Want A PREDICTABLE Sales Pipeline? Here’s The Secret…

Jason Bay is the co-founder and chief revenue officer at Blissful Prospecting.

In this episode of The Salesman Podcast, Jason shares how it’s not all that difficult to have a predictable sales pipeline and the steps to build one.

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Featured on this episode:

Host - Will Barron
Founder of Salesman.org
Guest - Jason Bay
Co-Founder and Chief Revenue Officer at Blissful Prospecting

Resources:

Transcript

Will Barron:

Coming up on today’s episode of the Salesman Podcast.

 

Jason:

Where I see a lot of companies and salespeople making mistakes when they approach prospecting is they either take one of two approaches. They either say, “Hey, I’m going to take the murder by numbers approach. And it’s all about the number of contacts on my email list. And I’m going to start cold emailing and sending a tonne of outreach.” And they’ll send thousands of unpersonalized messages to people. And most of the responses they get back from people are telling them to either F off, or it’s people that are interested that are not a great fit.

 

Will Barron:

Hello Sales Nation. I’m Will Barron, host of the Salesman Podcast. The world’s most listened to B2B sales show. If you haven’t already, make sure to click subscribe. And with that, let’s meet today’s guest.

 

Jason:

My name’s Jason. I run a company called Blissful Prospecting with my wife, Sarah. And we help small and midsize business-to-business companies reduce the stress from prospecting by doing it for them.

 

Will Barron:

On this episode of the show with Jason, we’re diving into how you can build a predictable sales pipeline. Predictable is the most important word in that sentence. That’s something that we all want clearly, but it’s something that is very difficult seemingly to achieve. Jason drills it all down into the most basic principles and makes it super easy to follow. And so with that, let’s jump into the conversation.

 

Is it Possible to Have a Predictable Sales Pipeline in B2B Sales? · [01:24] 

 

Will Barron:

I think we’ll get into many things today, but I want to start the conversation with asking you about predictability within our sales pipelines. Is it possible, not necessarily in an ideal world, but in the reality that we all live in, is it possible to have a predictable sales pipeline in B2B sales? Because I’ve never managed this before. And if it is possible, I’m intrigued to learn how to do it.

 

“Where I see a lot of companies and salespeople making mistakes when they approach prospecting is they either take one of two approaches. They either say, “Hey, I’m going to take the murder by numbers approach. And it’s all about the number of contacts on my email list. And I’m going to start cold emailing and sending a tonne of outreach.” And they’ll send thousands of unpersonalized messages to people. And most of the responses they get back from people are telling them to either F off, or it’s people that are interested that are not a great fit. Or what I see people doing is putting so much thought into what the messaging should be and who they’re going to reach out to that there’s just no volume at all.” – Jason Bay · [01:49] 

 

Jason:

Yes, it’s definitely possible. And I think that where you have to step back and think about, and where I see a lot of companies and salespeople making mistakes when they approach prospecting is they either take one of two approaches. They either say, “Hey, I’m going to take the murder by numbers approach. And it’s all about the number of contacts on my email list. And I’m going to start cold emailing and sending a tonne of outreach.” And they’ll send thousands of unpersonalized messages to people.

 

Jason:

And most of the responses they get back from people are telling them to either F off, or it’s people that are interested that are not a great fit. Or what I see people doing is putting so much thought into what the messaging should be and who they’re going to reach out to. There’s just no volume at all. So there is a certain volume play to this. But I think a really good place to get started, and for whatever reason, even large companies don’t really think about this is what’s your ideal client profile?

 

“Just because your solution would work across multiple industries doesn’t mean that you should segment your outreach like that.” – Jason Bay · [02:43] 

 

Jason:

And it can’t be, we’re a solution that’s industry agnostic. That’s one of my biggest pet peeves is when companies say that. Just because your solution would work across multiple industries doesn’t mean that you should segment your outreach like that. So for example, we sell prospecting services, right? A lot of companies need prospecting. And if we just said, “Hey, if you sell a business-to-business service, we can work with you.” That’s much less appealing than if we’re like … So, for example, nonprofits are an ideal client profile of ours.

 

Jason:

If we’re like, “Hey, nonprofits have a really big challenge with being tapped on resources. And they typically don’t have business development people that are actively building partnerships. So where we can come in is help them identify what their dream partners look like and help them create a little bit more predictability in that partnership pipeline so that they can increase their impact.” So they use words like impact versus revenue. They use words like partner instead of clients.

 

“If you could really dig down that deep and look at all the clients you’ve worked with in 2018 and up to this point and just look for some similarities. Who did I like working with? Who had the shortest sales cycle? So in other words, who is the easiest to sell that really understood what we do and why it’s valuable to them? And most importantly, who’s most profitable for you as a service or a product provider. And then who seems to get the most value? What are the repeat customers? If you take that list, you can segment that into the ideal client profile.” – Jason Bay · [03:38] 

 

Jason:

So if you could really dig down that deep and look at all the clients you’ve worked with in 2018 and up to this point and just look for some similarities. Who did I like working with? Who had the shortest sales cycle? So in other words, who is the easiest to sell that really understood what we do and why it’s valuable to them? And most importantly, who’s most profitable for you as a service or a product provider. And then who seems to get the most value? What are the repeat customers? If you take that list, you can segment that into the ideal client profile.

 

Jason:

So you’ll start seeing patterns in industry, employee count, specific things you might identify on their website, for example, specific technology they might use on their website. And I think that that’s … To answer your question on the predictability part, you got to take the time to really understand who your customer is so that you can craft the right messaging and reach out to the right people. Once you have that going, you can then create a machine of, “Hey, I have this lens that I look through to identify the right company.” And you can start hiring help, whether that’s virtual assistance, someone in-house, a firm like ours.

 

Jason:

They have something repeatable that they can always be going after. It’s like conducting experiment. You want to limit the number of variables. You have something that can be consistent and constant the entire time while you’re plugging in new companies, new people that meet that, and you can refine the messaging.

 

Will Barron:

All of this seems like complete common sense yet I’ve never really done this. My issue doing this in medical device sales was probably that there was only probably 50, 60 potential customers each year that I could go after in that there was say a hundred accounts, and I already had half of them on board. So perhaps didn’t need to do this as in depth as someone who was selling perhaps SaaS software to midsize organisations.

