
27 Jul 2026 · 1h 13m · 34 chapters
How AI is changing SaaS and sales execution, especially “build vs buy,” pricing/seat models, centralizing AI via RevOps, and using AI for coaching/roleplay and pipeline generation (pipe gen) including outbound phone strategy.
John Attell is Chief Growth Officer/CRO at Orum. He previously served as CRO/Chief Revenue roles at Demandbase, Canva, WP Engine, Spiceworks, and Rackspace. He has 20+ years in revenue/sales leadership across enterprise SaaS, PLG, and cloud sales. Host Jason Bay is CEO of Outbound Squad.
Written by AI. May contain mistakes.
Discussion on the implications of the build versus buy decision in AI for SaaS companies.
“Talking to a prospective buyer that we're looking to hopefully bring on board here soon about not just build versus buy with AI.”
Jason discusses his experiences working with various sales teams and partnerships with Orem.
“So I was in Austin a couple weeks ago, did a whole big batch of interviews and got to meet a bunch of people in person.”
Jason shares an opportunity for listeners to access a free outbound masterclass designed to enhance sales skills.
“I got two things to give you before we get to the interview.”
Jason shares an opportunity for listeners to access a free outbound masterclass designed to enhance sales skills.
“The goal with that is we just want to get that into as many hands as possible if you're a rep.”
John shares his unconventional path into sales, emphasizing autonomy and the lack of a predetermined path.
“Was that the case for you or how did you get into sales?”
An exploration of what it means to be a Chief Revenue Officer and the unique challenges in that role.
“And they were willing to commit to the grind and do the do the work.”
John discusses current challenges and trends he's observed in sales organizations, particularly regarding AI.
“So let's get into some of the fun stuff that we were just talking about.”
Discussing the difficulties of maintaining software and the importance of building workflows.
“And, you know, it usually fails because, like, people don't want to upkeep the software.”
Exploring the concept of headless systems in sales tech stacks and their future.
“Because if you think about, as you were sharing that, I was thinking about the sales tech stack right now.”
Analyzing the challenges of sales tool adoption and the shift in management culture.
“glue that can bring the pieces together here, you know?”
Discussing the changing role of RevOps and its evolution in the context of AI.
“And that, you know, we also bought these tools, kind of put them out there and said, Hey, we recommend you use this for that.”
The trend towards centralizing AI applications within sales organizations.
“So many areas that I want to talk about.”
Sharing insights and lessons learned from implementing AI tools at Orem.
“But we, you know, we recently, you know, rolled out Claude to the entire company.”
Strategies for reducing complexity in sales processes through AI tools.
“And that way also when new hires come on board, you're not hoping that a year later they catch up to this top rep, right?”
Explore how organizations can simplify outbound processes for sales reps.
“They don't just live in silos or pockets there.”
Discuss the limitations of AI in addressing fundamental sales challenges.
“One thing I wanted to ask you, though, is like, dude, one thing I'm super bullish on is there's a Derek Sivers quote that says, if information were the answer, everyone would be a billionaire with six-pack apps.”
Learn about the concept of the 10X seller and how to leverage their skills.
“You know, I think we need to, and that's why, you know, some of these checkpoints and some of these, you know, kind of comments around like, how do we standardize at certain, you know, areas here?”
Understand how AI tools can enhance training and support for sales reps.
“And so, you know, unfortunately, leaders, you know, have really big spans of control right now.”
A shift in focus on pipeline generation and its implications for sales.
“I love that it's creating a coaching culture.”
Explore how to effectively balance inbound and outbound sales efforts.
“I'm curious for you, How as a CRO do you think of and have you thought of like the pipe gen pie chart?”
Explore the optimal mix of outbound and inbound sales strategies for effective prospecting.
“That's where I start to think like, you know, 60, 40, you know, kind of 50, 50 starts to make more sense.”
Learn how organizations can structure their approach to pipeline generation at different levels.
“you know, how you guys sort of drink your own champagne, eat your own cooking, like that sort of stuff.”
Discover the significance of dedicated prospecting time and team accountability in sales.
“I think if you don't focus on it and block it, it'll always get deprioritized by other things that come up.”
Understand the importance of in-person events and innovative strategies in sales outreach.
“I mean, I think, you know, obviously, you know, the, I would say moments of connection and in-person are resonating.”
Learn how to create engaging events that resonate with executives in the sales community.
“Can I ask you related to this, just as a senior exec yourself, what makes you want to participate in certain things?”
Learn how thoughtful seating can enhance interactions at events.
“you know, really put a lot of thoughtfulness into like, table arrangements and who sits by each other.”
Explore the evolving perceptions and strategies for cold calling.
“So I want to, we got to talk about the phone.”
Understand the challenges faced in outbound sales and the shift in strategies.
“Dialing strategy is like lost on a lot of folks, right?”
Discover the proper use of dialers and common misconceptions surrounding them.
“of cells, you know, and being able to understand where they are and how to get a hold of them there.”
Learn how to enhance conversation quality and call effectiveness with technology.
“You know, I think that, you know, my story of joining Orem, you know, was for all those reasons, but I think like AI got more, you know, you know, prominent and, and people kept overusing email and LinkedIn.”
Gain insights on overcoming call screeners and making impactful connections.
“And so I think you're going to the conversation with everything you need to have a great conversation.”
Understand the significance of touch points in establishing customer connections.
“And so it's a good way to, you know, kind of find yourself in a conversation.”
Learn how to effectively decompress and protect personal time after a busy workday.
“And look, it took me a while to figure it out.”
Find out how to learn more about Orem and opportunities within the company.
“Before we take off, where can people go to connect with you, learn more about Orem?”

Get the gist, explore an idea or ask about something said.
On Outbound Squad, what are the key points of this episode?
Automatic transcript. May contain errors.
0:00Talking to a prospective buyer that we're looking to hopefully bring on board here soon about not just build versus buy with AI. That's a really big thing right now, right? In software, what we haven't really had to deal with to this extent is the build versus buy question where, hey, we could vibe code something like extremely fast, not just build it in-house. We could do it way faster with fewer resources. Well, they're dealing with some of the downstream effects of that. It's not only build versus buy. It's, hey, we happen to sell a solution that helps with security for product teams and for developers.
0:41And if we have this environment right now where they're being told and experiencing efficiency gains where they can have 20, 30, 40, 50 % less headcount and we have per seat. We sell seats instead of usage. That kind of screws us. That screws the entire business model up. And these are some of the really big things happening in SaaS right now that I don't know if anyone has like the answer to, but you can see a lot of the teams shifting their pricing models and we're dealing with all kinds of different objections. And that really affects outbound because that affects whether people are going to take meetings to even talk about our solution.
1:20So I'm really excited to dig into this today with chief growth officer at Orem, John Attell. Before we get to that and the topics, thanks for checking out Outbound Squad. My name is Jason Bay. I'm the CEO at Outbound Squad. We've worked with some really great sales teams, 250 plus of them in the last five or six years, folks like Shopify, Zoom, Rippling, Gong, and a ton more. And we've also worked with a lot of startups as well. So think of like your series A, series B, building out your first BDR team, maybe pivoting the organization to be more outbound centric. And that's what we talk about on this show.
1:55sales sourced or BDR sourced pipeline and all of the different ways that you can do that. So if you got a BDR team or an SDR team doing a bunch of cold outreach, or maybe they're reaching out into the customer base to expand, you're in a good place. If you have AEs that you want to do more self sourcing, or maybe you're moving that market and being more enterprise and you need to break into those accounts, you're definitely in the right place. So I was in Austin a couple weeks ago, did a whole big batch of interviews and got to meet a bunch of people in person. John was one of the people I got to meet.
2:27We've been really working on our partnership with Orem because of the dialer. There is a significant decrease in pickup rates with cold calling and it just goes down every single year. Orem has done some really good things around just their dialer and there's obviously the parallel dialing capabilities, but just their hot numbers. We work with a lot of the same clients, and there's sort of a peanut butter and jelly sandwich kind of thing going on. So I was really looking forward to getting to meet with John in person to really foster that partnership a bit. Anyways, John has been a previous CRO at a ton of companies.
3:09His thing is building out sales teams and scaling out, whether it be partner, scaling out the enterprise motion, whatever it might be. but he was previously CRO at our chief revenue officer at Demandbase. He was at Canva, WP Engine, Spiceworks, Rackspace. His freaking resume is insane. But we talked about build versus buy. We talked about the centralization of AI. Instead of getting cloud accounts for everyone on our sales team, we're centralizing that and thinking about it from a rev ops standpoint. We talked about pricing, the skill conversation. Reps still need skills in order to execute this stuff.
