Jason Bay is the Chief Prospecting Officer at Blissful Prospecting. He’s on a mission to help reps and sales teams turn complete strangers into paying customers. In this episode of the Salesman Podcast, Jason explains what is and what isn’t working in the world of cold email sales outreach in 2022.

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Featured on this episode:

Host - Will Barron

Founder of Salesman.org

Guest - Jason Bay

Chief Prospecting Officer

Resources:

Blissfulprospecting.com
Jason’s LinkedIn
BombBomb – Video messaging platform

Transcript

Will Barron:

Hi, I'm Will, and welcome to the Salesman Podcast. On today's episode, we're diving into successful cold email trends for 2022. And our guest is Jason Bay. Jason is the chief prospecting officer over at Blissful Prospecting. He's on a mission to help reps and sales teams turn complete strangers into paying customers. And with that, Jason, welcome to the show.

Jason Bay:

I'm excited to be back, Will.

Will Barron:

I'm excited to have you back on, mate.

Jason Bay:

We were just talking. It's been a couple of years since we jammed last on a podcast, so I'm looking forward to being back.

Will Barron:

A couple of years. You are perfectly suited for this topic of cold email, cold outreach. Perhaps we'll touch on other areas of cold outreach as well. We'll dive into some trends.

Will Barron:

It'd be interesting to see the difference between what worked last time we spoke and then what's perhaps working in the marketplace right now in, what? We're in February 2022 as we record this. So let's start by setting some benchmarks.

The Average Cold Email Response Rate in 2022 · [01:00]

Will Barron:

We want to measure our cold outreach. We want to see if we're having success or not. I don't know if you've got finite numbers on this. If not, the gist of things will be more than appropriate. Jason, what is an average cold email response/reply rate in 2022? And then what should we be aiming for? How do we know if we're having success?

Jason Bay:

Yeah. It's really hard to find good data on this actually. Clearbit's got some stuff that you could take a look at. I've noticed a downward trajectory in the data in the last two or three years.

Jason Bay:

So Clearbit's data says less than a 1% reply rate to a cold email. And you think about that, and I don't know about you, that's a lot of work to get a response. You've got to send a hundred emails out to get a response. That's a lot of work.

Jason Bay:

Right now with Outreach, Salesloft, any of the traditional sales engagement vendors, they're all seeing a very similar pattern of that reply rate going down. Now, what is good? Depends. It depends on what you're selling, the transaction size, how many meetings that you need to get, the level of personalization.

Jason Bay:

And to give you a range here, if you were selling enterprise, let's say, some of my clients, and they're selling, let's say, a customer experience or employee experience solution into a large company where the deal size might be 500,000-plus at a minimum size, I'm going to expect 10% to 20% reply rates on those emails because I'm working 20 accounts at a time.

Jason Bay:

And I'm taking the time to actually look for triggers in the company, I'm researching the individual. Maybe I'm listening to a podcast interview with them. I would expect the reply rates to be much higher on those and meeting volume to be much lower in that case.

Jason Bay:

And at the very other end of the spectrum, you have people selling stuff that's very transactional, very SMB type of thing. And if what you're selling has at least a 10,000 to 12,000-plus US dollar… I don't know what that translates into to the rest of the world's currencies.

Will Barron:

Don't worry. Everyone talks in dollars on the… I'm a British company. We sell our product in dollars. That's where the world's at, I think.

“If what you're selling has at least $10,000 or $12,000 annual contract value, it's worth doing a little bit of customization on the emails. But you're not going to spend an hour researching someone to sell them something that's a thousand bucks a month. You don't have the time to do that.” – Jason Bay · [03:03]

Jason Bay:

Okay. If it's at least $10,000 or $12,000 annual contract value, it's worth doing a little bit of customization on the emails. But you're not going to spend an hour researching someone to sell them something that's a thousand bucks a month. You don't have the time to do that.

Jason Bay:

So you might have reply rates more in the 3% to 6% range, and then you have everywhere in-between. So I think you need to do some sales math and think about how many deals do I need to be closing on a quarterly basis? You've talked about this a lot.

Jason Bay:

How many deals do I need to be closing on a quarterly basis? And how does that backtrack into my closing rates and how many qualified opportunities that would need, how many intro calls that would be? And then you backtrack into the outbound metrics. How many outbound activities does it take to create a meeting?

Jason Bay:

You've got to work your sales math a little bit in order to really figure out what is a good or bad reply rate for you. But I can tell you, regardless of the scenario, 1% is not good. That's a little too much work.

The Difference Between Cold Emailing 100 Prospects and Spamming 100 Individuals · [04:03]

Will Barron:

I love it. I was going to bring it back to what you said, and you ended with it then, Jason, it's a lot of freaking work for not a lot if you are sending… Well, are you sending a hundred emails at that point or are you spamming a hundred emails at that point? I guess we need to define what spam is to discourage people from doing it to a certain extent, right?

Jason Bay:

Oh, yeah. Definitely. So the difference between spamming someone and cold-emailing them is… I think it's the accountability. A lot of these automation tools, the part that's kind of tough is oftentimes you don't really hit Send to that person. You might hit the Send button and it goes out to a hundred people, but you're so removed from what you're actually doing.

Jason Bay:

The way that I would compare it is, not to get political, but any kind of politician that is making a big decision that impacts a lot of people, whether that's going to war or something that impacts taxes or underprivileged people, they're so far removed from most of those decisions, the way that we do it here in America at least, where they don't really feel the accountability of their actions.

Jason Bay:

In a very small form, we're doing that with our sales engagement tools where we hit Send in a sequence to a couple of hundred people, we didn't actually hit the Send button to Will Barron, the chief revenue officer at this software company I'm trying to get a hold of. And we wouldn't normally hit the Send button on a lot of the stuff that we're sending.

Jason Bay:

So the difference between spam, I guess, and cold email, to answer your question, is how purposeful am I in reaching out to this person? Did I pick out this person, this company? Am I reaching out to them on purpose? And am I making it evident to them that this was intentional?

