EPISODE 657: Seven Tips for Better Sales Prospecting Using AI from Vlad Oleksiienko from Reply.IO

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Today’s show featured an interview with Vlad Oleksiienko, VP of Growth at Reply.io, a sales engagement platform provider.

Find Vlad on LinkedIn.

VLAD’S ADVICE:  “Great salespeople know their customers. They get into the prospect’s head, and they will use AI to become more effective and productive. Automations help us be more productive. The same with AI. I’m confident we will just increase our productivity and be more effective with AI.”


Fred Diamond: Well, I’m very excited. This is the second show we’ve had with our guest, Vlad Oleksiienko. He’s the head of growth at Reply.io, and if you recognize that name, it’s because he was on the show in 2023 and we had a great conversation about the current state of sales prospecting, and we were beginning to talk about AI and a lot of the tools that are out there right now. You can go back and listen to the original show at salesgamechangerspodcast.com/replyio. Again, Vlad, it’s great to have you here. I need to ask you the first question, and we talked about this on the last show. You’re in Ukraine, and again, we’re doing today’s interview in the beginning of March of 2024. A lot of people reached out to me after we posted the show. Give us a little bit of an update. How are things going for the people that we love in Ukraine?

Vlad Oleksiienko: Thanks, Fred. Thanks for having me, first of all. Thanks for the question. I wish to say it’s getting better, but again, it isn’t. It’s getting even more rough, I would say. Unfortunately, we aren’t on the first page of newsletters and articles, blog posts, but it’s pretty much the same. We are trying to stay strong and with the support of the whole world, we’ll go through this eventually.

Fred Diamond: Well, again, I’m broadcasting right near Washington DC and the outreach that I had in the original show we did with you last year in 2023, people were very supportive and wishing their well. We’re continuing to do that and we appreciate the opportunity to talk to you because your company is doing some amazing things. You’re on the leading edge, I think, of sales prospecting and usage of tools, and you gave us so many great tips the last time. We’re going to get a little bit deeper. We’re going to get a currency on this. I’m excited about that.

We talked a little bit about AI and sales. First question, give us your thoughts before we get deep into tips for improving prospecting, what are your insights right now as it relates to AI? What are some of your insights into how AI is being used in the sales prospecting process?

Vlad Oleksiienko: Well, I guess it keeps changing since we had our last conversation a few months ago. It’s changing so fast that it’s super hard even to know to check all these tools basically. By the way, there are probably a few hundred brand new sales tools with AI superpowers, and they ‘re adding them every single day, there are more and more tools. But when it comes to AI and sales, especially in cold outreach, prospecting, outbound sales, stuff like that, I would say that we are getting closer to a new sales tools category called AI sales agents or AI SDRs. It happened because of lots of shifts in B2B sales in the past few years, and B2B data became more democratized.

It’s getting cheaper to buy B2B data. There is no need to buy 10k per year licenses anymore. You can get started with a simpler and cheaper solution. Data is getting cheaper. It means that we can find emails, phone numbers, relatively clean and cheap data. Then we can use some kind of signals. Then we can use generative AI to write semi-personalized emails at scale. AI SDR is a combination of B2B data, generative AI and cold outreach automation tools, all of them in one place. Then that’s how they can write personalized emails at scale for every single prospect in your list based on data from their LinkedIn profiles, maybe some updates about their company, company news, company updates, stuff like that. Emails feel more personalized, but again, it’s not perfect yet. Smart salespeople, smart SDRs will still outperform AI SDR agents. But again, we’re talking here about improving our average results. That’s where AI SDRs and AI sales agents come in. That’s probably the biggest update.

Fred Diamond: Actually, I was listening to a podcast yesterday on this topic. Someone said that AI will get you to the last mile, or I guess for your perspective, last kilometer. Yesterday, just last night, I was just playing on ChatGPT, the most common AI tool that there is, of course. I was just looking for prospects for the Institute for Excellence in Sales. We have a very successful Women in Sales program. I just searched on women in sales companies with women in sales ERGs, employee resource groups. You had to refine the search a couple of times so that it understood what you were looking for. But after five minutes, it shot off a hundred companies that have ERGs for women that are prime targets for us. I know you have a bunch of tips for us. I know you have seven specific tips that you want to bring up, seven tips to improve the prospecting process. Let’s start getting into it.

Vlad Oleksiienko: Well, some of them might be too technical and too into detail, so maybe it’s going to be even hard to explain them during the conversation, because probably I need to show things. But when it comes to tips already, my perspective and probably at least building tips, they’re all about thinking how to make cold emails more relevant to prospects. Because again, it’s getting relatively easy to personalize emails. Let’s assume everyone sends personalized emails, but what is more important here is that we reach out to prospect in the right time. It’s not just about personalization at scale, but it’s about relevance at scale. When it comes to relevance, my prospective tips here are to use some intent-based tools that reveal an interest, that reveal that signal trigger that indicates that prospects are in a buying mode, basically. They’re ready to discover your product or your services, stuff like that.

