SaaS Breakthrough – Featuring Jason Bay

demio saas breakthrough featuring jason bayAbout Jason Bay:

Jason Bay is the Chief Revenue Officer at Blissful Prospecting.

He does not believe that prospecting is “just a numbers game” or that it has to suck.

Jason and the crew at Blissful Prospecting help sales teams remove the mystery of what to say in their outbound calls and emails.

Learn from top SaaS marketers inside of the new SaaS Breakthrough Community​​​​  Facebook Group.  Join today:

Show Notes:
Growing Outbound Sales
The Three Buckets Of Outbound For SaaS
The Problems In Cross Department Communication In SaaS
"You have sales people being forced to say something that they know is not going to work because they're having the one-to-one conversations and marketing is having the one to many."
Two Practical Ways to Improve Cross Department Communication
The Right Mindset For An Outbound Campaign
"We always say don't prospect to make a sale prospect to start a conversation. It's the whole point is to start a conversation with someone."
A Framework For Approaching Messaging: The REPLY Method
"R is for results. It's to get the prospect's attention. So again, get them to go from what's in this for me to this looks interesting."
The Balance Between Automation and Customization
A Testing Strategy
"E is for empathy. (...) What we need to do at this stage is show the prospect, you're one of them. We need to get them to go from, you're not one of us to, you're speaking my language."
"P is for personalization. (..) What's important is that you want to show the prospect that your outreach was intentional."
"L is for laser focus (...) get to the point and people have very short attention spans these days and they're just getting, they're getting murdered with cold outreach."
The Little Hack To Make Your Emails Shorter
"Y stands for You. So what we want to do is make sure that we make the prospect the hero."
Analysis Of A Bad Outreach Email Example
Analysis Of A Good Outreach Email Example
When To Choose Automation Vs Personalization
KPIs and Benchmarks
Lack of Empathy Is The biggest Missed Opportunity
2020 and Beyond: Outbound 3.0
"We have to move beyond outbound 2.0 with multichannel and personalization. And now what we need to do is we need to build thought leadership. So salespeople can't just have a push strategy, they need to do push and pull strategy and the biggest opportunity for that right now is LinkedIn."
Ligthning Questions

DA: 02:40
Hey Jason, thanks so much for joining me today on the SaaS Breakthrough podcast. So excited to have you here. How you doing today?

JB: 02:46
I'm excited, David. Yeah, I'm doing great, man. It's a Friday as we're recording this and it's been a long week with little sleep, so looking forward to get some sleep this weekend.

DA: 02:57
Yeah, I hope you get a really great, that's a big part about being a founder, right? Is getting that kind of balance of rest. We here in Tampa this weekend is actually a crazy holiday, so probably not much sleep for me. It's Gasparilla here in Tampa.

JB: 03:09
Oh, that sounds fun. Crazy pirate festival pirates, man, that's, that's funny. I never pictured you to be a pirate kind of guy.

DA: 03:22
I'm not but if you're in Tampa, that's the city. That's the city thing we do. Cool. Well, you know, let's kind of jump right in here. I know you are not necessarily running a SaaS company, but I wanted to bring you on because you work with a ton of SaaS companies and you're doing some really interesting and powerful items for sales and marketing. For those of our listeners who have not heard of your company, why don't you give us a little bit of a background on Blissful Prospecting?

JB: 03:48
Yeah. The reason why, you know, we started as a company was really, it was a pain point that I had when I started consulting. When I left my full time job in 2014, one of the pain points I had was, you know, outside of doing some marketing and creating some content and getting up podcasts and networking, I wasn't really able to get the attention of clients that I really wanted to work with. They just weren't really coming to me and I wasn't running across any of their stuff. And it's a natural pain point that a lot of, you know, early stage businesses come across too. Once they found product market fit is like, how do we let everyone know about us and how do we kind of adopted push and a pull marketing approach where we're not just waiting for people to come to us or doing advertising and how can we can, how can we make outbound and inbound work together, is really how we started. And in terms of like working with SaaS companies, I've always been a big fan of SaaS companies and this whole outbound thing kind of started in SaaS with Salesforce doing a lot of this kind of stuff, selling software and moving to the cloud. So SaaS is one of the industries that I love working with because they're very tech forward and love adopting new approaches to things as well. So yeah, that's kind of how we got started, man.

DA: 05:04
When did you and your co-founder startup, or were you just working with a single client? How did that kind of whole process go?

JB: 05:10
Yeah, so this is a really interesting thing for consultants, is the, what you want to do. The Holy grail as a consultant is to get into a productized business and to make it bigger than your name. So when I was consulting, I did that for three or four years and what I started doing when I perfected my approach for outbound and was working on that naturally a lot of the clients I started working with were like, Hey, that was kind of a cool email you sent me, or Hey, your approach is really interesting. Can you do that for us? And then a light bulb went off and I'm like, okay, cool. I think that I can do this. I know how to do it for myself. I've worked, I have, you know, 10 years of experience training and working with sales people, so let's give this a shot. And it worked really well. So we took four or five clients that I working with as a consultant and rolled that into Blissful Prospecting,. And Blissful Prospecting as a company just kind of happened to be the packaging on the outside. We were already doing that stuff prior.

DA: 06:06
That's really cool that you guys kind of just found that pain point through that consulting journey. It makes a lot of sense. Most people are finding the problems as they're, they're building out themselves. And you found this new value. So what type of companies are you actively working with and what does it look like when you go into that company?