 

Why Aren’t Salespeople Prospecting Based on Their Ideal Client Profile? · [05:45] 

 

Will Barron:

Clearly, there are thousands of accounts to go after, so we need to drill down on this. But other than just that one distinction where it’s more applicable perhaps for some individuals than others, why don’t we do this? Why isn’t this the starting point? Why aren’t we given, or seemingly organisations that … For the audience who email me and are asking about prospecting, why aren’t they given a playbook of sorts with this at the top of it? Because it seems like real common sense.

 

Jason:

A lot of this is common sense. So it’s hard for me to really take credit very much when I’m just telling you things that you already know that you should be doing. But the reason why people don’t do it is, one, I think it takes work. People aren’t lazy for the most part, and you got a lot of other things that you’re working on, but really it starts at the top with leadership. And leadership gets a lot of pressure. So sales managers, VPs of sales, chief revenue officers, especially at a SaaS, you have a lot of pressure to hit quotas because your investors have invested millions of dollars and you need to hit your sales targets.

 

Jason:

So what that does is it puts you in a very scarcity mindset, very short-term thinking, we need to hit our sales numbers. There’s nothing wrong with doing that along, because you got to hit your numbers and you got to pay the bills and all that, and keep the lights on. There’s nothing wrong with doing that. But also in tangent, being like, “Hey, what can we do that’s a little bit more intentional?”

 

Jason:

So if nothing else, if the least you did was say, “You know what, maybe I don’t need to do these ideal client profiles. Maybe I just create a profile or a list of a hundred companies that are my dream clients.” These are the people that would have double the deal size of our average client. They really, really need what we have to offer, et cetera. And just focus on those 100 companies and think about, what are the patterns in those companies? Building the list. How would we approach this? And use that as an experiment.

 

“The thing that I’ve learned in my sales career selling stuff for the last 10 or 11 years is that not all advice is great advice, and stuff might not work for you. So just try it.” – Jason Bay · [07:35] 

 

Jason:

And the thing that I’ve learned just in my sales career of just selling stuff for the last 10 or 11 years is that not all advice is great advice, and stuff might not work for you. So just try it. Use that as a test. Test it with a hundred companies that are your dream clients. And if that works, then start doing that, and apply that to the rest of what you’re doing.

 

Jason’s Understanding of Being Intentional with Your Prospecting Efforts · [07:55]

 

Will Barron:

So Jason, you said a word here, which is five years ago I would have called you a hippie or thrown some … Not really, but I would’ve thrown some abuse at you, even if it was just in my own thoughts if I’d heard you say it. Now, it’s becoming more and more important to me as I’m selling the database of the podcast, as I’m gearing up to sell the sales school to the enterprise and to corporates on a larger scale. That word would being intentional. So again, a few years ago I’d been, “Well, it doesn’t really mean anything,” but now it is a focus for me. So what does being intentional about your prospecting mean to you?

 

Jason:

It’s no different than like when you go to the gym. I lift weights, and when I go to the gym, I don’t just say, “Hey, I’m going to wait until I get there and then I’m going to do a little bit of chest, do a little bit of arms, do a little bit of legs.” It’s like, no, I have a routine that I go through on a weekly basis, because I have very specific goals. I don’t want my muscles to be out of balance. And a lot of people approach this like going to the gym and not having any idea what they’re going to do, except for the amount of time that they’re going to spend there. And they don’t make any progress towards their goals of losing weight or building muscle or whatever.

 

“Sometimes we’re so much in the day to day, in the weeds doing stuff, we don’t think about how we’re doing the things that we’re doing and why we’re doing them.” – Jason Bay · [09:29] 

 

Jason:

So being intentional, it can be as small as take a step back and saying, you know what I’m going to do is I’m going to block off the first 30 minutes of every day, and maybe start with one day. I’m just going to remove distractions, not respond to emails, Slack messages, phone calls, anything like that. And I’m just going to be thoughtful about what I’m doing. And sometimes we’re so much in the day to day, in the weeds doing stuff, we don’t think about how we’re doing the things that we’re doing and why we’re doing them.

 

“One of the most valuable things that you can do in sales or business is just take a step back and think about, this prospecting that I’m doing, if I was the prospect, how would I respond to this? We have to challenge ourselves to do this too, even though we’re prospecting. And we got to think about, if I was the prospect receiving this email, would I respond? And guess what? A lot of times the answer’s no.” – Jason Bay · [09:36] 

 

Jason:

And that’s one of the most valuable things that you can do in sales or business is just take a step back and think about, this prospecting that I’m doing, if I was the prospect, how would I respond to this? We have to challenge ourselves to do this too, even though we’re prospecting. And we got to think about, if I was the prospect receiving this email, would I respond? And guess what? A lot of times the answer’s no. But if you don’t step back and say, “Hey, instead of sending all these emails and reaching out to all these people or running all these sales calls, let me think about how I’m doing this.” If you don’t actively block off time in your calendar to do that it’s just not going to happen.

 

Will Barron:

Love it. So there’s two things here that essentially … Exactly what you said. I agree with. And just another way perhaps I think about it. I can’t remember who said this. I think it’s probably a famous quote that’s been recycled, but that is to always try and keep the main thing the main thing. I think you described it as people get in the weeds. I’m like this, because just my personality type, it is the entrepreneur personality type, it’s the debate personality type. If you look at the Myers-Briggs testing, I like to change topic and change pace and change … I make a great lead of an organisation because I can be high, I can have a vision on things, and how an industry’s moving and we can create projects and stop projects.

 

Will Barron:

But the reverse of that is I find it very difficult to stick to the main thing. So the main thing for the podcast is great content and growing the podcast. It’s no more complicated than that. It doesn’t need prettier graphics. It doesn’t need better audio at this point, yet I will still spend two hours pretty much every week trying to research the perfect graphics overlays or whatever it is or the latest trend in graphic design to try and make it 1% better on that front when I could spend that time getting more downloads, bigger show, bigger guests. And there’s a flywheel approach to that. So two things here that I really took in when you were going through that, Jason was keep the main thing the main thing.

