It can be a challenge to have your voice heard among the plethora of sales calls, texts, and emails. Sometimes even the best practices for connecting with prospects can be drowned out in the overwhelming tide of sales pitches prospects receive every day.

However, now is not the time to fret! Help is on the way.

For the first time on INSIDE Inside Sales, Darryl is joined by not one, but two powerhouse guests. Amir Reiter, the Rockstar CEO of CloudTask, and Tom Jenkins, CloudTask’s innovative Director of Marketing, offer their wisdoms when it comes to not only standing out, but developing a relationship with their clients. If you are looking for an edge when it comes to being singled out from among the crowd, you won’t want to miss this episode!

Not in the mood to listen? No problem, you can read the transcriptions below.

Host:  Darryl PraillVanillaSoft

Guest: Amir Reiter & Tom Jenkins, CloudTask


Darryl Praill:   Thank you Paul. Good to hear, see, talk, connect with everybody here again. Another episode of INSIDE Inside Sales. I am your host Darryl Praill. And today is an interesting conversation because it’s something that’s near and dear to my personal heart. I’m a big advocate that a lot of your success depends upon how you represent both your employer, or your company that you work for, as well as yourself. And there’s multiple reasons why that’s important. A) People buy from people, that’s number one, not companies. The company is almost secondary. But again, even when they look at you, they’re gonna do a couple things. They’re gonna say do I trust you? Do I like you? Can you and I do business together? And then they kinda leave you and they go back to the company and say do I like this company? Can I do business with this company? Any kind of sale, any kind of engagement, is all about trust. It’s all about a relationship. It’s all about working together as partners.

Darryl Praill:   So even though a lead, a brand new cold, unqualified, pick them out of the contact database that’s probably three years old, that lead they may start off cold, but when they become a customer of yours, by that point in time, you will be best buds. It’s the journey in between that dictates a lot of that success. That journey starts with how you package yourself. And today we’re gonna talk about how you can stand out in a crowded market. And when I say it’s a crowded market it’s not just you, right, it’s you and your competition. Many of us are offering products and services where there are multiple providers. In many circumstances, there may be so many providers that it’s almost a commodity. There’s only two ways you can win that business quite often. One is on price. And if you’re winning business on price chances are you’re probably not making the margins you need to succeed and grow. The other way you can win out is just on who you are and what you’re about and what you’re offering.

Darryl Praill:   Hence, today’s conversation how to stand out in a crowded market. I have got not one, for the first time ever on INSIDE Inside Sales we have two individuals to have that conversation. And we’re gonna meet them right now. First up is my good friend Amir Reiter. Amir is the CEO at CloudTask, and if you don’t know what CloudTask is check ’em out right now. Go to He’s gonna correct me if I got that wrong, but they are a managed workforce solution for B2B sales, customer success and customer support. Amir is the CEO. He’s the founder. This is his baby. He takes a lot of pride in it. He knows first hand how to stand out in a crowded marketplace. He’s gonna share his wisdom with us today. Amir, welcome to the show my friend.

Amir Reiter:    Thanks for having me. Excited.

Darryl Praill:   You’re excited? You sound excited. You sound like you’re pumped.

Amir Reiter:    I am. I am. I’ve got my Social Selling still open. I have to stop. I’m over here always on LinkedIn. But that’s good, ’cause we’re talking about that today.

Darryl Praill:   I love it. We’re talking about that, exactly. And joining Amir is Tom Jenkins. Tom is the director of marketing at CloudTask and one of the reasons we brought Tom here as well. You know if you will, Amir, he’s the CEO, he’s the founder, he got this puppy going. It was really all about him. But then as the company grows Tom is the guy who makes sure that all the people publicly are projecting the right differentiation on behalf of the corporate brand. So, again, all about how to stand out in a crowded marketplace. Tom, welcome to the show sir.

Tom Jenkins: Delighted to be here. Looking forward to it. And yeah, I’ll be bringing my sales and marketing hat to this call to help all of you out.