JB: 06:24
So we're working with SaaS companies. Typically under 500 employees sort of in that zero to 25 million, you know, kind of stage. And then every now and then we'll work with bigger companies that have large sales teams and just want to do this type of approach better. But it's probably the SaaS companies professional services. And then we also work with nonprofits. So one thing I'm actually really passionate about with nonprofits is getting their development teams to think and act more like sales and marketing teams to get aggressive with the types of corporate partnerships they want. And not be afraid to reach out to fortune 100 companies, fortune 1000 companies that don't know them or haven't heard of them before. And, and really putting their mission out there and pointing out ways that it would be beneficial for the company also to partner with the nonprofits. That's something we've been really passionate about lately as well.

DA: 07:12
That's awesome. That makes a lot of sense. And when you typically go into, let's say a SaaS company, like what kind of, what kind of packaging are you giving them? It's like a sit down with their team or what, what is the actual package about?

JB: 07:24
Yeah, so typically the way that we look at outbound is in three buckets. So we look at it, there's an identified bucket. So there's the first fundamental of outbound is being able to identify accounts that you want to go after and being able to find the contact information for the personas. The second bucket that we look at is engage. So that's your ability to engage those prospects with simple conversation starters through phone, through emails, social, whatever it may be. And then the third bucket is their ability to convert those prospects into opportunities. A demo in this case, if you're a SaaS company and that sort of thing. So the very first thing we start with is an outbound assessment. We're actually going through and grading them in each of these areas and most importantly we're looking for where the biggest opportunity is. So then we don't always start at the beginning of like, are you identifying (inaudible) prospects and that sort of stuff.

JB: 08:15
Maybe they have a conversion problem, maybe they're doing a really good job except for when they get people on the phone, they don't know how to handle objections very well. So we would identify the buckets where the biggest opportunity is and then we'll usually help in one of two ways or a combination of the two. It's from really through coaching and training, we're going to be coming onsite and delivering workshops and training and working one on one with their team and coaching theirs, their sales managers and that kind of thing. Or we're doing a combination of coaching and consulting where we might be getting our hands dirty too and helping them actually write a lot of this, helping them develop better processes around things that are maybe a little more custom to their business, that sort of thing. But it's typically one or two of those approaches. But really getting started with an outbound assessment and, and helping them figure out where the biggest opportunity is in their outbound approach right now.

DA: 09:04
I love that and we have kind of a similar process internally. We call it like our big impacts. Like where can we make an impact right now? Kind of an audit of that. So it makes sense. You're talking about these three kind of distinct ICPs as well, the nonprofit, the SaaS and the other tier company. And I guess when you first started this whole thing and you rolled in those first four clients, were they across the board, those different kind of personas or were you working specifically with SaaS, did SaaS kind of come in later and you've had to evolve the process for that? I guess I'm just trying to understand where that kind of SaaS product market fit ended up or how you got there.

JB: 09:40
Yeah, we started working with professional services actually, nonprofits we worked with on accident. One of our nonprofit clients just came to us and said, Hey, this looks really cool. I think this approach would work really well for me so that I don't have to do, you know, the type of, work that we're doing right now and can get into bigger companies and that sort of thing. And then SaaS, honestly, at first I was, you know, everyone is working with SaaS in our industry that does sales, you know, coaching and consulting and especially on the outbound end of things. So being honest, was a little intimidated at first to approach SaaS. And the way that it adapted was, you know, SaaS companies have a huge need for growth and to do it quickly, especially if you've gotten funding. So a lot of them just naturally came to us when I was posting stuff on LinkedIn about what we're doing.

JB: 10:30
And that's how we started working with them in terms of how we adapt the approach. I mean, I look at prospecting and outbound. The, the goal is the same no matter what industry you're in, you're trying to land an appointment with a qualified prospect that you can start a sales cycle with. So being that that's the goal in SaaS, you want to do a demo, but in professional services, they also like to sort of demo what they're doing. So the process is I would say way more similar than it is different. The only other nuances obviously with SaaS is you're selling a product, you know, versus a service. So it's a little bit easier to, in my opinion with SaaS to talk about specific, you know, if you've heard of jobs to be done, it's a little easier to figure out specifically what those pain points are that your product is fixing and how that intersects with the prospect's workflow versus delivering a service to someone.

DA: 11:25
I love that. I also think that it's pretty interesting that you obviously started with, you know, your set target demographic being professional services and then it evolved out of there. I always love to see that kind of focus and then it becomes expansion. Obviously SaaS also means you have to learn a lot of new vocabulary.

JB: 11:42
Did they love their, they loved their abbreviations and that kind of stuff in SaaS man, it's, it's a little crazy.

DA: 11:49
Yes, definitely, definitely. Of course, like you said, SaaS has, you know, where you're selling product. And I think with that becomes a lot of these departments, especially when you have funding now you have bigger companies with big, big, teams that are kind of spread out. And I know one of the core things in that three tier process that you work through is just making sure that you have solid communication, especially like cross department communication from your product team to sales to marketing and making sure that everyone's speaking the same language and just aligning there. Because as you're doing outbound, you know, your marketing team may not be saying the same thing as your sales team, which may be a different, you know, benefit from the product team. So when you're coming into these SaaS companies, what are you finding as like a common issue when you jump into these, these kinds of audits?

