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Episode · Mar 26, 2025

Cold email is dead — unless you do this. Harris Kenny on what replaces it.

Outbound is breaking for the same teams that made it work two years ago. Harris Kenny (CEO, Outbound Sync) walks through why volume-first outbound dies in 2025 — and the trigger-event motion that replaces it.

Discussed in this episode

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Welcome back to another episode of Bridge the Gap powered by Revenue Reimagined. We have Harris Kenny with us today, who is the founder of Outbound Sync. I think it's a super cool tool because it solves a problem that I'm dealing with right now: how do you attribute revenue, sync activities, manage block lists from tools like SmartLead and Instantly that do outbound at scale that don't historically tie back to your CRM?

Prior to that, Harris ran a Gold Tier HubSpot Solutions Partner agency. We could certainly talk about that because we do that as well. He was one of the first Clay experts and spent past life scaling hardware companies and selling ERP consulting. Man, you've done a little bit of everything. Welcome to the show.

Thanks. Great to be here. Yeah, I bounced around. It took me some time to figure out what I'm doing, but I'm also not young, so that helps.

All right. I mean, Dale's old. I mean, you're not young. I'm not young. Dale's old. It's definitely true. Although now that I shaved my beard off, I'm a little bit younger. But well, if you—I mean, one of our clients did send me a Slack yesterday being like, "Oh my god, Dale looks so young without his beard." True story.

That's great. Well, if you follow Brian Johnson, you know, maybe we can extend our lives a bit here. We'll see how it goes.

Yeah. Second person this week to tell us about that. True story.

Yeah. Yeah. I follow Brian a little bit. Adam's like, "Who is that?" So we're trying to get Adam into the 21st century on taking care of himself, but we'll see how that progresses. Jim, every morning, man. Harris, you know, one of the things—one of the big things that we've always been struggling with and actually the market's struggling with—is like outbound at scale or top of funnel or any of these things that we talk through. And it's a problem that you're trying to help solve with partnerships like Instantly, SmartLead, et cetera. Where should people be starting to think about outbound at scale? Is it as they're building? Is it after product-market fit? Where is it in the lifecycle of building an organization?

Yeah. Well, I think where we're at—so a little bit about Outbound Sync. We've got hundreds of companies using our product now. We've synced tens of millions of records. So we do have some visibility into where we're seeing things working.

And I do think about this. I split this in my head of: are you working with an agency or not? Because if you're working with an agency, it's going to fundamentally change the types of plays you can run and what you can do with the data and frankly how quickly you can move versus if you're a direct team. And the types of resources and the types of people required to be successful.

Why do you split it that way? Why do you think about it that way?

Well, I mean, we just see a really big difference on our side—the amount of time it takes for a team to move forward, for example. We have a company we've been talking to. I don't want to name them here. I'll just say they're using a conventional sequencer and they're like, "Look, we're landing in spam. We know we need multiple domains. We know that Instantly solves this problem for that." They liked Instantly for their use case. We know Instantly solved this problem for us. Problem is we went to go cancel our contract and they autorenewed us automatically, right? So you have these variety of things that a traditional team has in place.

Now in this situation, they have a really strong internal person. I would say that is the X factor of like: do you have an internal person that themselves can drive this entire conversation across the internal org around like, "Hey, here's the problem"? They need to be able to pick up and learn really quickly about deliverability and these other things and have the kind of guts to be like, "What we're doing right now is not working. I'm going to be the one to say it out loud."

You know, and then they have to do the research and they have to find—there's a lot they have to be able to do. And then if you're working with an agency, it's not the agency themselves—they bring a lot of skills, but also the decision to hire an agency seems to suggest that a decision has been made, a commitment has been made: let's bring in someone to solve this. And so we just find that companies that do that are able to get stuff off the ground faster. I'm not saying it's better or worse, but so then the question of like, at what stage do companies do this kind of outbound that starts to affect it—because if you're working with an agency and you have a really clear goal of like, "I want to test my positioning or I want to test a couple different ways"—then you can do it earlier with different expectations. But if you want pipeline generated, yeah, there's some traction, there's some offers—you have to know what to put into Clay to get the right lists, you know, the numbers to dial. And then you do validation, you do have reps that can do calling. It's definitely becoming a game for companies with more resources, I think.

So I think what I'm hearing you say is like the agency model will just get you there faster, more efficiently, more effectively versus if you're doing it internally, it's almost like a side project. It's like, "Okay, do all your other work and then by the way, we also have to figure this out on a scale-type motion."