Darryl Praill:   Now this call is a fun one right? So let me see if I get this right. We’ve got Amir, and Amir you’re American by citizenship? Is that correct?

Amir Reiter:    That is correct.

Darryl Praill:   All right. So originally American. Then we’ve got Tom, who’s originally British. We’ve got me, originally Canadian. And then you guys are, right now, your offices are outside of all three of those countries I believe. You’re currently hanging out in Columbia, is that right?

Amir Reiter:    Yeah. We relocated about two and half years ago to sunny Medellín Columbia.

Darryl Praill:   So that’s-

Tom Jenkins:  Yeah.

Darryl Praill:   I love it. I just love the diversity, and that’s something that’s really important about this right? It doesn’t matter where you are or where you’re located, or where you began your lot in life. You’re gonna learn how to stand out in crowded market today with these five people. So, Amir, we’re gonna start with you a little bit, right? So one of the things that is really prevalent when we’re trying to develop business is connecting on the phone. So let’s start with that. What is the best way to connect and succeed on the phone? And, as I’m doing that, what are some of the challenges to stand out in a crowded marketplace? Because I know for a fact, as successful as CloudTask is, you do have competitors that claim to offer similar offerings. So the phone becomes that first kinda touchpoint on how you’re different. So what lessons have you learned, what tactics did you apply?

Amir Reiter:    Yeah that’s a great question, and the phones are definitely not dead as many would say. In fact, when people say that a specific channel might be dead it’s in fact the opposite, because people stop using it and it’s a wide-open game. So the phones are back. That’s step one. And then when it comes down to connecting there’s two things, right. I think typically a lot of salespeople, or sales professionals, were looking at the number of dials, right? Did you call 100 people today, and did you dial 150 dials? And that used to be a great KPI maybe ten years ago, but I think now it’s all about actually connecting.

Amir Reiter:    So I think before you actually pick up the phone, making a small investment in a licensed,, which costs about $100 bucks a month, can give you direct numbers about 50% to 60% of the time. So I think first, before even picking up the phone, having a resource to make sure that you have the direct number and you’re not fiddling through a company line, because company lines tend to lead you to a voice mailbox or a gatekeeper. So getting direct cellphone numbers at is definitely a big step up. And there’s other obviously database providers, like ZoomInfo and DiscoverOrg, that also provide cell phone numbers as well. So there’s a few providers out there. But having the direct number is step one.

Amir Reiter:    And then having a good understanding of the persona you’re speaking to. And having that challenger-style conversation really tends to work, where you could bring up to somebody like hey Daryl. I work with a lot of CMOs like yourself in your space and from my experience I’ve seen that some CMOs are experiencing XYZ. And that’s kind of that authority, I think, is what people are looking for on the phones, because everybody has a short attention span. And I think the direction that people want is just do you understand me? Do you understand my product? Show me that you’re an expert in this space, and if you can display that on a call you can have a conversation.

Amir Reiter:    I think it’s the methodology of I’m gonna dial, and then I’m gonna have a feature-led benefit conversation, it just doesn’t work right? Nobody wants to hear about your features and your benefits. They don’t wanna be pitched on the phone. But I think that’s a good opportunity for people, just really learning how to understand the real pain points and be a professional in the industry. And those are the successful people on the phones these days.

[bctt tweet=”Nobody wants to hear about your features and your benefits. They don’t wanna be pitched on the phone. 📞 ~ @AmirReiter” username=”VanillaSoft @CloudTaskLLC”]

Darryl Praill:   It’s funny you say that, because … And by the way, Tom, jump in at any time ’cause Amir and I will just totally hog the conversation. But it’s funny you say you said Amir, because some people listening to that may say well that’s just kinda like yeah, of course, it’s obvious. But in fact it’s not. And you touched on it and I wanna circle back on what you talked about. You said the whole concept of just doing a feature pitch of what you can do is not relevant.