JB: 12:37
Yeah, this is a really interesting thing that we talked about previously and that I've noticed very strongly actually in the last couple of weeks of client work is we were running a workshop and it was really cool because the client wanted sales, marketing and product in the same room, which I thought was really proactive of them. Well, what I started noticing right away is that the marketing and product people weren't having as many one-on-one conversations with their prospects as the sales people were. Yet the marketing people were the ones writing the email copy and telling sales what to say in a cold call for example. This is like the ongoing debate right now in SaaS especially, and the reason why that's problematic is you have sales people being forced to say something that they know is not going to work because they're having the one-to-one conversations and marketing is having the one to many.

JB: 13:29
So it's extremely important that we get on the same page cause I think everyone can learn from each other. So when we get into these situations really what we're trying to show is that, Hey, your marketing copy and your conversion on your landing pages and lowering your cost of acquisition through the marketing channels. It all has to do with language. And if you can work together with the sales people, what you're going to get that you're not going to from looking at the conversion rates is what are these sales people saying and what challenges are their customers having, the prospects, excuse me, when they talk about the specific situations that come up where they need a product like yours. So I'll give you an example. Like, let's just look at Calendly. Really simple software app. As a salesperson, if I have these sales conversations, what I can hear prospects say is things like, yeah.

JB: 14:22
So when I'm opening up my email and I'm going back and forth, one of the things that's really frustrating is I have to manually look on my calendar for two or three times the prospect to meet with me. I have to put those in there. And then what sometimes happens after that is none of those times work. So the prospect and I get in this email battle back and forth and I ended up losing the opportunity because there's too much back and forth. That right there is it an extremely specific challenge that marketing could talk about on a landing page or in an ad. Hey, ever across a situation where you have to email the prospect back and forth three or four times and ended up losing the opportunity because of that. That's something very specific they can learn. And it goes the other way too.

JB: 15:04
Where marketing can bring in these meetings to the sales people. They can say, Hey, here are the things that we are seeing it's working really well from a conversion standpoint. Here's the social content that we're posting and the blog content. It's getting a lot of click throughs and a lot of engagement. Or here's the podcast episode that was the most popular, et cetera. And this goes on and on and on. And marketing can look at these statements and these, patterns in what people are responding to. And that's really, really helpful information for salespeople as well. And it's just like one of the many, many things that you can do. But the reason why is this so important, it's like everyone can learn from each other cause you're interacting with your prospects in different ways.

DA: 15:44
Yeah. And to add to your point, I think product as well, right? Like being able to give data on which features and functions are being used and how those are resulting in certain areas, which then can influence how the marketing team can speak about them and the benefits and the sales team can talk about the problems to benefit to product feature solution. So that's a, you know, super enlightening and very helpful. What are some of the solutions you would advise for SaaS companies to look at to improve that cross department communication is just, you know, more meetings together. Is it trying to have like a alignment through, I don't know, maybe like a quarterly review? What do you think helps?

JB: 16:25
So there's two really practical things that you can do. One of them is to create a recurring meeting that I suggest happens at least once a month for an hour where you get everyone together. And the second thing is you need some sort of document. It could be a Google doc that people share together. One person needs to be in charge of it. So put someone from marketing, product, or sales in charge of managing this document and the protocol after that and the habits that you're trying to create here are every time sales hears a situational challenge or situational pain in a sales call. That word for word text gets uploaded into that document. So the document is going to have two sections, results and it's going to have challenges. So the results is what do prospects tell you that they want to accomplish? And the challenges are what gets in the way of them doing that.

JB: 17:15
You're going to have all these word for word phrases that sales is going to put in there. Marketing's going to do the same thing. Hey, we noticed this article, this hyperlink to this article. This is the most popular thing we've ever put out. And here's some little snippets that we find that people really respond well to or here are some comments people left on there with things that they wanted to see more that they resonated with and then product do the same thing. So you have this document, this working draft, it will just get better and better and better over time so that anyone that goes to write a cold email or create a landing page can look at this document and say, what are we trying to say? And they don't have to guess from their perspective what it is. They can just look at what their customers are actually saying. So the really important transformation from a habit standpoint that needs to happen is everyone needs to be thinking buyer centric messaging or prospect centric messaging versus me centric or product centric messaging. It's a big transformation that you need to make and you need to document this stuff, need to get it on paper.

DA: 18:16
Wow. That was so helpful. That's really, really great insight. I love the cross department like team mentality there. The dynamic aspect of this document and Advanced B2B, an episode that we had a couple episodes back, also talked about some of their highest converting marketing copy was literally just using word for word statements from those sales calls or marketing calls or just surveys. So it's a great resource to have regardless whether you're in sales or marketing or product. That's amazing. So love those two insights. Thank you so much for sharing that. And now that you kind of have that document and you create this kind of cross department messaging and marketing is ready now to go out and do an outbound campaign drive new MQL for your sales team. How do you typically go about creating a campaign that works, like a reply- oriented campaign? One that's built for engagement, for getting results so you can generate those MQL to SQL processes.

JB: 19:11
So the mindset going into this, that's really important to wrap your head around first. Cause I think mindset really drives the process is we always say don't prospect to make a sale prospect to start a conversation. It's the whole point is to start a conversation with someone. And anytime we are doing cold outreach, we're trying to figure out if we can help the person not can, how can I help you? Because that would imply that you can actually help them. We don't know. We don't know what the prospect's situation is or what they're going through. We need to figure out if we can help them. So the whole premise of what I'm about to share right now is figuring out more about the prospect and learning more about them to figure out if I can help them not how can I sell to them or what product features they might be interested in. That kind of stuff. So we came up with a framework for approaching messaging called the REPLY method, which I can run you through here. So I guess David, the first thing is you're on the receiving end of a lot of cold outreach. What's the first thing that's going through your head when you get a cold email from someone?

