovered the same thing too. We call them the in-thread replies. Mark:    Yup. Marylou:    I think a lot of people because they’re so busy, when they see the in thread reply they first thought, “Oh, I didn’t see that,” or “Oh, what is that?” They’re going to go from that subject line to the first line at least to see what it was about. Word to the wise there is that your first line is really important, it’s not just the subject line. It’s that first line so that people will say, “Oh, let me go read the next line.” We call it the slippery slope of reading the email but you’re essentially wanting them to slide down towards to call to action. When you do these replies, do you embed another call to action or are you just saying, “Hey, want to make sure you saw this,” and add some value statement at the end of that. What do you normally do? Mark:    Actually, we try to keep it to two sentences. We usually will have a call to action. “Hey, would you like to get together and talk about this.” Or, the call to action would be a more soft one which is, “Did you read the below, do you have some reactions to the below, can you get back to me about the below.” We found that to be highly successful. I don’t know what it is. I get them too and I feel a pull when I get them. Marylou:    Yeah. Mark:    These little two sentence bumpers. I think that slippery slope analogy is very accurate. I’ve read enough now that I can I slide into the first message. Now, I’ve spent so much time I might as well reply. I’m not a good litmus test for that. I believe that the Sales Guy code. I read almost every sales email I get. If they’re good, I reply. Marylou:    My code of ethics is if you reach out to me, I will respond because my whole world is starting conversations with people we don’t know. Mark:    Yeah, right. Marylou:    When people reach out to me on LinkedIn and they say, “Hey Marylou I’ve read your book,” or whatever, I will reply. I love those people because they’re making that effort. Mark:    Yeah, right. I agree. Marylou:    Word of advice everybody, don’t be afraid to contact me. Connect with me. That’s great. That’s really good. Are you blasting through response rates? Because the Predictable Revenue book, we shot for 79% response rate. That was really on email number one. We’ve been able to maintain that. But through the course of the cadence, we’ve gone to double digits now. Are you pretty much way past that? Mark:    I would say on our big sequence, the one that we used with our best account, right now we’re at 28% reply rate. Marylou:    That’s awesome. Mark:    A reply would count as a phone call answer or a LinkedIn connection request that was approved or something like that too but an engagement activity happens on behalf of the customer. Marylou:    That’s even better because 79% response for Predictable Revenue was positive, negative and neutral. Mark:    Yeah. Marylou:    If you’re getting neutral to positives in the 20% range, that’s wow. Yay! Mark:    I wouldn’t say that. Maybe I misfocused. At least we’ve got 28% right now. It might be 31% on the one. I would say 35-40% of those are positive. Marylou:    Okay. It’s still like the one third but still that’s a lot of people going through that you’re maximizing the conversation which is great. From there, you get them into what kind of sequence after that. Is it more template based or? Mark:    After they’ve responded to the initial one? Marylou:    Yeah. Mark:    No. We have a tool that’s designed for salespeople. Typically once you get a reply, then you need to write something that’s actually from your brain with your fingers on the keyboard. I go back to the Sales Guy code and there are certain things that I expect as a sales guy that I act towards others salespeople. One of those is like if I’m going to send you an email or reply to your cold outreach to me, I do not expect you to send me a template or a deck back. I want you to actually respond cause I’ll typically ask important question. I want an answer to that question. For us, that’s how our team works. We’ll send an appointed response but then we have something we call a follow up sequence. A follow up sequence is if I don’t get a reply to this handwritten email, I’ll give you some statistics on that. They don’t reply to this handwritten, customized email within two or three days or if it’s really important within four hours because you can set it to however you want to, then they’re going to get this little bump again, that two sentence, “Hey, I didn’t hear back from you yet. Are we still going to do this?” We usually bump them three to four times on something like that when there’s a reply to a reply on our inbox. Marylou:    What’s the stats you’re getting on those? Mark:    It’s super interesting. First of all, I want you to guess what percent. This is probably across 17,000 emails the last time I looked at it, a pretty decent sample size. Tell me, if I have any reply in my inbox and I reply to it to somebody, what would you think the reply rate is on that email that I sent? Marylou:    We hope it’s somewhere about 30% response. Mark:    You’re