 

Will Barron:

The other one is the gym example. I’ve never put these two together for prospecting, but this works perfectly. So I’ve been half assed training for years now. It’s only now that in the past 12 months I’ve been training Brazilian Jiu-Jitsu relatively regularly and getting battered three times a week by bigger, stronger blokes and occasionally bigger, stronger women, that I’ve got, I need to get, not perhaps leaner, but definitely stronger and in shape. And there’s a guy, I like his methodologies. He talks about intermittent fasting. And we won’t go in the weeds of all this, but he uses the term called, and you have to excuse my language, both Jason and Sales Nation. He a term called fuckarounditis.

 

Will Barron:

He says, this is the disease that plagues most gyms. Most gyms are full of people who will do 10 minutes on a treadmill, as you described. And then they’ll do arms and some random exercise that doesn’t do anything. Then they’ll do something else. When all most people have to do is squat, bench, overhead press, and then probably get out of there unless you’re training for a specific sport. You do that, eat more and you’ll put on weight. It’s as simple as that. And he uses the term fuckarounditis.

 

Why Salespeople Need to Focus More on Doing the Most Impactful Things Instead of Trying to do Everything · [10:11]

 

Will Barron:

And I feel like this is 100% appropriate for prospecting. Because I’ve done it in the past. I was like, “Well, today, I’m going to do some research.” And then I forget about the research or I lose the spreadsheet that I’ve done it on. And then I just start sending these emails and I forgot about the … I’ve never tracked the messaging from any outreach I’ve done selling the advertising space on the podcast. I just recreate it every time. And I’m just messing around. I’m not testing it appropriately. And so I’m guilty of this myself. And that just summed it up nicely. Have you got any thoughts on that to add before we get onto the messaging side of the conversation?

 

“You can’t in one day get really good at Jiu-Jitsu, obviously. It takes months and years to do that, but it’s you showing up every day with intentional effort that gets you the results that you want. Prospecting is the same exact thing. You have to make it daily, and it has to be intentional, and you got to do it a long time and have faith in the process.” – Jason Bay · [13:28]

 

Jason:

Jiu-Jitsu is a great example. I’m a huge fan of mixed martial arts and UFC and all that other stuff. And I haven’t done Jiu-Jitsu, but I’ve done Muay Thai. But it’s the same thing. It’s what you do on a daily basis that will actually get you the results that you want. You can’t in one day get really good at Jiu-Jitsu, obviously. It takes months and years to do that, but it’s you showing up every day with intentional effort that gets you the results that you want. Prospecting is the same exact thing. You have to make it daily, and it has to be intentional, and you got to do it a long time and have faith in the process.

 

Jason:

I think where most people mess up, it’s no different than going to the gym, if we keep using that example. You got to actually just sit down and think about what you’re trying to accomplish and just put together a process for that. Doesn’t have to be complicated. With prospecting it’s build an ideal client profile, find companies, find contact of those companies, build messaging, send messaging, rinse and repeat. It’s just a five-step process. It’s not that complicated. But if you don’t approach it with that process and say, “Well, every morning, here’s exactly what I’m going to do. I’ve already built my dream client list. I already have the companies that I want to reach out to. I already know the people. I’m going to send those emails.”

 

Jason:

And maybe it’s five personalised emails with videos per day. That’s it. But you got to be intentional about doing that. And then obviously software. The type of software that’s going to help you AB test and keep things organised and all that good stuff.

 

Will Barron:

Sure. We’ll get onto tools towards the end of the show, Jason. But say now we’ve gone through step one in the process of building our ideal … And we could probably talk about this for four hours, so I appreciate we’re glossing over some of this. But we’ve built our ideal customer profile using the impact that we can have on the organisation, whether we like working with them, whether they are repeat customers and the other things that we’ve talked about at the top of the show.

 

How to Create Effective Messaging Campaigns That Will Bring Predictability to the Sales Conversation · [15:26] 

 

Will Barron:

We’ve linked that with other organisations of company size, do they serve the same customers? Are their customers’ customers the same? And we can go down at a funnel on that route. And there’s tools that help us with this as well. So the next step seemingly then is the … And we’ve got all the contact details and there’s plenty of tools that we shouldn’t be doing this manually. There’s plenty of tools that can give us contact details. So the next step seems to be the messaging. And focusing down on this word, process. How do we create messaging that we know is going to bring predictability to the conversation? Even if it’s only predictable for six months and then we need to change it, how do we create somewhat predictable messaging?

 

“I think the big mistake people make with messaging is thinking that a one-size-fits-all approach works. Especially with the way things are moving, all the data shows that the number of quality conversations per day is going down and the number of attempts to reach a prospector going up. Any data that you look at is going to tell you that.” – Jason Bay · [15:48] 

 

Jason:

So you do have to make sure … I think the big mistake people make with messaging is think that a one-size-fits-all approach works. Especially with the way things are moving, all the data shows that the number of quality conversations per day is going down and the number of attempts to reach a prospector going up. Any data that you look at is going to tell you that. So to stick through the clutter, things really need to be segmented. So before you create messaging, make sure that you not only have those ICPs created, but the people you’re reaching out to … I recommend another thing. Have you heard of Selling Above and Below the Line?

 

Will Barron:

It sounds familiar, but I couldn’t define it for you.

 

Jason:

There’s a book called Selling Above and Below the Line by William Miller. And essentially what it is, he says, the above the line people at companies, C level and VPs, have very different goals and challenges than below the line people, directors, managers. And the reason for that is that above the line, they’re typically focused on quotas and revenue and profit. Below the line is actively probably doing the thing that you could help them with, and are more interested in how they can save time and improve productivity and make their job easier.

 

Jason:

So that’s really important to know, because both above the line and below the line might have just as much influence on hiring your company. So when you approach the messaging, you got to think about, well, who am I sending this to? Is it a decision maker that’s above the line or below the line? So that’s the first step. Second step. There’s a couple different things that I recommend doing with the persona exercise.

