Jason Bay

Chief Prospecting Officer at Blissful Prospecting

19 Insights · 6 Questions · 13min Read · 18min Listen · Connect with Jason on LinkedIn

“Inbound-ish.” Dial in the content. How to get people to ask for help when they need it. Getting people to take action on what they learn. Regret minimization. Socratic method. Bite-sized content that is immediately actionable. Myself as a bottleneck. How to systemize and get a team around me. What if I'm wrong?

Here’s what Meghann Misiak said about Jason:

Jason Bay is someone I work with very closely. He is the king of outbound. He's a great prospecting trainer and he has a program called Outbound Squad. The results speak for themselves. He has a lot of incredible followers and is a great trainer. —Meghann Misiak, Founder of The Path to President’s Club → Listen

What are 3 ways that your team converts your market into revenue?

1) Inbound-ish. I teach companies outbound, but I don't do a lot of outbound to get business. I've been fortunate in that regard in the last couple of years that the inbound engine works pretty good, but I still do a form of outbound. I call it “inbound-ish”. The way I look at client acquisition is you have inbound methods on one side and outbound methods on the other side. If you're listening, imagine a piece of paper, you’ve got inbound on the left, outbound on the right. What I look at on the inbound side is the organic content that you create. That could be blog posts, stuff on your website. Then there's also guest content, there's third-party content. Getting on guest webinars, guest podcasts, et cetera. What I do is, I try to use those forms of content that I create, whether that be through LinkedIn content or being on someone else's podcast like this or a webinar, and I use that to drive traffic to my website, or if it's a LinkedIn post, I use it to get likes and comments on my LinkedIn post. Then I'll proactively reach out to those people. I'll still do outbound on those. It's just a little bit warmer. That's a really big strategy.

2) Posting daily on LinkedIn. Where I get most of my business from is posting daily on LinkedIn, every weekday, posts, so that people will engage on it. A lot of them are already target market. I'll just reach out to them directly, to set up sales calls. Or to get them in my programs.

3) Partnerships and co-marketing efforts are really big thing that we do and webinars have been huge. We just did a webinar with ZoomInfo last week on cold calls. We got almost 2000 people to sign up for it. Again, I'm building my list at that same time. I'm able to see who reached out and signed up for this webinar. And who can I engage with directly and kind of do this “inbound-ish”, this warm outbound, so that I can get clients.

What are 2 hard problems that you recently overcame?

Where to start? This one made me think a bit. Dude, running a business is hard. It really is. It's a lot of fun because, for me, I sort of grew up in sales. That was my career. And then I spent two or three years in marketing. But if I had to do a job where I only did sales, or only did marketing, or only did some sort of fulfillment, it would be really boring for me. The thing that makes this hard is also the thing I love about it.

1) Dial in the content. Specifically, we have a client program called Outbound Accelerator. It's six weeks. I'll take companies like Gong or Zoom, who’ve been some of my clients, through a six week accelerator with their team and it's really hands-on, “How do we outbound?” What I've really focused on is, how do I reduce the complexity of how I do this so that one, it doesn't drain all of my willpower fulfilling this, but two people get better results and it's just easier for them to do, so I think trying to figure out how can I teach less and say no to more things and really dial in the content and really, really focus on, hey, what are the handful of things? If there was one thing each week, during the two, one-hour training sessions that I needed everyone to take away, what's that one thing? And really distilling it down and simplifying it. It's just been so hard to find those things that will move the needle the most. We completely revamped our course content. Again, a lot of it is, how do we take 10 hours of content and whittle it down to the best two or three hours that's going to get the best results.

2) Figuring out how to systemize and get a team around me to support me. Another thing that's completely unrelated to that is our marketing. Just like you, I have a podcast and what we'll do with our podcasts is that, we'll take that, we'll chop it up into video clips. We'll re-share it on LinkedIn. I'll share it to my email list, getting mileage out of content. It sounds really nice in theory, to be able to re-share it all these places, but you need good systems in place. Otherwise, I end up being the person to spend all the time to do that. Figuring out how to systemize that and get a team around me to support me has been a really hard problem that we recently figured out how to do.