DA: 20:17
Yeah, no, it's a great question. I mean, I'm at the point now where I'm getting probably like 10 a day. So, quite honestly, you know, when I'm even checking email, which has become less and less now, just because it can be overwhelming. It's, you know, a quick scan. What is this about? Is this worth my time? Do I even want to look at this right now?

JB: 20:37
Yeah. So you said, what is this about? So the very first thing that we need to do is get the prospect to go from what's this about? Or what's in it for me really, is this looks interesting. So the very first part of reply, so it's an acronym, is for results. It's to get the prospect's attention. So again, get them to go from what's in this for me to this looks interesting. So the way that we can accomplish this is through a few things, but the most important part is that we need to talk about the results that we can create for the prospect or for the people that tend to use our product. The best way to do that is through case studies and social proof. Where I see people really missing the mark on this is they'll be reaching out to a business like mine.

JB: 21:21
It's got two employees and we work with six contractors and they'll say, Hey, we've worked with Google and Amazon and I'm like that's cool I guess, but I'm not a fortune 50 company. I don't relate with that. So segmentation is extremely important and having case studies and success stories and social proof that you can share with the prospect that are companies that are similar to them. It's really the thing that you want to do. So make sure to segment by industry or employee count, some sort of way and then make sure to share relevant results with companies that you're helping that are similar to theirs.

DA: 21:59
All right. Is there a way to automate that process? I think the biggest reason that campaigns fail, at least listening to what you're saying right now is that you just have an email campaign set up in like It's generic. You're doing some dynamic words like company name, email name, whatever, like the actual first name and then it goes out to everyone. So of course it's going to be canned and say we work with companies like this. How are you segmenting this? So you're getting it through automation or are you doing a lot of this prospecting that kind of manually?

JB: 22:33
Yeah, really good question. So it's kind of, I think where you're going is what's the balance between like quality over quantity? It's really kind of the approach here. Like do we do the murder by numbers approach or do we do quality and if so, how do I do this in a way where I don't have to write every individual email? So it's a really good question. So the way that I approach segmentation is typically by niche or industry. So let's say that, let's say that you have a product that does automated like bookkeeping.

JB: 23:01
That's, that's one of our clients right now. They have different segments. So one of them is marketing agencies that they want to work with. The other is health and wellness companies. The other is, you know, more product based maybe e-commerce companies. So I'm going to segment and create sequences for all three of those. So the sequence I sent to a marketing entity is going to be very similar to health and wellness, but I'm going to say things that are more oriented towards a marketing agency in that sequence. I'm not gonna talk about our work with health and wellness companies. So now I have like a base sequence that's templated but it's a customized template for that niche. So I'm segmenting based on an account level is what we call that based on industry or niche.

DA: 23:44
That makes a lot of sense.

JB: 23:45
And then I can go in and plug in some of the personalization on top of that, which we're going to talk about here in a second. Does that answers the question?

DA: 23:51
Yes it definitely does. And my last question as a follow up on that, before you start creating these sub segments, are you testing a template? Cause I can see like even if you did by industry and then you did it by like industry and company size, you can get really specific. How do you know those are going to work? Like is the template itself tested on one niche and then once you kind of see it's working, then you spray it out?

JB: 24:13
Yeah. Another really good question. So I, I always recommend starting with like look at your portfolio of users right now and say, Hey, like for our product, where is it strongest in terms of industry or employee count or whatever other pattern that you can look for. Typically it's going to be industry for most people. So once you figure out that industry or niche, I'm going to, that's going to be the very first thing that I do. And I only do one at a time. And then once I make that work, I can move on to the next one and then I can move on to the next one. And if you're feeling like you've got a lot of time to do this and attack this, you might do two at a time so that you can AB test. So yeah, start, start with like small numbers and make that work and then move on to the next niche.

DA: 24:55
Perfect. Makes sense. Okay. I didn't mean to cut you up. I know you were through the R of the REPLY method. So what's next in that framework?

JB: 25:02
No, this is good man. Then I don't have to just talk to you. So, so E is for empathy. So one of the things that we're wondering when we get outreach that the kind of on the receiving end as a prospect doesn't make us feel, very good and kind of put us on edge as if we feel the person reaching out to us doesn't really understand us. So what we need to do at this stage is show the prospect, you're one of them. Yeah. We need to get them to go from, you're not one of us to, you're speaking my language. The way that you do this is by having really, really good understanding of your prospect's pain points, frustrations, or challenges that are related to your products. I gave the example of Calendly earlier where if I can lead in and say something like, Hey, you know, I'm not sure if you've ever run across this David, but a lot of the people that use our product tell us that they've run into this challenge and we're very specific and situational with like what happens when you're experiencing this challenge?