 

“There’s a couple different things that I recommend doing with the persona exercise. But the way that I like to think about this is the person I’m reaching out to, what is this person’s responsibilities and higher level objectives? So, what are they trying to accomplish? Are they pushing revenue? Are they managing salespeople, whatever might be. And then I look at what are they trying to accomplish? So their goals, their obstacles that are keeping them from doing that, and any fears that they might have associated.” Jason Bay · [17:22] 

 

Jason:

So there’s a lot of different ways that you can approach this, but the way that I like to think about this is the person I’m reaching out to, what is this person’s responsibilities and higher level objectives? So what are they trying to accomplish? Are they pushing revenue? Are they managing salespeople, whatever might be. And then I look at what are they trying to accomplish? So their goals, their obstacles that are keeping them from doing that, and any fears that they might have associated. So goals, fears, obstacles.

 

Jason:

And the way that you approach the messaging and the way a sales cadence … So a sales cadence is a sequence of messages that you would send to a prospect. The way that that would work is it would be set up like this. So you would want the copy to address gausters and obstacles. You also want to make sure that you’re not making the assumption that the prospect already knows that they have a challenge or a problem. So in other words, make sure that you approach this from an educational standpoint.

 

“The first outreach I send, that first email is more of a, here’s who I am, and here’s why I’m reaching out, and some sort of social proof. So if I’m selling prospecting solutions to a SaaS company, for example, I have some personalization, either a video or a couple sentences, but I’d say, “Hey, I’m reaching out because what we do at Blissful Prospecting is we help SaaS companies like yours remove the stress from prospecting. And what we do is we help them get the attention of the clients they’re trying to work with. I’m not sure if that’s a challenge you’re having right now, but if it is, you might find this resource helpful. PS, we’ve worked with this company, this company, and this company. Here’s a case study if you want to check it out.” – Jason Bay · [18:14] 

 

Jason:

So the first outreach I send, that first email is more of a, here’s who I am and here’s why I’m reaching out and some sort of social proof. So if I’m selling prospecting solutions to a SaaS company, for example, I have some personalization, either a video or a couple sentences, but I’d say, “Hey, I’m reaching out because what we do at Blissful Prospecting is we help SaaS companies like yours remove the stress from prospecting. And what we do is we help them get the attention of the clients they’re trying to work with. I’m not sure if that’s a challenge you’re having right now, but if it is, you might find this resource helpful. PS, we’ve worked with this company, this company, and this company. Here’s a case study if you want to check it out.”

 

Jason:

That’s what the first outreach feels like. From there, I’m going to start making sure that the rest of the cadence addresses fears that this person might have, not hitting their sales quotas, salespeople quitting on them, not getting the attention of their dream clients, whatever it is. I’m addressing those. And hopefully I have a content piece which is great. You have awesome content in your podcast. I would be sharing specific things in snippets. One of the things I love about your content is you do those three to five minute recaps where it’s a specific topic with four or five different guests.

 

Jason:

That would be a really great example. If I had that for prospecting, I would share something like that. Like, “By the way, here’s some really awesome tips from some people that really know what they’re talking about. I thought you might enjoy this.” And it’s addressing those goals, fears and obstacles. And then from there, you got to make sure to have some empathy in there. And I’ve already been doing that. It’s just show empathy and like, “Hey, I understand you’re probably feeling a lot of pressure to hit your quotas and things like that. So I’m hoping that this resource will make that a little bit easier. Are you interested in chatting about how we might be able to help you out?”

 

Jason:

So that’s getting started. I’m sure there’s a lot of places you want to dig into deeper, but that’s how we approach getting started.

 

When To Expect Replies in Your Cold Emails When Building a Predictable Sales Pipeline · [20:15] 

 

Will Barron:

Is the goal with this then … Because that’s the formula of a marketing funnel or campaign, not necessarily potentially what a traditional sales cadence is, “Will you speak to me? Will you speak to me? I’m going to voicemail you. Will you speak to me?” And then you text someone. You email them, then you just keep spamming them with random nonsense. That’s how most salespeople do it, myself included. So this is what we do talking about here is a formulaic approach to almost build momentum throughout these emails. So are we expecting a reply or are we hoping for a reply on the first email, or are we expecting that we’re only going to get a reply on the third or fourth after we’ve had that cadence with them?

 

Jason:

So this is totally dependent on the industry, and I wish I could give a stock answer there, but it depends on the industry and who you’re reaching out to. So what we’ve seen that’s very common is if we have a messaging cadence that’s really, really dialled in and we have something that’s really repeatable, we’ll get a response in the first or second email, interested or not interested. That’s less common. And in most cases, it’s emails or outreach for that. Six is where we’re getting most of the feedback, yes or no.

 

“There’s a lot of great studies on this and a lot of great content out there on the B2B buyer’s journey. And everyone talks about it a little bit different, but essentially the first three steps are awareness, consideration, and interest. So awareness, you have to create awareness around a challenge to get them to consider what the solution might be and that you might be the company and get them interested in talking to you. You can’t start at the very end and assume that they’re already interested and know who you are. Otherwise, you’re literally spamming them. You’re not taking any time to get to know them. And guess what? Probably 99% of your competition is doing the same exact thing. So you don’t stick out from anyone else.” – Jason Bay · [21:38] 

 

Jason:

And I want to comment on what you said about this is different than the sales approach where it’s like, “Hey, are you interested in talking?” “No, no, no.” It’s like a murder by numbers game. You got to be aware of there’s a lot of great studies on this and a lot of great content out there on the B2B buyer’s journey. And everyone talks about it a little bit different, but essentially the first three steps are awareness, consideration, and interest. So awareness, you have to create awareness around a challenge to get them to consider what the solution might be and that you might be the company and get them interested in talking to you.

 

Jason:

You can’t start at the very end and assume that they’re already interested and know who you are. Otherwise, you’re literally spamming them. You’re not taking any time to get to know them. And guess what? Probably 99% of your competition is doing the same exact thing. So you don’t stick out from anyone else.

 

Will Barron:

Because I want to wrap up the show talking about video, but this is a true way to differentiate yourself. And I get emails every day from people saying, well, my product is commoditized. Maybe it’s a fantastic product. Perhaps you’re talking about CRM, and there’s a million different CRMs. There’s Salesforce at the top. There’s perhaps HubSpot, because Salesforce cover everything because they just acquire any company that’s doing anything. And there’s obviously strategy behind that. It’s a platform. There’s perhaps then HubSpot for small to medium size enterprises, which dominate that market.