There are a bunch of intent-based tools. Number one is Sales Navigator. There are a bunch of filters there that you can use. For example, an employee changes their job in the last 90 days, or company is hiring new employees, or company is drastically growing in a specific department, let’s say sales team. Their hiring lots of salespeople means they need lots of tools. Or let’s say when they’re hiring software engineers, it means they need way, way, way more tools there, and maybe services as well. Or opposite to this prospective team, maybe they don’t have a specific role at all, for example, SDRs. It means maybe they need outsourced SDR services, et cetera. It’s all about intent and signal-based cold outreach.

Tip number two, there are a bunch of other signals, for example, technographics, hiring content, social listening, for example, when they mention specific keywords on social media. For example, you are a CRM consulting agency. When someone from the company mentioned something like, “Which SDR tool is the best one out there?” Then you can listen to this signal and then reach out and say, “Hey, we are implementing CRM X, we think it’s the best one. Let’s have a conversation because probably you are going to implement it.” Social listening is number two.

Tip number three, I would say it’s copywriting basically. When it comes to cold outreach and cold email templates, it’s about details. You can add things like I would say use curiosity, which, for example, saying, “Hey, I’m curious, have you already implemented solution X?” Or use tentative tone, for example, “I’m not sure if you’re in the market.” Those copywriting tips we can talk about a lot. It’s all about those small details that make your email more human.

Fred Diamond: I want to go back on some of these things. People forget sometimes when they’re doing sales outreach and sales prospecting, the most important thing isn’t the process. The most important thing is what is going on with the customer? What does the customer need, and what is the customer striving for? What is the customer’s company challenged with? Every sales customer that I’ve spoken to, and I’ve spoken to thousands of them, they all say the same thing, “It’s about what I need.” It’s not about your process. The great sales professionals, especially the newer ones who are earlier in their careers as an SDR or BDR, they need, I love the way you use the word curiosity, they need to focus on, first and foremost, what is going on at the customer? What’s going on in their industry?

We were talking yesterday, it used to be if a guy liked golf, you would talk about golf, and that would help accelerate the relationship. They don’t care to talk to you about golf anymore. They want to talk to you about changes in their industry, new regulations, economic global impact on their business. Again, we’re talking to Vlad Oleksiienko with Reply.io, who’s in Ukraine. There’s so much going on in Europe because of what’s going on there. If you got to put yourself, first and foremost, in the customer’s mindset, you’ll have a lot more of an opportunity to write better content that’s going to have more of an impact.

Vlad Oleksiienko: Well, I agree with you. For me, I’m a millennial here, but again, we millennials and maybe Gen Z, younger generation, we think that software and tools and engineering will save the world. But in reality, it’s not true. Because nowadays salespeople are trained like, okay, so we need more tools, we need more tech stacks, we need polished processes, data migration, stuff like that. AI will save us. It helps. But from what I learned so far, from what I know so far, I would say that foundation remains the same. Basically, it’s all about people. It’s all about knowing what they want. It’s knowing about the pain points. It’s knowing about, as you said, the news in their industry, knowing how industry and economics will change their industry, their vertical, their company. How it’ll impact, how your services and product can help overcome those problems. It’s more about knowing them rather than explaining how your tool, or your product, or your services are cool. My rule here is our jobs as salespeople is to get inside someone else’s head and understand what they’re thinking about, basically. Our sales people mindset should be there.

Fred Diamond: As we’re talking about this, whatever tools you can use to help you understand that, but then I’m going to correct a little bit what I said before. Then you have to have the right process to get the message to the customer, and you have to say it in the right way so that it’s not about you. The Sales Game Changers Podcast, for example, we’re over 700 shows. We’ve had four main interactions. I get a lot of outreach from companies that do podcast stuff. Either they place guests or they can create 10 videos that are ready for TikTok or Instagram from one longer form, if you will.

They always put something in the beginning. They’re getting a little bit smarter. “Hey, I really love the Sales Game Changers Podcast, especially your interview from last year with Vlad Oleksiienko at Reply. We offer a solution that allows you to blah, blah, blah.” Then I always reply back, if I choose to reply, “What exactly did you like about that show?” I know you’re scamming me. I get it. I know that you’re thinking that I’m going to be intrigued because you were able to pick a show I did from 2023, but I could tell that it’s illegitimate. The challenge isn’t getting me excited that you listen to my show, although I want people to listen. It’s that you can help me get more outreach, or you can help me help Vlad get his message out. The reason we do the Sales Game Changers Podcast is to help sales leaders at companies like Reply.io get their message out to further help them build their brand. That’s three. Let’s move on to number four.