JB: 26:03
Not, Hey David, a lot of our users tell us that they don't have enough time to prospect. Okay, that's super generic. I think a lot of people could say that that was their pain point. But if I get really specific with that situation, the prospect will be like, Oh, this person kind of has an understanding of what I do and where we can get into trouble as sales people and marketers is we've never usually done the job of the person we're reaching out to. Unless you're one of those products that is, you know, for salespeople, by salespeople or for marketers, by marketers, we've never done the job of the person before. So typically where you're going to get this information is recorded discovery calls or demo calls. So this is another way that sales and marketing can work together is like processing those recordings and looking for those little snippets of where customers share their challenges. Product, same thing if you're doing product interviews and those are the challenges that we can lead with when we're doing outreach. So we need to address their challenges and we need to do it in their language and be very situational with that. Otherwise it's not going to really resonate with them.

DA: 27:12
Love that.

JB: 27:13
All right, so P is for personalization. This is sort of what we talked about earlier, David with quality over quantity, but are you pretty good at sniffing out whether an email has been touched by a person or not and like actually has a tiny bit of personalization or a lot potentially. Are you getting pretty good at that these days?

DA: 27:34
I am because I think it kind of goes back to what I said before where people are just kind of mass emailing with a small snippet of personalization, like the company name, email with some (inaudible) or something like that.

JB: 27:47
Yeah. So you, so marketers and salespeople are especially getting, you know, getting onto this and catching onto it and most other people are too. People are starting to realize how easy it is for 19 bucks a month to send mass outreach. So it's personalization. What's important is that you want to show the prospect that your outreach was intentional. The best analogy I could use here is if you've ever been on the receiving end of those company page invites on Facebook, a lot of people don't click on those and actually click on follow for that company unless they really know the person. And it's because I don't really feel like the person was thinking about me and why it would be valuable for me to follow that company versus if I send a private message to someone and said, Hey, I think you'd really get a lot of value out of following Blissful Prospecting cause it looks like you're in sales.

JB: 28:35
And from what I can see you're really into, you know, prospecting and learning better ways to do this kind of stuff. You seem like a growth oriented person. That's going to work much better obviously than me just sending a company page invite with no message on it. So that's a lot of what we're doing in our outreach is like sending out these generic invites to respond to us and it just doesn't work that well. So we really need to show that it was intentional and that we did our homework. So the way that you can do that is typically in an email is those first couple of sentences , where you need to provide some context to why you're reaching out and how it's connected. So if I'm doing a cold email, I'm just going to keep using Calendly as an example cause it was brought up.

JB: 29:13
If I'm going to send an email to someone I'm going to talk about in that personalization piece, I'm going to talk about something that I noticed about them related to sales or something I noticed about how maybe they enjoy using technology to save time. I'm going to look for something on their LinkedIn profile or something about their company that would indicate that they would also be into these conversations in shortening the email back and forth. Just schedule a meeting. I'm gonna look for something that's related that. The other thing that you can do too is use a tool like Vidyard and send out a personalized video in that first email to them and that works pretty well.

DA: 29:49
That's awesome. We started doing that with Loom videos on a personal touch point for trial customers. Not on the same scale. It's like an outbound email, but those personal videos work incredibly well, especially if you have someone that can take the time to do that well. What's next in this process?

JB: 30:05
So the L is for laser focus and this one's pretty straight forward, it's just get to the point and people have very short attention spans these days and they're just getting, they're getting murdered with cold outreach. So they're getting tons of cold calls, tons of cold emails. And what we really need to do to stand out is make it really easy to figure out what it is that we're trying to say and what we want from the prospect. So there's a couple of rules of thumb. What's your cold emails? We want them to be three to five sentences or less than 120 words. Voicemail should be less than 30 seconds. And when you're making a cold call at the very beginning, in about 15 or 20 seconds, you should be able to explain who you are and why you're calling, and get that out of the way as soon as possible so that you can start asking the prospect questions.

JB: 30:50
The other big mistake that I see in emails too is when people have like three or four call to actions, you should limit your emails to one call to action. So if you want the person to schedule a meeting, ask if they can schedule a meeting. Don't also ask them to look at a case study and ask them about a challenge they're having or tell them to do anything else. If the point of that email is to, for them to look at a piece of content, the entire email should be geared towards clicking the link to look at that content or replying and saying, yeah, send the content over to me. So be very, very specific with your call to action and limit it to just one if possible. And the rule that I always use is cause a lot of people have a lot of trouble cutting down their emails. Is what you have in the email doesn't help the prospect see a result that you can create for the, empathize with them through some sort of challenge or provide context in the personalization, you just need to get rid of it.

DA: 31:44
I've had the hardest time cutting down emails and for some reason I'm always overly wordy, especially when it comes to emails. So I could totally see, you know, having that kind of limit or being a great way for you to just say, okay I need to cut something down, this as a benefit is, this helping them understand like just having that framework is so critically helpful cause you can get wordy fast. It's easy to do.

JB: 32:07
Yup. One little hack that works pretty well for a lot of the people that we work with is reading it out loud and having a, like I have to be able to in a conversation say what's in this email to the person sitting next to me. So if you start reading it and you're like short of breath when you're reading it, you know that these sentences are too long, it's too long winded and if it feels awkward saying it to another person in conversation, you need to change it. So try to match your conversational tone as much as possible with what you're writing in the emails, which is a skill in and of itself.

DA: 32:38
It definitely is, but think that's the personable aspect of it. And I guess if you're reading your email and it's been like five minutes, you've probably written a novel and not an email. That makes sense. What's the letter there?