 

Jason’s Thoughts on the Effectiveness of Reaching Out to Prospects Using Different Mediums · [23:02]

 

Will Barron:

And then there’s an incredible amount of different companies underneath that. And so if you are selling for one of those organisations, everyone’s marketing bullet points will have some differentiation, but it’s all to the end user pretty much the same. So reaching out in a different way to everyone else’s I feel … And tell me your thoughts on this, Jason, but that might be a key differentiator in getting the deal done.

 

Jason:

Yeah, it could be. It could be one of the things. CRMs, for example, I think it’s a great example to use because it’s in a red ocean. Everyone knows what a CRM is. The company you’re reaching out to is probably already using a CRM and you don’t need to really over-explain and educate on what a CRM is. But what you need to have in that cadence is you have … For example, there’s lots of tools you can figure out if someone’s using Salesforce or HubSpot, especially HubSpot, because it’s a marketing tool. It’s going to be embedded into the code of their website. Why don’t you call that out in an email?

 

Jason:

Hey, I noticed that you’re using HubSpot. Here are a couple of customers that we’re working with right now that switched from HubSpot to Pipedrive, if I’m Pipedrive. And the reason for that was this. Are you having any sorts of challenges like that? Are you able to talking about that, or would you be open to a quick demo, or could I record a quick demo video, a personalised demo for you? Or if I recorded a personalised demo, would you watch it? That’s the type of way that you can start a conversation.

 

The Difference Between a Blue Ocean and Red Ocean in Sales · [24:18]

 

Will Barron:

So two things here. One, just for anyone who isn’t sure, can you explain super briefly what the difference between a blue ocean strategy is versus going into the red ocean?

 

Jason:

So blue ocean, an example of that actually is when we started Blissful Prospecting, a lot of my background has been in marketing and sales. So I was like, “Well, let’s start a marketing agency.” And the blue ocean strategy there was well, there’s thousands of marketing agencies. If we want to work with marketing agencies as partners and also differentiate ourselves from them. If we brand ourselves and position ourselves as a prospecting company, it’s a little bit more of a blue ocean strategy.

 

Jason:

And when we started Blissful Prospecting, I could make that case. Now it’s a little harder because a lot of companies are doing prospecting. Red ocean is you’re selling something that’s highly commoditized. Everyone already knows exactly what it is. And you can’t really position yourself as something that’s different, because in the prospect size, you do the same exact thing everyone else does.

 

How Little or How Much Time Should We Be Spending Focused on Converting Accounts Versus Going After Brand New Accounts? · [25:32] 

 

Will Barron:

Perfect. And then one thing that you mentioned here, which I’m starting to cover more. I’ve actually done a few shows on it in the past couple of weeks, and it starts to become more and more of an imperative for us to cover because I feel like we’ve totally neglected it. And this goes for prospecting, doubling down on this more than anything else. How can I frame this? So you talk about getting someone to switch from or discuss switching from one competitor to another. How little or how much more time should we be spending focused on converting accounts versus going after brand new accounts in the content of someone who’s already spending money is already pre-qualified. They may be spending more money. They may be spending less than what you’d be charging them. There’s plenty of opportunity to get in.

 

Will Barron:

You can source all this out. There’s been a purchase in the past. So there’s been a buying process put in place. There’s people who are perhaps happy and unhappy. For me, it’s the best accounts to go after. And most large enterprise accounts will have whatever you are trying to sell them already. So this goes double down for them. How important is it to prospect those accounts versus what I feel most people do is they go after accounts that are brand new and need educating from the very get go of all of this?

 

“If you’re going to really get serious about of prospecting, I would probably save 20% of your outreach for those dream clients that are those enterprise companies that it might take six plus months or more to sell this company. But if you sell them, this could be a huge account, and it could be a huge social proof for you. And you’re going to do extra stuff for them. You’re going to do extra personalization. You’re going to send these videos, you might send direct mailers, et cetera. The majority of your prospecting though, you want to be in this middle range of probably mid-market companies that may or may not already be using your solution, but are going to understand what it is. And you’re not going to have to deal with a really, really long sales cycle because one of the most disheartening things about prospecting is having to wait six to 12 months in order for it to work.” – Jason Bay · [27:27] 

 

Jason:

This is why it’s important to segment your prospecting outreach. So if you’re going to really get serious about of prospecting, I would probably save 20% of your outreach for those dream clients that are those enterprise companies that it might take six plus months or more to sell this company. But if you sell them, this could be a huge account, and it could be a huge social proof for you. I’d probably make that about 20%. And you’re going to do extra stuff for them. You’re going to do extra personalization. You’re going to send these videos, you might send direct mailers, et cetera.

 

Jason:

The majority of your prospecting though, you want to be in this middle range of probably mid-market companies that may or may not already be using your solution, but are going to understand what it is. And you’re not going to have to deal with a really, really long sales cycle, because one of the most disheartening things about prospecting is having to wait six to 12 months in order for it to work. So I think it’s really-

 

Will Barron:

I could see there was a downturn in your voice then of your own realisation of this of like, “Oh, it does take 12 months for this to work.” And everyone listening as well, Jason went, “Oh, it does take 12 months,” but that’s sobering, right?

 

Jason:

Yeah. And the thing is if you can find that middle market … And again, this requires testing with your ideal client profile. And it depends on what you’re selling with sales cycles and stuff. But you could find people that you could start working with in one to three months, a sales cycle versus these enterprise companies. And it depends on what your company is and what you’re selling. So going to take this with a grain of salt. But what I would really do is segment the outreach. Don’t treat every prospect exactly the same.

 

Will Barron:

I think that is a good way to wrap up this part of the show, Jason. And that’s what I’m taking away from it of, I don’t think marketers … And this from your background in marketing. Marketers segment everything, and they are trying to become salespeople eventually with the use of chatbot, with the use of just mass data. At some point it’ll be somewhat difficult if someone’s just spamming, cold outreach and not really making that much of an effort as a human salesperson. A marketing email’s going to do almost as good a job, if not a better job eventually over time.

