Episode 133 Successful (Not Stressful) Prospecting – Jason Bay

Predictable Prospecting
Episode 133 Successful (Not Stressful) Prospecting - Jason Bay
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Just the idea of prospecting can be stressful. Calling strangers can take a real toll on you, and it’s easy to get discouraged and believe that prospecting isn’t right for you. But within a predictable framework, prospecting doesn’t have to be so difficult. That’s part of what today’s guest is here to talk about.

Joining the podcast today is Jason Bay. He is the Co-Founder and Chief Founding Officer of Blissful Prospecting, a company that works with clients to create a predictable prospecting system. Listen in to hear what Jason has to say about how he got into prospecting, his approach to creating personas, and how to address common errors in messaging.

Episode Highlights:

  • What prompted Jason’s interest in prospecting
  • Mixing modalities
  • How much time Jason spends in the planning stages with clients to develop messaging
  • Jason’s approach to personas
  • The ideal client profile identifier
  • Applying the research to one-person consulting businesses
  • Errors in messaging that Jason sees frequently
  • Jason’s REPLY method
  • Incorporating personalization in messaging


Jason Bay

Blissful Prospecting

Selling Above and Below the Line

Free Guide to Getting Started with Video Prospecting

Marylou: Hey, everybody. It’s Marylou Tyler with a very hoarse voice today. I’ve been out weeding in Iowa and the pollen is falling so if I sound guttural, sorry, I’ll try not to clear my throat too much.

Today I have a wonderful guest, Jason Bay, he is the Co-Founder and Chief Founding Officer of a company called Blissful Prospecting where he and his wife, Sara, work with clients who are interested in creating a predictable prospecting system. He does a variety of different things and I’ll let him elaborate on what his firm actually does.

The reason why I wanted him to come on today was to really talk about prospecting and how to take that stress out of prospecting that when you hear that word, there are so many people that just get crazy, their stomach starts hurting, they don’t want to really do this, they think no one wants to talk to me, they’re rude. I think if you listen to Jason and how he goes about preparing  for prospecting, and how they put their systems together for a predictable framework, you’ll get away with some really great tips on how to do this.

Also, he has other programs, a Do It For You program for those of you who are qualified for that, not everybody is. He has the ability to take that off your shoulders should you desire to look at some type of outsourcing, but you will go through a rigorous onboarding process just to make sure that you’re a good candidate which is really important because if you don’t understand your messaging then it’s very difficult for anybody to do it for you. Without further ado, Jason, welcome to the podcast today.

Jason: It’s really good to be on, I’m really excited for this. That was one heck of an intro.

Marylou: So tell us, prospecting is not a sexy thing and for all the pieces of the pipeline you could pick, the prospecting piece is probably one of the hardest, I would say closing could also be hard. Some people argue with me about that. But opening doors and starting conversations with people that you don’t know repeatedly, consistently, routinely, predictively, is really tough to do. So what got you interested?

Jason: It was really out of my own personal pain, actually. At the end of 2013, I just finished working with the company for six years that I started working with in college. It was a company where they taught college students how to run a house-painting business. That’s what I did in college was go door-to-door, sell house-painting services and that sort of thing.

I ended up becoming a sales manager, and a VP of sales there. I wanted to leave and help other companies sort of with the sales and marketing stuff that I was doing for them. That was a business to consumer brand, then now I had to learn how to do the business-to-business. I didn’t really know how to go about that because when I was selling house painting services, we either had a call center team that can do a lot of cold-calling and that sort of stuff, or we would go have marketing teams canvas door-to-door. I didn’t really know at the time what the equivalent of that was for business-to-business.

The big pain point I had was I’ve been to one too many meetup groups where I just wasn’t in front of people that I could actually do business with. That’s when I actually read Predictable Revenue, Predictable Prospecting, I read some of those books. I just noticed that, hey is there a way that I can scale this down a little bit to make it work for myself? A lot of the clients that I was getting that sold business-to-business said, “Hey, that was a cool email that you sent me,” or, “Hey, that was a cool video that you sent over to me,” or, “That was a cool LinkedIn message, can you do that for us?” That’s when I started just as a consultant working with some clients and really figured out that pretty much everyone knows that they should be doing more prospecting and everyone really kind of hates it.

Marylou: Yes.

Jason: That was the concept of Blissful Prospecting–how can we take the old way of prospecting that sucks, just get over it, make more cold calls and really take a more methodical approach to it which doesn’t have to suck if you’re intentional about it. You don’t have to have a cold-calling-only approach. You can send email, social, and videos. How can I find out and do more research on these people so I can make them something of value instead of feeling like I’m pestering people on having to play a numbers game. There’s really, from my own pain points that I experienced in consulting, getting clients that Blissful Prospecting was born, I guess you could say.