Darryl Praill:   The fact that if you reach out to your prospects, whether by phone, email, social, whatever it might be, and you physically are able to connect with them on what their pain points are. Either you research that and so you know, ’cause you’ve seen them talk about it or the company has shared those things. Maybe they publicly trade it and you know what’s going on. Or, in the lack of that information, you know the target. You’re talking to a head of marketing, you’re talking to a head of sales, you’re talking to a head of R&D, whatever it might be. Whatever your persona is you should, based on the industry and who their competitors are, you should be able to make a very quick assessment of what their top three, exactly to Amir’s point, issues are.

Darryl Praill:   When I get emails, when I get phone calls where they say we typically help organizations in your situation, in your role, who have challenges with problem A, problem B or problem C, and if you have something there let’s keep on talking. Otherwise, I’ll bail and not waste your time. You’ve already differentiated and stood out in a very crowded marketplace and salespeople trying to get my attention and my budget, ’cause most don’t do that. Now I’m curious from your point, Tom, because you own the message, is that what you’re seeing as well?

Tom Jenkins:  Yeah 100%. I mean one thing I just wanted to add quickly, just before we move on to other topics, in the first part of the call is do not rush it. I’ll come back to your point in a sec, but so many people just get straight on the call and just be like hello this is blah blah blah, and they just keep talking for 30 seconds. Feel free to just take a step back, introduce yourself, give the prospect time and then slowly and clearly articulate that benefit. That’s one thing, that one piece of advice I really love to leave with people. And then yeah, it’s you have to take the time to understand exactly what the business is. And from your owner research, from your buyer profile research, understand if one, two, three challenges that you are having. And be able to clearly show that authority directly to them from your past experiences, from your connections, from your referrals, wherever you’re able to get that authority and experience to them that’s gonna be relevant to their needs.

[bctt tweet=”🗣 ‘Hello this is blah blah blah,’ and they just keep talking for 30 seconds. Take a step back, introduce yourself, give the prospect time and then slowly and clearly articulate benefits. ~ Tom Jenkins” username=”VanillaSoft @CloudTaskLLC”]

Darryl Praill:   So let me throw this at either one of you, whoever wants to answer. When you’re bringing on a new sales development rep, and you’re trying to coach them, how do you teach them? Because one of the common complaints we hear from sales development reps is that maybe they don’t have enough life experience yet to be able to articulate what their problems are.

Amir Reiter:   What we do here at CloudTask is we actually have what we call group assessments, where we bring in anywhere from five to ten candidates. And in that group assessment we’re actually setting up role plays, and we give them time to prepare. And we do a role play from right from the beginning, and it really sets the tone for the engagement that they’ll have in CloudTask. Where we’re gonna be role playing with each other, we’re gonna be giving each other positive feedback, we’re gonna be helping each other.

Amir Reiter:    And I think that’s something that, when it comes to training reps, is really the core right? I think you can’t get away from the role playing and simple practice, right? Because when you’re role playing you’re able to make mistakes, you’re able to feel a little bit more comfortable. And the feedback that you get is it comes off in a way where we’re here to make you better. How do you feel about the role play? How do you feel like you learned? And that never stops, right, and it keeps going through the journey. But we start that right in the beginning just so that’s part of our culture.

Tom Jenkins:  And one more thin cloud is when we get live as well. So after doing the role plays all our reps will be starting off. We do a lot of lead scoring, lead priority here. And when the rep’s starting out, making their first few calls, we’ll be doing them on the sort of the coldest, lowest-quality leads, just so they can begin to warm up through the day just like an athlete stretches out his muscles. SDRs, EDRs, need to stretch out theirs. And then you’re building that confidence on the phone, and by the time you’re getting to the top-quality leads then you know you’re really warmed up and firing and ready to go.

Darryl Praill:   What I love about this is that you guys were talking about a lot of processes, processes at the company level. So if a sales rep is listening to this podcast right now they should be reflecting upon does my company train me? If not, who do I need to talk to to make that happen? Because it would make all of us more successful if we could learn together what the right message is. I love that you’re doing that from the recruitment side and the initial side.