JB: 32:49
So the last letter is Y and that stands for You. So what we want to do is make sure that we make the prospect the hero and what we need to go from is the prospect thinking, Hey dude, I get it like you're really awesome. You're talking about how great your company is, how great your product is, and how many cool companies you work with. We really need to get them to transform from that to like, Oh, like this could help me. I see how they make their clients and their customers and their users of their product, the hero. And it's really about them more than it is about the salesperson. So what I always like to say is no one wants to be Alfred. Everyone wants to be Batman. So figure out how you can make the prospect the hero. And a really tactical thing you can do is just look at how many times in the email you're using you and your versus I. And if you're using I more than you and your, you're probably talking too much about yourself. So make sure to tell the prospect what's in it for them and how they can win.

DA: 33:46
I love it and this is a really awesome framework. Everything makes sense. And obviously from a strategy perspective it's very strong. I think the best part about this podcast in particular and also just like how I particularly learned is through like a tactical like detailed understanding of how it, how it looks or an example of it. I would love to hear maybe an example of like what a good, a good email looks like with that framework and then a bad one. So maybe start with a bad one then get the good one but that's super helpful having that extra detail layer on top of the strategy.

JB: 34:19
Yeah, I'll read this off cause these are two cold emails that got sent to me from SaaS companies and the good one I just want to preface, it's not perfect. It doesn't like, it's not perfect in any way, but it has all of these elements to it. So here's the bad one. The bad one says, Hey Jason I saw you're the co founder and chief revenue officer of Blissful Prospecting and I wanted to reach out and ask you if you're looking to improve your trading tools and outcomes? Here at (inaudible) we developed the world's first action based learning platform that's centered around feedback, coaching and peer mentorship. Our platform helps companies such as Blissful Prospecting, turn their existing training programs into unforgettable learning experiences. I'll be happy to chat, will any of these times and they link to their calendar, work for you. A terrible email for several reasons.

JB: 35:02
One, let's just go through the REPLY method. There's no result. They just say we developed the first action based learning platform that's centered around feedback, coaching and mentorship and it helps companies turn their existing training programs into unforgettable learning experience. I'm not really sure what the result is did they can do, there's nothing measurable that they talk about. There's nothing related to us. There's no case study, success story, nothing. There isn't any empathy into it either. They don't talk about a challenge that companies like us would be having, there's no personalization either. They used merge tags for my title and for company name, but there's nothing else on top of that that provides any context. Laser-focused actually did a decent job. The email, it looks like four sentences so it looks to be in line length wise and they kind of talk about how they can help me that you part, but they don't really make me or any of their users the hero.

JB: 36:01
They really focus on how they develop the world's first action based learning system. Which that whole sentence right there, you could just remove. It's not necessary.

DA: 36:11
Kind of confused by that sentence.

JB: 36:12
Yeah. It's got a lot of, you know, one mistake I see and hear people make too, is use a lot of like business jargon. You just remove all the tech or business jargon out of there and like really, really stay as human as possible with how you would talk to someone that is happier about what you do for work.

DA: 36:29
I like that. Talk to them like it's happier. Yeah, that's great. That's awesome.

JB: 36:32
Okay, so here's a good one and I'm going to read this off. Like I said, it's not perfect, but it really got my attention for a couple of reasons. So this is a company that has a SaaS solution for call coaching for salespeople. So he said, Hey, Hey, hello Jason had a look at your website and after diving a little bit deeper into how you're helping B2B companies and nonprofit organizations, I couldn't really not get in touch. I also see you follow (inaudible)) their company, which I'll give them a plug here. So you may be aware of the benefits already. So first off, what I like about how he opened up, and again it's not perfect, but he's talking about how he noticed that we help B2B companies and nonprofits. That's only something that he would have gotten from looking at our LinkedIn or our website. So he's already doing this personalization piece pretty well because he's talking about how we help those companies with prospecting and that's essentially what (inaudible) can do is help with cold call analysis. He also goes on to say notice that you specialize in coaching and one-on-one workshops and really keen to understand how you're currently conducting these and to share a few ideas about how other sales consultants are demonstrating their proof of impact and reinforcing their coaching remotely.

JB: 37:41
So he doesn't do the best job of like sharing the results in terms of like a percentage, but it's pretty clear what he's demonstrating, like how he can help. I mean like reinforcing their coaching remotely. We do a lot of our coaching remotely, so that resonates with me right there. I feel like the empathy piece is here too because he's not really like talking about a huge challenge, but I can tell that he understands what we do and it's using that language where it could be a little stronger is talking about how hard maybe it could be, do you do remote coaching, if you can't be there in person to listen to the calls, that might be something he could add to that. Laser focus. It's a little longer than I'd like it to be, but I don't really mind because I can tell you really took the time to reach out to me. In the you part I feel like he definitely made me the, the focus of the email instead of his software solution. And in the PS section he said, Hey, I'm also a big fan of the UFC. Did you make the QB versus (inaudible) fight? So I put this on my LinkedIn profile that I am a big fan of UFC. So he mentioning that shows me that like he paid attention and he actually knew of a fight that was going on that week that I did in fact watch. So I definitely took a meeting with this guy because of those reasons. And again, it's not perfect, but it kind of has the elements of the reply method in there and it doesn't have to be executed perfectly, but it really made it about me and did and did a ton of personalization. And I can tell that this was intentional.

JB: 39:08
I could tell this wasn't just plugged into a sequence.

DA: 39:12
I was going to say, I can definitely just feel from the first one or the second one, which one was plugged into a mass email sender with an email and which one was personally crafted, looked at your profile, took the time to research the company, understand how that company can help you. And again, using that REPLY framework for the craft of a nice email. So, I mean is there a time, and it goes back to my question before, is there a time and place when you should use that automation versus that second kind of email structure? Cause it sounds like, you know, maybe it's just a question of take more time, create more crafted, smarter emails and do less volume.