more pessimistic than I am. I would think 70% or 80% of the people reply to my replies. They’ve already replied to me. You know what I’m saying? Marylou:    I know, but they get to see. Mark:    We find it 50%. Marylou:    50% is good. Mark:    It’s not bad. Marylou:    I would be a hero if my clients have to 50%. I have everybody trained at around 30%. Mark:    Sell low, deliver high. Marylou:    Wow, that’s great. Mark:    It’s good but that still means half the people that are unhooked get off. By doing that follow up sequence where we automate the touches afterwards and we do four, five touches over ten days or something, what we end up with is we capture half of the people that didn’t reply to the original ones. We actually will get 75%, low 80% maybe of replies on people that are already on the hook which means that we keep people on the hook. That’s the hardest thing to do as a salesperson is to continue fishing while keeping all the fish that are on the hook on. Marylou:    Once they move from that cold status to working status, where we’re trying to get the AWAF call which is the are we a fit sequence that start. I call it disqualification but it’s a qualification call to get them into the pipeline. Our benchmarks are low. Mark:    I don’t know. We’ll see. You’ll never know. I think that as certain techniques proliferate, they become less effective. You have to constantly be thinking about your game. Marylou:    Yes. The other thing that we do too is the handwritten email that you talked about. We do really want our folks to research about the person because they are people on the other end of that email. Mark:    Yeah. Marylou:    And find out as much as you can about them. Include that in that reply email. We do give them a template. We do give them the sales conversation that we talked about that slippery slope. It’s embedded a little bit further down as to the why. Why should they change? Why now? And why us? We do it in a way that’s very respectful. We help the business developer really choose from a template of choices, which pain point they think would resonate most with that person to start. We actually organize the pain points one at a time but we put it into template format that we do expect them to customize. Mark:    Yeah, we stole that 100% from you. We’re do the exact things. We say keep it to two, three sentences at the top. Show them that you’ve done your research and that we actually care about them and can help. Marylou:    It makes such a difference. Just thinking about the emails I get now. When people actually make an effort and put one little thing that maybe in my LinkedIn profile even. I’m just blown away that they took the time to do that. I will respond. We are sales people. We are a little bit of a different breed. Even IT people, when you get something that is of value to them, or something they’re passionate about, or something that interests them and you include that in the email, you are more likely to get a response from them or just build a fun relationship. What I call squirrel feed them, get them further into the pipeline with more meaningful conversions as you go along. Mark:    Yeah. I totally agree. We don’t sell to IT guys, thank God. Marylou:    I have one client. He’s a HR. He thinks IT is hard. Mark:    I’ve heard about HR. Marylou:    It’s a challenge, definitely. They’re like I guess the best purchasing agent, they’re like that personality a little bit. Mark:    Oh, yeah. Marylou:    Yeah. Mark:    As salespeople, we love those guys too. Marylou:    Definitely. Tell me, how have you been since you know this process so well? How have you shortened the lag in your pipeline overall. If something needs to take sixty days to close, where are you at now? Mark:    I don’t know if we do that. I can definitely explain how we do that. I don’t think it has necessarily to do with messaging if you wanted to stay on that topic. But quite honestly, it’s the thing we’re just talking about earlier, keeping people on the hook. If you go in thinking this person that’s engaged is only going to reply to my email 50% of the time, they’re gonna do it at their leisure even when they do that. If you have seven or ten interactions with that person and they procrastinate just a few hours each time, you’re taking a week to a week and a half that you are pushing out a close just because they’re taking their time to get back to you. That’s fair, we’re all busy. I think that when you stay persistent and you’re on top of your game, first of all if you do it the right way, people perceive it as thoughtful and like, “Hey, this guy’s really trying to empower me to make a decision.” I think that those follow up sequence that we were talking about for us definitely. I know that when we brought those on as a feature of the product, it shrunk our sales something like 20 days or something like that. Marylou:    Oh my gosh. Mark:    Yeah. Marylou:    Your tool is completely automated. It’s not like you’re setting tasks to remember to do stuff. It does it for you, correct? Mark:    Both way. Some people, like in tier one account, super important