Marylou: Yeah. I’ve heard a couple of things in there that I want to make sure listeners also noted. One is that you’re all about adding more value, so this is not about going into an email engine or voice or social or even video and asking for things all the time. You’re adding value, there is a place for the ask, but there’s also a place for the value add.

The second thing I heard you say was you’ve mixed up your modalities. A lot of times I see people–this came off a client recently–where there was a heavy reliance on email and that’s also not a good thing. I love the fact that you apparently knew to mix the modalities of different touches of maybe social or voice or email or video mixed with email. That is probably one of the biggest lessons and I’m glad that you said that so the audience can start learning that consistency is important but mixing it up is also important.

Jason: Yeah, and one of the really cool resources out there is all these sales engagement platforms, people send millions of emails and setup tens of thousands of cadences through their systems. insidesales.com had a really good–I think it just came out a couple of weeks ago, I think it’s called The Definitive Guide to Sales Cadence, and they just talked about there’s about a 9.5% success rate with one channel and it goes up to about 22.5% with two channels. Just adding one other channel will double the effectiveness of your prospecting efforts.

It makes sense for a lot of reasons. It’s like you can only do so much persona research and only so much of that will ply. You don’t know what a person’s preferred method of communication is unless you try a couple of different methods.

Marylou: You also mentioned the term persona. In your work at Blissful Prospecting, how much time is spent in the planning stages with your clients to develop this messaging together?

Jason: This is something we spend quite a bit of time on. A lot of the clients that we work with are your SMBs, so they aren’t running enterprise Fortune 1000 type of companies where they’ve been around for a long time and really know their personas. And to be honest with you, I don’t know if you’ve found this–a lot of the larger companies don’t do a very good job with it either.

Marylou: You’re absolutely right on that one.

Jason: It’s really important. The approach that I like, I don’t know if this guy came up with it but a guy named William Miller wrote a book called Selling Above and Below the Line, and that’s the approach that we take with personas. One of the big mistakes, when people come to us, they’re having challenges with prospecting is they’re sending the same exact message across different ideal client profiles to different types of personas.

What William Miller suggests in this book is if you visualize a horizontal line, that’s where the decision is made, some people call the power line. But the above the line personas are your VPs and c-levels that are really strategic in thinking. Then you have your below the lines which are junior directors, managers, people that are like the tacticians that are going out and executing.

The reason why it’s so important to separate those is because we want to create and segment the messaging copy, too, because they have very different goals and challenges. That’s one of the things we spend a lot of time on with our clients. You’re talking to these people everyday. What are these people trying to accomplish that’s related to your product or service? What are the challenges they have doing so? What fears do they have? What are the big wins that you deliver?

When you do that research and really think about it, if you’re a sales person for each of this personas, it almost gives you word for word what you would plug into an email or a LinkedIn message or your content. We spend quite a bit of time. I feel like this is the most overlooked part of prospecting. People just want the email templates but really what’s more important than what you say is who you’re saying it to and understanding. Then the email copies relatively, I don’t want to say it’s easy because writing emails are not easy, but it becomes much easier when you know exactly who you’re reaching out to, what challenges they have, how to connect your value prop to that, all that good stuff.

Marylou: Yeah, what we do in Predictable Prospecting, in chapter three, was we talk about the influence map. We add a third level to what you discussed. There’s decision makers, leadership, the people who are responsible for the bottom line. The next level out in the bullseye are direct influencers who have the ear of the decision maker. They could be people who execute, they could be people who utilize the product that they’re putting in, but they’re very instrumental in influencing decision.

Then we have another ring, for prospecting we always have that last ring which is indirect influencers. They may not warrant a full cadence or sequence but we want to know who they are because we want to be able to call in around that piece to get some warm referrals, to get our foot in the door. While they may not be people that we’re going to spend time crafting a lot of messaging for, we do want to have the introductory here we are, why should you change, why now, why us, and get that type of I guess a script, for lack of better term, but get those bullets down to talk to those people so that they can refer us in.

Now we can add that to our sequence with a referral email saying, “So-and-so recommended I speak with you. They were really excited about our conversation, suggested I talk with you so let’s get on the calendar and do this.” That way, we have some social proof that we have some of them in the company. But you’re right, we really spend time crafting email messages and messaging in general for the decision maker and then the direct influencer, bullseye people.

