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Episode

Tim Bradley's Trifecta: Three Videos That Compress B2B Sales Cycles

With Tim Bradley/April 22, 2026/46:29 listen/Hosted by Jordan Lally

Tim Bradley is the co-founder of Pennant Video Co., a mid-funnel video marketing agency. Pennant works primarily with B2B SaaS brands, producing everything from script to screen, with a focus on building buyer trust rather than generating top-of-funnel awareness. Bradley has been working in video production since finding a role on Craigslist in 2011, and has spent over 20 years across action sports, live events, outdoor programming, and B2B brand work.

The conversation centers on the Trifecta Framework Bradley uses with clients: anthem videos that express why a brand exists, explainer videos that show what it does and how, and endorsement videos that validate those claims through customer storytelling. His argument is that each piece answers a distinct set of buyer questions, and that having all three removes the need for salespeople to repeat themselves. When a sales objection keeps coming up in calls, he treats that as a clear signal to build a video asset around it.

Bradley also covers how Pennant approaches client retention through proactive account work, mapping annual client calendars so they are proposing work ahead of deadlines rather than reacting to last-minute requests. On new business, he describes outbound as a rudder and inbound as wind in the sails, and explains how he uses LinkedIn, Sales Navigator, and communities like Exit Five to map org charts inside existing accounts and expand from one contact to several.


What You Will Take Away


About the Guest

Co-Founder, Pennant Video Co.
Tim Bradley

Tim Bradley is the co-founder of Pennant Video Co., a mid-funnel video marketing agency that produces anthem, explainer, and endorsement videos for B2B SaaS brands. He has worked in video production for over 20 years across action sports, live events, outdoor programming, and B2B marketing. Pennant focuses on compressing long sales cycles by building buyer trust through story-driven video assets.


In This Episode


Full Transcript

Full transcript of the conversation, published verbatim. Speaker labels come from the recording itself, not from an automated guess.

0:00 · Intro

Jordan:0:00
Welcome back to the [High Ticket AI Systems] Podcast. Everyone, please welcome the winner known as Mr. Tim Bradley. Tim, how you doing today, my friend?

Tim Bradley:0:08
doing great. Thanks for having me, Jordan.

Jordan:0:10
Absolutely, it's our pleasure. Now on our initial phone conversation, you and I actually have, I believe, very similar strategies when it actually comes to outreaching and to landing clients. Now, before we dive into all that fun stuff, can you just give us an overview about what you guys do and who you guys sell that to?

Tim Bradley:0:32
Yeah, yeah. So I'm the co-founder of Pennant Video Co. So we're a mid-funnel focused video marketing agency. So that means we have writers and creative directors and motion designers, and we do production, sort of everything like script to screen when it comes to producing video, right? But the mid-funnel focus is really the sweet spot for us because it's really about like, building trust with audiences, right? And like helping our clients, especially our B2B clients that have like long sales cycles, like recognize like these are the most common sort of FAQs that need to be answered. And how can you do that with story and branding and tone and sentiment and things that really work on behalf of audiences, know, desires to make a decision, right? Like this is all about empowering decision-making at the end of the day.

1:27 · How Tim got into video

Jordan:1:27
And absolutely, yeah, videos are such a key asset that I think are underutilized in all sales, but specifically B2B sales. How did you manage to get into this field specifically? I guess what spawned the idea, yeah.

Tim Bradley:1:39
Yeah. Yeah, yeah. I mean, I like to throw it way back to my childhood where my dad had one of those like big clunky VHS camcorders, right? And he was like, you know, I was like fortunate enough in that way. And he let me use that every once in a while to like do little, you know, make believe things with my brothers or like do stop motion animation with like my Legos or action figures or whatever. Right. And so just kind of that early know, exposure to the medium was awesome. And then I just fast forward to like coming out of college where I went to school for communications. And, you know, I was like, did some radio, did some print journalism and video. And was just like, man, this is really just the future, right? This digital video. And so I opened that first credit card and bought that camera and that MacBook Pro and was like, I'm just gonna, I'm gonna do it. You know what I mean? really just kind of immersed from the jump, but that was a mix of like, know, action sports and lifestyle and that type of world. And then we did some, you know, a lot of like live streaming and events and things. And then I did some editing for outdoor programming, like hunting and fishing shows, and then et cetera, et cetera. It was just kind of a big mix of like experience the first kind of like, you know, handful of years. But then I, I found this role as a video production specialist on Craigslist of all places back in 2011 for a PR, a burgeoning PR agency, right? Now I call it that 2011 not to show my age, but to more be like, this is a really specific moment in time, right? Like YouTube was only a couple of years, two, three, four years old. still known as the destination for cat videos. A lot of the brands that we were talking to, you know, were really reserved to be like, video, like we don't do TV commercials, you know, like just sort of the presence of digital hadn't really like connected yet. But fast forward to now, then like video is prevalent absolutely everywhere. It's like the preferred medium by audiences everywhere. It's on every channel. It's like,

Tim Bradley:4:04
you're all doom scrolling on socials and et cetera. So it's just like, it's very prolific and therefore expected, right? And so when it comes to the brands that we're working with, it's like helping to identify sure, like the right strategy around channels and where the audiences are. But like often that's already sort of like established because these are prominent businesses. And now it's just more like, what's the right way to express that this brand and make you stand out and be different and demonstrate your value propositions and validate what you're saying with customer storytelling, you know what I mean? So it's really sweet niche for us to be in. take a lot of pride in like the work and the craft and all of that. That's kind of like the table stakes, but it really the benefits is for us is like seeing the work work in our our, you know, client brand sort of channels and ecosystem at large.