3:51We talked about pipe gen and how he thinks about that. We talked about different kind of pipe gen plays and stuff that they're doing to generate pipeline, like going on the road and meeting with people in person. We talked about current and future state of the phone, state of SaaS, all kinds of really great things. John was a really good interview. I think you're going to really enjoy this one. I got two things to give you before we get to the interview. One is free. We just came out with our outbound masterclass a few months ago. I sat in a studio for six hours and we walked away with around three hours of content and it is our very best stuff.
4:26And it's all of the tactical things that you as a rep or if you leading a team of reps would need to do to find and prioritize their accounts, knowing what offers to leverage, how to use the phone, email, social, et cetera, to secure that first meeting and build pipeline. That's an outbound squad.com slash masterclass. Again, it's free outbound squad.com slash masterclass. The goal with that is we just want to get that into as many hands as possible if you're a rep. So if you're an SDR, AE account manager, maybe going into existing business, you're going to find a ton of value from there. And then lastly, if you listen to this podcast or you've been a listener and you're like, you know what?
5:02it's like time for us to really develop our outbound shops and create more systemization and scale around this. And we want to implement a lot of these things. I would love to talk to you. Jason at outbound squad.com. Just shoot me an email. I'd love to talk to you about how we've helped some really cool companies like Shopify, Zoom, Rippling Gong, either build out their outbound programs or scale their outbound programs. And really the number one result that we deliver and promise is a 20 % or more increase in qualified pipeline built within 90 days. So we build the system and the playbooks. We train your team on it.
5:39We work with your managers. We work with your enablement team. And we just give you the latest and greatest stuff that you can run with from an outbound pipe gen standpoint. Cool. That's all I got for you. Let's get to the interview.
5:59I have to ask you, because most people get into sales on accident. Yeah. Was that the case for you or how did you get into sales? Bring us back to John back in the day. Yeah, that's so funny. This is actually like one of my favorite things to talk about. And so, yeah, I didn't realize we'd have this in common here. I have a running joke that sales is a profession that chooses you. You don't choose it. which is my way of saying, you know, usually people don't, you know, kind of start with this end in mind. They have a different path. And so, yeah, a little unknown fact about me. I went to school at UT Austin, studied biology.
6:36I was supposed to be a doctor. So, you know, look at me now. You kind of have the doctor look. If I saw you at the doctor's office, I'd be like, okay, cool, I trust this guy. Good, good. Bedside manner, hopefully, you know, translates there. But no, I mean, I, you know, I was good at math and sciences, you know, you know, my family didn't come from, you know, they were they were small business entrepreneurs. So, you know, you know, didn't really have a path to follow that was like predetermined. And so it just seemed like the right answer for me. And I got into it in four years into my, you know, kind of career of, you know, studying biology.
7:07I was like, I don't really like hospitals and like this is just, you know, not my my jam. And so it was interesting. You know, I was so far along in the degree. I was like, I got to finish it. you know, but I kind of knew like, this isn't what I want to do. And if you have a biology degree, you go into like a lab, you go into, you know, all these other things that I was like, even less probably my interest. And so it was interesting. I, you know, worked in the hospitals and did internships and things like that. I also waited tables and bartended. And so I think like some of the things that informed my decision was like, I'd work nine to five, you know, Monday through Friday in a hospital and I would get X at the end of the week.
7:45And I, you know, would work on the lake here in Austin, you know, and I'd pull a double and, you know, work the weekends, you know, Friday and Saturday. And I could make like, you know, 10x what I could make in that week. And so I was like, I really want a job that doesn't fix my income, you know, to the hours that I work. Like, I really want something that aligns to like the quality of work I put in and the amount of energy and effort I put into it. And so, you know, those were kind of like some of the deciding points that led me down the sales path. I also came out of school right at the like height of the dot-com bubble, not knowing it was a bubble at the time.
8:15And so, you know, it was pretty easy for me to say, like, I think I want to go chase this, you know, gold rush that's tech and I want to get into sales. And so, you know, I think also something that I've seen is I've, you know, hired and, you know, managed and developed a lot of high performers. You know, there's a lot of things that kind of make us, you know, the, you know, folks that are successful in this profession, you know, who they are. And I think some of it ties back to that story and that I didn't have a fallback plan. Like I was like, you know, soon to be engaged, had a long-term girlfriend.
8:43You know, I was like, gosh, I like have this life I want to live. And, you know, the path I was on isn't the right path. So like I'm going all in on this sales thing. And there was no there was like a burn the boats moment. It was like there's no fallback plan anymore. And this has to work. Right. And so, you know, I think sometimes as I talk to a lot of high performers, like they had that same kind of motivation and chip on their shoulder of like I went down a path, you know, for a different profession. And I made this pivot. It means I made less money, but but it had to work. Right. And they were willing to commit to the grind and do the do the work.
9:13work, right? And, you know, so I think that was, you know, an element of my story that I, you know, love to like look for seeing others, people that like, you know, see this as something they're all in on and they're committed to just for that reason. Yeah. And it sounds like a big part of you for you too, is the autonomy that you get in sales is so much different from a nine to five or any other kind of hourly or even in most salary jobs too, where it's so performance oriented, where it's like, that's the most important thing. We're not going to, outside of you working a really high transactional, you know, high volume kind of thing, we're not going to really micromanage, you know, and all if you're hitting your number.
9:52My other question before we dig in, because I'm curious, so you've decided to not only take the leadership route, but the CRO route, which is like, a lot of people are like, cool, I'm just, I'm cool with being a head of sales or VP of sales and the CRO is obviously it's a very different muscle that you're flexing there. Why the CRO route? what's particularly interesting for you about that? What energizes you about being a CRO? I think it's not for everybody. And I think sometimes when you start - You have to take your hairline than I do at least still. So you've been able to manage the stress somehow.
10:22I appreciate it. I've gotten good at that. And I was going to say, it takes definitely a lot of being able to manage those aspects. But no, I always like being challenged as well. I feel like if you look at my career progression, And, you know, it's not been it's not been linear in some ways. It's not, you know, traditional in that I worked at like, you know, all the same SaaS kind of companies and I just moved to different brands. Like I was always like I went from like enterprise SaaS to, you know, PLG, you know, I've done, you know, kind of cloud sales, which were, you know, kind of highly, you know, dynamic units that you were selling.
10:58And so I just always enjoyed like the challenge, I think. And so I think that's, you know, got to be someone, you know, who wants to be continuously challenged and actually in my current role at Orem, I have marketing rolling to me too, which is - Yeah, I forget. That's a whole nother thing that's - Totally. Maybe becoming a little bit more common, but it's not super common in my experience. Yeah, no, it's not what I'd even done up until this point. Like I'd always partnered really well with a great CMO and, you know, like really, you know, was pretty good about, you know, staying in my lane. And so this is just another moment of like, you know, if you enjoy being pushed out of your comfort zone and like always learning, like, you know, that's probably some of the things that I think led me here and, you know, it really kind of kept me engaged in doing it.
11:39Yeah. So let's get into some of the fun stuff that we were just talking about. So you were just at Outreach Unleashed. It sounds like we had a killer time there. There are some really big themes that emerged from that. So, and I think that both of us have a unique advantage point in our companies too, because we sell to sales teams. So you get to talk with a lot of sales leaders. You see the inner workings of all of these sales orgs. Just from that vantage point and then from the Outreach Unleashed conference, what are some of the high level things that you're seeing sales orgs and revenue orgs focus on right now and talk about and have challenges with?
12:16Yeah, yeah, no, good question. And it's definitely timely here, I would say, you know, I share your sentiment on this as well. Like, I really do value and appreciate where I get to sit right now at this moment in time, because I think like this is, you know, like, you know, talk about like radical, you know, transformation and tectonic shifts in our industry. This is like definitely, you know, one of the biggest I've ever seen. And I've been doing this for 20 plus years. And so it is kind of fun to just get to like talk to other leaders, get to talk to other teams, get to talk to like companies that are driving the transformation.
12:50Like it is a really fun, you know, seat to be in. And I would say, look, I think everybody I talk to, you know, first off, like feels like they're behind, feels like they're, you know, out of their comfort zone. You know, it feels like they should be doing more with AI, right? You know, like there's this intense pressure we're all feeling on that. And, you know, and I'd say, honestly, like, you know, I've talked to hundreds of companies in the last six months. And, you know, I don't think anybody's got it figured out. So I'd say, like, that's the, you know, the first magic. Despite what you see on LinkedIn.
13:19Yeah, magic epiphany. Yeah. No, no. I mean, the best companies out there don't have it figured out. And I think that's at least somewhat comforting, you know, because I think that there's probably people who will listen to this and be like, okay, I feel and, you know, you know, get all the stress that John just mentioned. And, you know, like good to know that, you know, this isn't, you know, the game's not over and there's still more innings and more, you know, things to be figured out. And so, you know, I think that's a fun thing. I do think like thematically things that I'm hearing, you know, over and over, you know, I'd say a lot of folks are bringing up build versus buy, you know, when they're making software decisions here.