JB: 39:51
Yeah, there's definitely a balance and you have to do a couple of things. Your ACV is really important to understand. So if you're, if your ACV is under 10,000 bucks, I have a really hard time telling you to spend a lot of time in personalization because it might not be worth it to spend 10, 15 minutes writing an email every time you reach out to someone. Some people are selling products that costs 100 bucks a month per person and it just, there's not really a huge deal size there. That's more of a templated approach in my opinion because it doesn't really make sense from a financial standpoint to invest that amount of time. Now if your ACV is 10,000 plus, I think it makes it, makes a lot of sense to personalize the approach, but I think you've got to be real and look at the numbers and like what makes sense. So once you just kind of use that point or to look at it, the next thing you'd want to look at is, is testing.

JB: 40:46
Let me test an approach where I spend more time adding context and writing more customized emails and enable AB tests at the same time with something that's, that's pretty templated with a little personalization. And let's analyze how much time it takes for me to get that end desired result, which is a qualified meeting with someone that I ended up closing, right? So do that test and let the test and the data between the two tell you where it's worth spending more time. My personal belief is that it's a blend between these two emails. You don't have to custom write the entire email every time if you get some of the points down right. And the best way to create an email template that you can use is to do with this guy Ryan did and write something custom the first couple times you do it and you're forced herself to the campaign without automation, you're going to write it completely differently. And then once you find what works, figuring out how you can repurpose that into your own customized template or you use tags in a sentence or two at the beginning to personalize it to that prospect, once you dial in the language. That's the approach I suggest.

DA: 41:51
Love it. That's so helpful. That's really, really, really helpful. And what about KPIs? I mean, are there specific winning numbers or benchmarks you're looking for? Like a campaign should have X open rate and X click rate and you should be getting, you know, X amount of, maybe demos or just replies or is it a kind of a case by case basis?

JB: 42:12
It's definitely a case by case basis, but most of the companies we work with have a $10,000 plus ACV. So these metrics are going to apply more towards that. You at least want three to 6% of the total accounts or companies that you reach out to to convert into, you know, those first round calls, whether you do a demo first or you do some sort of qualification or discovery first, so three to 6%. That's sort of the bottom range that you want to be in. That's the only thing that matters that we measure. Now there's also leading indicators up to that rate that are going to drive that conversion rate and we don't use click through rate. I don't like using it in a cold email because these emails are not mass blast emails and if you're using click tracking, it's much more likely to go to the promotions or updates or the spam folder.

JB: 43:00
So we don't do any click tracking. I don't really share a lot of links for the people to click through. Really what I want to know is if people are opening and replying. So it's reply rates. You want to be five to 10% plus ideally you're in that 10 to 20% range is that sweet spot of reply rates. And then open rates, you want to be 50 plus percent. But again, everything works back down to how many of the accounts that I'm reaching out to. Like how many of those are actually converting into a meeting, like a qualified meeting that we can do and then work backwards from there with your open and reply rates.

DA: 43:35
That's super helpful. And I know you said that's for 10,000 plus ACV, but that's still a really good kind of benchmark for those of us who are doing outbound. Just kind of have in our heads as we go about it. Cause I know I've done an outbound campaign and did not get to 6% results there. So, very helpful. And I guess, you know, looking over maybe the past year, any lessons learned from working with companies, coming in to help them with this outbound processes. campaigns that didn't work out the way you expected them to or missed opportunities?

JB: 44:07
So everything comes down to knowing your customer better. Because like when I hear sales team say, Oh, we really know this. And like, here's what I would say versus well, Hey, let's step back real quick and think about our prospects. Like what's, what's the experience that they have? It's so different than like people on product thinking about user experience, what is the user experience for the prospect on the receiving of this outreach? What are they thinking? What do they want to see? It's that lack of empathy really I've seen to be the biggest missed opportunity.

DA: 44:39
Really. Definitely understand that. I think that thoughtfulness is something that so many of us miss, especially when we're looking at numbers like total sent, total opens and you're just kind of seeing it as numbers on a screen and you kind of forget about that experience behind it. So that's really valuable insight. And looking forward here at the start of a new decade, new year, 2020, are there challenges or opportunities that you're super excited for, for outbound, for the companies you're working with?

JB: 45:05
Yeah, I'm excited for what I call outbound 3.0 so outbound 1.0 was you know like nineties and like early two thousands where you could just mass blast. So if you have people's email addresses and can mass blast it worked extremely well. You could set a ton of meetings off of it, didn't need to do any personalization, that kind of thing. And then we entered outbound 2.0 in like this, like maybe 2008 2010 to like 2016 or 17 where Hey people don't respond to mass blast anymore. You need to add context. And you need to personalize the approach, multichannel started to becoming a thing. So you can't just make calls or just make emails anymore.

JB: 45:45
You have to work those two channels together. You have to have a sequence that includes email, phone and social outbound 3.0 now. And where I think things are really moving in the next decade is we have to move beyond outbound 2.0 with multichannel and personalization. And now what we need to do is we need to build thought leadership. So salespeople can't just have a push strategy, they need to do push and pull strategy and the biggest opportunity for that right now is LinkedIn. So you need to be publishing content and interacting with your prospects on LinkedIn and those become the people that you call. So you don't have to do a cold call. Look at the people interacting with your content, interacting with your competitors content, visiting your profile, look for people showing some signs of intent or interest and focus your prospects and efforts on those people. That's the biggest opportunity there is for sales teams right now.