The other thing I wanted to say was the way that you build the value proposition–I love that. We have a grid in the book that talks about time, money, quality and quantity. Those are by columns on a spreadsheet; columns B, C, D, and E. Column A are all the pain points that we come up with. Then we put on the top the persona, who is this person? What is their daily activity that is influenced by our offer? Then we fill that grid in as to this pain point. Are they affected by money? Are they affected by time? Are they affected by quality or quantity?

Then we also take it to another level saying, “Is this something that affects them financially, or strategically, or personally? Once we have this beautiful matrix, you’re right, it is essentially the schematic for us to be able to craft messaging for any type of channel and we have to go through that regardless if you are a two-person company or a thousand-person company. We really need to have this series of connect-the-dots, this actual map that will give us the ability to craft any type of message and any type of pain point for those sequences.

Jason: Then you have a foundation that you can build on, you have a working draft. The more you figure out about the persona, the better we’ll get and the more precise the messaging will get, and the more effective your prospecting campaigns will be. You guys take it to a whole other level that’s so important, especially when you’re selling really high-end to really large companies where there’s lots of decision makers. You have to do all of this research and really understand this stuff.

Marylou: And really weed out who are those top people that we need to talk to. If you’re a smaller company like the ones you work with, you may have the owner of another company. Or you may be selling into large companies but you may have the owner and somebody else, but still the same process applies. And you are right when you said in larger companies, when I ask them for their persona profiles, I get a marketing persona.

Jason: Yeah.

Marylou: We can use that, but that is not what we need for prospecting. Prospecting, think about it, we’re one-to-one, we’re belly-to-belly. Marketing is one to many so they’re building their personas as if they’re casting a wider net. We’re building our personas as if someone’s sitting right across the table from us and we’re having a conversation. We’re also trying to get the appointment, they’re trying to get someone to engage. For those of you who are out there thinking, “We have our personas, they’re at marketing,” you have an incomplete persona. You really need to finish it up with some of the things that Jason was talking about in terms of getting that persona ready for prospecting.

Jason: You mean that Marylou wakes up at six in the morning, and she drinks coffee, you don’t think that’s useful?

Marylou: I gave a presentation once where I have nine coins of why the marketing personas are not prospecting personas. There are nine things. I can’t tell you what they are on top of my head anymore because they’re a while ago. I’ll include it in the show notes.

Jason: Yeah,  I’m definitely interested in taking a look at that for sure.

Marylou: Very good, that’s great. Now we have our grid. What do you call this thing that you create that your clients can now take into the next step which is start the messaging process?

Jason: We don’t have a fancy name for it. Ideal client profile identifier, and it’s got the ICP information, the persona information, and all these goals and challenges and all that good stuff. I don’t know if you’ve experienced this challenge but it took a while to figure out how to organize the information in a way that would be really easy to plug it into the email copy.

Marylou: Yes, I had the same issues. I came up with a contract called compel with content which is in I think chapter five in the book, which is a story arch for email essentially. I still look for somebody who from direct mail. They had a story arch for direct mail that was a little bit too complicated for what we want to do so I narrowed it down to five steps.

Basically, when you fill out that persona profile and the challenges, you come up with an OOO Document which is the obstacles, the outcomes, and the opportunities. Basically those are the three main constructs of compellable content. And then there’s a trigger, an emotional trigger that gets them interested. It could be, again, based on a persona. It could be curiosity, mystique, alarm, prestige, depending on what motivates this person to move those eyeballs from the subject line down to the next line. Or when you were doing a voicemail to jolt them out of their complacency.

That trigger is added to the compel content, and then the call to action. The book ends through those three OOOs are the trigger to get them leaning in and then the call to action which is the next step that we suggest for them to know more.

Jason: That’s great. I wanted to comment quickly on something else you brought up too. Even the smaller companies that we work with still want to reach out to larger companies so this research is very applicable even if you’re a one-person business doing consulting, this is very applicable.

Marylou: Yes. The other thing to tell you because I’m a solo person, I have an army of one reaching out to companies. What I do is I have maybe three pain points that I think are the top ones. If I have an eight-touch sequence, I’m going to mention these three pain points and lead them into the conversation over the course of the emails, one pain point for email or one pain point per social touch. You don’t have to come up with 8-10 things, is what I’m telling you. Three is good and you just repeat but do it in a different way and bring up a different problem that relates to that pain point.

For those who are thinking,  “Oh my gosh, I need this gigantic thing,” no, you don’t. You really need two to three pain points per persona and then work on the obstacles or challenges, as Jason said, they have in their work day. The term what keeps them up at night, people hate that term but it really resonates into, “I was up thinking about something the other night. I’m up at night, worried about something.” That’s something that you want to consider. That’s a challenge.