13:53And, you know, which is really unique. Like that has been a theme, you know, in my 20 plus years, it's come up three, four different times, right? It's come in different waves. And, you know, it usually fails because, like, people don't want to upkeep the software. I think, you know, you and I were talking about some of the stuff you've coded as well. And, like, you know, sure, you can ship a product and you can do, you know, some of the most impressive work these days in, like, you know, a few minutes if you know what you're doing. But the maintaining, the upkeep, you know, the modification and then the security piece.
14:25Yep. So, you know, look, I think it but I think it's an interesting one. And I like the people are talking about it. I think actually, you know, I don't think it's, you know, maybe build all these point solutions. I think it's going to end up being building workflows and connection, you know, and making the tools work together. And so, you know, it is fun to hear, you know, one, everybody talking about it and trying to understand where they are in the journey. And I think many folks are, you know, build versus buy curious and they're trying to, you know, future proof whatever decision they're making in that moment.
14:56And so I think if you're trying to sell to them, being able to have a story about how you can enable that journey and be a partner to them, should they build versus buy, I think is a really strong vantage point and viewpoint to have here. And so I think that's a big one there. Can I ask you real quick about that? Because if you think about, as you were sharing that, I was thinking about the sales tech stack right now. And if we just think about the outbound tech stack, there's a data provider that people are going to interact with. There's their CRM. There's possibly sales nav. You got Orem in the tech stack.
15:33You have a sales engagement tool. You maybe are using something else for call recording. I mean, holy shit, that's like six things already. And what I'm hearing from you there is sort of this thing that Salesforce has been talking about a lot. It's almost like this headless kind of thing, where it's like, is there a world at one point where people are using Orem and they never even log into it? You know what I mean? Because it's just like there's something that people have vibe coded or built internally that's like, here's our hub where we do everything. And it just leverages all the back end.
16:07I'm curious, one, on your thoughts on that. And two, the narrative that needs to be put out in the marketplace, I think, is really important. And that's, I always say with Outbound and with PipeGen, the ceiling of that is really your marketing engine. It's like the thought leadership you're putting out and the point of views. And it can never really long-term, in my opinion, outperform that. Does that need to be something that these go-to-market organizations are thinking of too and getting ahead of this and really shaping the narrative and how their buyer thinks about it? Yeah, yeah. So much good and the multiple layers to that question there.
16:43I, yeah, I'm a big proponent of like, you know, the, the topic of headless, you know, and I think, you know, you're right. Like the, the ability to have these tools working together, you know, with a workflow that could be, you know, coded by, you know, the team there, you know, that becomes the interface. Like, I think that's a, that's an interesting and, you know, magical utopia there. And so, you know, I think the, you know, thought that, you know, everybody's going to live and work in your system, you know, and they have 10 others that are all believing that they're going to live and work in that system, right?
17:14The, you know, like system switching, you know, kind of tax has gotten really high. Oh, it's been the reality for sellers for like a decade now. Yeah. And so I think like, you know, if you can cut that down and get, you know, again, like other thematic things that just keep coming up, like that single pane of glass or that single view on a customer where you can launch these actions, like that would be, you know, I think the ultimate utopia that everybody would love to get to. So I think that's where we're all kind of heading. And I think the, you know, I've, I've had a lot of moments of like AI is now the glue that can bring the pieces together here, you know?
17:46Um, and so, you know, I think in, you know, many times in my career, people have talked about, you know, headless, you know, and, and I think it actually could become a reality because of the, you know, ease of use to build that and by, by coding the connection, you know, and the workflow is the, is the cool thing to think about there. You know, so it is, yeah, it is definitely, I think, where things are going. But I think there's people all over the place on this journey, again, back to like, nobody's got it figured out, you know? And so I think that's a big one. I think, you know, kind of, you know, also going down that line, like, we all overbought tools, right?
18:20You know, I think we, you know, I also make the joke of we're one sales tool away from being perfect. And, you know, like, next time I buy a tool, it's like, all right, we're still one more tool away, right? It's just like a never ending journey. And I think that's what kind of led us here. And, you know, now it's, you know, really hard to sell software because I think people overbought. Right. And so people are really scrutinizing every decision. They're trying to cut back, you know, some of that, you know, kind of switching, you know, situation. They were trying to, you know, drive adoption.
18:50And so I think that's super important. You know, I think one of the other key conversations that I had at the outreach conference was about adoption, you know. And, you know, someone mentioned, you know, my job depends on, you know, all these sellers, you know, doing the things that, you know, I ask them to and like many aren't right, you know, and I think there still is a lot of reluctance and resistance. You know, maybe it is, you know, like, you know, personal reluctance, you know, style, like their own style doesn't fit this. You know, maybe it's also they're just not informed. Like I think you and I chatted about the, you know, being distributed and working from home.
19:25you know, you're not able to look over someone's shoulder and see their workflow, right? You know, and so you're hoping, you know, that they went to the training and, you know, they went to the enablement session and then they're using it now in their day to day. But I would say like the large majority, you know, has some really good pockets of people that are doing it the right ways, but there's still a long tail of others that aren't right. And so, you know, I do think sales leaders that will win in this, you know, kind of era are going to, you know, start to shape that point of view and, you know, they're going to switch from a, you know, recommended to required culture is my kind of thought on this.
19:59And that, you know, we also bought these tools, kind of put them out there and said, Hey, we recommend you use this for that. And, you know, this will make your life easier here. And I think we need to be a little bit more prescriptive, you know, in some of these instances of like, you know, let's define, you know, what is our sales process and how is it different and how do we all follow, you know, at least certain elements of like, you know, base case and make sure that we're using the tools in the right way. And, uh, you know, I think that's going to, you know, be a big, you know, kind of big shift that needs to happen there.
20:30Um, and then RevOps, like I think RevOps, you know, needs to be a major fulcrum point right now for us. I think, um, you know, I sent my RevOps leader off to a, uh, uh, you know, a, you know, big session that he sat through and, you know, his big thing that came back was that, you know, RevOps orgs need to become more like product orgs versus analytics orgs. And that really resonated and put a bow on a lot of the things that I'm, you know, kind of seeing and thinking right now, because I think who is better suited to, you know, kind of, you know, be able to set that platform and, you know, make those build versus buy decisions, you know, alongside their leadership and then make sure that, you know, adherence is, you know, managed with the leadership team, it's RevOps.
21:13And so I think there's going to be a major transformation and shift. And, you know, I think the RevOps team of 10 years ago is not going to be the, you know, RevOps, you know, team of the next decade. It's going to, you know, you're seeing it already with a lot of them hiring, like, go-to-market engineers and, you know, different people to kind of be AI, you know, workflow evangelists. But I think, you know, their job no longer is to measure, It's to make sure that this kind of new way of adopting and using these tools and implementing them the right way happens here. So many areas that I want to talk about.
21:47There's a lot to unpack. What I'm hearing is a theme around centralization of AI within the org versus last year. I feel like at the beginning of 2025, the thing was like, just get ChatGPT or Cloud wasn't even as popular then. or Gemini, just get the seats for the reps to use. So is that what you're talking about? There is a trend more of like, let's centralize this. So instead of, yeah, we should have reps that use Claude, let's say for their account research and stuff, but how much can we pull back into the org and leverage RevOps, let's say, and leverage AI to do things the rep never has to even really interact with.
22:28So like an example of that would be a client of ourselves to construction companies, local construction companies, house painting companies, et cetera, reps should not have to be going on Google Maps and Yelp to find these companies and find their phone numbers and the service that they do. Like we can do all of that with AI. Is that sort of where you see it going? And what does a first baby step maybe in that direction look like for an org that's like got the chat GPT licenses and the cloud licenses, but hasn't started to centralize a bit? Yeah, no, it's a big, it's a good one. Look, I'll pick on myself here too.
23:06Yeah, how you're thinking about it too. As much as you can share or feel comfortable sharing would be great too. Yeah, we get it right, you know, a number of times and we screw it up just like everybody else out there at Orem. And, you know, again, it's fun to see some, you know, some mistakes that I even made as a seasoned operator who's, you know, been through some of these things. Like, you know, again, I'll make my own, you know, rookie moves here, you know, from time to time. But we, you know, we recently, you know, rolled out Claude to the entire company. And we, you know, we threw it out into the wild, kind of like everybody probably did, as you were mentioning there.
23:40And it was a really interesting experiment. And I think, you know, you know, we learned, you know, some things really quickly. Like, I think one of the things that I would say is just kind of like the negative downside is that we had a rep who like, you know, token maxed on the first week. Right. And, you know, I'll talk about token maxing as well as another kind of, you know, part of this here. But, you know, it was interesting. You know, it's like, wow, we just put it in their hands. And, you know, this guy was able to hit his max limit in the first week. Right. And, you know, so I was like, well, before we advance it, like, let me sit down and talk to him and understand like what he did.