Darryl Praill:   But what I also love and you’re getting at, Tom, is the fact that you’re recognizing that they are effectively athletes. They are professionals and they kinda need to build up and get their rhythm going and get their comfort level going. And you’re minimizing the risk and you’re saving your quality stuff for later on when you’re in full swing. And that’s a very intentional tactic to stand out when it matters most, when the pressure’s on the most. I love that. Okay. Let’s take a commercial break. We’ll be back in not too long. And we’re done talking about channel number one, the phone, and when we come back we’re gonna talk about the next channel. So don’t go anywhere. We’ll be right back.

Darryl Praill:   Okay. So we’re back.  Next one up here is phone is done. Next channel to talk about social selling. I’ve heard it called social marketing too. But when it comes to social selling, how do you advise a sales rep to stand out in what can be a very crowded market? Who wants to start this one?

Tom Jenkins: Oh so I’ll start this one off, and I’ll come in with number one on more of the marketing side of the social. And that’s getting your face out there, getting your name out there, and getting leads coming to you. So instead of adding reaching out to people pitching, if you’re posting top-quality stuff on your news feed, videos. We just put out a video yesterday that’s got thousands of views, over 100 likes. And people are messaging us directly ’cause of that. Make yourself a leader. Know what your prospects, your profilers, are reading. Know what their pain points are. Put stuff out that’s completely relevant to them, and they’re gonna be coming to you.

Amir Reiter:   I think that this is a good topic, right, because this is how we met. We met through social. So I think the first thing to start off with is the-

Darryl Praill:   It is.

Amir Reiter:    The word social selling-

Darryl Praill:   Yes.

Amir Reiter:    Right? I think what I like to call it is social engagement, right, but I think any time we’re selling we’re really gonna get nothing right? Because I think selling is not helping right? Selling is it’s I’m selling you my features, right, not engaging you. So I think one of the big things is that people need to stop selling, right, they need to stop pitching. If I had a dollar for every web development message I’ve gotten about a company that had XYZ developers I’d be a wealthy guy. And those just never work right? And I think being real and authentic is priceless right? Just saying to somebody hey I saw that you commented on this so-and-so post and I agree with you on that topic. It’s a good topic to discuss. Do you have any more resources on the topic? It’s a way to get a real conversation going, right?

Amir Reiter:    And I think the conversation I had with you was something along the lines of I like the software company that you’re with. I think it’s got some context of what we’re doing. I’d love to connect and maybe learn more about what you guys are up to. And that wasn’t a sales message, right? It was a message that kind of pointed out that I’m in a similar field, I work with marketing leaders, and I have interest in knowing what you’re up to. And you responded to that and that’s kind of how we built this friendship, right, and why we’re here today. So I think one of the things is just don’t look for the appointment as the goal. Look for the engagement as the goal. The appointment will be a by-product of a quality engagement. If you can, in fact, understand someone’s business, and if you can potentially help them, it will be natural to say those things and ask for their time to connect right? But without the engagement first you really are just trying to hit your number and people can see that right away.

[bctt tweet=”Don’t look for the appointment 🗓 as the goal. Look for the engagement as the goal. The appointment will be a by-product of a quality engagement. ~ @AmirReiter #SalesEngagement” username=”VanillaSoft @CloudTaskLLC”]

Darryl Praill:   That is the most important piece of advice. You nailed it guys. I love the word that you’re using, engagement, because it’s truly what it is. You can engage with content, exactly as Tom says, and that could be your company content, it could be your content. But that content should not be a pitch. The content that you guys shared recently, Tom, if I recall, it was kinda like five tips. You guys should be doing these five things. If not hey let’s talk about it. It wasn’t a company pitch about CloudTask. You were sharing and I loved it. And you had different people in your organization so we got into understanding who you were. We could see them smile and their personality, and who wouldn’t want to work with CloudTask because they looked like fun people right? And so that was really cool.