Yep. So it's a matter of—and I say this a lot with sales and marketing like: salespeople can help you generate awareness outside but it could take you 12 to 18 months to do that where marketing may take you 6 months. And I think that analogy is probably the same as like, if I brought an agency in, because they do this all the time they know all the modifications, because things are changing so quickly right? It's like just because it worked today, a month from now whatever you did today is not really going to be working. And you guys are on top of that all the time.

Yep. Yeah. I think the side project analogy is exactly right. Because that's what I mean. I look, I get an email at 8 o'clock from head of sales, an email at 8 o'clock at night being like, "Okay, I did a bunch of research about how to set up domains. Can you tell me about DKIM?" And it's like you obviously just put your kids to bed. I know because I just did the same thing, right? And now we're getting online for our second shift. So I think the side gig analogy is exactly right. Our second shift.

That's funny.

Does outbound at scale work? And let me piggyback off that for a second. So there's a gazillion AI tools out there, right? There's a gazillion agencies out there all claiming, "We could enrich everything amazingly through Clay and like we're going to get you this great data," but you're still going to send out 10,000 emails and you're going to get a 1% response rate. Like, is outbound at scale worth investing in? And I understand you're a little biased based on your product, but like, does it work? And if so, where?

Yeah. Well, I would say with our product, sometimes customers use our product to disprove that, you know, to say, "Oh, outbound is not working." And that's okay, too, right? I mean, our—my core belief is as long as they pay the subscription, I don't particularly care what they use it for, right?

Right.

And that's part of why we're going to be looking at moving it, supporting other channels, because it's like, well, maybe email isn't working or maybe this, you know, and so it's like, "Okay, what about LinkedIn? What about phones?" But I mean, like our core—my core thesis has been like, "Look, this—we had the early sequencers for whatever five to seven years and Outreach created the category I think, and Salesoft and these other players. But that—like one rep in one seat with that—one ZoomInfo seat and they have one sequence with one domain with one CRM seat—that era is over basically. I'm not saying that people aren't continuing to use all of those tools, but the use case is different than it was before.

And so the question is like, what is this new? What is different now? And when people switched to different tools to get deliverability edge or to get different, better data, maybe more segmented custom data with Clay, there is still this phone home problem. And so I think the main thing that we're trying to solve right now is that people chose new tools to get an edge, but then those new tools on the edge don't phone home. And so they can't say confidently whether it's working or not.

And even like, what is success? Is it positive reply right away? What if outbound influences a lead that converts through another channel like paid ads? Does that count? Does the outbound get credit for that? Well, we don't know because there's no record that we emailed them in the first place. So that's kind of where I think where we sit where the market is.

Is. I think the market's very, it's very early in a lot of ways for these new tools in my opinion. So I hear you, and I hear everything you're saying and I agree with you. But where does outbound at scale work and where doesn't it? Like I'm looking for a very, very definitive answer. Like I'm a Series A or Series B or Series C or I have three BDRs. She thinks I'm talking to her and I'm not. Um, where does outbound at scale work? And to piggyback Harris, I love that you said we could use to prove that it doesn't because I'm a big believer there's places where it doesn't and you have to be able to track the activity to know that it doesn't. Well, I can give some examples of people that are real companies that I see in Slack that are booking meetings right now. You don't even have to name them. Yeah. Yeah, I won't name them because I can't.

I understand. But like, okay, there are types of products where customers are repeat buyers. So there's a company that does well, they've talked about this publicly so I can say this publicly, an agency that we work with called C7. They work with a merch company called Jamo. And so Jamo is a little different because they have really, really high quality merch. Like if you want to buy merch, most of the companies like it's really cheap and it's flimsy and it's hard to get good stuff. And so they take a more of a higher value approach. And so what C7 did was they developed a really good offer. So okay, so like ingredient one of why this is working is that companies are repeatedly buying merch. So if they're not buying it right now, they might be buying it in three months, right? So that is like a prerequisite to this being a thing. There's an acknowledgement of a problem. There's typically a set aside budget. They're kind of in motion. There's a little bit of friction because they've got a commitment to maybe a certain vendor and they've got a preconfigured shirt design with an existing shirt printer. So okay, we got to get them to consider doing something else besides clicking the reorder button. And so what they did was they developed a good offer and the offer was we'll develop, our designers will develop for you a custom, they call them jams but like some custom looks basically with some of our higher quality merch, some of our fleeces and things like that. If you're game, like I can send it to you and you let me know if it looks cool and it's like a very, very low-risk offer. And so they are crushing it on that campaign. I mean they're booking a ton of meetings and it's extremely successful for them because it's something compelling. People like to see their brand used in different ways. A lot of times the person that's designing the shirts and ordering the shirts, like they're looking for new ideas on how to do things and they want to keep it fresh. They don't want to just do the logo with like the founder designed version of merch, which is like the logo is like 300x blown up on the front of the shirt and that's the whole shirt. So that's one example where I can tell you for a fact that's winning.