24:13And, you know, there were some really, I think, magical, unique things. Like he was like, I don't, you know, customer presentations used to take me, you know, 30 minutes to an hour to do, to prep before a call. And are they leveraging co-work like the agents? Is that what's using the credits up? Yeah, yeah. There's a couple of things that caused him to burn it. But, you know, he was able to create like beautiful customer presentations, you know, in half the time, right? He was using Glean plus, you know, Claude and, you know, pulling all that in and was able. And they looked like, you know, as marketing roles to me, like I've seen also stuff come out of there where I'm like, oh my God, none of this is on brand.
24:49And like, you know, we loaded it with our brand standards and guidelines. And some of it looked better than what marketing had been putting out before. You know, a lot of it looked better than, you know, what reps were creating on their own sometimes. And so like that was a huge, huge leap forward. There's almost, sorry to interrupt you, there's one thing to point out there is, I wasn't really thinking about it this way, but there's almost a, because I don't run a large sales org, a governance component to it where it's like, hey, we can keep things on brand a little bit easier and have a little bit more control over how things look and the messaging and like all of that stuff that would be really, really hard to do when the main creator is someone taking a slide deck.
25:31It's all in here and then I'm going to start there versus, you know, starting it here, rolling it into AI and then rolling it down. Yeah. That's like a big, big part of it, it sounds like. Yeah. Yeah, totally. And so it really was like impressive, you know, some of the output. So there was like, you know, tons of little positive things that this guy did. But then there was a lot of stuff that he, you know, was actually kind of like vibe coding shortcuts here. Right. You know, and so I was like, well, what was this? And he was like, well, you know, like I can do this in outreach, but it takes two extra clicks to do it in outreach.
25:58So I just did this. Right. You know, and so I'm like, all right, well, we have outreach, you know, like let's not, you know, do that. And I think like, you know, there was a couple of other ones here too, but I was just like, wow. But I think like, you know, my biggest takeaway was I was like, wow, he spent a whole week basically working through this. Like he went deep down the rabbit hole and, you know, he wasn't prospecting, you know, he wasn't building pipeline, you know. And, you know, he had some really good ideas, some bad ones, some good ones there. But that was like lost productivity in my mind, right, because we threw it out there.
26:32And, you know, we didn't give any kind of like, you know, feedback on like, here's things that we, here's the base case of things that we think you can do with this. Like, go. Here's like the starter kit. Yeah. And so, you know, yeah, I was like, we, you know, it'd be my worst nightmare if, you know, my, you know, 30 sellers, you know, all spent, you know, a couple of weeks going down the rabbit hole, you know, in a tough quarter when it's, you know, really tough to sell. So like, you know, I want to be kind of clear because I think this is a weird topic, too, and that's, you know, there is some degrees of freedom that sellers need.
27:06I do think that the best sellers are artists, like they're creative and, you know, they have their things that make them unique. And so I think, you know, there is a, you know, there's governance, you know, there's some best practices and there's some, you know, things that we could have done through RevOps to make this go smoother. while, again, maintaining the artistry of what they do and keeping that on point. And so, in retrospect, what I would have done was work with RevOps to roll it out and build 10 base case agents of saying, hey, we heard the feedback, and these are the things that you really hate about your day-to-day, and they really slow you down and take you away from doing the things that you want to do.
27:47So here's 10 agents that we rolled out with Claude, you know, in the initial rollout here, right? And that way also when new hires come on board, you're not hoping that a year later they catch up to this top rep, right? You can roll those things into their onboarding and you can get them started off on that right foot. And so I think like that's where it needs to, you know, have like a great partnership, you know, to be able to set up, you know, things that go, you know, across, you know, the team. They don't just live in silos or pockets there. Yeah, we have this concept that we call eating complexity.
28:22And eating complexity is like, if we just use outbound as a simple example, I have identified the account that I want to reach out to and I need to secure a meeting. There's dozens of steps and things that happen along the way. and eating complexity is as the org, you know, because we're a professional services firm that does a lot of what we do is training and process creation. But the other part is like getting them to get the outcome. And we always ask ourselves, how can we eat complexity for the rep? Like how many of those things that can we remove either like thinking or steps or whatever?
28:58And I think that people with the AI thing, we cannot forget that this is a tool like any other tool that needs to be enabled and workflows need to be created and we have to eat complexity for the rep because like to your point we'll have someone that just spends an entire week going into a rabbit hole which is like something I would do um so I think like that I the future of rev ops I'm so excited about because that's like this should be really exciting for rev ops like you get to use your freaking brain versus being not that when you analyze data you're not using your brain but you're going to help with the operationalization, if that's a word, the operational-ing, whatever, of the data.
29:38One thing I wanted to ask you, though, is like, dude, one thing I'm super bullish on is there's a Derek Sivers quote that says, if information were the answer, everyone would be a billionaire with six-pack apps. and I feel like with AI, we're getting very excited about, okay, cool. We can spoon feed everything to the rep on a silver platter and say, this is the account. These are the triggers. Here's exactly what to say. But in my experience, that's not really the problem. Is that hard? Yes, it is. But the problem is, and I think you would appreciate this just with Orem, it's like, hey, when the person says hello, what happens next?
30:18My tonality, how I show up, how I make all of this stuff my own. So I'm just like the AI stuff I'm excited about, but I'm like, I don't know if it fixes the real problem. And the real problem is like, how are we leveraging AI to enable? This is why I'm excited with the coaching stuff that you guys do, because the coaching is that's enabling the rep and improving their skills. The skill I feel like is the bigger problem. I don't know. I'm just curious on your thoughts on that though. No, no. Yeah, no, you're absolutely right. Like I think, you know, there is a scary utopia that comes out of this as well of like, you know, again, we'll automate everything that makes a seller a seller, right?
30:56You know, and everybody will become vanilla and the same, right? And like, you know, I think that that's not, you know, what AI should deliver on here. You know, I think we need to, and that's why, you know, some of these checkpoints and some of these, you know, kind of comments around like, how do we standardize at certain, you know, areas here? It's so important. But look, there is, you know, I truly do believe that there is a, you know, the concept of the 10X seller. I think we talk a lot about the 10X engineer, you know, but we all have a 10X seller, right? Someone who's just like innately good, right?
31:28You know, that is, you know, completely different from the rest, right? You know, you're like, you know, the one that you're always talking about, like, if I could just clone, you know, you know, this person, like we would be a better team, right? And so I think those people will still exist, you know, and, you know, I think that's what's really cool. you know this does actually i think really make good on the promise of like but how do you close the gap between you know an average seller or a really good seller uh yeah do you even think that that is the game anymore of like turning a c player into a b player or is it we have these a players how can we get 10x the results because you can get like i think 10x i don't know if you mean that literally or not i think literally we could get a three to four x multiple on a great rep though, by just getting the hell out of their way, getting them great context and all of that kind of stuff and just like removing all of the busy work from them.
32:22But what do you think? Is that? Yeah, no, I think you're, you know, I mean, 10X is obviously like something that the, you know, the Bay Area, you know, made infamous. And so we'll all, we'll all use it there. But I look at those, those people exist, right? I think, you know, the, the, the numbers less the, the story, right. And I do think, you know, we are going to be able to find, find them, you know, faster. I think we're gonna be able to identify them I really do I'd get excited about coaching like I do think you know as we started this conversation a lot of folks end up in this career with you know high aspirations and hopes right and they have to kind of wander through the wilderness to get to the right you know spot there yeah and so the ability to be able to like you know coach train develop them you know even more effectively is is so powerful you know I can't tell you how many times like you know like especially the worm you know I In every given sale, any given sales team, there's, you know, a thousand calls that go on at least in any given week.
33:16Right. And so, you know, unfortunately, leaders, you know, have really big spans of control right now. And it's just not humanly possible for them to sit across a thousand calls and critique them. You know, and so what ends up happening in typical one on ones, you know, usually is, you know, they sit down with their leader and they're like, you know, I had a good, bad, you know, indifferent week. What should I do differently? And usually that leader is just like, I think you should try this, you know. And it's just like they hope they got it right. But now being able to look at the scorecard that comes out of the week that shows how they're tracking against themselves, how they're tracking against their peers, what are their top five moments that they did really well, what are the bottom five things that they need to get better on, the ability to be able to assign calls from Jason where it's like Jason really nailed that objection.
34:05And that's what has been flagged as something you're struggling with here. And so you can listen to it. And then, you know, we rolled out our, you know, kind of AI role play. And look, candidly, when we rolled it out, I actually was like, this is gimmicky. It's going to, you know, it's not going to stick. You know, I think it's going to be a here today, gone tomorrow thing. And it has been one of our more wildly successful, you know, products. And, you know, I think a lot of it, you know, tracks back to, you know, we align mainly to the SDR organization, you know, and some AEs. But, you know, SDRs are the ones that are the greenest of the green, right?