5:02 · Who owns distribution, agency or client

Jordan:5:02
Absolutely. Thank you for the context there. So when you do work with clients and you're crafting these middle of middle of funnel videos, are you is your team in charge of distributing that content as well? Or you kind of create the assets on behalf of your clients and they do as they please with those assets.

Tim Bradley:5:21
Yeah, it's usually depends on the seat at the table, but more often than not, we know we're working with the head of product marketing, or head of customer marketing or head of marketing or CMO, right? And like, we're making sure we understand like the goals and the purpose of sort of this moment. Like most of the time, when we talk to clients, they're at like a bit of an inflection point, right? Like they have new positioning, they've gone through a rebrand, they have a new industry they're trying to break into or a new client, the new logo that they want to show off, you know, in their marketing and, or they have their annual sales kickoff. Like this is like really like where we do a lot of work is in those annual cycles of like aligning like minds and building that sort of momentum and motivation for the year, you know? So with that in mind, it's, it's, it's, you know, you said it early, like video is really complex, right? It's like, it can be challenging. to produce. like, we come to the table with that objectivity, we're working on behalf of the audience as much as we are, you know, the client that's paying the invoice, right, but it's like, making sure we're using the right style aesthetic, is that live action production? Are we pointing cameras at things like, or is it more motion graphics and designed in that way? Or is it a combination of both? Like, we do so much work with like B2B SaaS, and it's like, yeah, of course, we're gonna show off your UI and like the new features and like functionalities of what that means or what it can do on behalf of the technology. But it has to relate to human beings. like, how do we show that, you know, show and tell like the human beings that are using this and receiving the benefits of this business, right? So for example, like right before we we hit record, I'm flying to Salt Lake City tomorrow to do a customer endorsement video. So this is that like, that case study slash testimonial type of storytelling where we're on site with our client's client and getting, you know, from the proverbial horse's mouth, their validation, validating what our client is saying their offer is, right? So that's a mix of, you know.

Tim Bradley:7:36
interview and b-roll and music and sound design and some motion graphics to show off the UI and all that. So it's very like complex. But so fulfilling at the end, right? You take what's sort of like a nugget of like an idea or an intention or goal, you know, for this moment in time, and like, putting it all together in this really, you know, this this complex format to have this like really powerful medium and tool and asset that that you know, sales and marketing teams overall can use and leverage for months or years to come is really satisfying, right? That like impact that we're all here for.

Jordan:8:14
But for sure, it's like you're a magician. You you pull, you turn nothing into something basically. It is super cool. You give me one second. I can definitely see how what you do, what the company does is really applicable to B2B SaaS. Cause I feel like there's a lot of like tech videos that kind of get involved, especially enterprise sales. In regards to

Tim Bradley:8:19
Yeah, exactly.

8:43 · Storytelling vs production, what matters more

Jordan:8:43
That's the question. What do you find to be more enjoyable? The storytelling aspects of the work or like the production side, turning it into life with motion graphics and production?

Tim Bradley:8:58
Yeah, mean, so, you know, being the sort of like operator of the business, I have my creative teammates that get to really be sort of like, in the thick of the creative and the in the producing of the thing. So it's like I, I love that aspect of it, like seeing someone run with a ball or whatever run with a baton to like, create create the thing. at the end of the day. So for me, it's like, I would have to, you know, in this sort of like strategic advisory role that I'm often in, it is like the storytelling aspect, right? That's sort of like, the question is always like, what's in it for me? Not from the client's point of view, but the audience, like, what did they need in this moment to like, on some semblance of trust? Like, how do we take them from, how do we take this audience from like they've...

And of you, they've seen you, maybe they've, they've clicked on a banner ad somewhere, and they've arrived at this destination, which is likely a landing page or a homepage, right? Like, how do we help build this journey? You know, like, how do we express the most common FAQs of like, why and what and how and who and where, right? And all that really boils down to story at the end of the day. So it's like, a lot of times, it's like, our clients, you know, for better and worse that they're, There's a of pressure. So these marketers have like arguably some of the hardest jobs. The sales folks have some of the arguably the hardest jobs, right? Where it's like, it's data, it's results, it's goals. It's so much like driven in that way. So to like come in and be that sort of creative partner to be like, hey, let's just tell a really good story that supports your audience's like experience in their journey with you and build trust so that when they, once they, know. get to that CTA or the number of assets we've created over a period of time, they're arriving at your doorstep ready to buy. There's no convincing because you've built so much trust in that way.