Then basically, you contrast that to the outcome of where they could be, where they should be, and give them the sense of the success to get there. Then you weave it in with your opportunity then the call to action. You have a nice flow, you switch from emotion to logic, so it does follow the story arch that we all grew up with, with fairytales and everything else, but it’s just concise and more incompacted for the smaller email or the smaller message that you’re going to do whether it’s LinkedIn, or voicemail, or video-recording of yourself. So, bite-size, very small, short and sweet is what we used to call it in Predictable Revenue.

Jason: Yeah, love it.

Marylou: So we got our thing, we’re now ready to do our messaging. What kind of things that you see now that people notoriously mess up on, over and over again you see the same errors. What are they?

Jason: There are so many.

One thing that I do, I try to do it every week on LinkedIn is called email breakdown because I get a lot of cold–I’m sure you get a ton of cold emails.

Marylou: I do.

Jason: It’s really kind of fun so I’ll pick out the ones that’s from a reputable company. I could tell it’s a salesperson that’s really trying, I’ll blur out their name and the company name. There’s a couple of things that I see and we have something, I don’t know if we’re going to get to this in detail but I came up with something called the REPLY method. It’s sort of this method for approaching email copy and taking all that stuff that we talked about.

The R stands for Results, and that’s where I see people making the first mistake, in which they think reaching out to me out of the company that has two employees and three or four contractors and saying that we work with Google and Amazon is really going to get me excited when I don’t relate to any of those companies at all. If you’re sharing a company like that that you got results and help them with their branding or their social media or what, it’s just all stuff that I don’t care about. That persona research and focusing on that first part, the R, the Results, is hey, after you know what the challenges are, make sure that you’re sharing social proof, other companies that you’ve worked for, case studies, whatever might be that’s actually relatable to the business goal they’re trying to accomplish so that the prospect, which was me in this case, goes from, “That doesn’t apply to me,” to, “Ah, this looks interesting. Let me check this stuff.” That’s the first big mistake that I see people making.

The second one, the E stands for Empathy, and this is something that I’ll call skies out for because I don’t know if it’s that we don’t have a lot of empathy, it’s just not necessarily something in our society for some reason that guys like seeing that they have, or work on, or is rewarded I guess. One of the things that I didn’t really focus on just in my personal life as well is just you’re trying to empathize with people a little bit more, and understand what they might be going through. That’s where the goals, challenges, and fears comes in. The messaging copy doesn’t relate at all like what the prospect might be feeling or experiencing or challenges that they may be having.

The goal there is to really get the person to understand that this person reaching out to me knows a little bit about my situation. There’s no way that you can fully know what’s going on, but hey, is this person using language that I relate to, in my industry and my role? Are they talking about challenges or goals that I’m actually having at this time? And I see that completely missing from most emails. Most of the time it’s we do this we get these results all the time. People don’t call on any challenges usually at all in the emails.

Marylou: Right, so important.

Jason: It’s very, very important. The third part is Personalization. One of my biggest pet peeves, I don’t know if I’ll ever respond to an email that doesn’t have personalization beyond like merch tags, like the first name and company name. People that don’t find a way to relate the personalization to what they’re actually talking about, like making it contextual, that’s another thing that I see missing. It’s either nothing personalized at all. One of the ways I know, because I use LinkedIn a lot, it’s like we categorize ourselves as a marketing and advertising for our industry. I get a lot of emails from people pitching marketing agencies. We will talk about ourselves as a marketing agency, that’s not something I really relate to.

When people are doing that type of stuff and it’s very apparent, it’s a mass email. This is very basic stuff but I mean that’s another big mistake I see people making. Either no personalization or the personalization is just of no context. It’s about I saw you like the Boston Red Sox when that’s not really going to get the person to respond if you don’t find a way that connect that personalization to something that they’re having challenges with or why you’re reaching out or how you can help, etc. That’s the third big thing that I see.

The L stands for Laser focus, this is just being concise. One of the things that I have seen in a lot of the data shows that everyone’s got personal preferences but emails should probably be under 120 words if possible and three to five sentences at most, and it needs to be easily read on mobile. A lot of the emails that I get are 180-250 words, they’re extremely wordy. There’s more than three to five sentences and there’s a couple of apps that I recommend like Grammarly and Hemingway App are really good, they’re both free. You can just plug your email copy into these tools and they’ll help you write it in a more concise manner.