34:41And, you know, the teams that were really, you know, adopting it, I remember actually sitting down with a table of SDRs who were using it. And I was just like, you know, what are you getting as far as value from this? Why are you using it so heavily? And one of them looked at me and said, you know, John, basically, you know, for me to practice and get better at outbound, I can do it with a customer or I can do it with my manager. And both of those have downside. You know, I'm going to screw up the customer call and cost the company business or, you know, possibly embarrass myself or the company.
35:12You know, my manager might lose faith in me and not trust me because of it. And so it's a safe place to practice. Oh, wow. I didn't even think about that part of it. Yeah. And so, you know, I think it is really neat when we turn on the coaching and role play, you know, a lot of like managers are like, I don't know how I did my job without this. And it's, you know, kind of back to giving them the ability to scale themselves to cover those a thousand calls and be able to give actionable feedback in the moment uh you know you're giving you know the the reps the ability to have the safe place to practice with the ai you know role play um and it does really show up and and i think the you know the neat thing is you know when we first rolled it out to like people were using it in one-on-ones top down uh and some of the best teams we have on the platform right now the the rep has already looked at the scorecards and showed up to the one-on-one and said like, I'm seeing all these things that I need to improve on and here's what I'm already taking, you know, steps and action on.
36:05And so like, it all of a sudden gives this power back to, you know, folks to speed up that journey through the wilderness and get to be, you know, closer to that 10X seller, you know, than someone who washes out. Right. And so, you know, we all probably, you know, can remember when we started, but there's such a high failure rate in this profession too. I think everybody, everybody wants to do it until they get into it and then they realize it's really hard. And so, you know, I think now like this will also probably decrease that failure rate. You know, the right folks will, you know, there'll still be people who make a, you know, make a decision and don't really know what, you know, this profession entails.
36:41But I think the, you know, the other positive side is like the right person with the right drive, the right motivation and the right intellectual curiosity now has these tools at their disposal. Love it. I love that it's creating a coaching culture. And that's the thing that I always love doing as a sales leader. And I do now with my team. To get coaching from me, you have to coach yourself first. So you have to attempt to help yourself. And there's a lot of sales cultures that are not like that, where it's like, what do I do? So I love that piece. Let's shift gears for this next part. Because we got to talk about pipe gen.
37:18We got to talk about the phone. It's all of that fun stuff. I'm curious for you, How as a CRO do you think of and have you thought of like the pipe gen pie chart? You know what I mean? Like I, oftentimes when we go into an org, the reason why they're reaching out to us, we're engaging is like, hey, our AEs need to now self-source 50 % of pipeline. And, you know, we need to move from an inbound led org to a more of a 50-50 split. And like, there's just a nice, simple narrative there. And I'm like, I always wonder, where does the 50-50 come from? You know, like it sounds a little too generic to me.
38:00And I'm just always curious because I've never really sat down with someone like yourself and just asked, like, how do you think about the pie chart in terms of, you know, channel versus marketing versus SDR versus self-source versus expansion? in. How do you, how do you kind of think about that? Is there a calculator that you use? Like, you know what I mean? Like, I just wondering, how do we arrive at the number that like sales needs to self-source this? Yeah. You know, this is what the sales team's going to be accountable for. Yeah. It's a good question. And I definitely have an opinion on this one.
38:36And I, I'm laughing about like, how did we arrive on the 50, 50, right? You know? And, and you're absolutely right. I do think, you know, historically, we've done a lot of tops down, you know, where it's just like we hire reps, you know, and, you know, hopefully marketing again is doing such great work that they're, you know, kind of filling, you know, their, you know, their funnel and giving them prospects to talk to, right. And I think largely, you know, for a long period of time, most people were building more inbound models, right, you know. And, you know, it's gotten tougher out there, right?
39:08And I think it's gotten to be, you know, more challenging. And so it has caused us to, you know, stretch and, you know, think about, you know, new muscles and ways to get there. I tend to always do, like, I think planning process is where you get this right, you know, and that's where that calculus happens. And I think, you know, usually, you know, if you've been around as an organization, you start to get a feel for like, what is your mix, you know, currently here, you know, and you've got things like your ASP, you know, you know, what, you know, kind of like, you know, average corporate or enterprise AE, you know, what is the amount of accounts that they can actually like handle and touch, right?
39:43Like you get a good idea of like, you know, what is the right amounts, you know, for them to work, you know, actively here, you know, and hopefully you'll get a good sense of like, what is, you know, you're inbound, right? And so like, yeah, then you can just run the math of like, okay, I know what a, you know, seller costs. So that usually dictates the quota math there. And so it's like, okay, of the quota, you know, do we have enough inbound, you know, to get there, you know, and I think the best sales teams, you know, don't have, you know, 100 % plus, you know, coming from marketing or inbound, right?
40:14It should be some stretch. I think everybody should be thinking about pushing some of the, you know, responsibility to AEs. Like I do think like they're unhealthy. And I know it can change based on the, or if you were advising, let's say the hundreds of companies that you guys work with at dorms or thousands, um, what percentage would you be a little bit alarmed like this is way too much of the pipeline coming from inbound is there like a benchmark or any kind of range that you might think about there yeah yeah I know you need to think about it across your different motions too yeah so usually like I have different benchmarks for you know like you know commercial you know enterprise strategic man to do all of these different ones yeah across all of these different sales motions and it shouldn't be the same right you know because I think like you You know, usually you have like a, you know, give it, you know, kind of small, medium and large, you know, for simpler terms here.
41:07You know, small usually is your velocity play, you know, a lot of times, you know, when I'm thinking through modeling here. And so it is like transactional, you know, it is like how do you help, you know, kind of speed the velocity there. And so those can be largely inbound fed, you know, and I think those are kind of like 80, 90 percent inbound fed. Yeah. You know, you do want to have an element of stretch, right? And so I think like it is like, what is the, that's the question you're asking is like, what's the right acceptable amount of stretch there? And so I'd say like for those like kind of like the small high velocity segments, like anywhere from like 10 to 20 % is usually kind of the right amount of stretch for them.
41:45Because I think, you know, if they are doing high velocity, then they don't have dedicated time to do outbound as much, right? You know, and so I think there is a little bit of like doing the work on one side, you know, comes at a cost to the other, right? You know, and so that's why you hit that balance, you know, kind of in that medium segment. That's where I start to think like, you know, 60, 40, you know, kind of 50, 50 starts to make more sense. Right. You want to get that good, you know, balance of you've got activities that they're working. So they're not completely just coming in cold.
42:15Right. You know, you want to give them momentum so that they are able to close some business and really start to feel some traction there. but again large portion needs to be you know like do we have pipe gen friday like are we going to get on the phones and are we going to give ourselves that focus time to you know continue to fill the funnel and then you know usually like large you know for me is typically like your strategic and large enterprise accounts like they don't usually come to your website like they can you know and that's sometimes the you know misnomer but i would say like if you're going to go in to try and like you know take a big contract down with an enterprise brand like they're not going going to typically come to you, come knock on your door.
42:54Happens on occasion, you know, but I wouldn't, I wouldn't model around that. Right. And so, you know, that's where you, you want to have someone who's got a majority of their time focused on prospecting, who's really working on, you know, building strategic plans to map their way into the organization to multi-threated decision. Right. And so, you know, those can be like, you know, 80, 20, 80 % outbound, 20%, you know, kind of inbound so that there is some, you know, things that are just going to naturally come through, but we're not banking on that. You can't make your number on that, right? You really have to have that muscle.
43:26And I think like the beauty of having three different versions of this, like it'd be great if I said, Hey, it's, you know, it's always one for all three, you know? But the reality is each business has a different, you know, kind of speed and course. And I think if you do this right too, they will build on each other so that, you know, your, your, your best, you know, rep at the small segment, you know, can eventually move into the middle segment, you know, and, you know, be able to ingest that new stretch of like, okay, now I've got to go from 20 % of my pipeline, you know, from outbound to now 50%.
43:56So that means I'm going to change a lot about how I structure my day, a lot about how I think about, you know, what accounts I go after here. And then again, you know, when they're ready to make the jump to the top of the pile here, you know, 80-20 doesn't, you know, feel so daunting, right? They've already began that journey and they're starting to kind of make that, you know, that understanding of how they spend their time and balance the trade-offs there. So once we've got that sort of math equation or pie chart dialed in, I'm just curious, you know, how you guys sort of drink your own champagne, eat your own cooking, like that sort of stuff.