10:57 · Psychology of conscious vs subconscious decision making

Jordan:10:57
Absolutely. And from a psychological standpoint, storytelling works far superior than just directly telling someone that they use as an example. And I kind of learned this from psychology class back in college a few years back, but our mind is kind of broken up into two parts, right? We have the conscious mind. That's how we talk. That's how we like, you know, make critical data driven decisions. And then we have the subconscious mind where all of our like habits live, our emotional state, all that fun stuff.

Tim Bradley:11:07
Totally.

Jordan:11:26
And humans, majority of humans tend to make decisions based off of emotions and justify with logic. And if you were to look at like the power of each part of our mind, conscious and subconscious, depending on who you ask, our conscious mind makes up like five to 12 % of our mind power and the subconscious is like 88 to 95 % of all of our mind power. So if you're able to tell an amazing story, What it actually does is it bypasses that five to 12 % of our mind and goes directly into the subconscious where we make majority of our decisions. So it's really powerful to do. Is it easy? No, I suck at telling stories. But if you sound like you are, if you can master that fricking skill, you will make buko bucks for your company and on behalf of other companies. So just wanted to acknowledge that with any man. That's awesome.

Tim Bradley:12:08
Yeah.

Tim Bradley:12:19
Yeah, I love it. No, that's super good. Yeah, and it's, you know, it's also just sort of like... you all of what you just described, it just takes time, right? And it takes attention. And it takes like, the right amount of care, right? And so like, building out that that sort of proverbial buyer's journey is that's why that's so critical, because it's not the way I've also heard described is like, you you need to you need to bring clients or prospects through a set of gates, you know what I mean? Like they have to go through each gate sort of respectively, along the way. So how do you build the right set of gates that like encourages them to move on into the next gate, know, because you can't really go from gate one to close necessarily, you know, as far at least it's like very, very, very uncommon. So yeah, a lot of that is in that emotion, right? And that's where a lot of the storytelling derives from. like, what is the best right emotion that we're trying to evoke here in this moment? We use a framework.

Jordan:13:09
Thank

13:24 · The Trifecta Framework explained

Tim Bradley:13:24
I think it's just a helpful, helpful thing to like, better understand a lot of what you and I are talking about here, right? It's like the trifecta framework is built around three key three, three key things, differentiation, demonstration and validation. And that's like really the point of it. You want to differentiate yourself from your, from your competition, right? And so that's sort of like, the top of the mid funnel in a lot of ways, but it's really that expression of why, like why you exist, why your audience should care, why you're different from the competition, right? So that type of work is very sort of like anthemic and mission driven. So we call them anthem videos if you're like looking at like from a deliverable standpoint. These speak to the hearts of that audience, right? It should be that sort of like reflection of your brand and your values and your purpose. to the audience, they should see themselves in you in that way, right? The next prong being different or being demonstration, right? So that's that explanation of what you do. It's what you do and how you do it, right? It's kind of classic explainer video that most brands have, because it's really fundamentally like helpful, you know, because it's like, as a salesperson or a marketer, you don't have to like say the same thing over and over again, like you leverage this tool to like the video to...

Tim Bradley:15:02
So that's like, you sort of most pure form of storytelling of like, how can you have your audience put themselves in your current clients shoes, right? And see this sort of like power of working with you. So this, the trifecta. differentiation, demonstration, validation. If you can come to the, you have no video, you just come to the table with like that type of strategy or framework in mind, you start knocking off the most commonly asked questions, the FAQs in that way. And now you've built your buyer's journey through these specific and videos, right? The anthem, the explainer and the endorsement or customer story.

Jordan:15:43
I think what you're saying is really, really important. And I don't think a lot of business owners in any stage, maybe understand that there really are, you know, depending on who you ask, three to six stages of the buyer's journey. And it's very rare, like you said, for someone to go to unaware, they have no idea that you exist in the world to the very next day of the purchasing, you know, $5,000 ticket item is very rare. Most of the time, they're going to go through the stages sequentially. What our job as marketers, depending on what you do for marketing specifically, our job is to compress time, right? Our job is to take someone from stage one to hopefully stage six as fast as humanly freaking possible, right? Because that's what makes our clients happy. And the way you do that is through videos, which I think are probably the most engaging thing to you can argue. You can argue, read if your subtitles are probably watch, right? Not a lot of people enjoy reading nowadays. Reading is sucks to say a thing of the past, but videos are everything. So you're capturing that, that demand. Now what I really want to say is, is in the videos that you make, it's not about what the company wants to say. You have to put the audience first, right?

Like not to sound like an asshole, but no one gives an F about what you miss your business owner wants to say care about what the audience, but your potential customers want to hear. Now, when you do that, when you put the audience first, the, the probability of them consuming the content goes up significantly. In addition, I'm sure, I'm sure, know, like a VsL is right. A video sales letter. You, you, you, I know what you are creating probably isn't exactly like that, but

Tim Bradley:17:07
Yes.

Tim Bradley:17:15
Excellent.

Tim Bradley:17:20
Mm-hmm.

17:28 · Turning repeat sales objections into video assets

Jordan:17:28
You said if the prospects are asking the same questions over and over again, if the salespeople are repeating themselves all the time, if you're getting all of these objections at the end of the conversation, then let's create a video asset and send that to the prospect beforehand. So it's just so it saves our salespeople time, right? And there's another way to compress time.