accounts with super high stakes, C level type people. Their time is valuable. It’s $100 an hour they’re making. To me personally, I feel bad wasting their time. We do things, we do manual stuff. Some of the stuff we do is automated, you pick. If you want it automated, you can do it automated and you can test it and see the results. If you want to do it very manual, you can test it and see the results. For us, we have a certain sales velocity we need to reach not in terms of sales cycle but in terms of the amount of meetings that we’re generating. We need to be a little bit faster so we do incorporate a lot of automation. Marylou:    Yeah. The other thing too is you could set up what I used to teach a long time ago in sales forces is to set up queue. You’d have your working queue, you’d have your call queue. When you came into the office, you would just start at the top and work your way down. Is there something similar like that that you guys are doing? Mark:    Yeah. For us, we have rules of engagement. In order for you to be “working” an account, we say that the account has to be in compliance with rule 52. Rule 52 says I’d come up with bunch of stupid stuff. People will find it all the time. Marylou:    I love it. Sounds like NCIS like gives. Mark:    I am not coming up with periodic tables of selling but I’m getting there. Marylou:    Yeah. It makes it easier to teach when you got everything in a little box, right? Mark:    I hear ya. Rule 52 says that in order to be working an account, you have to have five people that you’re reaching out to at one time, and at least two of those need to be of a manager/director type level. That way, we’re not just prospecting the bottom drags, the easy ones and we’re not putting all our eggs in the basket of like the CFO is gonna respond or email, right? Marylou:    Right. Mark:     We have a report in Sales Force called Rule 52 Compliance. This is the number of contacts in the account and this is the number of contacts that are currently in a sequence. It turns the number red, yellow, or green, depending on how many people they have in a sequence. If it’s green, they know I’m good there. I don’t have anything to do with that. I don’t need to do anything with that account other than some tasks that might be queued up to do it. But if they’re red or yellow, then they know they either need to go prospect again and get some more prospects in there or hook more people that are already in Sales Force into a sequence. They’re our job in the first hour of the morning, we call it account planning, is to look at the Rule 52. Anything that’s yellow or green, get it into the green. Marylou:    Oh, that is great. I love that. When you just said in the morning they do it, it’s habit. It becomes a daily routine which, as you know, at the top of the pipeline. That’s really what we’re looking for is the consistency of habit. Mark:    Yeah, yeah. Marylou:    The same thing with phone calls. Mark:    Yeah. We do the block thing, too. I’ve always believed in time blocking. It’s just I don’t understand how people operate when they just go willy-nilly from one thing to the next and, “Oh, I don’t feel like calling after 12 minutes,” and then you get off on some tangent and you make 13 phone calls that day, it doesn’t work. I don’t think so. We have to have a three-hour call block each day. The first half hour is actually role playing. We break that half hour block into three blocks, three ten-minute blocks. One is drilling where if we say, “Alright, hiring.” That’s one of things that we help solve. When we see somebody is doing hiring, you taught me this, we have a whole content based on a research. We got what we call research buckets so when we go look at an account, we find the bucket of research that this one applies to hiring, a certain technology, bad quarter, new leadership, new product. And then, we have right here two or three open-ended questions that you can use to start a conversation in an email or a phone call. Here’s two case studies that you can use that apply to this particular thing and then here’s a quote from somebody in those case studies that you can use so that they set our customers for us, we don’t set for ourselves. Again, you taught us that. Now, all they do is they just look at the research buckets and then they drill, hiring. Boom! You got to tell me two open-ended questions. You gotta tell me the quote. You gotta tell me the case study. Marylou:    Oh, great. Mark:    And then we have fifteen or sixteen buckets, it makes it very simple for our sales people to know how to start a conversation with somebody that they’ve done research with three months ago. Marylou:    Awesome. I’m so proud of you. You took this to a level that I love this conversation. Mark:    Yes. Marylou:    Tell me, the Mark of a year ago. What would you say to him? Mark:    I’d say to that guy make sure you show up to your meetings with Marylou. I think the main thing is this that I don’t know if it was a mistake. It was definitely a lesson learned is that I think that sometimes you start moving so fast. For us, we are very blessed. We