44:30How do you facilitate as an org PipeGen? You mentioned PipeGen Fridays. I'm curious if you do something like that, like what is happening at the org level around like the rhythms, the weekly, monthly, quarterly rhythms around pipe gen outside of just, hey, we expect reps obviously to do some of this on their own, et cetera. Like what is facilitated at the org level? Yeah. And I think actually I'll hit that, but I would say like one thing I left off that I'd be remiss if I didn't hit back on is like when you are doing this bottoms up math. And I think like, you know, we, you know, once you get to a certain level of maturity, you're doing the tops down and it should be informed by bottoms up, right.
45:06You know, And that as a sales leader, then you're able to say like, okay, we can't add 10 new reps, right? Because we don't have enough marketing inbound to hit, you know, that's, you know, 50, you know, 80 or, you know, 20, right? And so like it starts to inform where you put resourcing, you know, or how you, you know, work with marketing and hold each other accountable to say like, we want to invest in enterprise. So we got to figure out how we get that up there. But I think when you get to that conundrum, you know, there are other avenues that I didn't talk about. and that was the thing I wanted to circle back on, like, you know, channel partners, you know, is a big one there that I always try to think about.
45:39Like, I think we, you know, when you're growing an organization, you can get very binary of like, you know, it usually comes through, you know, knocking on our door, us knocking on theirs. And I think like, you know, there is a strength to be developed around, you know, partnering and how to, you know, facilitate those deals. And so, you know, then you have to think about, or what are the investments we make in partner to make sure that we can add, you know, 10 % to, you know, the mid-bucket here to offset maybe some of our deficit there. And so that's where the, you know, the calculus gets, gets fun.
46:07And, you know, you get to develop, you know, I think other kind of like, you know, channels, you know, for you to work through there. But yeah, I think once you, once you get that, then it's really down to the leaders to set, you know, the standard and the course. And so back to your, you know, how do you set your day? Like we, you know, we drink our own champagne and, you know, we definitely do like a lot of our team meetings and get togethers on the sales floor, which I think is great. Orem is a fully distributed company. We don't have headquarters. And so I think tools like a digital sales floor is such a great way to facilitate the bullpen or environment that we had in office.
46:46And so I think if you don't have an office, that's a great thing to do. You block dedicated time. I think if you don't focus on it and block it, it'll always get deprioritized by other things that come up. It's just kind of human nature. Is there mandatory blocks? Yeah. How do you do that? Yeah, we do it by team on Fridays. You know, I think that's kind of the big one for us. I love that it's on Fridays, too, by the way. It can be any day, but it's, you know, usually. And look, I think the team commits to doing it on their own, but Friday is when we do it together, right? And I think there is something to be said about, like, the joint accountability, you know.
47:22Just like if you're training for a marathon, right, join a training group, right? Because if you're doing it on your own, you know, it's really hard, you know, and you're going to hit, you know, roadblocks, obstacles, you know, you're going to learn together. And so, yeah, we will jump in there and, you know, block four hours on a Friday, you know, and just, you know, pound the phones to the team, you know, with the team. And it is, you know, where a lot of like the idea sharing happens because, you know, while the dialer is going, there's downtime. I think there's, you know, good moments of like catching up on wins, you know, catching up on weekends, you know, plans and things like that, which I think really kind of gels the team and connects them.
47:54But I think you got to make it, you know, kind of regularly part of your discipline and and look measure against it, too. Like I think as a manager, you know, making sure when you have those one on ones, it's not just about what have you closed and what are you going to close? It's, you know, where is the pipeline? Because that tells the story of, you know, what next quarter is going to look like and, you know, the rest of the year is going to look like. Yep. So the PG Fridays, the prospect, you call them prospecting Fridays or PG Fridays? PG Fridays. PG Fridays. I think what's really important there is that you have, I mean, you guys are able to use Orem for this, like that you make that time productive.
48:27A lot of the companies I've seen that struggle with that, it's like it's an it becomes a really unproductive four hour block that everyone hates to do. So having like the right data, having tools to make this efficient, the training, the process, all of that kind of stuff is definitely big. Like having executives, you know, give them open, you know, ability to pop in, you know, I'd say like, yeah, I enjoy it. Like if I find myself on a Friday, you know, with a calendar hole at the same time that one of the teams is dialing, like I want to sit in and I'll occasionally dial with them, you know, and so that's kind of fun.
49:01Jason, our CEO, you know, is also, you know, a former sales guy as well. And so he really gets a lot of energy off of it. You know, I think that, you know, the more folks you can bring into it, I think that's how you make it. you know not something you need to do and you're dragging your feet about it's like it becomes fun and it becomes you know motivational and like i think when others get to see it and you know be a part of the action like and celebrate you know great calls together like that that reinforces itself here my old vp called that rubbing shoulders yeah getting in the pit with the reps it's like yeah you got to do the thing too um a couple quick things i wanted to ask you around just other pipe gym plays you guys are seeing some success with like the roadshow strategy And I just want to know, outside of doing good old-fashioned outbound and hitting the phones and sending the emails and doing the digital thing, what outside of that are you seeing work right now from a pipe gen standpoint?
49:52Yeah, yeah. I mean, I think, you know, obviously, you know, the, I would say moments of connection and in-person are resonating. I do think, like, there's this weird dissonance that's been kind of created with, you know, AI where I think people don't trust, you know, emails anymore, right? It's like it doesn't feel like it was written for me. It feels like it was written by AI. But I think that, you know, that the pandemic, you know, hangover of no events, bringing them back, I think, has really created a thirst and like a, you know, hunger for people to get together. I think, you know, so I think all these things are really coalescing.
50:26And I do think, you know, it's neat to see, you know, how that is working. I think everybody is valuing in-person time. I think you've got to be really thoughtful about it, make it interesting and make it fun and worth their time to spend with you because everybody's time is precious, right? And so, yeah, we've been doing some fun things around that. And I think it has been, we do city by city takeovers right now. We do one session focused on executives and it is 30 people invite only and it is - Is it like a dinner type of format or what's the - Yeah, it's kind of like a small group setting salon style.
51:03Like we did one here at a wine bar. My events team is always thinking of creative ways, again, to make it like something they've never done before. Because I think if you're doing the same things everyone else is, I think like people will stay home. Yeah, people will stay home. And so, you know, I applaud like, you know, teams that are thinking about, you know, new creative ways. And, you know, like our events person is brilliant, but she like has a thought of like doing it at a house, you know. And so it's almost like a dinner party, you know, catered there. You know, we did this last one at this, you know, wine bar that was really kind of a cool, intimate setting there.
51:33But I think, you know, the conversation was the best part. And it was like, you know, let's bring in, you know, folks from some of the biggest companies, you know, in the world. And let's talk about, you know, honestly around AI, what's working, what's not, you know, what's fact and what's fiction. And, you know, it was funny. You know, I think there's definitely a lot of like collective eye rolling because AI gets talked about so much. But I think the space to say, like, here's the stuff that's totally not worth its time. You know, here's the products that we've used that, you know, didn't really meet the mark.
52:04Here's the ones that were really great, you know. And so, you know, I heard a lot of executives come out of it and just say, man, that was awesome because I thought I was, you know, I was in this struggle alone and that I was the only person who was in this spot. And so hearing, you know, this big company say they've got the same challenges, like really helped me test my thinking and made me feel, you know, like really good about the path we're on. And so I think like, you know, that's been interesting. And then, you know, we, we work with, you know, SDR leaders, SDRs, you know, AEs. And so we've been doing this fun event where it's almost kind of like the anti-networking event, but we call it the dive bar tour.
52:37You know, I just feel like every sales team always kind of finds the best dive bars nearby the office, you know? And so that was kind of born on maybe a rant I had with the marketing team. And they were like, we should totally do that. And, you know, it is, you know, like the first hour is, you know, kind of like get together and network and meet with the community. And I think, again, people are really, I think, you know, missing that. I think there's not as many of those moments. And then we bring in, you know, we brought in bands and, you know, actually like, it's like almost like, you know, going to a concert with, you know, kind of new friends that you just made at this.
53:09And so it's been resonating in a lot of ways because, you know, we actually are not making them sit through a, you know, a timeshare pitch. We're, you know, not, you know, making it the Orem show and it's about how do you go meet and network with others. And so I think just try and find ways to give value back to your audiences. I think that's how you get people out. So I think, you know, a long-winded answer to say events have been really successful for us. Can I ask you related to this, just as a senior exec yourself, what makes you want to participate in certain things? What makes you not want to participate?
53:41What just you personally? Yeah. Because a lot of people want to do the dinner thing and it's really hard to pull off a good dinner, especially with 30 people. Like to get the level of seniority that you want in that room can be really tough. Making sure they have a good time can be really tough. I mean, this is not an easy thing to do, what you guys are doing. For you personally, when you think about it, what catches your attention? Like, oh, I'm going to check that out. What feels productive for you when you participate in this kind of stuff? Good question. I got invited to one tonight that I'm going to totally no-show on.