Tim Bradley:17:43
Yes.

Tim Bradley:17:49
Jeffy Zierer.

I'm super glad you brought that up because that is like one of the most clear signals to create is like when you find yourself saying the same thing over and over again, it's like, this is that moment to take pause and to craft a script and a video to like support that moment, right? And like, basically like expose that that sort of bottleneck in that way, right? And like, release it and then yeah, you're off you're off to the races. That's awesome.

Jordan:18:01
Absolutely.

Jordan:18:19
Question do you I guess have you niche down on the style of videos or like the numbers of the number of videos that you produce on behalf of your clients or if you feel like you know there's an asset you can create for this specific situation you will suggest that and they will pay you for that video

Tim Bradley:18:38
Yeah, it's predominantly the former, right? So that like trifecta that I just described, like those Anthem videos, explainer videos, endorsement videos, like that is so pure mid funnel, right? It's like this type of work, cause it's not advertising and it's not sort of like thought leadership, drum beat, employer branding, event coverage type of work, right? Like that's sort of more like you've already made the sale at that point, right? So this like mid funnel is, so pure to those types of work, right? Like, speaking to the heart, speaking to the minds, like, doing that sort of helping, you know, prospects with their gut check is the way I like to describe it right with that that trifecta. So yeah, for us at Pennant, it's just like, we love existing there because we know this work is is, is working really hard to build trust in this moment. And it's going to have a pure like impact on the work versus awareness and advertising that's like, sort of like vibes and feels, you know what I mean? So yeah, and to that end, though, it's like, I've been in this game for 20 plus years. And so it's like, I know and can help advise what is the best right tool based on the moment, like that inflection point or that hurdle or goal or bottleneck that exists in this moment, right? Because we've produced all sorts of stuff, the episodic series of things, the commercials and everything in between. But our niche and focus on mid funnel is just like, know the work works and that's what's important to us.

20:13 · Client retention through proactive leadership

Jordan:20:13
Absolutely. Yeah, if you know where it's why I kind of deteriorate not to be able to like detour off that path Kind of want to jump topics here when it comes to client retention and keeping clients happy What do you feel like has been the key indicator of success? For that because I know you know the longer you can retain clients obviously still providing value the more enterprise value you have the more profitability the company has so you have any tips tricks pointers on on that what you guys do in terms

Tim Bradley:20:19
Yeah. Yep.

Tim Bradley:20:25
Mm-hmm.

Tim Bradley:20:44
Yeah, a lot of it just being as proactive as possible and not in like, Hey, do you need this type of way? But more like recognizing the patterns that are annual, you know, there's like the annual cycles, like, you know, there's going to be a sales kickoff, you know, there's some semblance of a customer event, you know, that there's two or three, like flagship events that they're hosting. There's trade shows, you know, there's hiring cycles, like, you know, if you, if ideally you're, you have align into the product marketing team and have a sense of like what products are rolling out throughout the year and those often align with these these key key moments in the calendar right so the pro activity is a huge thing because it shows that you care because you do because you want to be in lockstep with what ongoing are happening over there but you also start to like be a bit more immersed in their ecosystem of like okay I see that they're their competition is showing up in this way here. see that this, this challenger brand is doing this over here. And so you can be sort of like on the, not like in the front lines, but like a big sort of advocate for that brand too, like a champion in that way for that brand and show them like, this is, this is what we're seeing in the ecosystem. Right now. It's not like the, we're trying to, you know, we're not

Jordan:22:00
Please stand by.

Tim Bradley:22:05
I hate to use like the fishing analogy, but it's kind of like, cool, we're casting lines for all these moments, we're not expecting to get a hit or to get a bite every single time. like, when we do, there's no sort of like, you know, we don't have to sell anything, we're just like, we're already aligned and like the moment and what this matters. And so it's like, sure, arrive at the scope based on the guardrails of time, budget and resources. But like, it doesn't, it doesn't, it's not like a big like mental lift or load to like, re onboard the team in this way, we're just sort of part of their another cog in their sort of like overall system, which is awesome, you know, and that's, when we look back, you know, we're now at the end of q1. So it's like, that's a pretty clear reflection moment. like, annually, just annually, just looking back, like, great, like, did our that our project, sort of margins increase time over time, did we grow this client in the percentages we'd hoped to write like, Did we let go of other clients or just not work with other clients and is that fine? Cause like it's, it's pointing us better in the direction where we aspire to go. So it's a mixed bag of that, like proactivity in being, you know, sort of in the same footsteps or lockstep with the clients that we have, but also like the reflection for ourselves and be like, does this align with like our sense of purpose and, and, and, and process and margin and all of that from a business standpoint.

Jordan:23:30
Yeah, I think taking a proactive leadership stance when it comes to client success is vitally important. You don't want to be a leader or reactive CSM. You definitely want to know, anticipate what the problems are going to be for this specific client. And before they reach out to you saying, hey, XYZ is going on.

Tim Bradley:23:38
you

Jordan:23:53
as the CSM, Client Success Manager, you would want to say, hey, I noticed XYZ is happening and we're taking ABC steps to solve this specific problem. I think from a client's perspective, it's like, damn, Pennant is taking care of business. I like that. And for whatever reason, from my experience personally, the problem could be the exact same, right? Problem X and problem X, same problem, okay? But.