⏳ Big revenue goals? Find out what GTM operators are doing now.

↓ Access lightning-fast interviews with go-to-market pros.

What are 3 roadblocks that you’re working on right now?

1) Myself as a bottleneck. In terms of roadblocks, me, I've always been the biggest roadblock in the business. I have three virtual assistants that work with me full time. I basically consider them full-timers even though they live in the Philippines, they work with me full-time, and then I have a couple of contractors I use to help with coaching. Those folks don't work with me full-time yet. I ended up being the bottleneck in most of the instances. I just got rid of myself as the bottleneck with marketing. I am trying to get rid of myself as the bottleneck with delivery and coaching and actually executing the trainings. That's a big thing that I'm working through.

2) How to get people to ask for help when they need it. I think engagement is really tough when you have a paid community of people, like in our Outbound Squad program, it's for individual reps. They pay a certain amount of money every month to get group coaching, course content, and then access to a Slack community. We have 85 people in there right now. Getting people to engage in a virtual environment. It's tough. It's something I'm still honestly trying to figure out, how to get people to ask for help when they need it. That's something I'm trying to figure out right now, actually.

3) Getting people to take action on what they learn. I am getting better at that, but this is what I've done the last 14 years, is coach and train salespeople. I'm still learning so much. A guy, Sam Ovens, he runs a company called consulting.com, what he talks about is “eating our customer’s complexity”. I thought that was interesting. A small example of that is, if I teach you Chris, “Hey, when you make a cold call use a permission based opener, it sounds like this: “Hey, Chris, Jason with Blissful Prospecting. I know I probably caught you in the middle of something, but you got a minute for me to tell you why I'm calling and you can let me know if want to keep chatting?” I could just say that to you. Or what I could do is, I could say that, scripted out on a piece of paper for you, on a document, and then I could share it with you and I can make it easy for you to not have to do any thinking, to take action on it. I think “eating the complexity of my clients” and spoon-feeding as much as I can, without doing it for them, is something I'm always trying to figure out.

What are 2 mental models that you use to do your best work?

I love that you asked this question. I've only recently gotten into my mental models. There's a really good book, I think it's called Mental Models. There's a couple of volumes that are pretty good.

1) Regret minimization. Most of these I use with my wife, Sarah, when we make decisions, either with the business or financial or career type stuff, one is regret minimization. That's a mental model from Jeff Bezos talks about that a lot. That's a really simple one. It's, you know, “Hey, 10 years from now, what am I doing right now that I would most likely regret?” And when you put that lens on things, it's like, oh gosh, wow. Me spending so much time and prioritizing work over family time, I would regret that in 10 years. So much, just starts to become really clear when you apply that mental model.

2) Socratic method. Another mental model that I like, that's really old is, Socratic Method. When you have to make really big decisions, just forcing yourself to think about a question I like to ask myself when I really want to do something that's kind of a big decision: “If this was the wrong decision to make, what would make that true? What would make that statement true? What would make this the wrong thing to do? Even though I think it's right. What other outside sources have I asked?” I think that's really big.

Let's go with those two for now. Those are the two big ones.

What are 3 techniques that GTM teams need to try?

This is a tough one, because I think there's so many.

1) Bite-sized content that is immediately actionable for your target market is super important. I always think of everything through an outbound lens. How can we make it easier for salespeople to start conversations with prospects? When you have nothing insightful to share, it's really hard to start conversations unless people are ready to buy. How do you do the equivalent of, I help salespeople with cold calling? How can I, with a sales leader, share something that's a LinkedIn post that has one tip that would take five minutes to consume and then immediately start using. That's really effective. I'm creating a ton of value for that sales leader and a ton of value for their team. How can I create more bite-sized content that helps people that's immediately actionable? Maybe it's a different way of thinking of something. Maybe it's a framework, maybe it's a tip or a technique or something they could forward to the rest of their team. I think it's hugely underrated.