Jason Bay:

I'm not approaching you like a list. I'm approaching you as an individual. And there's ways that you can do a hybrid of both. But that's how I look at the difference between the two.

“I like to think of cold emails as would you send that email to your mom? Would you send that email to a friend? Would you send that email internally to someone in your organisation? And if they would just click Spam, then it's probably a crappy email.” – Will Barron · [06:07]

Will Barron:

Yeah. That makes total sense. I like to think of it of, would you send that email to your mom? Would you send that email to a friend? Would you send that email internally to someone in your organisation?

Will Barron:

And if they would just click Spam, then it's probably a crappy email. Leave it to marketing to send those emails and to warm up a client list if that's what you need, as opposed to… It's a terrible use of a salesperson's time to go about it that way.

How to Gauge the Success Rate of Your Cold Email Campaigns · [06:35]

Will Barron:

Just on these numbers… And I want to get into trends and what's working, what isn't working, what's changed in a second. But is this a rubbish way… Having asked the question and listened to your response, Jason, is this a rubbish way to measure success of the response rate of a single email?

Will Barron:

Should we be looking at the response rate of a campaign or a cadence that probably includes social selling, LinkedIn? Whether that's cold calls included, knocking on doors as well. Should we be looking at our success and response rate from starting cold outreach to then giving up on cold outreach with a prospect versus the response rate of a single email?

Jason Bay:

Yeah. I'm so glad you asked this question because we do have to step back and take a 10,000-foot view. So I look at outbound, I like to think of it as a game of odds.

Jason Bay:

So right now, when you look at this in terms of probability, I already mentioned that email, there's a 1-in-100 chance that you get a response to your cold email. With cold calling, it's not much better. According to Gong and what I see across sales teams, it's 1.48%, sometimes I'll see it around 3% or 4%, but of a chance of a positive outcome from a cold call, not even getting a meeting, just the next step of some sort. So basically, the person didn't ask you to take them off your list.

“The number one thing that we are driving with outbound is we want a qualified meeting. So we want a meeting that has a chance to turn into some sort of opportunity. So outbound is a very simple equation where number of qualified meetings equals volume times quality.” – Jason Bay · [07:55]

Jason Bay:

So I don't know by you, I don't really like those odds. Those are really low odds. And the thing that we have to think about is that the number one thing that we are driving with outbound is we want a qualified meeting. So we want a meeting that has a chance to turn into some sort of opportunity.

Jason Bay:

So if you look at outbound as a very simple equation of number of qualified meetings equals volume times quality, and there's a few things that go into that quality metric, but you can manipulate that equation any way that you want. You just have to start with the number of qualified meetings that you want to get.

Jason Bay:

So if we use some really simple math, you can say, hey, it's five qualified meetings that I need to get because I sell enterprise, let's say, and I'm an account executive, that I need to get per month. A lot of times, the way people try to manipulate and get to that number is they really focus on the volume piece.

Jason Bay:

So they might have a 1% conversion rate into a meeting, let's say. So that volume is like 500 prospects. That's one way that you could do that. And I'm pretty sure 1% of 500 is 5. You can correct me if I'm wrong, Will.

Will Barron:

I feel that the pressure is on me now to double-check all the math in real-time. I'll have my Post-it note with a load of equations on it.

Jason Bay:

Yeah. So that's one way that you could do it. But the other side, the quality side is really what I help most companies with. And that's a combination of your message, whether or not the prospect is a good fit, so the prospect fit, and it's also your soft skills.

“I look at outbound as a three-part framework of identify, engage, and create. So we can get to that qualified meeting mark by making sure that we identify good-fit prospects. And then that middle part, engage, that's our ability to start a conversation through emails, phone calls, all of that kind of stuff. And then the create part of that equation is how do we secure a meeting and turn this into a qualified opportunity? And typically, we're going to have to objection-handle in order to get the number of meetings that we need.” – Jason Bay · [09:27]

Jason Bay:

So if we look at this as a framework, and this is where we can kind of go in and out, you mentioned cadence, I look at outbound as a three-part framework of identify, engage, and create. So we can get to that qualified meeting mark by making sure that we identify good-fit prospects.

Jason Bay:

So it doesn't matter how clever or great your email is if it's not going to the right person at the right company, and that we know about the language in which these people talk about their priorities and problems, which we should spend some time on.

Jason Bay:

And then that middle part, engage, that's our ability to start a conversation. So that's your emails, your phone calls, that's how you sequence, all of that kind of stuff. And then the create part of that equation is how do we secure a meeting and turn this into a qualified opportunity? And typically, we're going to have to objection-handle in order to get the number of meetings that we need.

Jason Bay:

So to your point, it's a combination of all of those things. The email is only going to be as good as the person that you're sending it to. It's only going to be as good as your soft skills of being able to write a compelling message. And then the actual message itself. How am I talking to the person about what they're focused on, their priorities, problems that get in the way, et cetera? Yeah.

Jason Bay:

So I want to look at all three of those areas. And I'm happy to get as tactical as you'd like to. I have example emails that we can talk about, all kinds of stuff. So we can get as tactical as you'd like, Will.

Will Barron:

Cool. Well, we'll use that framework for the rest of this podcast. Now, one thing that's just cropped up in the mind of maybe 70% of the people listening to this, the 30,000 people that are going to listen to this, they're driving to work, they're going, “Jason, this sounds great, but it sounds like a lot of work, mate. That sounds like a lot more work than what I'm doing just clicking Send to spam 10,000 people that marketing have just given me.”

This is Why You Should Customise Your Emails and Not Just Spam the Marketplace · [11:10]

Will Barron:

Can you just reiterate, you've already touched on this, but can you reiterate the numbers here of maybe it seems like a lot of work up-front, but you're going to send way less emails to get the same or better results? Just to any naysayers who would like to spam, just to knock that on the head before we get into the tactics.