Darryl Praill:   And you can make your own content, but again the content is engaging, exactly to what Amir said. Too many people are going for that quick will you buy my product, as opposed to playing the long game of let’s engage and grow together in a relationship that’s mutually beneficial. And when the time is appropriate you can reach out and say hey you know I think you might benefit. Let’s have a conversation. And with Amir and I that’s exactly what happened, if you will. We talked and we saw … He checked me out, I checked him out, because our mutual content caught our eyes, and we said yeah there’s a connection here. Let’s talk. And that led to a live phone call, which of course was our first channel. So two channels down. Next channel. Let’s talk about the power of chats. Amir, do you wanna open this conversation?

Amir Reiter:    Ooh. I do. I do. So chat has been around for a long time, right. I don’t think that chat is a new technology, but I think the way people are using it is new right? And if you look at chat we have chat everywhere right? We have chat for sport, we have chat on Facebook, we have Drift or Intercom on websites. But what it’s really allowing people to do is to get information now and not to go through a slow process. It’s not every process is supposed to be I download an ebook, I get marketed to, I have someone qualify me. It gives people the ability, from a sales perspective, to ask questions right away and to build trust, because you trust people who give you answers right away right? If somebody says I can’t answer that question, you have to go in a meeting, it’s kinda fishy. You really have to go in a meeting to answer this question, right, you can’t just tell me how much your service costs?

Amir Reiter:    So it gives you the ability to break down that stereotype of you’re in a sales cycle, right, and it lets you just really naturally speak to people and just be honest and genuine. That’s what people want. And they call it sales chat, support chat. Well, it’s not really any of those. If you look at the buyer’s journey, which is really a wheel right if they’re in the awareness/consideration/decision stage. It lets somebody tell you where they’re at right? If they can come into a chat and say I’m about to buy. I need a quote today because I need to make a decision today, right, then you’re gonna handle that person differently than someone who says I’m just looking for some good information. Can you send me some articles to do research, right? So it lets the visitor or the person engaging, really tell you where they are and that’s what people want. They want control of the sales cycle. They don’t wanna be in that same cycle all the time.

Amir Reiter:    And chat is really picking up on all areas. I’m actually,… Let’s consider Facebook Messenger the same chat channel. But believe it or not I’m getting actually about three to four inbound inquiries on Facebook Messenger, right? And a lot of people say Facebook’s not for business, but it is if you connect with business leaders and join business groups right? I think you can make it what it is. And then from that, it’s easy for them to maybe visit my website. And then they’re talking to a rep on Drift, right? So it’s your chats everywhere, but the concept of just having people have open conversations is what’s priceless. And then what you do with those conversations can be endless from a marketing perspective, as you qualify and gather information on somebody who might not be ready now, but is telling you hey you can email me information every week or every month right?

Amir Reiter:    So we love chat, and I think chat’s gonna continue to grow. And I don’t wanna name drop multiple tools, but I’ve recently found some applications that allow you to connect 13 different channels, WhatsApp, WeChat, Facebook Messenger, all into one channel. So there’s gonna be a lot of good tools out there to help people control multiple chat channels, and I’m just excited to see chat continue to grow.

Tom Jenkins: And just to throw in its power in terms of monetary value, we work with a company called Ipswitch. We run their chat for them. And in the last 15 months now we’ve generated over $6 million of pipeline through it all and closed over $1.5 million of new revenue. So giving a financial figure to the power, that’s really what it can do.

Darryl Praill:   So the big thing there for any sales reps listening to this is you wanna use the right channel based on the individual. Some will prefer chat, some will use phone, some will use email right? So you gotta adapt to your prospect. If you can adapt, and you understand though many people are just fixated. I’m only gonna do social and I’ll never pick up the phone. That’s wrong. The power of chat is that it gives you a chance to add value. It’s not unlike social where you’re kinda playing the long game. How can I help you? What do you need to know? And you’re helping them solve a problem. So if you stop the pitching and start the helping, start the solving. Don’t sell. Solve. Chat is really incredibly powerful. Let’s bring it home to the fourth channel. I talked about this already. Email. We all agree, still key. Maybe we’ll start with Tom. What are some top tips we could offer the sales development reps to stand out in the crowded market using email?