Vlad Oleksiienko: Maybe some of them are number four, number five, I don’t know, because as I said, lots of intent-based ideas out there. I would say for at least seven categories that we can scale, predict, and be relevant and scale with those intent-based outreach. I would say localization. I’m not sure if it’s super relevant for the US market only, but it’s super important for European prospects. What we realized and what I realized, and we had a few conversations about this a few weeks ago, what do I mean about localization? When you reach out to specific segments, to specific countries, markets, localize your sequences and localize your cold outreach. Don’t use English. For example, when you reach out to Poland, use Polish language. When you reach out to France, use French language. That’s how you can easily increase your reply rates by almost probably 2x.

This is what happened in my case when we reached out to Brazilian market. We used Portuguese, if I’m not mistaken. What we did there, we actually added a localized landing page in Portuguese as well. That’s how they can relate this content to their language. But probably the hardest part here, you definitely need salespeople who speak that language then so when they decide to get in touch with you and jump on a call, it’s localization here.

Fred Diamond: Tell us what Reply.io does.

Vlad Oleksiienko: Reply is an AI-powered sales engagement platform that helps you automate multichannel cold outreach at scale. You can automate emails, follow-ups, so you can build a sequence of different touchpoints, emails and probably LinkedIn, maybe phone call, manual tasks, manual touches. That’s how you can automate everything. Then you can use AI to maybe localize your sequences. You can use probably something ChatGPT-like interface to create sequences, to improve them, rewrite them, change the tone, change wording, stuff like that. Then you can use AI that will personalize intro lines, PS lines, based on data from their company, from the news, from their LinkedIn. That’s how you can personalize at scale. Basically, Reply I would say is the first iteration of AI agents and AI SDRs nowadays. It’s not just a cold outreach tool anymore.

Fred Diamond: Where are your customers? Around the globe pretty much, or?

Vlad Oleksiienko: Yeah, it’s all about all around the globe, but I would say 70% are from the US.

Fred Diamond: I like the way you keep talking about intent-based outreach. Again, in sales, our job is to close business, or to get it to the next stage with the account executive, whoever it is, whatever the internal process is. I like the way we’re talking here and how you keep bringing up that sales reps, SDRs, BDRs, et cetera, they need to understand what the company does as it relates to how it benefits customers. I think when an SDR understands that, a lot of times they don’t in the beginning, their job is get on the phone, get on the computer, here’s how you send emails, we talked about personalization, et cetera. We talked about how to prospect and they tool out of that training. A lot of times companies forget to teach their frontline people why we provide value to customers, and here’s the intent of what we’re trying to do to get them to be more successful. I know you got two more strategies or tips, let’s get to those.

Vlad Oleksiienko: I would say tip number five here, it’s not just AI personalization, but I would say visual personalized outreach at scale. Meaning we can use, for example, personalized images. We can use personalized gifs. We can use personalized links, landing pages. Here’s how it works. There are a bunch of tools out there that, again, just like in cold email, you have those curly brackets, variables, we call them first name, company name. But what we can do here, we can use those variables and insert them on an image and make them personalized. For example, on an image itself, we can say, “Hi, first name,” or maybe we can use their company logo or their company website screenshot. That’s how we can be even more personalized and make our outreach warmer, basically.

It works. I know it works because sometimes we A/B test things. For example, one of our follow-ups is just, “Hi, first name, any thoughts?” Then variant B is, “Hi, first name, any thoughts?” Then we add a personalized image with their name and saying, “Hey, have you seen our previous email?” That we can easily increase reply rates. Visual, personalized cold outreach, images, links, gifs, maybe screenshot, stuff like that. It’s tactical stuff.

Number six, I would say simplify your language. Again, it’s all about cold emails. I’m not sure about cold calling, but with cold emails, it works. Here’s what I mean. Sometimes I see email templates like, “Hey, we are number one in,” and they specify their vertical or services. For example, “We are number one in PPC advertising,” for example, stuff like that. Then they send us their Clutch reviews saying they are number one, number two. But again, prospects typically don’t care about this. That’s how we can just remove this and simplify your language and say, “Hey, we are helping companies like X and Y,” instead of saying, “We are company number one in something.” Just remove abbreviations, remove jargon, buzzword, marketing slang. For example, sometimes they can say, “Hey, we can help you increase your MQLs by providing AI/ML,” stuff like that. Don’t use those abbreviations. Just say, “We will help you get more leads.” MQL is basically marketing qualified lead, but we don’t care. We’re all talking about leads here, so don’t use those cool words, prospects don’t care about them.