If the client has to reach out and confront the team, the company about this problem, they're to be pissed. And I have found that again, with the same problem, if I take a proactive leadership response or the team does, and they reach out before the client says anything, it's almost as if their anger or their unhappiness, their displeasiveness is like subsided or not as strong because we are already on top of it. And I think that alone, that proactive leadership, as you were saying, It does wonders for the team.

Tim Bradley:24:52
Absolutely. Yeah, it's kind of like.

I don't know. It's like that mental load. You know what I mean? It's like, we can take a little bit of the mental load off and just being proactive, man. It's just like, it does wonders for everybody, you know? And like similarly, or adversely rather is like, if a client's come to the table with this like need for video in this moment, it's usually almost too little too late, right? Like, so we have a newer client that we haven't really had a full calendar year with. They have their flagship event happening. like today actually, but they came to us like less than two weeks ago and like, Hey, we need a, we need a hot start video for our event. And you're like your event, you, you know, this happens every year. Why are you coming to us with less than two weeks to like pull this off? You know, we should have taught us started talking two or three months ago. So it's like the, that proactivity like has a sort of like secondary or like tertiary impact of just like education, just like educating the client on like how long it takes to like thoughtfully and effectively produce whatever it is we're producing and doesn't feel rushed or, know, we took too many shortcuts or something to get there, you know, so it is helpful in that way. Right. I also find in the productivity, like you just get to understand that the individual that you're working with so much more. So it's less like brand or logo that has their their overall goals and mission, etc. It's like the individual marketer that we're working with in this case, right, you get to like, you have such a rapport with them, you start to understand like their individual pain and or their individual like, where they aspire to go as a professional, you know, and it's like, all right, now, how can we help? How can we be a champion of this person beyond just the brand, right? And like that person becomes a two way street of

Tim Bradley:26:45
of advocacy, right? They are advocating for Pennant and the work that we're doing. And we're advocating for them because we want them to succeed in their role too, because it's clear that they care about what they do. yeah, it's man, productivity, man. It's super powerful. It can just be hard when you're like, only have so much time.

27:02 · Scaling the team, creative vs operations

Jordan:27:02
Thank Absolutely. In regards to like leadership, right? Because it sounds like you have a couple of employees that are on full time. How has that transition been for you when it comes to being a solopreneur just starting the company? I know you have a co founder, but so it's being you know, just you two to now having like a full staff, a full team where you kind of delegate more than you act, if that kind of makes sense.

Tim Bradley:27:15
Mm-hmm.

Tim Bradley:27:32
Yeah, yeah. Yeah, I mean, a lot of it's just like being really concerted in your decision making, right? Where it's like, you know, I knew that I was going to be flying pretty much solo for the first year. You know, I was like, this is how it's going to be. They're just like, how can I be successful with the couple hands that I have? then it was like, I know my first two hires have to be really senior and creatives and.

Tim Bradley:28:04
And then it's like, okay, grow in the creative front, eventually we have to grow in the operations front. So the analogy I've been using recently is like a ladder, right? If you're like climbing a ladder, it's scary or unsafe to try to climb both rungs with both hands at the same time. need to have, structure and like balance. like one hand at a time, one hand, like one rung over the other. So for me, that's creative and operations. And so how can we climb those two rungs? How can we climb with both hands like thoughtfully, which is where we are. So yeah, we're, actually hiring another motion designer right now. And next up will be that account director person to help us like build depth with the clients that we have. build that retention that we just talked about,

Jordan:28:57
For sure, for sure. Do you feel like it's more important to have a stronger foundation for operations opposed to like the team that guess produces the work? Like what's the...

Tim Bradley:29:08
Yeah, I mean, I, I do. Only because like the operators tend to be really aligned with the client and like the relationship and like making sure that every sort of like decision day over day is like on behalf of building trust of that that client, right? Whereas creative like really, really concerned so much care in the craft, you know what I mean? So it's like, it's I don't know.

That's really good question. I love this one because it's like the the craft is obviously super important and it is like kind of the table stakes, right? So it has to be sound and really good. But for us, like we can work with the right creative for the moment, right? Like, okay, we need this specific director of photography to capture this style that we want. That's really important to this brand and how we portray that. Or we need to work with this specific 2d motion designer or this 3d motion designer because it's the the work needs it, right? So they go hand in hand, of course, and it's all like sort of, they just go hand in hand. So the operator, though, just like working on behalf of trust and retention and all of that, I think just is what builds a business at the end of the day.

Jordan:30:34
It's almost like what came first, the chicken or the egg, you know? It's like, yeah, it's like, they're both really important, you know?

Tim Bradley:30:37
Totally.

Yeah. Yeah. You saw my hesitation. Like, man, I hope this is like coming out right. Cause it is like you obviously need both. That's why it's called creative process. Right. You can't have one without the other, but I think to answer your question and just like operator assures that the business is staying sound. And that's, that's the goal. Right.