“When you have to spam 500 people in order to get a meeting, you’ve potentially alienated hundreds of people that will never do business with you just simply because you're an email spammer. I think people don't take into consideration that when someone hits Unsubscribe or wants you to take them off your list, you can't ever communicate with them again.” – Jason Bay · [11:42]

Jason Bay:

Yeah. It's like, why should you even care about having quality as a side of your approach? For sure. It's a fair question. I think about a couple of things. One, when you have to email 500 people in order to get a meeting and you look at the conversion rates on that and all of that other stuff, you potentially alienated hundreds of people that will never do business with you just simply because you're an email spammer.

Jason Bay:

I think people don't take into consideration that when someone hits Unsubscribe or wants you to take them off your list, you can't ever communicate with them again. If someone asks you to take them off your list, you can't communicate with that person ever again.

Jason Bay:

So if your goal is you're selling enterprise and you need to talk to chief technology officers or CIOs or whatever, you're putting yourself on a blacklist where your company can never contact these people ever again.

Jason Bay:

I've had clients before I come in and work with them where their entire domain of email addresses is blacklisted. So they're trying to reach out to this company and nothing from the @company.com name will even come through to any of their email inboxes. That's how serious these companies are about it.

Jason Bay:

So I like to think about… This is called second-order thinking is the mental model behind this. It's the consequences of the consequences. Right? It's the effect of the effect, in other words. So a way that you can think about this is what will the result be in the next one hour? What will be in the next one day, one week, one month, one year?

“Just because something will get you meetings here in the next hour or next day doesn't mean it's good over the long-term of what's going to happen over the next year. So we have to separate decisions versus outcomes. Also, just because we can get an outcome that we want in the short-term doesn't make it a good decision, and vice versa.” – Jason Bay · [13:06]

Jason Bay:

Just because something will get you meetings here in the next hour or next day doesn't mean it's good over the long-term of what's going to happen over the next year. So we have to separate decisions versus outcomes.

Jason Bay:

Just because we can get an outcome that we want in the short-term doesn't make it a good decision, and vice versa. Just because we don't get a good outcome short-term doesn't make it a good decision to get long-term results. So we really have to think about that. So you run the risk of burning out your market.

“I’ve also noticed that the people that respond to very spammy types of emails are never really great prospects.” – Jason Bay · [13:34]

Jason Bay:

The other thing too that I noticed is that the people that respond to very spammy type of emails, they're never really great prospects.

Will Barron:

Yep. I knew you were going to say this. This is exactly my experience and exactly my experience with the students in our training programme that come in from just spamming cold calls, spamming cold emails. They're like, “Why does everyone I speak to hate me? This sucks. I'm just getting rejected.”

Will Barron:

And they're coming with this hard, thick, emotional shell. And then they're unable to have empathy for the customers that aren't, by happenstance, the right place with the right product at the right time.

Why You Never Want to Be Identified as the Spammy Salesperson by Any of Your Prospects · [14:15]

Will Barron:

It makes me laugh so much the fact that you almost counterintuitively, by spamming people, you're starting the relationship as the spammy salesperson. And you've got to do so much work then to get just to level grounds with them to be able to have an adult business conversation.

Jason Bay:

Yeah. Let alone the quality of that prospect. A lot of my clients are selling into chief executives at Fortune 1000s or large companies with 5,000-plus employees. And these C-level folks are really smart. You're not going to get any meetings with smart people that know that you're spamming them, that can tell you did zero research. You're just not going to get meetings with those people. You're going to get meetings with all the garbage in that list.

Jason Bay:

So I would think about that. And we can address the time thing too because, basically, what we're doing is we're saying, hey, if we're going to do some up-front work and set up a system, we then can maintain over the long run a lot easier. But this is a lot more work to set up in the short-term up-front than for you to just write a couple of really bad email templates and to hit Send. So it is more work up-front for sure.

Will Barron:

But then you get, you might have enough analogy for this, but I like to call it the Flywheel Effect. And this is HubSpot terminology. HubSpot talk about this all the time, the main sponsor of this show.

Will Barron:

That you get that flywheel spinning and you start to build that momentum and you get a few deals from it, and then you're going to get referrals because you've sold appropriately and you've added value. Then you've got insights from your original customers that you can then share via cold outreach as an appropriate message. This industry insight that only you have as a salesperson, you can share that. And it goes bigger and bigger, and bigger.

Will Barron:

And then you've done so much work six months ago, the leads that you spoke to that were like, “Oh, it's not the right time, I'm not going to respond to this,” they then have the problem, they have some kind of critical issue within the organisation and you're top of mind, you've done all the work, they reach out to you.

Will Barron:

And this isn't as glamorous and as sexy as the idea of the Wolf of Wall Street where you're just calling people. Two grand, two grand, and you're just going through these numbers and crushing it. But I don't know that that's ever been a thing. And certainly, I'm 35, I've never seen that in any companies I've ever worked in that you were capable of doing that. I think that's a Hollywood stereotype of salespeople as opposed to what's really possible in the modern world.

Jason Bay:

Yeah.

Will Barron:

Let's get into tactics because that's what we're all here for. We're 15 minutes into the show and I think we're doing a bit of selling now, hopefully, to convince people because I think we're on the same wavelength with a lot of this stuff.

Applying the The 80/20 Principle to Your Cold Email Activities · [16:47]

Will Barron:

How do we go about identifying who are… This is a whole episode in its own right. I appreciate that. For the specifics of cold email outreach in 2022, what do we need to know about a customer? What's the 20% of things that we need to know that's going to get us 80% of the results so that we can then send an effective cold email to them?

Jason Bay:

Yeah. This is a great question. You wanted to know about trends in this episode too. This is the trend that I have seen really in the last couple of years is a lot of the tools are allowing you to sift through information a lot quicker.

Jason Bay:

So what I want to do, I call this the perfect fit identifier, is with any type of cold outreach, whether that's cold email or I'm running a cadence or sequence or whatever it may be, what I want to think about is how can I retrace past successes? So where has my company had the most success? And I'm just going to reach out to companies and individuals and follow that same exact pattern and then I'm going to build upon it.