 

How and Why to Use Video When Sending Out Cold Emails · [28:50]

 

Will Barron:

So we need to differentiate ourselves. And I think also sub-segmenting into smaller groups than perhaps what even marketing does is the way we can go about that. But one final thing that I want to wrap up the show with, Jason is video emails, because you reached out to me with video email, it got my attention. And I’m seeing it more and more frequently when I’m doing business prospecting, when I’m selling out space on the show, wherever. As we’re gearing up to start selling the sales school to the enterprise and different things, I’m experimenting with all kinds of different emails or texts or just cold calls or adding someone on LinkedIn, and then messaging them on LinkedIn and then follow them on Twitter and doing all this nonsense social selling stuff, which may or may not work depending on how in depth you want to go with it all.

 

Will Barron:

The thing that is working right now for me is just sending a quick video from the studio. So not everyone has this, and this adds social proof, it adds credibility and different elements to the video itself. Because when someone gets a video from this they go, “Oh, this dude isn’t messing around with his podcast. Clearly it’s a full-time venture.” With that said, why is video so useful? And why is it, I would say, and I won’t put words in your mouth, but probably the best way to reach out to people right now in 2019?

 

Jason:

The reason for that is that growth hackers and salespeople and all this other stuff, once they find an email template that works, what do they do? They write a blog post about it, especially if you’re one of these email service providers that has cold email software. So what happens is people start regurgitating the same exact templates and people are sending all of these things. And when you look at the tech stack that a company uses for prospecting, if you’re just doing email, you’re doing what 85, 90% of your competition is doing. If you’re just doing LinkedIn, which is starting, growth hackers are … And I’d throw myself into this category too. We’re ruining LinkedIn right now. You’re probably getting a lot of cold messages that might have the first name personalising them more so than you were getting a year ago.

 

“The reason why video is important is that you can’t fake a personalised video. You really cannot.” – Jason Bay · [30:51] 

 

Jason:

So it’s becoming less effective because you’re getting more people that you don’t know requesting to talk to you using the same exact outreach. So the reason why video is important is that you can’t fake a personalised video. You really cannot. And one of the things that it allows you to do in an email that I really like is like the email that I sent to you in the thumbnail, I was holding a little whiteboard on a piece of paper and it had hi, your name on it. So you see that thumbnail in the video and you’re like, clearly this looks personalised.

 

Jason:

From there, what I can do too, and why I think this is so powerful for you with video and why this is working is that people can see you, they can see your personality, they can see and determine even if it’s subconscious, if you’re a credible person and if you would relate to them, and if they would enjoy talking to you. So video allows the prospect to actually empathise with you. And I think that word empathy is something that I’ve really learned. Sarah and I have learned the hard way with our prospecting campaigns is that we weren’t putting enough in there and allowing the other person to put theirself in our shoes or to look at us and be like, “Would I want to work with this person?”

 

“When you’re hiding behind the text of an email, unless you’re a very, very, very talented copywriter, your personality’s not coming across. The video’s a really easy way to do that. It’s a really easy way to show that you did your research. And we have tools now that make it really, really easy to plug it into an email. I think that video a year or two from now is going to become the minimum expectation to get someone to respond.” – Jason Bay · [32:14] 

 

Jason:

When you’re hiding behind the text of an email, unless you’re a very, very, very talented copywriter, your personality’s not coming across. The video’s a really easy way to do that. It’s a really easy way to show that you did your research. And we have tools now that make it really, really easy to plug it into an email. I think that video a year or two from now is going to become the minimum expectation to get someone to respond.

 

Will Barron:

I agree. And I literally did a video yesterday. One of the regular sponsors of the show, I won’t name who it is, just in case the deal doesn’t come through. But I’m trying to build a centre basis adobe proposal for them. I want to work with them on a new podcast, a new feed that we’re doing, salesleadership.org. It’s essentially everything that we’re doing on the Salesman Podcast, but for sales leaders. And so I reached out to them, sent them a proposal, and then I followed up with an email with a video in it created by Soapbox. And I’ll ask you your thoughts and opinions on the best software for creating these videos in a second.

 

Will Barron:

But with Soapbox, you can go from just the webcam to then the screen, and then your face on the screen … Your webcam alongside the screen content as well. So all I did was just to basically go through the proposal as if I would if I sat next to that individual and just say, so this is this, this is this, this is why X, Y, Z is here. This is why there’s two tiers. Basically due to the fact that your quarter ends in a different quarter than ours, so you might want to budget one side and budget the other. But to put that in an email, it’d be about 15,000 words and no one would ever read it. It’d be boring as heck.

 

Will Barron:

And especially when you’re talking about contracts or proposals of 12 months worth of work. I feel like if someone’s written down in an email, it’s going to be documented, it’s going to be shared around. If you’re using creative copy at that point, it might not look at professional on page. But over video, you can be yourself and you can use, not slang and colloquialisms, but you can be more relaxed about the language that you’re using versus how it’s documented if it’s going to be shared around. And I’ve seen that that video has been shared 15 times. Before I clicked record with you today, Jason, it’s been shared 15 plus times in the past 24 hours.

 

Tips for Effectively Using Video in an Email Sequence · [34:22] 

 

Will Barron:

So that video clearly has virality in itself, again versus going, “Pam, can you read through this 15-page document and tell me your thoughts on it?” It’s, “Pam, can you watch this two and a half minute video and give me your thoughts if this is a go or not?” And hopefully, it’s going to be a goer. So with that said, Jason, where does video … The cadence is what I’m getting at here. Is the first email video, then the second email’s video, and there’s a video the whole way, or is the quick introduction just to get attention via text and then we get into video, when we know the individual has been opening the emails so that we can lower the amount of work we’ve got to do on the video front? How do we frame all this up in our sales cadence?

 

“The reason why it’s so powerful is oftentimes, if you’re selling in a digital world like we are where you hop on a Zoom call with someone, that person you’re interacting with is likely not going to be the only person that has decision making that’s going to contribute to the decision making process. So if you have a video, the other person that needs to help them make the decision, which might be their boss, if they see you and your personality, that might be all that they need to pull the trigger. So just keep that in mind. Make it easy for them to have a conversation outside of the sales call.” – Jason Bay · [34:53] 

 

Jason:

Great question. And I want to quickly comment on what you said too, that video is so underutilised in the sales process as well. And the reason why it’s so powerful is oftentimes the person … If you’re selling in a digital world like we are where you hop on a Zoom call with someone, that person you’re interacting with is likely not going to be the only person that has decision making that’s going to contribute to the decision making process.