You ever get an email you open up and you just kind of glance at it before you even read it and like, “Oh, god. How do I even get started here?” People have found a way, and it’s really easy with tools, but this is something you got to work on with your writing chops. It’s just being concise, 3-5 sentences, less than 120 words, if possible.

Then the last part, the Y stands for You, making it about the prospect that you’re reaching out to. I always recommend that the you and your ratio to I and we needs to be at least one to one or greater. You need to at least be saying you and your more than I and we. Ideally you don’t really say I very much in the copy at all. It should really be about you and your goals, and your challenges. Most emails I see is. “Hi, I am so-and-so. I do this. We help companies with this. We can help you with this. I’d like to get on the phone call with you,” and it’s just so me-centric that it doesn’t really make me feel they want to help at all, or that they understand what I’m going through.

So those are the five really big mistakes that I see most commonly. A lot of them–I’m sure your experience has been similar but these are pretty straightforward stuff. People just break all of these rules all the time.

Marylou: This is a great way for people to remember too, I love when you associate with an acronym of some sort. I want to ask you about the personalization. One of the things that I get a lot of push back from from clients and people even contact me is this personalization at scale. Can you help us understand, if we’re trying to mechanize, and systematize, and leverage technology where it makes sense, how do we incorporate personalization to do that in a way that it’s seemingly on the receive side? Is that we are crafting a […] type of message?

Jason: Yeah, you can definitely systemize the approach. I would look at personalization in two ways. You’re going to have, and this is one of the big things I recommend from a prospecting standpoint, is to prioritize your prospecting efforts. A lot of sales teams are working in companies where they have people that are like their dream clients, like the really big deals. Then they have prospects that are more your small or mid-sized deals.

The stuff that’s really big or has a logo from a company you really want to work with, I would do the out-of-the-box personalization that might not be really repeatable. But maybe you’re only reaching out to 10 or 20 of those accounts per month. We don’t do any personalization that we can’t scale. The way that you do that is you just come up with personalization templates.

If we’re reaching out to marketing agencies, for example, I know that one thing marketing agencies really have a lot of pride around is their portfolio. If you have some sort of template, and we have something like the blank project on your portfolio, was really impressed with this specific thing. Like you can use that, that’s repeatable, you can use that over and over again, and it’s different for every person that you reach out to. That’s something that you can have virtual assistants do for you, as long as their writing chops are good.

Marylou: Wonderful. I want to be respectful of our time, how do people get a hold of you? What would you say would be a good next step for people listening to this conversation who want to get to know you better?

Jason: Sure. There’s a couple of things you can do. We put together a PDF, for you guys. It’s at blissfulprospecting.com/marylou. What you’re going to find on that is a guide to getting started with video prospecting, in 5-10 minutes, what tool to use, what to say, etc.. It’s how I reached out to you. That’s really quick videos, really effective. It depends on the persona but most personas are going to be pretty receptive to personalized videos if you do it correctly. I would check that out, that’s something that you can start using immediately.

The other place is just our website blissfulprospecting.com. In terms of things that I would suggest that you guys do next is I would really listen back to REPLY and use that as a checklist. Those five things that we covered, are my emails talking about the right result? Am I using empathy? Is it personalized? Those two things are probably the things I recommend that you could do relatively quickly and see a significant spike in results if you’re not already doing some of this stuff.

Marylou: Wonderful. That’s great and I’ll be sure to put references that we talked about, some of the books that you mentioned, and we’ll get those links so that we can add these to the show notes so that people who want to read the books you mentioned, we’ll put them there for you. That way you guys have the reading you need in order to start really working on this.

For the things that I want to share, I’ve been doing this now for 32 years, a bit more. The messaging piece, planning of the messaging, what we say to who, how, when, on what channel, on what position on the pipeline is utmost importance for us to really get. It doesn’t require that we have any magical tools for this. We have to really know our business, why we matter, why people should change now and why people should change now, and why they should change to us.

If we can get the core of that done, then everything else just naturally falls into place. We have these conversations with conviction, we’re very confident because we’ve worked through the reasons why people want to work with us. That’s really the crux of it all, right, Jason? It’s not about the email template. It’s about what goes into the message that gets people to sit at the edge of their seat to want to engage with you, to want to have a conversation with you. That’s what prospecting is all about–getting that first conversation started and then painting a picture at a very high level of what success could mean for them should they take your hand and start walking down the path or the pipeline for us. Jason, thank you so much for your time today. I really enjoyed our conversation and I hope the audience did as well.

Jason: Thank you. This is a lot of fun.