Jason Bay:

So there's three kind of areas if you were building a Venn diagram that you'd want to look at. There's perfect fit on the account level, on the persona level, and then there's the values level. The values one I'll talk about here in a second, that's the most overlooked part, and it's also a way that you're going to customise the approach.

Jason Bay:

So on the account level, let's say that it's one of two scenarios. People are usually either assigned a bunch of accounts or it's a bit of a free-for-all at your company. And maybe you have a territory you're working and you can reach out to anyone that you want to. Either way, you're going to have more opportunities than you can reach out to at a time.

Jason Bay:

So on the account level, what I'm looking for is who best represents our case studies, our best success stories, the shortest sales cycles, biggest average deal size. I want to look for the verticals, the industry verticals, and the types of companies that best represent where it's going to be easiest for me to sell to, I have case studies, we have lots of content to show them.

Jason Bay:

I want to be able to reach out and to cold email and say, “We've worked with companies exactly like you and they've dealt with these types of problems, and here are some of the things that they're doing. Can I share a case study with you or can I share a piece of content with you?” Whatever it might be.

Jason Bay:

So I want the prospect to feel like, “Hey, we've worked with tonnes of people like you before.” On the second part of this, on the persona level-

Will Barron:

Just before we move on from that, Jason-

Jason Bay:

Oh, go ahead, Will.

Will Barron:

… What does that look like practically? Is that we go through our CRM, find the top 10 biggest deals, and then go to those companies' competitors and say, “Hey, we've worked with X. We can do the same for Y?”

Will Barron:

Do we look through the top 100 deals that we've ever done within the organisation and go, “Well, they were this company size in this kind of location, and we spoke to these individuals within the company?” What do we need to do very literally to put that into practise?

Jason Bay:

Yeah. Good question. So CRM is a good place to do that. That's where I would start. And if you've closed a decent number of deals, I would just look at the deals that you've closed because those are the best stories that you can tell.

Jason Bay:

But yeah, CRM, your deals that you've closed, your company's closed, whatever it might be. And I'm going to put those companies into a tool like LinkedIn Sales Navigator and I'm going to look at patterns across some of these companies. So, industry, employee count size, department growth, what's in their tech stack, et cetera.

Jason Bay:

And then I'm going to look in my prospect list of a hundred accounts, let's say, and I'm going to look and see, out of these a hundred, which 20 or 30 are going to be the best to prioritise first? Because they best represent what's in our CRM and what we've closed, they best represent the case studies that we have. And again, I'm looking at industry employee count and demographic types of things.

Jason Bay:

The other thing that you could look at too is some folks sell a solution where you can go onto someone's website, let's say, and you can see if they need it or not. So let's say you sell something that's a customer support type of solution or customer experience solution, and maybe part of what you do to make sure an account is a good fit is you go on their website and if they use a chatbot instead of an actual person, that makes them a good fit. So you're going to look for those kinds of indicators. So that's on the account level.

“People reverse-engineer closed deals, but usually, they only reverse-engineer from what happened in that first call or what happened in the second call, but they don't reverse-engineer how the meeting was landed for some reason. I don't know. People just never focus on that, yet it’s such a valuable process.” – Jason Bay · [21:14]

Jason Bay:

On the persona level, I really want to… People reverse-engineer closed deals, but usually, they only reverse-engineer from what happened in that first call, what happens in the second call, who did we multi-thread into this? They do all of those things, but they don't reverse-engineer how the meeting was landed for some reason. I don't know. People just never focus on that.

Jason Bay:

So take those deals that you looked at, those clients that you've personally closed, let's say, and what I want to do is reverse-engineer the outbound motion. So literally, who did I decide to reach out to? Who responded first? Who was the first meeting with?

Jason Bay:

So I want to look at champions, influencers, and then decision-makers. And people can be a combination of one or all of those things, depending on the size of companies that you sell to. But I have a company that I work with that sells an automated welding solution. It's hardware as a service and software as a service. So they want to reach out to people in manufacturing and operations.

Jason Bay:

One of their big champions they noticed they get the first conversation started with is at these manufacturing companies, it's plant managers, it's people that manage a plant. They're most impacted by the labour shortage around welders, for example.

Jason Bay:

So I think another big mistake people make when they're figuring out who to target is they'd be like, “Well, I need the chief operating officer to sign off on this, so I'm only going to reach out to those people. They have all the decision-making power.”

Jason Bay:

And you're like, “You know what? The chief operating officer is not even going to be in the plant where this tool would be installed, and they wouldn't be working with the people running the software either.” There's such bigger things that this person would be working on that they're not really going to care about that kind of stuff.

Jason Bay:

So you need to have a mix. Theirs, it's manufacturing and operations. And the VPs in both of those areas are typically the biggest champions and influencers and decision-makers in the group, and then we have plant managers and folks like that that we would talk to.

Will Barron:

That makes sense. I've had a bit of a revelation on this in the past 12 weeks or so, Jason. And this might be useful for you if you're selling to teams as well, sales teams. The person that is signing off on a lot of our Selling Made Simple Academy, the audience know where to find that, our training product, in the corporate environment for more than five to 10 people upwards are HR.

Will Barron:

I would've never thought to sell into HR. And it's only that people come on as individuals and then they go, “Well, our company should be using this and I should be getting it for free. I shouldn't be spending my own money.” So they go and sell it internally on our behalf, we give them a commission for doing so if we get a deal done.

Will Barron:

And HR is signing off on loads of our deals for onboarding new reps. So they're buying it for their entire teams and then buying extra seats for new people that are coming on board. I've got no data on this, no track record. It's only that I saw it happened twice in November, two decent size deals for us.

Will Barron:

And then I sent an email to everyone who… We have a list of people who are in the product and who are trying to upsell it within their own organisation. And I said, “Hey, maybe you should drop this to HR.” We did a bunch of deals in January via HR. The CSO or CMO still signed off and had the budget, but it all went via HR.