DA: 46:39
That's huge, super helpful. I absolutely love that and I totally agree. First of all, LinkedIn is a huge opportunity right now and we can do a whole podcast episode just on how you're using it and lessons learned there. But based on time, what I want to do is move to our lightning round questions. Just five quick questions that you can answer with the first best thought that comes to mind. You ready to get started?

JB: 47:02
Let's do it.

DA: 47:03
All right, let's do it. What advice would you give for an early stage SaaS company starting marketing today?

JB: 47:10
Talk to your, your customers. I've already said this before and regurgitating it, but like have actual conversations. Don't just run tests on click, pay-per-click or on social or anything like that. Like physically, like have conversations with the people that you're marketing to.

DA: 47:26
Yeah, absolutely. The earlier the better.

JB: 47:29

DA: 47:30
Awesome. What skill do you think is vital for marketing teams to improve and build on today?

JB: 47:36
I already said empathy earlier, so that was going to be my answer, but the next one would be just copywriting, better writing skills, writing that matches the conversation and writing that reflects their customer's pain points and challenges versus their own biases.

DA: 47:52
Like you said before, right. Like you would be talking at happy hour. That was such a great line. That's awesome. What about a best educational resource you'd recommend for learning about marketing or growth?

JB: 48:02
I got two. Neil Patel, I love for content and conversion and that kind of stuff and I really love Seth Godin for the less tactical stuff and more like positioning. He is just such a master at how to look at how you position your company and your offer and that sort of stuff. And I love Seth Godin, his work.

DA: 48:23
Yeah, those are both absolute masters and experts. Great recommendations. What about a favorite tool you can't live without?

JB: 48:30
For us right now it's and that's a tool that you can use too. It's essentially set LinkedIn sales navigator on steroids so you can build account lists, find contacts, and then you can run your sequences through the same exact tool.

DA: 48:44
I love that question. Every episode I learn a new tool. That sounds amazing. I'll have to check that out. What about a brand business or a team that you admire today?

JB: 48:52
This is funny. This is a competitor of Apollo, Really good example of a highly successful SaaS company, but what I love about Outreach is they eat their own cooking, so they sell a tool that helps us sales engagement and prospecting, and they do a really good job of that themselves and what they do a very good job of that. I don't see a lot of SaaS companies, even successful ones taking advantage of is thinking about how they can leverage success stories with their customers and create content with their customers so that they can learn how to use the tool better. One thing that I love with Outreach is like I can listen to their podcast, I can watch their webinars and it's people using their product and talking about different interesting ways that they're using it to just get massive results. And that's what I've love hearing and I think they do a great job of.

JB: 49:43
The other thing they do really great job of, it's hiring women, so they make a huge proactive focus to hire more women in sales, to interview more women in sales and to spotlight more women in sales, which I think is super cool and a really big missed opportunity because a lot of the stats out there will show you that women have higher closing rates than men. So a lot of the companies, that's what they experience internally. So really what it comes down to is I don't think that necessarily maybe that men are better than women or women are better than men that necessarily, it's, it's having diversity on your sales team. It's not having a bunch of one gender or one race. It's having a mix of people with a mix of experiences that can help each other. That's really what it's about. But Outreach, they just totally practice what they preach in that department.

DA: 50:35
I love that. It sounds like a lot of social proof and awareness on both sides from a team here that's very diverse. The Demio team is very diverse. I think the one thing that I take away from that in the most is we all have unique experiences from our cultural or you know, gender specific views and it really helps to make a better company. Just a more well rounded thought out. And, and I love that. I love the push for diversity from gender or you know, racial perspectives. But I just want to stop there and say, Jason, you know, thank you so much for coming on today. This was a little bit of a longer episode, but I think we went through a ton of great strategy and tactical. That cold email breakdown was fabulous and super helpful as well. So thank you so much for coming on today.

JB: 51:18
Absolutely. I had one quick thing I wanted to share, with the listeners here and you know, if you're listening to this, like at the gym or driving and whatnot, we went through the REPLY method and went through pretty quickly. And if you want the guide I one page cheat sheet that you can use for your cold outreach, I put together a page for you guys at, so that's free. You can grab that, that will give you a really good idea. once you download that, like different ways that you can, work with us. So a lot of those being free. So that REPLY method guide, we have a ton of that stuff. I post daily on LinkedIn so much stuff you can check out. And there also be a link in there if you want to see what it'd be like getting our help, that opportunity to be there for you as well.

DA: 52:01
Well, thank you for sharing that. I think that's awesome. I'm definitely going to also follow you on LinkedIn. I think there's a lot of lessons to be learned there and I will say that Jason did do an outreach to me for this podcast. Definitely got you a spot here, so you've done a great job of that as well.

JB: 52:17
Thank you.

DA: 52:18
Awesome. Well thank you again for your time, Jason, and we'll talk to you soon and have a great day.

JB: 52:22
Awesome. Thanks, David.

DA: 52:24
Oh man, that was an incredible episode. Like I said, it did go a little longer, but we were able to really jump in to both the strategic overview of that REPLY method and some of those tactical examples, which I think was really, really helpful for anyone here doing prospect and your outbound campaigns. (...)

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