 

Jason:

So if you have a video, the other person that needs to help them make the decision, which might be their boss, if they see you and your personality, that might be all that they need to pull the trigger. So just keep that in mind. Make it easy for them to have a conversation outside of the sales call. So, yes, a really interesting question. And this is something we do a lot of experimenting with.

 

Jason:

So where I would start is … It obviously depends on how much time you have. And most of us don’t have enough time. So you really want to 80/20 and prioritise this. So what I would do is your dream client list, so that 100 companies that you’re like, “Hey, if I landed this company, this would be a total game changer for me as a salesperson or for my business,” I would start out with a video. So for us, getting a podcast is a really big deal right now. And you have a great podcast in a huge platform, especially for this space.

 

Jason:

So I want to send a video on the very first outreach so that I can make a good first impression, because that might be the only impression I get to give you, right? So segmenting those dream clients, I would start out videos with them. And then the rest, what I would do is prioritise that based on engagement. So with tools, it’s really easy to see if people are opening emails. If you have click tracking on, if that’s something you do, you can do that too. And you can say, “Hey, I sent out a hundred emails last week, 40, 50% of the people opened them. These are the people that are highest engaged, that opened the most, clicked on the most links. I’m going to send personalised videos to these 10 or 15 people that already got a couple emails from me. I’m going to throw it right into the middle of the cadence.” That’s more often case the times how we do it.

 

Best Practices for Sending Out Video Emails · [36:48] 

 

Will Barron:

That makes total case. And we’ll wrap up with this. What’s the context of the video with regards to, is it 30 seconds, is it five minutes? If you’re experimenting on all of this, are we just regurgitating what we would say in an email anyway, or are we using a video in a slightly different manner?

 

“A good rule of thumb though is keep it around 30 seconds. And the reason for that is they don’t know who you are and people have really short attention spans. And if you’re going to ask for more than 30 seconds of their time, it’s just too big of an ask.” – Jason Bay · [37:13] 

 

Jason:

I’ll tell you what’s working for us, but again, it’s test it yourself and it’s going to be industry specific. So good rule of thumb though is keep it around 30 seconds. And the reason for that is they don’t know who you are and people have really short attention spans. And if you’re going to ask for more than 30 seconds of their time, it’s just too big of an ask. So the way that we do videos and what we say is it could be something like this, say, “Hey, Will, this is Jason with Blissful Prospecting. First off, I want to say I’m a big fan of your podcast. I listened to this episode with Jeffrey Gitomer and got this out of it. Reason I was reaching out is I thought that if you’re looking for guests, we could talk about video prospecting, how that’s working for us, how that might work for your audience and how that might be valuable for them.”

 

Jason:

And then give some times to talk and then say, “Hey, look at the email,” and then that’s it. 30 seconds, keep it real short. Who are you? Why you’re reaching out, one or two sentences, your value prop, how you can help the person and why you want to chat, and then have a call to action. Keep it very short and sweet. And try not to be too wordy, smile, all those good stuff.

 

Will Barron:

And I’ll tell you what I got from the video that you sent over directly. For the audience, we’ve not discussed this before the show, but I got that you were calm, collected, clearly comfortable in front of the camera and on the mic, which is a huge positive, because otherwise I’ll have people on who aren’t comfortable in front of the mic, but I typically have to coach them for 5, 10, 15 minutes before the show and it makes my life not … It makes my life harder, but sometimes it’s worth the effort of doing that.

 

Will Barron:

So I was like, interesting. You said something. I can’t remember what it was specifically now on the spot, but you said something that I was like, “That is interesting.” And then it all tied it all together and I was like, “Oh, this person isn’t …” And this is a huge compliment. This person isn’t an idiot. Because I get so many people reaching out to me that have wrote some nonsense e-book and then spamming all these different podcasts just to get some attention.

 

Will Barron:

And I’ve learned my lesson in the past of having these people on, and then there’s no depth to the conversation. But just to be able to get on video and be happy and confident and smile. Maybe I’m overthinking it, but that is probably where you gut feeling comes from where you go, “Oh, I can probably trust this person.” There’s an element of trust to all of this, and rapport building, which you just can’t get over from a text email, right?

 

Jason:

Yeah. And trust, that word is so important in sales. Everything is based on trust. It’s trust in you, trust in your product or service, and trust in the company. And you can get a lot of those things taken care of in a 30 second video if you do it right.

 

Jason’s Advise to His Younger Self on How to Become Better at Selling  · [40:10] 

 

Will Barron:

And you can get it wrong, just for the context. I do get occasionally emails where I go, “That person is an idiot.” And I thank them for their time, thank them for the video and say, “This isn’t the appropriate time to have you on the show,” or whatever the nonsense excuse that I give them is. So with that, Jason, and just for context of the audience that it can be done badly. We do need to think about this before we start spamming videos out 24/7 to individuals that we want to be in front of.

 

Will Barron:

With that, Jason, I’ve got one final question mate that I ask everyone that comes on the show and that is, if you could go back in time and speak to your younger self, what be the one piece of advice you’d give him that would help him become better at selling?

 

Jason:

I would say the biggest thing is making sure to have more of my style and personality in the approach. And I think when you’re getting started, you need a foundation of some sort. So you read books and you listen to a podcast and you watch YouTube videos. And you’re like, “I want to be like this person. I want to be like Gary V, or Grant Cardone, or Jeffrey Gitomer,” or all the other people that we’ve been talking about, instead of I really like what they’re doing, but how can I do this for myself so that I can be authentic?

 

“People can smell desperation or inauthenticity, if that’s a word, from a mile away. And they can see it in your body language, it comes out in your voice.” – Jason Bay · [40:53] 

 

Jason:

Because people can smell desperation or inauthenticity, if that’s a word from a mile away. And they can see it in your body language, it comes out in your voice. And if you just really own the process and be like, “I get conceptually I need to do these things in order to make a sale, but how can I make this mine and make it my own?” I wish I would’ve done that much, much earlier on in my sales career.