Will Barron:

And again, this is a trend that has probably existed for 10 years. I've only just picked up on it. Maybe it's just me being dim and not seeing the trend and not noticing these people in on the meetings on the email threads. But we've driven a couple of hundred grand in revenue just via noticing that alone. So finding out these trends can be incredibly powerful, and I'm talking from my own perspective here.

Jason Bay:

Yeah. That's really interesting. I haven't noticed that before. And you gave me a little hack, actually, I need to start using.

Will Barron:

Yeah. [inaudible 00:24:43] talk about it off-air. I'm explaining the pathway of it. The audience would find it interesting. You might find it interesting. But yeah, HR, not their budget, but they're the champions because they seemingly, in these enterprise companies, are organising a lot of the onboarding for new sales starters rather than you'd think a sales manager would be sat next to them going through all this.

How to Find and Get the Most Out of Your Internal Champion to Win the Deal · [25:04]

Will Barron:

So I made the assumption that we are selling to VPs of sales. In reality, even though VP of sales, CMOs, CROs have the end budget, HR is the one going and doing the work on our behalf and grabbing that budget and getting these deals done.

Jason Bay:

And that's really what you're trying to figure out when you think about the person is I'm trying to find the person that is working in a department that's going to have a lot of energy and passion around making this happen. Who cares about this the most? That's what the champion is.

Jason Bay:

For me, it's always been sales managers. These are typically the people I interact with the most throughout the sales cycle, and they're able to do the work for me outside of our sales call time together to organise the troops, get their VP sold, all that kind of stuff.

Jason Bay:

You bring up a really good point here in that you got to find those people. With the HR folks, for example, so this is kind of a messaging thing… Actually, well, I don't want to… I should probably finish this. So there's a third part of this before we get to messaging. But I think the HR one is a really good example that we can use.

Jason Bay:

So we have accounts, personas, and then values is the other big one. This is the one where you can reach out to a company that seems like the perfect fit, you're talking to the perfect person, but they just don't really care about your solution. So I'll give you an example. Customer experience was something that I talked about earlier.

Jason Bay:

If I'm reaching out to a Walmart, let's say, nothing against Walmart, but their value prop is being the lowest-cost provider, it's literally on their website. So it's not that they don't care about their customers. It's that, to be the lowest-cost provider, that doesn't typically mean that you're investing a lot in the customer experience.

Jason Bay:

There are other things that are more important to them to hit that mission, that value of being the lowest-cost provider. So that would make Walmart not a great account in most cases if you're selling a solution like that.

The Three Personalization Buckets You Should Know About · [27:09]

Jason Bay:

So the values, what I'm going to look at, is three buckets, and these are the three personalization buckets that we would use too. It's education; so what are they educating their customer base about? That's going to be a little bit more applicable if you're selling to companies that are also B2B.

Jason Bay:

I'm going to look at accomplishments; so what does this company brag about? So that might be company awards. It might be workplace awards that they've won. It might be how they're so awesome with certain things. It might be testimonies. It might be case studies.

Jason Bay:

And then the last bucket is investing; so where are they investing their dollars? Are they hiring people right now? Are they acquiring companies? Are they merging with companies? Are there new products coming out, new services, et cetera? And tech stack is a really big part of that too.

Jason Bay:

So if we were looking at that customer experience solution again, I would be looking for customers… Or accounts, excuse me, that have clear signs that they care about customer support and they care about customer experience. So are they really proud about displaying their response times and their 100% guaranteed policy? And have they won awards around the level of customer service that they add? Do they have content about the service, et cetera?

Jason Bay:

So I'm looking for those three buckets as well, and that's going to drive a lot of the messaging that I'm going to send these folks.

Will Barron:

Got it. Got it. The answer to the following few questions for me is sign up to Jason's course training. And this is, obviously, more in-depth there and he'll hold your hand and help you through it.

The Messaging Matric: Understanding The Engagement Elements of a Cold Email Outreach · [28:51]

Will Barron:

But let's assume now that we've got what we think… We can use the scientific method to make a hypothesis and test and refine some of this over time, right? But we think, via our hypothesis of what our product does, the value, the account, the personas within there that we're in… We've got the right people. We've got a list of 10 accounts.

Will Barron:

What does the engagement element of this look like now? How can we take what we've learned and turn that into an email? We'll stick with email specifically. But an email, or it could be cold outreach [inaudible 00:29:11], but we'll stick with email. An email that gets a response, that elicits some kind of reaction in the buyer.

Jason Bay:

Yeah. So we want to create what's called a messaging matrix. And this messaging matrix is going to give us swipe copy for emails, it's going to tell us what to say in a talk track, et cetera.

Jason Bay:

So what I want you to imagine is I want you to pick a prospect out and I want you to imagine that the prospect is on a path. I call this the prospect path. So they have a current state. And in this current state, they have priorities.

Jason Bay:

So there are initiatives. This year, in 2022, as we're recording this, there are two or three things that are at the top of their priorities list. And what you're going to find is there's actually a pattern across all of the people that you reach out to around what they're typically trying to accomplish.

Jason Bay:

And then there's things that they're doing to get that job done right now. So there's the solutions that they're using, strategies, tactics, competitors maybe that they're using to help make way on those priorities.

Jason Bay:

And then somewhere along that journey, they run into problems. These are things that get in the way of those priorities, these are things that are impeding their team's progress. And then they have aspirations, so things that they're trying to accomplish six to 12 months down the road.

Jason Bay:

I want to give you an example of what some of this sounds like. And then what we can actually do with that is I'll talk to you about how that translates into an email. So I work with a company that sells into VPs of human resources. And it's not a staffing company necessarily. It's more of a company that has a software solution where people can go in and hire some of these factory workers and people working on the floors and that sort of stuff.

Jason Bay:

So with these VPs of HR, what we found out about the prospects is they want to accomplish a couple of things. So there are two big categories and priorities of things that they want to accomplish. And I'm looking here at their messaging matrix. So one of those is employee satisfaction and productivity, and the other is HR effectiveness.