Fred Diamond: A lot of times we throw around acronyms and not everybody knows. I love that tip because we live in this world of acronyms, we live in a world of technical jargon, and not everybody knows. Especially at the customer side where people might be new or they may refer to something different. Make it as simple as possible. I love that.

The thing I’m listening to here is, again, it’s hard. It’s easy, but it’s not simple, or the other way around. You got to be good at this, but you got to get the message to the customer. You got to do it the right way. You got to understand their challenges. Every customer on the planet, especially in B2B, where most of we deal with at the Institute for Excellence in Sales and Sales Game Changers Podcast, they’re dealing with complex issues. There’s so many macro things. We’re still coming out of the results of the pandemic and supply chain hasn’t fully gotten back together. It might take 2, 3, 5, 10 years before we get to pre-pandemic from a supply chain perspective. Every customer on the planet in the B2B world is dealing with challenges. The great sales professionals are the ones who understand that they’re going to be more successful if they frame their wording, their emails, their parlance in the nature of what their customer is dealing with. You keep hitting us over the head with that, which is great, and giving us some ideas on how to be more effective at doing that.

Vlad Oleksiienko: You’re right. It’s easy to learn, but it’s hard to master pretty much everywhere. Tip number seven, I would say reengage leads in your cold outreach or sales engagement platforms. Because people, typically what I see when we’re having conversations with SDRs, they’re typically always looking for new leads and they forget about some potential warm opportunities out there. Here’s how it works.

Let’s say you reach out to 100 prospects and you have this data in your sales engagement platform. Then what you can do here, you can filter this list and sort it by number of use of your cold emails. Then you will have the most viewed emails on the top. Then you can just grab the most engaged ones and add them to a separate sequence saying, and be honest here, “Hey, I saw you opened my emails, but haven’t replied yet. I’m curious, are you having a conversation in your organization? Maybe let’s have a chat. Maybe we can help you with X, Y, Z.” Just try to reengage the opportunities you already have.

Fred Diamond: I remember when the pandemic first started, we were asking people for tips and everyone said the same thing. The smart sales leaders said the same thing, go to your existing customers because you’re not going to get new customers, except if you were selling PPE devices or whatever it might be. But you’re absolutely right, the cost of getting a new customer is so much more prohibitive than getting an old customer. We’re doing today’s interview in March of 2024. Companies are still dealing with the challenges of the last four years, and they’re also dealing with macro challenges, what’s going on in Europe. Again, we’re talking to Vlad Oleksiienko, he’s the head of growth at Reply.io. He’s in Ukraine and we talked about the challenges there.

Of course, everyone listening to this understands there’s challenges obviously in the Middle East. In the United States, there’s an election coming up in November. There’s things happening all over the place, global climate change, et cetera. Everyone is dealing with stuff, and sales professionals need to understand that. You need to understand how the customers that you’re talking to are dealing with this. I love your last advice, which is figure out a way to get back to your existing customers and to go back and to find them again and to recommunicate to them, because you may have things today that are going to help them get through the challenges that they’re dealing with.

Vlad, I just want to send our well wishes from everyone who’s listening to the show. We’re all in support of Ukraine. It’s been going on for over two years now. A lot of people forget that. We appreciate what’s going on with your company and your family and all of our friends there. You have our support. Give us a final thought, final action step, something specific that people listening to today’s Sales Game Changers Podcast should do to take their sales career to the next level.

Vlad Oleksiienko: First of all, thanks for having me today. Thanks for your support and kind words, and congrats on almost 700 episodes. I can’t imagine how much value you’ve brought to the world. I would say that great salespeople know their customers. They get into the prospect’s head and they will use AI to become more effective and productive. This is the word, just like with automations. Automations help us be more productive. The same with AI. I’m confident we will just increase our productivity and be more effective with AI.

Fred Diamond: AI is going to get you to the last mile as they say. But you still, salespeople listening to this, SDRs listening to this, no matter what stage you are in your career, you got to put the customer first. You got to be thinking all the time about how is the world affecting the customer? How is the customer dealing with their own challenges as well? I remember during the pandemic I spoke to one of our guests, his name was David Morelli. This was early on in the pandemic, and it’s still true. He said, “Everyone on the planet is dealing with the effects of the pandemic, they’re dealing with the financial effects, and then whatever their company is dealing with.” That’s still true. If you think about your sales processes in that context, always, what is going on at the customer, then you will be successful. Companies like Reply.io provide tools to help you even accelerate that success. Vlad Oleksiienko, thank you so much for being on today’s Sales Game Changers Podcast. My name is Fred Diamond.

Transcribed by Mariana Badillo

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