Tom Jenkins:  Yeah. So number one from me would be people receive thousands of emails per day. Keep it short, keep it direct, keep it to the point is number one. Number two is you’re gonna get so much more success with personalizing, the more information. Use their LinkedIn. Get on the company’s blog. Anything you can do to tie in your email directly to their pain point, directly to what they’re looking for. You may not always know exactly what they’re looking for, but you should some, from all your training, have a good idea and be direct about it. Be clear. Again, offer value as well. Don’t just go straight in with a let’s book an appointment. But maybe I saw your post on LinkedIn. This is a pain point of you. I thought this piece of content would be great. And yeah, just leave it with them to take it forward and follow up a couple of days later. Use a different channel if you don’t get a reply and eventually you will get there.

Darryl Praill:   Okay, Amir. I mean you’ve seen a lot of good and a lot of bad as you’ve grown your company. Any wisdom you wanna share?

Amir Reiter:   I think that with email I think the simple is better right? I think leave the complex informational emails to the marketing team and really make it really simple right? Like why not send an email and actually say I’ve been trying to reach ya. Is there a better time to connect? It’s regarding X, Y and Z, right? Sometimes people are still just putting … They’re putting features in their emails and they’re really not making it a goal to engage. Everybody knows that we work for businesses and we live in a world where service is a product, so it’s things, right, we’re selling each other. So there’s no surprise there. So the surprise is when people actually feel like you’re trying to build a relationship first. Then they’re shocked. So I think in the email, I think, don’t try to go for the appointment. Try to go for that engagement and the relationship and ask a question, send information.

Amir Reiter:    And I’ve received some good emails from people that have been after me for quite some time. And I received one, I think the other day, and I’m gonna actually pull it up to read it because it was good. And it was good because he wasn’t trying to sell me. He actually sent me something. And it’s from Human First and you can see they’ve left an impression on me. I didn’t give him the appointment ’cause I’m busy, but it’s from a man named John ***** from Human First. And he goes, “Amir hi. No rush to view, but I sat through this webinar yesterday and thought of your salespeople. This webinar makes sense for sales agents who might not have a thorough sense of what their sales have been doing and what’s going on.”

Amir Reiter:    And all he asked for was I hope you found this procedure helpful. Let me know what you think. And he sent me something of value without asking for anything that was on his agenda. And what that did for me, as a leader of a company, was it made me feel like the person is actually trying to help me and that they’re trying to build a relationship with me. And with that I’m happy to give him an appointment. Not only am I happy to give him an appointment, but with someone like that I would refer them business if I can’t become their customer. Because he’s won me over already just by being professional and not trying to book an appointment. So I think giving value in your emails and trying to build a relationship first, is really important.

Darryl Praill:   I had that conversation with my team last week, exactly the same thing. Stop asking for that meeting in the first freaking email you know? Add value. Like by exactly the email you just got he added value. He’s already set a tone with you and it’s starting to develop a relationship. He will eventually go for the ask, email number three, but he’s playing the long game and building up trust with you. All right. With that we’re out of time.

Darryl Praill:   Tom, Amir-

Amir Reiter:    I’ll let Tom answer that.

Darryl Praill:   If my audience wants to reach you guys, what’s the best way to get ahold of you? Is it LinkedIn? Is it the website? What is it?

Amir Reiter:    Well it’s all of the above. Email [email protected]. Website Speak to our live chat. Find Amir and I on LinkedIn, we’re always there and just reach out to us on the phone as well. The number’s online and yeah, we’re here to serve, we’re here to help.

Darryl Praill:   If you and your organization could benefit from an additional provider to help you guys really hit your numbers and then grow, you don’t have to do this alone. Organizations like CloudTask, Amir, and Tom, will walk alongside you and help you hit those numbers you need to hit. Thank you guys for joining us today on another episode of INSIDE Inside Sales. We love your feedback. Don’t be shy. Send us comments. But until the next episode, we wish you a wonderful day. You take care. We’ll talk to you soon. Bye-bye.