Jason Bay:

They got this information because we looked at all the sales calls, all the discovery calls that they do, the demo calls, and we just asked prospects, “What are your top two or three priorities this year? What would make this conversation relevant for you?” Et cetera. All you got to do is ask.

Will Barron:

I know I'm interrupting you, Jason.

Jason Bay:

Oh, go ahead.

Why You’re Likely to Get More Done By Simply Asking Your Prospects What They Want · [31:30]

Will Barron:

And I'm sorry to keep butting in here, but I think that needs reiterating. How much of a hack is it just to ask your prospects what they want or previous customers what they wanted and what you delivered on and what got them interested?

Will Barron:

Salespeople just never… Companies never do this. This is how we found out about the HR hack, getting our product into these enterprise organisations. How important is it just to ask your prospects and ask your best customers, “What did you want from us? What did we provide? What made you reply to an email?”

Jason Bay:

It's the oldest advice I could possibly give someone that creates any type of content, right? You're 35, I'm about to turn 33. It's the advice we read about 10, 15 years ago or whenever we got into sales around the language, right? Just ask your customers.

Jason Bay:

And there's a bunch of different things we don't have time to get into with how you can find that information. But the bottom line is I would just ask. Every sales call moving forward, before you dig into it, hey, just to keep the conversation relevant for you today, what are the top two or three priorities that are most relevant so I can make this conversation as useful for you as possible today? And people will just share them with you and you're going to find patterns, and you need to write them down word for word.

Jason Bay:

So I'll go through one of these. So for the VP of human resources, it wasn't just employee satisfaction or productivity. It was how do we take care of existing employees to increase our workplace ranking and retention?

Jason Bay:

So it was very specific around how do we demonstrate that we're a great workplace to work for so that we can win awards and use as a recruiting tool? How can we retain people so that we have great Glassdoor reviews and we have positive references and things like that?

Jason Bay:

So the current way that they're getting that done, so that's the next part of the messaging matrix. We got priority, how they're getting it done right now. They're relying on in-house employees to get the job done. So they have an in-house team of recruiters that are going out and finding these people.

Jason Bay:

The problem with that is that their current solution leads to a lot of turnover and burnout, workers don't feel valued, and there's a lot of job abandonment due to poor working conditions, long hours, and shift inflexibility. So this is stuff that's happening on factory floors like let's say an Amazon, for example.

Jason Bay:

So once I know that's the problem, then I'll look at the aspirations. So what do these people, when they come into sales calls, what do they tell us they're trying to accomplish in six to 12 months? They want to be able to focus on culture, diversity, and inclusion, to hire and promote from within, and increase employee satisfaction and retention.

Jason’s Guide to an Effective Cold Email Strategy · [34:10]

Jason Bay:

So that was a lot of information right there and you might be like, well, how the hell do I turn that into a cold email, dude? That's a lot. So the cold email structure, I'm going to give you an example. I'll read off the email. I'll give you an example of what it sounds like first and then we can deconstruct it a bit.

Jason Bay:

So here's the email. And it actually follows a very close kind of template to the messaging matrix. “Hi, Andrew.” Personalization. “Saw that you're offering a $1,000 signing bonus, on-demand pay, and retention bonuses for the positions you're hiring for right now.”

Jason Bay:

So you remember the three values that we talked about around education, accomplishments, and investments? Well, one of the signs of investment is hiring people. And when you look in those job ads, you can see how they're incentivizing people to work for their company right now.

Jason Bay:

So that was that first line. Saw that you're offering a $1,000 signing bonus, on-demand pay, and retention bonuses for the positions you're hiring right now.

Jason Bay:

This next part is I'm going to speak to the priority of these VPs of HR that I talked to. This got me thinking about how you plan on increasing the speed of hiring and reducing the cost of acquisition, a focus I'm hearing from many VPs of HR in a similar position.

Jason Bay:

So all I did was circle back to the priority, the thing that people are trying to accomplish. And this actually is in alignment with that second priority, the HR effectiveness. How do we improve our hiring practises to increase the speed of hiring and lower the cost of acquisition? This is exactly what they would tell us, word for word. So I'm using their words in the email.

Jason Bay:

And then I'm going to drop a couple of names of companies that we've worked with. Coca-Cola and Good Foods are using our help to avoid running into labour bottlenecks by keeping hiring costs down and hiring timelines short.

Jason Bay:

So that was the big part that they talked about was a problem. And again, this is actually from that second priority, not the one I listed off earlier. They said costs are high, candidate quality is poor, timeline of hire is too long, it's very labour-intensive, and candidates are not responding to our job ads. So I addressed that right there.

Jason Bay:

Coca-Cola and Good Foods are using our help to avoid running into labour bottlenecks by keeping hiring costs down and hiring timelines short. Can I get an opportunity to share how this could be helpful for you at ABC company? Jason.

Jason Bay:

So I've incorporated, in that email, all of those elements. I've talked to the priority, the thing that they're trying to accomplish. And I'm going to read that second one off right now, just so it's less confusing.

Jason Bay:

So the priority, again, was HR effectiveness. How do we improve our hiring practises to increase the speed of hiring and lower the cost of acquisition? What am I doing to accomplish that right now? I'm working with an outside firm or I'm using an in-house recruiting team.

Jason Bay:

That's a problem because costs are really high. When we work with an outside firm candidate, quality is poor, timeline to hire is too long. Or an in-house recruiting team, the problem is that it's very labour-intensive and candidates are not responding to our job ads. And what do I want? And I want to improve our hiring process so that we never run into a labour bottleneck ever again.

Jason Bay:

These companies are literally having to put production on hold and turn away orders and business because they can't hire fast enough. So my email is just addressing all of those things in that order.

Jason Bay:

We can go ahead and pause there. I'm sure you have a lot of questions on the email. We can go in-depth and break it down. But an email like this would get a 5% to 10%-plus reply rate. If we send it to the right person, we look for that hiring trigger. And we know that the language is really sharp too because we tested a bunch of iterations of this.