2) Personalized videos I think are really, really big. I'm working with a client right now that has a solution. It's primarily for software companies, but with complex solutions, like a DocuSign, let's say, when people need to figure out how to do stuff, they go to the help file. And usually they can't find what they're looking for. And when that happens, people get really angry and they churn. They don't use the tool as much, so they help get rid of all that. One of the triggers that they look for is people talking in public forums about complications they have with the tool. That would be a really cool to put in a video. I reach out to you. “Hey Chris, I noticed that there's a bunch of people struggling to find XYZ feature on your product. I wanted to show you how we eliminate this problem for other companies by doing X, Y, Z.” Being able to visually show someone's really powerful.

3) Messaging matrix. This is something really simple that can be repurposed across departments. But what I find, is that there is a lack of clarity around the customers of the business and what they actually care about. Nothing against marketers. I am one by trade and I do a lot of marketing, but most of the time, when I see a persona built by marketers, it's very, “Oh yeah, Chris is, he's a typical persona and, he's a white guy (from your appearance). It's, I don't know how old you are, but there's this age demographic. He likes to wake up early in the morning and, and get Starbucks.” That's not really that useful. You know what I mean? I think the big thing is, you want to build what's called a messaging matrix and you want to have these four things on it: priorities. What do these people think about, care about, on a daily basis, independent of your solution? If I was to ask this person, “What are your top two or three things that you care most about in your current job right now?” What would those things be that they would say, and then I want to talk about current solutions. How are they getting the job done on those priorities right now? Are they using tools? Do they do it in house? Is there spreadsheets they use for it? What is the way that they're getting it done right now? What are the problems that get in the way of that? What are their aspirations? What do they want to accomplish? When you have those four things across your personas, you have something that can be used to make content. Salespeople can use it to sell better. People can use it to prospect better. There's all kinds of things that you can do that are really effective. If everyone just teams up, does a couple of workshops, style sessions, someone takes ownership over it and leads it. And you say, “Hey, we're going to come up with our personas in the language that they talk, in their words, in our customer’s voice.”

What are 3 questions that you love to ask and why?

1) What if I'm wrong? I alluded to that earlier with the Socratic Method. I like asking that, because it makes me think from the other side.

2) What's this person feeling? I think that's something that's super important. I think we tend to, in sales, especially with bigger deals, where there's a lot of money on the line, we tend to just think about the numbers. Most of the big sales that I've landed, there's a very emotional aspect to that VP of Sales and why they want to bring me in. Yeah, the numbers need to sort of make sense, but a lot of it is them trying to prove something within their organization, to leverage for a promotion or some sort of power, in a lot of cases, too. That's a question that I like to ask myself a lot.

3) Are you having fun? The last one I would say is, are you having fun? I ask myself that question a lot. I've tried really hard. Fun is one of my theme words for this year. I tend to take my work very seriously and forget that, dude, life is short and you can be really serious about what you do and, and, make some good money and also have fun. Those things aren't mutually exclusive. “Are you having fun?” is a question that I ask myself a lot.

Who are 2 operators that should be our next guests and why?

1) Ethan Parker. He is VP of Revenue at a company called AltiSales, and he's also Head of Sales for me here at Blissful Prospecting, for our Outbound Squad program. I think he would be a good person to talk to because he's just got a lot of experience with this type of thing. I mean, he sold a $40 million deal as a sales rep. Pretty cool stuff. He's doing a lot of really cool stuff now with account executives and with outbound on our side.

2) Belal Batrawy. He's another good guy to talk to. He's Head of GTM at GTM Buddy. He is just the master at provocative messaging. So coming up with ways to come up with email messaging or cold call openers or marketing messaging, that's provocative and gets people's attention. He's pretty good at doing that. So I'd recommend reaching out to him too.

Learn from Jason → Blissful Prospecting

Follow Jason on LinkedIn → Connect with Jason on LinkedIn

Listen to Jason’s podcast → Blissful Prospecting Podcast

May 2022 · Interview by Chris Morgan, Host of Market-to-Revenue

Market-to-Revenue Podcast 🚀 Rocket-fast interviews with GTM operators in sales, success, product, and marketing.