were able to really drive revenue and close a bunch of deals and it just seems like the momentum never stopped, the velocity kept picking up. For me, I needed to slow down some. While the rest of my team can be on that kind of super-fast acceleration, for me, I need to slow down and be much more thoughtful. I know my CEO is the most empowering person I’ve ever worked for and he told me one time, he goes, “Mark, when is your wide space?” I’m like, “What do you mean wide space?” He goes, “When is the time during the week where nobody can access you, where you go into a room by yourself and that’s when you just think about things?” He’s like, “How do you get your eyes above the wave?” Everything’s tossing and turning, how do you get your eyes above the wave so you could see the shore that you’re sailing to? I wish I would’ve started doing that a year ago because that’s when I really start to collect my thoughts, gather my senses about me, and then concept the direction and the priority of the things that we’re trying to do. That’s probably the biggest thing. Marylou:    Yeah, that’s great. That’s great advice. To think a lot of times we are running a million miles an hour and you need to go to your happy place. Mark:    Yup. Marylou:    I’ve been lately going down to the river here in Des Moines, Iowa, and just sitting and looking out and so many ideas come to you. Mark:    Yeah. Marylou:    It’s just incredible if you let your mind just chill. Mark:    Something about stillness and rest. Marylou:    Yeah, definitely, and mulching. Mark:    Yeah. Marylou:    We’re getting close to mulching time. Mark:    Are you coming to my house this year? Marylou:    No, I have three truckloads coming in April so I’m going to be very busy. Thank you very much. Mark:    Yeah. Marylou:    Was there anything else that you’d like to share with our folks because I’m sure they’re all like, “How do I reach out to this guy, he’s got it figured out.” Mark:    I don’t know about that but yes, the easiest way to get a hold of me is LinkedIn. I don’t understand Twitter. I tried, I just don’t get it. Marylou:    Yeah. Mark:    I actually got into a nice groove where I was following a bunch of people and they were putting up a lot of content but I think they all got together and decided, “Let’s retweet everybody’s stuff that they post,” so I’d literally read through a hundred of the same exact thing and I just couldn’t filter it enough. But anyway yeah, LinkedIn is the best way to get a hold of me. mark.kosoglow@outreach.ios. People can always email me, too. Marylou:    Yes. What if before we go, what plans do you have? This might be too long of a question. You talked a lot about these processes that you have in place for your sales teams. Are you empowering your clients with similar teaching materials and things so they can come and hit the crowd running and be successful? Mark:    We asked earlier about how we shorten sales cycle. That’s kind of like our little secret sauce. We treat people like customers before they actually sign a deal with us. I believe to do a true evaluation, each party has to have skin in the game. We actually have a pilot agreement that you have to sign in order for us to let you on the platform because a frivolous evaluation is just a waste of time for everybody. Part of that pilot process involves us giving you a solutions consultant that looks and knows exactly how my team works and all the things that we’re learning we constantly share with them the things that we’re learning. They will help the company take what they want to do in their sales process and then graph our best practices on it and propose to them. This is the way that we think that you could really scale up. We just took a very large life insurance company, this is no joke, Marylou. This is insane. He said that it used to take him eight hours or thirty hours a week to do one task and we got them down to four hours. Marylou:    Wow. Mark:    Basically, it freed up an entire week worth of time because we’re able to say “Alright, how do you want to do things?” This is what we think are some great ideas to help you then let’s built it out in the tool that can increase your productivity. Marylou:    That’s so great. We’re not talking hundreds of transactions here, people. We’re talking right now in the hundreds of thousands transactions and email sent and what are the numbers looking like, millions? Where are they? Mark:    I haven’t even seen the, I know in January of last year we we’re sending three or four million emails a month for people. I wouldn’t be surprised if it’s fifty million now, I don’t know. I don’t even know. Marylou:    For those of you listening who are numbers people, fifty million transactions are gone back and forth. This guys really know what they’re doing. You need to contact Mark and that team over there because it’s a great tool that appeared really serious about outreach and starting conversation for net new business. That’s a great tool for that. Thanks Mark. It’s great talking to you. Mark:    You too, as always.

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