54:12Sorry, you couldn't. I was like, no, I think it's, you know, it is important. And you're hitting on something really good there. I think like the audience matters, you know, the topic matters, you know, I think like, you know, the event space matters too, you know, in some ways, like the environment matters, right? You know? And so, you know, kind of thinking about those things I think is super important, you know? And so I sometimes will be like, okay, is this a vendor that I think is doing really innovative things? And do I, you know, trust that they've garnered an audience? Because a lot of times you can't see the guest list, you know, but I've seen people do that where they're like, you know, look, there's already confirmed, you know, four or five people from, you know, X, Y, Z companies.
54:55And I think that's important too, because it's like, okay, I get to, you know, hopefully be in the same room with people that I look up to, you know, that's, that's important to me. I met with, yeah, actually, and I go through like pockets of, you know, going to dinners where I'll overdo it. And then I'm like, all right, I got to take a couple of weeks off or a month off. And then I'll go back right back to where I started again. And I went to a partner's dinner here in Austin and it was, it was really great. And it was interesting. They booked it at five, uh, you know, which in Austin, you know, getting across downtown at five o 'clock, like, I mean, the restaurant was probably 20 minutes away, you know, but at five o 'clock was impossible to get there.
55:33And a lot of us showed up late and he was, you know, he was like, Hey, we intentionally did drinks, you know, to, to give everybody time to get here. Um, but what I thought was really neat he was like, you know, I hate it when people do dinner sometimes at seven, you know, that go till like 10, 11 at night, you know, because some people have, you know, families, kids, right, things that they need to get back to, right. And so he's like, I intentionally, you know, want to do from five to eight, you know, and get everybody out of here. And so I think like, I applauded that, you know, you know, that partner who put that event together, he, you know, really put a lot of thoughtfulness into like, table arrangements and who sits by each other.
56:08Uh, and I think you're right. Like, uh, getting the right mix, it's almost like planning a wedding, you know, it's like, okay, who are the relatives that can't sit together? You know, who are the ones that I know will hit it off, you know, just by their personalities. And so I think, you know, if you get known for curating those things, you know, that is really good. Um, you know, I've, I've, I've been to a couple for, uh, you know, Nick Mehta's infamous for Gainsight and he's a big boisterous personality, but yeah, he does his a lot of times very much, you know, like a, like a dinner that you would have with friends.
56:41Right. And he gives topics and discussions and, you know, makes it engaging there, you know? And so, you know, I think you just have to be thinking about all those nuances, right? You know, it is, there's a lot of pressure. So no pressure tonight. And let's get a super casual. Yeah. I'm kidding. You picked a good group too. And so, yeah, for those who are watching, Jason and I are getting dinner tonight. And so I had to give him grief on that. But yeah, no, I think it does, you know, it does matter. Right. And I think we have seen more, you know, I think others are probably, you know, would witness this drop-off rate is a thing.
57:15You know, I think a lot of folks with best intentions say yes. And then, you know, more so than ever, I think people are like, you know, I didn't think about the soccer game or this, you know, at home commitment. So, you know, you have to just kind of constantly think about those elements and make sure you're giving value to the audience. Yeah, 100%. Got maybe five-ish minutes left. So I want to, we got to talk about the phone. Yeah. I would love to get your take on future of cold calling and how you guys think about the positioning against cold calling is dying or dead, like it's been doing for the last two decades or however long now.
57:49And then I would love to just hear, I would love to debunk a few things with dialers specifically. And for some reason, people think that I hate dialers. I've said things publicly around poor use cases of dialers that I believe you would also, that Orem would disagree with as well. And one of those is parallel dialing through a list of CROs or senior executives and not doing research and having a populated field where you can still have an intelligent conversation. That's what I was making an argument against. So I just want to make that clear. Like I'm a fan of Like dialers, like there's a great use case for them.
58:26There's obviously the coaching and being able to listen and like all of that kind of stuff. But cold calling, give me your take on this. And maybe the two or three most common misconceptions on dialers and really the proper way to leverage these. We would be remiss if we didn't talk about it. I appreciate it. I was going to say I agree. Dialing strategy is like lost on a lot of folks, right? And so I think like that has become a big mandate for us internally too. is like, you know, when you turn these tools over to the team, you know, kind of back to, you know, recommended versus required, like, don't just hand them over to them and let them go nuts, right?
59:00Like, give them some, like, you know, some advice and guidance, because I think that's where dialers get a bad rap, you know, in a lot of these cases. But look, I think my origin story coming to Orem is kind of an interesting one in that I, you know, during the pandemic, you know, was at, uh, was at Canva and then demand base, uh, and demand base, you know, also works with sales and marketing teams. And, you know, we had a pretty massive SDR organization and I was just seeing this pattern of like, you know, our SDR team at the time and other customers, SDR teams, you know, we're seeing a massive drop in their performance.
59:35It just seemed like every year it was eroding and getting, you know, kind of, uh, more and more challenged. And I think it's still, you know, continues here in different ways. And it just speaks to, You know, the world shifted. People don't go into offices as much anymore, and they definitely didn't, you know, at the beginning of the pandemic. So that means you don't have a desk phone to call people, and they don't sit at a desk with a phone that they can answer, right? And so, you know, it meant that you had to have accurate numbers for, you know, kind of cells, you know, and being able to understand where they are and how to get a hold of them there.
1:00:05You know, it really, I think we went distributed as well. And so that was a new muscle, you know, for leaders to embrace there. And, you know, I think that, you know, when you're not together, you know, you don't have those moments of intentionality like a PG Friday. Right. And so, you know, for all these reasons, you know, and outbounding is just hard in general. I think it's one of the hardest skills to develop, you know, and such an important one. People are pivoting away from it. So I think like as I talk to more and more people, it's like, yeah, we're not really using the phone. We're just sending more email and LinkedIn and, you know, hoping we get a response.
1:00:38And the problem is everybody was doing that. Right. And so I remember actually going to a conference thinking, oh my gosh, you know, my team's not using the phone as much as they should and used to. Others aren't. And this is a problem. And I think like, you know, for clarity to like the one I always get nailed on is people always want to ask me like, what is the one channel, you know, that that you'd use for outbound? And I'm like, I can't pick one. It's like picking a favorite child. Right. I think the beauty is using all of them with the right discipline and understanding, you know, how to use them in those different ways again.
1:01:11And so, you know, my kind of moment then was, you know, we were losing this muscle and, you know, I think it's leaving a channel wide open, you know, that we needed to fix. And so I actually ran into the Orem team at a conference and, you know, my faith was immediately restored because, you know, Jason, our founder, was at Rubric and he, you know, was building sales teams around the globe. and he was buying a lot of tools and he was like, I kept looking for what was Orem and it didn't exist. So that was his reason to go. It's the best origin story. It is. Yes, it is. And again, I connected with him on that because I was like, okay, you saw it faster than I did maybe, or you were a step ahead of me on this, but so glad we connected.
1:01:49And so he and I connected and the rest is history. And over time we developed a friendship and now now we work together, which is great. Um, but I do think like it needs to be there. You know, I think that, you know, my story of joining Orem, you know, was for all those reasons, but I think like AI got more, you know, you know, prominent and, and people kept overusing email and LinkedIn. And I look, I'll just tell you my own inbox. I check it at the end of the day or the beginning of the day and the end of the day. And like, I dread going in there and I feel like My eye is just scanning for like what's important, you know, what was written for me.
1:02:27And I can spot AI written copy now. Like my brain just knows like, you know, filter that, folder that, you know, go find the things that are written for you. And so, you know, look, it's definitely made it really hard to get people's attention in the inbox there. LinkedIn, I think, like became another inbox for us, you know, and it's the same problem. And so like, I'm probably less in there if I'm honest too. And so I think like the teams that haven't picked up on this, that just keep, you know, maybe I'll just send five more, you know, touches in these channels are going to get the same outcomes.
1:03:01They're not, they're going to get nothing. And so, you know, magically the teams that have figured out the phone, you know, are seeing, you know, sometimes five to one or better in, you know, engagement there, you know, you're having real conversations, which I think cuts through the process. of like, you know, am I talking to a robot or am I talking to a human? It's like, you know, it's a voice, it's a person, it's, you know, someone who can connect with me. And so it's magically clicking, you know, and it'll change. You know, I think like over time, you know, these channels will, you know, have other nuances that happen to them.
1:03:34And so I think that's why you want to do all of them, you know, with the right discipline. But back to your point, like, I think I actually, like, I've had bad experiences with dialers in my past as well. I do remember, like maybe the 10 years ago dialers, you know, I kiddingly said it was like hooking up like a phone machine gun to an SDR and just, you know, setting it off, you know, and, you know, that wasn't a good experience, right? You know, the reps didn't have a chance to prepare for the calls, you know, they were just, you know, just going through the motions. And so. Well, the technology has gotten much better too, where there's not such a delay.