Jordan:30:59
Absolutely, and if I can articulate it this way, it's almost like building a house, a foundation of sand, if the operations of the freaking business are not in place or order. Because I am pretty aggressive when it comes to growing the company. At least, I'm still aggressive. I was way more aggressive in the past where operations were just not in check. But I'm like, I think I'm more clients, I got more clients, know? And that shit did not work out well. But.

Tim Bradley:31:09
Yeah.

Tim Bradley:31:25
Love it.

Jordan:31:26
It's like get the foundation in place first, get the foundation in place, then scale, then the foundation, and then scale.

Tim Bradley:31:33
Yeah, that's all right. Build one floor at a time type of thing. Yeah.

Jordan:31:36
Exactly. Let's see, kind of going over to, um, to Legion for you and the company, you actually got pretty excited whenever you and I first spoke about this, but can you please explain how you guys generate clients for, for Pennant and why it works so

Tim Bradley:31:53
Yeah, so I have this maybe kind of silly like metaphor of a of a sailboat. OK, so the wind in your sails is that inbound, right? So and I'll get into that. But it's like the mechanics of your inbound. But it is still wind, right? Like you you can't really control it. Sometimes it can be like gusting super forceful. You're you're flying right. Other times it's there's nothing. And so it's just flat and calm and still and that's part of that's part of your your operations. And then the other that you're outbound is your rudder, right? It's like pointing you in the direction that you're trying to go as a business owner, right? And so, of course, they go hand in hand a lot of time. It's just like, how can you assure you have the right attention to each so that the sailboat has like a proper and predict more predictive sort of like cruising speed, you know what I mean? So for us, really started with inbound functionally. was just like, I need to be visible, we need to be visible, my teammates need to be visible. We just like, we have to show up in the places, which for us are primarily LinkedIn and a few communities, online communities, and in-person communities too, like showing up with enough like regularity there with like, thoughtful attention to what's happening in the sort of like current state of things, the ecosystem, sharing behind the scenes, sharing process, sharing wins, sharing anecdotes from conversations we have with prospects and clients, like just being very thoughtful in the way we show up and are being visible in that way. And that's been huge for us. It's like that's most of the work that those first couple of years is because we just like showed up. and just made an impression in that way. Now that we're like, we have a body of work, we have a deep portfolio, we have an impressive roster of clients, we have our new website that's coming out next week, hopefully. Now all of this is like quivers to attack the outbound of where we want to go. And so a lot of that is in the systems, the systems of being a

33:04 · The sailboat analogy for inbound and outbound

Tim Bradley:34:17
thoughtful to my time and the time blocking and like showing up for current clients showing up for perspective clients, targeting and making lists and like being proactive and sales navigator and just sort of all the places and like understanding the work that we have in the background, like fortunately, we're creative. So we have so much like client work to show off, we have our own like reels and and pieces of work that support the sales sort of mechanics that we have the business development mechanics we have in place, right. So just that system is like, you have to be so attentive to it, you have to put gas in it and oil in it whatever like that engine to like make it work. And a lot of that it's just like, like holding guard to your time, you know, and being really deliberate to like how you show up and put that energy into it each day. And being reflective to and like making sure that like, cool, these winds that we're getting are they are they is this rudder pointing us in the right direction back to the boat analogy, right? Our sailboat analogy. So, yeah.

Jordan:35:23
I feel like the more aggressive you are with outbound and whenever you accumulate revenue that way, and obviously profitability, it allows you to scale up inbound because for sure inbound is going to have warmer leads. They raise their hand, you know, they're coming inbound to your company opposed to outbound. That said, I freaking love outbound. It's really, really cheap to do. I feel like I'm kind of pulling money out of thin air in a way.

Tim Bradley:35:48
Yeah, no, speaking of magicians, right? Yeah.

Jordan:35:51
So that is a great analogy when it comes to inbound do you are you spending any? advertising dollars on Facebook Instagram YouTube

Tim Bradley:36:02
not currently. We're, we're in talks of actually advertising on a podcast, because it's like very specific to the B2B SaaS. I just think that's like, the closer you can get to the buyer decision maker, right? The better. So yeah, I mean, that's just it. It's like everything to date has been sort of like homegrown in that way. So I, like our visibility strategy is like part of our

Jordan:36:08
sure.

Tim Bradley:36:30
sort of whole system and hiring process and things like that. It's not necessarily an expectation, but we want to empower our people to show up and have a point of view and express themselves through the channels that we're on. Because it's that gentle reminder that these are human beings working very thoughtfully and carefully on behalf of the creative work that we're producing for our brands, our brand partners.

Like that is like a habit type of thing. Whereas outbound is also a habit, but it's like a habit that like I own more so than the team. So I think it's like that balance, right? Of like, well, inbound can be shared by a lot of voices that are inside of our four walls. Whereas outbound, you need that kind of leader that's like really taking aim and like sort of attacking the places you aspire to be directionally in a leadership way.

37:27 · Tim's outbound system for B2B

Jordan:37:27
No, for sure. Do you mind giving us an overview of your outbound strategy and why it works so well?