So yeah, we can go through some more. Other people that I'm seeing winning are that are combining multiple channels. So they're using paid ads plus email or they're using phone plus LinkedIn touches and things like that to find the right channel for the right person because not everyone. What you just said is key though, it's not just email and I tell this to everyone. Outbound at scale, I think has its place. There is a place for brand awareness. I'm also a big believer the goal of any campaign is to book a meeting, right? It's to get a response. Yes or no, to get a response and ultimately to book that meeting. And I'm super curious your thoughts on this. If you go outbound at scale and we're going to email 10,000 people and hope that we're going to get great response rates and they're going to book a meeting and all we're going to do is email them, you're going to be, pardon my French, fucked. If we do outbound at scale and couple that with a multi-channel approach and we add in phone calls, we add in LinkedIn and we make sure that those emails are high value, that's where I think your outbound at scale has its place. But if you are just outbounding, barring very few niche industries, do I think people are going to be like, "Holy Harris, I have been waiting for your email for the past three months of my life. The timing is perfect that you sent this and I cannot wait to get on the phone with you." No.

Well, so okay, let me drive a bus through that. I agree, but let me drive a bus through that except niche industries thing because I do think there are a lot of industries and I will also say like geographic markets where the recipients are less, let's just say cynical, maybe or less like fatigued with outreach where we do have agencies that are using alternative data provider sources like scraping Google Maps directly and going to other places, state scraping like public databases of business registrations and different types of like liquor tax registration, restaurant, whatever things like that where they are succeeding with single channel. But like others, you know, we have a customer that where they saw the contractors and a lot of those contractors like they don't even have websites at all, you know, and they're using a Gmail address kind of thing. But then if you find him on Angie's List, you see, oh, actually this is a very good roofing company that has tons of reviews and they could totally use this product. So yeah, I mean I think that specialized industry, like what does that mean? That can also mean different geographic markets. I know that we have some agency partners in Europe who are absolutely printing money because they're sending their cold emails in Dutch to people that speak Dutch and it's like you turn back the clock and it's like it's 2016 and people are like, "Hey, oh my gosh, like thanks for emailing me. This is great." They are treating you like that because they don't ever get emails like that. So it's like the future is here but it's just not evenly distributed.

So it works outside of B2B tech.

Yeah, definitely. Oh, definitely. And Dale, I know you're like, "Fuck, dude. Let me talk." But that's another thing that I don't think people realize. We work with a lot of tech companies. We talk to a lot of tech companies who see email at scale every day, who see 100 cold calls every day. There's lots of industries out there. Even LinkedIn is the same thing where none of this exists. This is so novel to them that people do respond.

Now, I'll let Dale speak. Thanks for getting my coffee this morning, man.

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I think it's more, I think it's like beyond that as well. It's like back to fundamentals and sales. Where do your buyers live?

Yeah. And if they live in a place like, we're working with a client that's in the construction industry as well and they, you'll get them on the phone much faster than you get them on email because they'll be on job sites or you know they'll be in the middle of something. So you can send as many emails as you want at that point but it may be a supplemental piece. So as you're going through, calling them, calling them, then sending an email versus like email first then call. So it's all about where the buyers live in the space.

Um, I want to switch topics a little bit here. So what was the pre, like why'd you say like let's build out Bound to Sync? What are the first three things when you were kind of like building out the foundational elements of your business that you found challenging that now you can like say good, I kind of put a bow on that and now I can move forward off of it?

Well, the first thing, I was running a HubSpot agency which we could talk about. Really was having a great experience being a HubSpot partner program and we were also doing outbound because I was originally doing outbound and then we had these clients that were also using HubSpot and I decided okay, well why don't we, why don't I join HubSpot partner program too. And so originally I was doing sales consulting. Like back in April 2019 I went out on my own and we had clients who were asking hey, can you get this outbound data? Like sort of like duh, can you get...