1:04:05Yeah. Yeah. And, and I think, you know, we're able to integrate with all the tools too. So they have, you know, they've got Jason's LinkedIn up, They've got, you know, the last, you know, kind of notes from the last touch point, right? You know, they have the different things that, you know, make it not a like, hey, Jason, you know, like delay then. Hey, Jason, you know, kind of thing. You're going right into a conversation. And so I think you're going to the conversation with everything you need to have a great conversation. And we've got, you know, another product that's just about to be released, but it's in-call coaching, you know.
1:04:35And I think the ability to, you know, when someone throws out an objection about, you know, like we're looking at XYZ competitor, like the ability to have notes pop up. Yeah, battle card pops up right there. Yeah. Yeah. It says that we've got three customers that chose us over that. Here's what they saw value in. So, again, like it does, you know, speeds up, you know, that rep's journey to have the details at their fingertips. It kind of replaces battle cards, which like would be a moment of like fumbling to go find the battle card and then try and skim it really quickly to talk to what are the competitors pain points, you know, or problems with going with that competitor.
1:05:09And so anyways, I think it's getting, you know, so much better there. But yeah, back to the dialer challenges, like I think just like dialing strategy, like I think, you know, we, you know, kind of preach that it's not about like, you know, just massive volume of calling. Like, I think we have teams that do 10, 20 calls, right? You know, we have technology that helps you understand, like, when is the best time to call Jason? And so how do you schedule your day and, you know, schedule that call at a time that you know you're going to connect with him? And so instead of, you know, make 200 calls, hope you get 10 pickups, you know, you can make 30 calls and get 20 pickups because you have the technology and the details and, you know, the relevant talking points to make it really land there.
1:05:50But I do think, you know, we, you know, in our own dialer, we've got, you know, click to dial, we've got power dialing, and we've got parallel dialing. You know, and I think what really gets fun about this, too, is, you know, we have different scoring of numbers for those that don't use Orem. So, you know, like, who are the hot prospects that are in the market there? And if I've got a hot prospect that I really, you know, want to land, like, I'm going to probably click to dial that. I'm going to do, you know, I'm going to know like it's Jason and Jason's available at this time. And like, I'm not going to try and do 10 calls at the same time.
1:06:21I'm trying to get a hold of Jason, right? Like that's my one shot, you know, and I want to maximize it. You know, power dialing is what we recommend for most folks. And I think we've actually thought about like, should we gate parallel, you know, to - Well, it might be interesting because it's kind of the same throttle that you should have on a sequence. Yeah. Yeah. You know, because like, so So related to parallel dialing, the one thing I wanted to ask you was showing up as spam and the spam risk and like all of that kind of stuff. How does ORAM mitigate for things like that? Yeah, I mean, and that's the beauty of it, too, because, I mean, you know, for all the reasons that I mentioned calling got hard, you know, regulations have changed.
1:07:01You know, again, the phone technology has gotten better. You've got, you know, you don't want to show up as likely spam or telemarketer because I'm definitely not picking that up. Right. And so we actually, you know, have technology that keeps the numbers clean, recycles the numbers regularly, allows people to work through the numbers in the right ways. And that obviously helps you. Right. You know, if you show up from an area code that I usually pick up from and it just shows up as unknown, you know, I may think it's my my vet calling to tell me about my dog or, you know, this or that. And so it's a good way to, you know, kind of find yourself in a conversation.
1:07:32If you call at the right time, you know, because the system says this is the best time to reach, like, it's like your odds just went up, right? You know, I do think call screeners are another one, too, that's just a hot topic. Like, I think, you know, everybody has been, you know, avoiding them since they were rolled out, you know. And I think, you know, it's seen as, like, another reason to say the phone is dead, you know, that we're all going to go to call screeners. And actually, we've seen some really fun stuff with our data. like, you know, over a billion calls have gone through our platform.
1:08:02Yeah. You know, many of them, you know, have been to people with call screeners. We actually, you know, found that if you are willing to put the time in and call those numbers, they actually are likely to pick up. They just want to know what you're calling about. Sometimes they have a higher pickup rate, too. Yep. If you know how to, you know, manage the three to five words that you get. Yeah. You know? Yeah. They actually, that's what we found. And so I think there's this, like, misnomer of, like, people who are like, oh, they've got call screeners set up. Like, I'm going to drop or avoid. And it's like, no, do it.
1:08:30One of our customers had the best point ever is like, you know, if you get good at the call screeners and you understand like how to really establish value quickly here, you know, one, they'll pick up. You got a good chance that's going to happen. So you're not leaving that opportunity untouched there. At a minimum, you know, and I say this about voicemails as well, that's an impression. Like they see the call screener. They see that it was Jason Bay calling, you know, from Outbound Squad, you know. So, you know, you registered with them, you know, a touch point, right? And so just like an email and, you know, a phone call and a LinkedIn message, you know, all those things kind of, you know, lead up to that six, seven touches that we need to get to a conversation.
1:09:10It's a touch point. So again, if you abandon, you lose the value of the touch point there. And, you know, voicemails as well. Like I hear teams say, like, I'm not going to bother to leave a voicemail. I'm a big fan of leaving a voicemail. I actually feel like because they get text transcribed, I'll read it. And if I'm in market for this or if I am, you know, suffering from that pain, then like that's a great opportunity. And again, another impression for you. 100%. We got to run. This was a great conversation. I loved all of the trends around build versus buy, the rev ops stuff, the skill versus AI and where AI is going and centralizing that.
1:09:46We talked about some great pipe gen stuff, the phone, of course. I just have one, you know, kind of rapid fire question, I guess, for you. Because, you know, running a business or a sales team or leading a group of people can be really stressful. I'm curious, what do you typically do to decompress after a long day, long work week? Like, what's that look like for you? Yeah, no, I'm big on this one. And look, it took me a while to figure it out. You know, I think like I grew up in the era of like white knuckling stress, you know, and just, you know, you just, you just, deal with it. And I think like, you know, finding outlets, you know, and protecting those, those, those outlets in time.
1:10:26So I think like one of the things that I, you know, I have in my calendar is, you know, I block workout time, you know, on Tuesdays and Thursdays. And I think like, you know, it was a hard one for me to get to because I think like I have kids, you know, I work a lot, you know, and so I think like, you know, the first thing to get compromised was, you know, you know, my time outside of work and, you know, putting it in there was like just something that like once you do it, commit to it, you know, hold it as sacred. I actually have a funny thing because when I did it, I put it in as CF therapy, which stands for CrossFit therapy.
1:10:57And, you know, for me, it was therapeutic to get out of the office and go like throw some metal around and, you know, do some workouts there. And it is kind of funny. Maybe it's my sense of humor, but I put therapy in there. And I think if you put therapy in there with, you know, people scanning calendars, like no one ever asked about it. No one ever booked over it. Like they just left it alone. And so, you know, it served a unique protection there. But no, I, you know, I went on a walk this morning with someone that I needed to catch up with. Like, you know, I often get asked to grab coffee and I feel like, you know, I'm always thinking about how do I batch things.
1:11:30And so usually I'll say, come meet me at the trail and, you know, I'll bring coffee and, you know, let's get a walk and talk in, you know, a big on sauna and cold plunge. I think you've got to figure out what is your thing and, you know, protect those things. It's a stressful game we're in, and I think if you don't manage those things, it'll eat you alive. So I'm glad you asked that question as well. Yeah. Before we take off, where can people go to connect with you, learn more about Orem? Are you guys hiring? All of that kind of good stuff. Yeah, absolutely. Thank you for the plug there. Yeah.
1:12:01Yeah, John Itell on LinkedIn, please reach out if any of this resonated or if you have questions. We'd love to chat and connect with more of the community. Orem.com, obviously. you know, for, for Worm, if you want to hear more about the technology that we have and, you know, are thinking more about outbound strategies and, uh, yeah, it's, uh, yeah, it's fun to be, you know, I think part of this community and, you know, kind of leading through this, you know, challenging time, it's hard, you know, but I think it's so important to be, you know, consuming content like yours, you know, meeting with leaders.
1:12:31Um, yeah, so hopefully it helps out others as they, you know, kind of, you know, work through these things and hope to, you know, end up in the right spot on the other side.
1:12:43Thank you.
In this episode, Jason and John Eitel from Orum, talk about why top sales teams admit they haven't cracked AI, how to centralize AI through RevOps without hurting rep productivity, why skill still beats tool stack, and the pipegen mix by segment that holds up from high velocity to enterprise.
Check out more free content and get help with outbound at https://outboundsquad.com.