Why Simple, Professionally Written Emails Yield the Best Results · [37:36]

Will Barron:

My question, Jason, is when this is done correctly and we've done the work up-front and we know what we're talking about, and we're making a few assumptions here that the salesperson is somewhat knowledgeable about the industry, their product, their space, otherwise, it'd be very difficult to come up with these other than asking.

Will Barron:

Obviously, any chimp can ask you your best customers, why they want to work with you and all this kind of stuff, and the problems that they've had, and trends that they might have in the future.

Will Barron:

So assuming that it's a relatively educated salesperson, they've been through the process that you've just outlined, and they've put all these steps into place, that was quite a simple, straightforward, logical email. Is that what it should look like?

Will Barron:

Because if I got an email like that in the circumstance that you just outlined, if I was that potential buyer, at the very minimum, I'd go, “Oh, that sounds interesting.” And if I don't respond right now, I'm probably not clicking the Spam button. And maybe it might take a few more emails because I'm just busy and you need to catch me at the right moment where I've got my calendar open, where I can say yeah, let's jump on a call.

Will Barron:

But should the email just be as succinct and as logical and as… That was quite a professionally written email as well. I'm assuming there was no weird GIFs in there and memes and stuff to try and grab attention, right?

“People think they have to be really creative but I like what I refer to as a boring approach. You don't want to bore the prospect to death, but I want to be so insanely straightforward and obvious about what my email is about that the prospect is not having to invest any willpower into figuring out what my email is about” – Jason Bay · [38:59]

Jason Bay:

No. Yeah. So you mentioned something really good. People think they have to be really creative. I like what I refer to as a boring approach. You don't want to bore the prospect to death, but I want to be so insanely straightforward and obvious about what this is that the prospect is not having to invest any willpower into figuring out like, I don't know what this is. Does this even apply to me?

Jason Bay:

There's some stuff going on on LinkedIn right now that I think is a little bit concerning, where the content is, basically, if you confuse the prospect, they'll respond to you. And I'm like, “I don't think so.” Especially an executive.

Will Barron:

You might get a response, right? But the response is what we talked about at the top of the show of you're now the spammy salesperson who's conned the prospect into getting on a call, and that you're immediately 20 steps behind where you could be if you sent a more appropriate, adult, conversational email where it's, here's where you are. Here's where you want to be. You're blocking your pathway. Perhaps here's how we can get you from one side to the other.

Will Barron:

A bit of social proofing that we've done this for other companies similar to yours, similar size, similar industry. Even better if it's a competitor because hey, you don't want them getting away from where you are. You probably want to work with us as well.

The Most Effective Cold Emails are Simpler Than You Might Think · [40:13]

Will Barron:

Are we over-complicating all of this, Jason, in the fact that that is just a straightforward professional email that can be templated in the idea of, you might do things differently, but this is how we structure our emails, of current state, future states, what's blocking them, how you get from one side to the other, social proof that they should listen to us.

Will Barron:

Is that enough to get attention? I'm asking you the same question again because I really want to double down on it. Is that enough to get attention? Or do we need videos? Do we need to be doing an email, immediately calling, adding them on LinkedIn, and then doing some weird bullshit on LinkedIn to get their attention as well?

Will Barron:

Or it's just a well-researched, well-written, professional, but still somewhat conversational… We're not being weird. We're not typing a letter here in 1984. But is just a professional, straightforward, conversational value-adding email like that enough?

Jason Bay:

I don't know if it's enough all by itself. I think that definitely couple it with a phone call. So the cool thing about this messaging matrix is those two priorities that I mentioned, employee satisfaction and productivity and HR effectiveness, that's the same thing I've used in my opener for a cold call.

Jason Bay:

Hey, Will. Jason with so-and-so company. You got a minute for me to tell you why I'm calling? You can let me know if you want to keep chatting. Will says yes.

Jason Bay:

Well, hey, I'm talking to a lot of VPs of HR right now and I'm hearing them prioritise one of two things. I'm really curious what it is for you. One is around employee satisfaction and productivity. So how do we take care of existing employees to increase our workplace retention?

Jason Bay:

Or two, HR effectiveness. How do we improve our hiring practises to increase the speed of hiring and lower the cost of acquisition? I'm really curious, which one of those two is a bigger focus for you right now?

Jason Bay:

So I think the messaging repurposed, this is how you can reduce some of the work. So if you repurpose that same message into phone, I could record a video too, Will, with that. I could say, hey, I could share my screen on the video and do something really simple and just narrate the research as I'm doing it.

Jason Bay:

Hey, Will, I was on your website. I saw that you're offering a $1,000 signing bonus, on-demand pay, and retention bonuses for the positions you're hiring for right now. Typically, what I hear from people like you is a focus around one of two things, bam or bam.

Jason Bay:

You're just repurposing the same message across a different medium. So repurpose. Repurposing is the big… I mean, it's a huge content marketing hack, as you know, right? You take these episodes and repurpose a best-of. Or you take five episodes on cold email and you just summarise your best parts of it and you put it into a video on YouTube, right? It's content marketing 101 to repurpose the stuff.

Jason Bay:

Statistically, less than half of people are going to open up the emails that you send. So make sure you're repurposing that content and reusing it.

Jason Bay:

So to answer your question, in email… And I don't think you were asking it in this way necessarily. I just want to be clear for everyone listening and watching. Sending one email, no matter how great it is, probably not going to get a response if you only send one email.

Jason Bay:

I need to send multiple emails to this person. I need to call am. I need to reach out to them on LinkedIn. But I don't need to do that in a way that is inauthentic. I could just repurpose the same messaging across those different mediums.

Jason Bay:

One of the things I really like to do is to bump emails and to not do it in a pesky way. So I would bump this email if they didn't get a response. And in two days I wouldn't say, “Hey, did you get my email? I noticed you opened up my email but didn't get a response.” Or, “Hey, I noticed I haven't gotten a response from you.” Just a simple, “Any thoughts?” Any thoughts? Question mark. Jason. That gets a pretty high reply rate.