This outbound data into HubSpot actually, and I was like, "Oh, that's a great question. Currently, no, I can't."

So the first question was: does anybody want that? Do people want the outbound data inside of their CRM or not? Because at the time, none of these tools had any integrations. Even now, a couple of them have introduced some very basic ones, but nothing like what we've built, because this is all we do. So we better make it better, otherwise what business are we doing?

We started to get requests of people being like, "Hey, I don't want your agency services. I just want the app." So that was kind of like that first checkbox, like okay, yeah, I think there's room for this.

And then I think the second big question was: okay, but how are bigger companies willing to use these new tools? And at the time, two years ago, that was not clear. None of these tools had SOC 2 Type 2. A lot of companies denied that this was even an issue. They were like, "We're landing in the primary. We're landing in the inbox just fine. What are you talking about?"

I believed, because of a couple of early calls that we had, that it would happen and that the midmarket would move in this direction, but that at the time was very unclear. Now that is definitely the case. We have some really great customers. We have quite a few Series D companies who are using our product. That growth hacking movement has gone mainstream, I think. So those were probably two of the big ones.

And then I think the third question was: okay, people agree they want the data in the system of record—they want it in HubSpot or Salesforce—but then what are they going to do with it? I think we are still in the process of getting better and better at identifying workflows and automation, how to set up call tasks, how to set up revenue attribution reports. That, I think, is going to be the long-term project: how do we help, and maybe the scary part is, how do we get too much data? Do we have too much data? How do we manage all this data? Is there a use for the data? So that's an interesting challenge.

Oh, definitely. Well, and I think tied into that, it's like what we're starting to see in the past three weeks or month—I've had three different people ask me about sending this data to Snowflake. So which to me is like, "Holy enterprise. There's a name I haven't heard in a long time."

You know, and so it's like, are we sending too much or are we not sending enough? Because what they're considering is like a CDP almost. They're like, "We're running tons and tons of paid ads and impressions. We've got an insane amount of data, and we want even more. We have this voracious appetite to push everything into a data warehouse, and then from there we'll take care of sending it where it needs to go."

And so on the one hand, you've got the CRM where it's like, "Okay, the CRM is sacred. We don't want to push too much in here." But then there's this other conversation of, "Okay, but what if every single data point is something that we want to capture?" So I don't know where that's going to go. It's only come up a couple times, but it's already kind of giving me that feeling that there's more there. It just feels exactly like, well, then you could just aggregate the data outside of the CRM and then only push in the calculations, the things you really want into the CRM, versus the raw data. The raw data is an interesting position for people that have a data warehouse—the question is, do we push it into a place where we aggregate it and give you the right data points versus having to aggregate it inside the CRM?

I think it's still pretty early days. And this is why I'm such a believer in agencies. This stuff is super complicated. Anything that's complicated enough, you've got someone to help you think through it, no matter what it is in life, you know what I mean? That's why I'm a big believer. Some people are skeptics of agencies in the space. They say, "Oh, agencies are going to die, or this type of agency work is going to die." I've seen some software companies be like, "We use agencies for our early validation, but now we're moving upmarket. We're moving on." And I fundamentally disagree with that. I do not think agencies are going anywhere. Sure, it'll change. Well, that's good to know. I really believe that. It's a huge part of our business model and it's a huge core belief of mine. I don't think it's just—this stuff is too hard. Sorry, you know, nobody has enough time to learn it like an agency does in my opinion.

It can't be a side project.

No. Yeah, it can't be a side project. You just don't have time for it. It's too fundamental to a go-to-market strategy.

But how does AI affect that? We were just talking to someone the other day who—an agency owner, for lack of better terms—who very much believes that agencies are going to be out of a job in the next three years because AI is going to build the playbooks and do this and do that. I have my opinion, which we could talk about in a second, but does AI affect anything that you're saying as the next two to three years goes on?

Yeah, sure. I mean, I'll take the other side of that bet. I'll bet against that for sure. I think maybe this is a hot take or not, but in a year from now, I think if you look at the org chart of an organization, the number of people in sales, revenue, and go-to-market roles, I think that number will be lower. But I think spend per person will be higher. It's possible that there will be fewer agencies or that the average agency has fewer employees. Sure, AI is huge. We use it all the time. I was playing around with O1—the reasoning model—where it does deep research. It was really awesome. This weekend I went on a long walk and I asked it a question. It was going and doing research and it was building it. It's really cool. But you still have to know the questions to ask and how to put it together. I don't think AI is going to fundamentally disrupt the existence of agencies, but I do think it'll change them. They'll be smaller, spend will be higher. The expectations will be higher.