Tim Bradley:37:33
Yeah, so it's, lot of it is like looking really thoughtfully at the clients that we have, right? So it's like, okay, we have this point of contact, we're building a rapport there. How can we like almost immediately get it like paint the picture of their, their environment, right? So lot of that is like, detective work, frankly, right? So it's like asking pointed questions, like what's your team makeup? Like, who do you report to sort of like one on one stuff in the conversation, but it's great because then you can use that to leverage.

LinkedIn, sales navigator, the org Apollo, like whatever that is to like really start making connections and like painting this sort of like diagram of the org chart. I'm like, okay, great. Let's say we're working with product marketing. Let's get the couple reps under our belt and, and, and, and, in the work, you know, like make sure the work is working and it's successful. But then once you use that to like, make the warm introduction to customer marketing or make the warm introduction to head of marketing, right? And to start like building that rapport inside the four walls. like that's like, as constructive a way as we can do it, like with work that is being produced. But then we also have like, you know, the sort of industry segments, right? And a lot of those, we, we relate more to like sense of values, right? So safety, security, sustainability. Those are the appropriate catch-alls for cyber security, health care, and life sciences, and med tech, and energy, and climate tech. So it's because we're really ingrained in those works, or those industries, and produce work for those industries, we can build individual sizzle reels to things. We can tell really specific stories and show up to those doorsteps via DM. the exit five is a B2B community that I'm a part of. Showing very thoughtfully in those ways and just making those introductions like, we exist over here. We do not expect you to buy from us today. We just want you to be aware that we're here and this is how we often support our clients. If you want any more information, let's connect. So it's a very thoughtful approach, but targeted to.

Tim Bradley:39:50
per the ICPs, per the industry sets, per the work that we're producing. So it creates this really healthy flywheel for us where, great, we have a new client project that's going live. We've already thought about how are we going to share that on one-on-one basis with prospective clients or people that we're nursing along in our own buyer's journey sort of way. You know what I mean? Does this answer your question?

Jordan:40:15
for sure. It does, but let me ask you a more specific question. And if I'm wrong, we can just edit this out. But didn't you tell me on our first initial call that you utilize cold email and you send like a custom video as a lead magnet saying, this is what we can do for XYZ company or for your company? Do you do that?

Tim Bradley:40:19
Yeah, let's do it.

Tim Bradley:40:36
We, you might want to cut this out. So we did do that. or like the beginning of our business, but I, I, I want to caveat that because it like, I have learned or I did learn that it was like, yeah, we, we did, we did that. So it like, we did cold email. We did a video, you know, it was like hosted on loom basically, right. To like show a bit about what we had going on.

Jordan:40:39
You

Tim Bradley:41:03
I think the maturity of our business at that time, it just wasn't the best right time to deploy that as a tactic. Because there wasn't much depth there. our website, it actually still is kind of the current website, only had a couple examples of work. So there just wasn't enough opportunity for follow up and storytelling and case studies and testimonials and all of that. So now, I think it'd be a bit more interesting because we have several more years under our.

I think there is a time and place for it. would just caution like doing it too, like deploying it too early might be like, might not be your best advantage. But just my own experience. know what I mean?

Jordan:41:49
for okay. Well, thank you for that. We can cut that part out. I thought it was bad, but I think I was just a little confused and I was like, yeah, my mistake, my mistake. But you, Tim, you said something pretty interesting.

Tim Bradley:41:52
You

42:07 · Advertising on B2B podcasts

Jordan:42:07
Tim, you said something pretty interesting. You said that you wanted to advertise on podcasts and I'm assuming that the channel, the podcast, their audience are B2B tech companies, B2B SaaS companies, right? That is such a fricking good strategy. Who, if you don't mind, who, I guess I can look this up, like which podcast did you have in mind specifically to advertise on?

Tim Bradley:42:31
Yeah, yeah, that's this one called the notorious B2B. So it's a very like sort of playful, news oriented show. So it's very like of the times, like these are the trends that are happening in B2B marketing, right? And it's co-hosted by two people that are very entertaining, right? And so what I like about it is that it aligns with our sort of brand, the perception we want our brand to have that it's like, we take ourselves seriously, but like, not too seriously, you know what I mean? And because it's such a recurring show, like timely show, that the listeners are really on the front lines of sort of like marketing and communications in this way. And they're all largely B2B SaaS people, you know what I mean? So it's like the work we most squarely do. So yeah, that's probably our second half of the year experiment in a way, right? It's like, see how that performs for us. we call.

Jordan:43:31
I think it will be pretty cool because I have another podcast. It's called the Ecom Growth Podcast where I sit down with like Ecom operators. There's this guy. Do you know the name Sheath Underwear?

It's okay if you don't. story short, he makes underwear and obviously, right, cheap underwear. And he does not advertise on like Meta or Google, but he pays a pretty decent amount for advertising segments on long form podcasts on YouTube, Apple, Spotify, et cetera.

And he says that crushes because the listeners are his exact demographic, his exact ICP, like men who like fitness, who probably want this style of underwear, you know. And if you're advertising on a platform where like everyone is a B2B operator or a B2B listener, like that is the exact podcast for I'm going to put my advertising dollars behind. So genius idea. And I just want to hype you up and say, probably going to work. It's probably going to work.

Tim Bradley:44:31
Exactly.