Jason Bay:

So a really simple bump email can work really well. There's another type of bump email that works pretty good too. So we did talk about GIFs. The best GIFs are the ones that you make. So if you could make a short video or a GIF of you holding a piece of paper that says, “Any thoughts on it?” And you're pointing up at the email.

Jason Bay:

BombBomb is a video platform, they popularised that approach, to give them credit. I've seen that work pretty well too, but I wouldn't send that to a VP of operations.

Will Barron:

No.

Jason Bay:

You know what I mean?

Will Barron:

I was letting you finish that, Jason.

Jason Bay:

I might send it to someone in tech.

Will Barron:

I was like, “Maybe don't send that to the CEO.” Maybe that you not send that to a Ballmer over at Microsoft or someone. But I really appreciate what you're saying there.

Will Barron:

We've not got time. We'll have you back on in the not too distant future to dive into this deeper because I think you might be into some of the psychology of this as well and understanding it. But when you share a similar effective message over and over, you add a layer of congruence to what you're sharing with the prospect.

Will Barron:

And it might be one, two, three. There might be layers and there might be layers of the same problem on you, so to speak, for the prospect. But when you're sharing one, two, maybe three different problems and how you can solve them for the prospect over the course of a week, a month, six months, whatever it is; depending on the size of the deal, what it's worth, and appropriate doing; you're congruent. And that shows the prospect that you're adamant in what you're doing.

Will Barron:

What a hack does is go, “Well, we can do this. And we've got a discount on next month. And then this week we've just added this feature which might not be relevant but might be relevant. Hey, can you get back to me on this and this?” And you go all over the place and you have commission breath, and it sounds desperate. You're just trying anything to hook them, to claw them in.

Will Barron:

Well, if you've got a great product that solved this problem for people similar to your prospect, it's almost going from all this, from a standpoint of, hey, it's almost inevitable that you're going to work with us. I'm going to keep following up because I'm a professional.

Will Barron:

And eventually, we're going to get a time booked in the diary. And whether that includes a GIF or not is obviously going to depend on the person. You can send me a GIF all day. I love GIFs.

Will Barron:

But you send in a congruent message with regularity. I don't know if that is a real word, I've just made it up. Over the long-term, it shows that you're a professional salesperson, as opposed to someone who's just going to do, as you alluded to before with this weird stuff that's going on on LinkedIn to trick people into getting on calls and follow up on emails.

How to Avoid Stone Age Selling · [46:26]

Will Barron:

You're not having to go back to the stone age of selling, which is manipulation, weird five-word hacks to get into someone's subconscious and drive up their 11 levels of emotion and all this weird stuff that happened in the '80s and '90s.

Jason Bay:

Yeah. You don't really got to do a lot of that at all. I think of this… Your sequence is like a personalised ad campaign. The average person needs to see an ad six to eight-plus times in order to even click on it. And that's from something that they might like actually. That might be a retargeting ad that they are seeing from Amazon or Nike.

Jason Bay:

So my advice is always, don't go into this situation where you're prospecting to someone and you expect to have better brand awareness than Nike or Google because they have to put multiple impressions in front of people to get them to click on stuff too. You're no different.

Jason Bay:

You're probably not working at a company that has that level of brand recognition. Most of us aren't. And if you are, that's awesome, but most of us aren't. So treat it like a personalised ad impression where you're putting a custom message or ad in front of someone.

Jason Bay:

They're not going to always click or respond in everything that you say, but that doesn't mean that that first email they didn't respond to wasn't a big reason why they responded to the third or fourth email or why they decided to pick up your call.

Will Barron:

Yep. It's almost like we're telling a story, right? It's progressing. There's going to be peaks. There's going to be troughs. We're going to try and raise emotion. We're going to try to add logic to it. We're going to make things simple. Maybe there's an element of making things more complex. And then you go back and forth, and it's going to be an experiment.

Will Barron:

And we'll wrap up with this. We're using the scientific method, right? We're making these hypotheses, we're testing them. What I find is that when salespeople get that message, they just can dominate a marketplace. Maybe it lasts six months, maybe it lasts 18 months, depending on what's going on in the market, your competitors, and what your customers are doing as well.

Parting thoughts · [48:35]

Will Barron:

But that's when salespeople hit target, hit target, do pretty well, make some money, and then just make stupid money for six months, 12 months, and when sales becomes an incredibly lucrative and fun place to be. So with that, Jason, tell us more about Blissful Prospecting. Tell us more about the work that you're doing over there and how we can get in touch and follow you, mate.

Jason Bay:

Yeah. This is super fun. This is what I eat, live, breathe. I prospect every week. Outbound is my thing. There's a couple of ways that you can get more of what we talked about today.

Jason Bay:

So blissfulprospecting.com, tonnes of free content on there. So we got a podcast. There's guides, webinars, all kinds of stuff that we're doing there on outbound. And then if you're a rep, we have a programme called Outbound Squad, and it's pretty cool. So you get coaching from me, you get a community that you get to interact with, and just all of my best course content that companies like Zoom and Medallia and some of my other clients see, same exact content there.

Jason Bay:

And then I also work with sales teams too. So if you're wanting to implement something like this, we have an accelerator programme where we take you through this. You get to work one-on-one with me over six weeks, and that's a lot of fun. And we deliver some good results there too. So blissfulprospecting.com is the best place to check out everything.

Will Barron:

Great stuff. We'll link to blissfulprospecting.com, your podcast, everything else that we talked about, and I'll probably link some blog posts of the specific things that you've mentioned in this episode as well where appropriate in the show notes of this episode over at salesman.org.

Will Barron:

And with that, Jason, I appreciate you, mate, for your time, your energy, your insights on this. The fact that I think you're a man after my own heart of putting this into frameworks and systematising a lot of it as opposed to just dumping it out there and hoping people can follow along.

Will Barron:

I appreciate that from you and your work, mate. And with that one, thank you again for joining us on the Salesman Podcast.

Jason Bay:

Yeah. Thank you for having me.

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Successful Cold Email Trends for 2022 | Salesman Podcast