 

Jason’s Moment of Realisation That a Salesperson Needs a Personal, Distinct, and Unique Selling Style · [41:21] 

 

Will Barron:

How did you come to that realisation, and then what did you redo, develop or work on to come up with a style? Because style’s important, right?

 

Jason:

Mm-hmm (affirmative). I think that really owning … For me, a interesting thing was I thought all successful salespeople had to have the gif of gab, be good talkers. Because I came from a background where my parents aren’t in sales. They aren’t in business. They don’t run businesses. None of my family really does that. So I didn’t even know what sales was before college. And the misconception I had in my head and the fear I had is that I know I’m not an extroverted person. I’m not a person that’s going to go to a networking event and really get a lot of energy from that and really be able to talk to people.

 

“The best salespeople actually are the people that are the best listeners and ask the best questions. You don’t have to be a good  talker.” – Jason Bay · [42:13] 

 

Jason:

I’m a great listener and I can ask great questions. And I think owning my introvertedness and really owning the fact that the best salespeople actually are the people that are the best listeners and ask the best questions. You don’t have to be a talker. I don’t know exactly when I made that realisation, but I started reading a lot of books about people that are introverted and studying people that had more of an introverted style and approach to selling. And that just really clicked with me that I can be myself, and that’s what people appreciate most.

 

Jason:

I think one pro tip that I would give is I always ask people, I did this … So I ran a house painting business in college. And as a freshman in college, one thing that I did always after someone gave me a sales, I asked them, “If you don’t mind me asking, why did you decide to hire me today?” And what they would tell me was way different than what I thought. I thought that they were going to say, “You seem really experienced. We loved your sales pitch. The price was right.” They were like, “No, I just really liked you. I trust you.”

 

Jason:

And I heard that over and over and over again. I’m like, you know what, it’s not about the pitch. It’s not about me having the best price. I was selling house painting services and I never even painted a house myself before. And I wasn’t doing the painting. I’d hire painters, but that was the big realisation I had, that people hire me because they like me. And I can really own that. And that’s going to work well because it’s authentic. And people want to work with people that are authentic and genuine.

 

Will Barron:

I won more business in my medical device sales job from just being, not the traditional salesperson than pretty much anything else. And it was only by naivety that I didn’t know what I should have been doing that I just started down that route. But in medical devices, in the role I was in, two massive companies. I worked for both of them at different times, and they both had their own stereotypes. One company, they hired … The last company I worked for, they hired mainly ex athletes and professional athletes that didn’t quite make it into the Premier League here in the UK, or didn’t quite make it to St. Rugby team or whatever it was.

 

Will Barron:

So they were driven. They were aggressive. They were assertive. I did not fit in that crowd whatsoever. The other company is Japanese company. They follow all the Japanese principles of business of 1% improvement and Kaizen and all that side of things. They’re all a bit soft, weak … No, weak’s not the right word, but a bit soft and wet and, “We’re just going to do this and this.” And there wasn’t any flexibility. I didn’t fit in with either. I found my place in the middle.

 

Will Barron:

And with all that said, when I learned to just be myself and not try and fit in with everyone else in one organisation or fit in with everyone else in the other, people would start commenting on, “Oh, we’re not having that jerk from your competitors in, because he was being dead aggressive on the phone and was pushing for this or that.” And ended having it from the flip side of, “We’re not having that person in from that organisation because they were just slow, monotonous. They couldn’t just give us medical equipment on loan. They had to go for all the paperwork,” which we should all go for the paperwork, but sometimes you’d help people out where appropriate.

 

Why Being Yourself is a Competitive Advantage in Sales · [45:31] 

 

Will Barron:

And as I said, I was always in the middle. And I got more compliments of, “I would just rather have you in the theatre with me whilst we’re using the gear than the competition.” Not that you are better at sales or you’re better at serving us or anything else, it was just like, “You could be a laugh and it’s nice having you around.” And that was pretty much it. And that was the feedback I got forever, every sales role I’ve ever done. And it’s not that I’m a better person than anyone else I was competing with or I was funnier or anything else.

 

Parting Thoughts · [46:11] 

 

Will Barron:

I think I was just … And this is really bad. I was probably just neutral. I was probably just acceptable to have in the room with people. And as I said, that was my competitive advantage in a lot of occasions. So just being yourself is just so important, right?

 

Jason:

Yeah, because at the end of the day, even though we’re doing business-to-business sales, you’re selling to a person. This person has individual fears, stuff that they’re self conscious about, things that they like in people, et cetera. At the end of the day, you just got to be relatable. Actually take the time to put yourself in the other person’s shoes, be likeable, be relatable, be genuine.

 

Will Barron:

Love it. Well, with that, tell us a little bit about Blissful Prospecting. And then you’ve got a link to share with us as well.

 

Jason:

Definitely. So I put together a guide for your audience on how to get started with video prospecting in less than five minutes. So it’s got the tool that I recommend, a process flow to follow, steps A through Z to do it. And then also a script of what to say. You can get that at blissfulprospecting.com/salesman. And what we do at Blissful Prospecting is we essentially remove the stress from prospecting by doing this for you.

 

Jason:

So we do everything up to the point of that introductory call. So we’ll help you build out those ICPs, get the accounts for you, mine the contacts, create the messaging, help you send out the videos. And we specialise in doing that for typically small and medium size organisations where the founder’s either really engaged in sales, or you might be a quota caring salesperson yourself and need a little bit of help hitting your quota or your team might, and we can help you out there.

 

Will Barron:

Amazing stuff. Well, I’ll link to that, Blissful Prospecting, everything else we’ve talked about. I think we’ve mentioned a couple of books in this episode. I’ll link to all that in the show notes to this episode over at salesman.org. And with that, Jason, I genuine really enjoyed today’s conversation. It went as well as what I thought it could have done from the initial video that you sent me. So with that, mate, I want to thank you for your time, your insights and all of this. Specifically on segmentation and specifically on your ideal customer or client profile, I think that’s really profound and useful for the audience. And with that, I want to thank you for joining us on the Salesman Podcast.

 

Jason:

Thanks for having me on. This is a lot of fun.

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