Yeah, I appreciate it. Yeah, it's, I think it's going to be worth it. And then we do other things too. Like we're, we're in talks of doing like a, well, too much backdrop. Like we, we have access to a cinema robot. So like one of those like really cool, like robot arms with a camera on the end of it. Right. So we use it for client projects a lot, but we're like, Oh, well, why don't we show up to this annual B2B event? that I've attended at, well, I've just been like an attendee before. I'm like, well, let's talk to the organizers there and we can set up a glam bot, right? So we can run, you know, sort of the classic like red carpet look type of thing, like slow motion shot of the individual attendees. And I think it'll be really impressive. Like not only just sort of like take away from an experience standpoint, right? Like that, that these, these, the event itself would have like, really cool visuals to support their marketing and the individual marketers that were there have like a cool piece for their own social channels. And I'll have like this little bit of a spark of a moment. But for us it's like, well, we can all, that's really beneficial for us. Cause we can just hand out business cards right then. And like explain what we do on a one-to-one basis to these like really targeted sets, you know? So yeah, we're just trying to like think about the experience of things that like, these marketers have with our brand, right? Beyond just like LinkedIn all the time, you know? So I think that's going to be really cool for our back half of the year, the way we experiment in that way.

46:11 · Advice to his younger self

Jordan:46:11
No, for sure. Last question for you, Tim. Looking back over your career, what is one thing that you want teach else in your shoes or maybe even your younger self on how to get to where you are faster?

Tim Bradley:46:26
Faster.

I think some of it is there are a lot of opportunities for inputs. There's a lot of people in your network. There's a lot of mentors. There's a lot of coaches. There's a lot of consultants. There's a lot of people on the internet. know what I mean? Every once in a you just got to turn a lot of that off and just go heads down and really build. I think it's easy to just be like, I just don't know yet. I just got it. I need to, I need more information. need more information. I need more information. You haven't like committed to yourself. You haven't just committed to the thing that you know in your heart and you're like in your heart of hearts can be possible because you haven't like done it, you know? So I'm like, for example, I'm like, funny enough, I'm sort of advising, another creative who's turned entrepreneur and he's like really focused on like building his website and like building all these materials and things. And it's like, well, that is important, you actually need to just start selling, you just need to go and sell like right now, just just go through the motions of that pain. you're, you're not, you know, you just have to figure out how you just how you your posture, like how you talk about yourself, how you talk about the business, how you talk about the value propositions that are allied to what it is you're doing. if you don't get those reps, if you don't go heads down and get those reps in, you're just you're just guessing, you know, you're just like throwing spaghetti at the wall with like the things you're creating. So Yeah, less inputs, more deliberate heads down output for yourself, think, will go a long way. Yeah.

Jordan:48:05
I cannot agree more, my friend. When you're just joining the entrepreneur journey, like sales reps, marketing reps, fail as fast as you can. Just get those hardheads hitting reps in. No offense to anyone out there, but the website is not the most important thing. When you're just starting, you know?

Tim Bradley:48:14
Yes.

Tim Bradley:48:21
No, not at all.

Yep, exactly. Yeah, yeah, I love it.

Jordan:48:27
Tim, you're the freaking man. It was such a pleasure having you on the show, bro. Safe travels to Salt Lake City and in Park City. So, winning with the bros. Yeah, for sure. Sounds like fun. Audience, we love you guys. We'll talk to you soon.

Tim Bradley:48:34
Thanks, I'll wave to you.


Questions This Episode Answers

What is the Trifecta Framework for B2B video marketing?
It is a three-part structure built around differentiation, demonstration, and validation. An anthem video expresses why a brand exists and how it is different. An explainer video covers what the product does and how it works. An endorsement video uses customer stories to validate what the brand claims. Together they are designed to answer the most common buyer questions without requiring a salesperson to repeat them.
How does mid-funnel video compress a long B2B sales cycle?
Bradley's argument is that buyers move through a sequence of gates before they are ready to purchase, and skipping gates is nearly impossible. Mid-funnel video answers the questions buyers have at each gate before a salesperson ever speaks to them. When prospects arrive having already seen the anthem, explainer, and endorsement content, there is less convincing left to do.
How does Pennant Video Co. retain clients long term?
The main method is proactive outreach tied to a client's annual calendar. Bradley looks ahead to sales kickoffs, trade shows, product launches, and customer events and brings proposals before the client asks. He also monitors the competitive ecosystem and surfaces observations unprompted, positioning Pennant as a champion of the brand rather than a vendor waiting for a brief.
What outbound strategy does a video agency use to grow inside existing accounts?
Bradley asks pointed questions early in a client relationship to understand the org chart, then uses tools like LinkedIn and Sales Navigator to map the people around his existing contact. Once the work is producing results with one team, he uses that as the basis for a warm introduction to adjacent teams such as customer marketing or the broader marketing leadership.
Should a new agency focus on creative talent or operations first?
Bradley describes it as a ladder where you can only safely move one hand at a time. He hired senior creatives first and built the operational layer afterward. His current view is that operators are what ultimately keep a business sound because they are the ones maintaining client trust and relationships day to day, even though the creative work is what gets the clients in the door.

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