What do you guys think? You run an agency. How do you see it affecting your business?

I think the expectations are already higher. When we started, we started with "we're operators, not consultants." Those days are gone. Two years ago, you could be a consultant and hand someone a pretty slide deck and people were very happy to pay you tens of thousands of dollars for it. I think that's done.

AI is going to help with things like how do I build a really complex workflow? ChatGPT can tell me that, and if you're relatively intelligent, you can follow the steps and build your workflow and it's going to get you 90% there. When it comes to things like how do I develop a comprehensive outbound motion? How do I get the right copy and the right systems and the right reporting? How do I build a go-to-market motion? How do I define my ICP? ChatGPT will tell you how to build an ICP. I don't think it tells you how to do it correctly, but it will. You still need someone to execute. Our moat isn't that we have the knowledge to tell you what to do. Our moat is that we can execute and show you how to do it because ChatGPT can tell you what you need, but not how to do it the right way.

And I'll go a step further. I think the second part of that moat is like it's going to be wrong the first time you build it. You're going to have to iterate on it based on feedback from the market, feedback from internal stakeholders, feedback from the market. This thought process—the market is never going to fail. They'll tell you whether they think your value proposition is the best or not. If you believe that you have some impact on people and people are like, "Nope, I don't like that impact," guess what? You're wrong. So you've got to take all that back into account and put it back into the mix.

Then come up with a new ICP or a new value proposition or ask the next question. Like when you have kids, you're like, the kids are like the three W's: "Do this." "Why?" "Because I said so." "Why?" "Because..." And like, finally you get to the real reason on why you want someone to do something. So that is in my mind where the agency world or the consulting or the operations world is going to be.

And it's as simple as like, we're working with a founder right now who's going through a funding exercise. Yes, you could go ask ChatGPT. We were talking about CAC and LTV and a bunch of stuff—yes, you can go ask ChatGPT what does that look like. But then you got to go build it in HubSpot or wherever you're going to do. You're going to look at what the iteration actually ends up looking like, and then you're going to modify it based on, look, we only have four records. That's not enough data points for you to get back to an investor. Maybe we need a data set of 10 to 20, so maybe we need to open things up. It's just that critical thinking of the plus one and not the initial conversation that I think will be the value.

Yeah, I agree with that. And I'll say, like, so we're talking about the nuance, right? This is where things get complicated. I think it's going to be like a little bit of a throwback to the system integrator from the earlier days. It's like, look, this is really complicated. And you start talking about things like, okay, why does this matter for maintenance and long-term? Okay, fine, let's say it works. Let's say your sales team doubles, and then someone wants to know, like, why this one random property in HubSpot keeps changing, and you're like, "I don't know. Let's go troubleshoot the workflow," and they're like, "Okay, well, the naming convention is just called, you know, 'Untitled Workflow 2021-01-01' or whatever." You know what I mean? So that's where I think, you know, you mean you should have a naming convention for your workflows? No, yeah. So you're going to start having GTM tech debt basically. You have people that, if they don't have enough background and experience, if they haven't done this and made the mistakes enough times, they're going to be creating tech debt for the go-to-market organization basically, where someone's going to have to come in and unwind this stuff and figure out what the heck is going on. And why did we give right access to Make and Zapier and Naden and Clay? And then you have these race condition problems where these different low code things are competing with each other, you know? So the complexity can really get difficult quickly. And again, to me, these are spaces why you bring expertise. And also sometimes it's wrong. I have spent time just, like, for no reason, just for my own, like, getting out my frustration, getting back at GPT and being like, "This workflow action doesn't exist. Stop telling me to do it. It's not real. It's not in HubSpot. You're completely hallucinating this."

I've run across that a couple times.

So that's like, let's say you can get past all of that, and let's say you still have this problem of how you're designing these systems. And I think, to your point Dale, it's like, okay, but then are you bringing some unique novel idea? And it's that listening to the customer. And it's a new company who's raising money. Fundamentally, they're going to do something new. You're raising money because you believe something is going to change in the market in the next five years, and that's why you're raising money to go build that business. So something that's built and defined by the past is not going to be able to as effectively break that deck with you and tell you what metrics are really going to matter.

Yeah, like I love AI. I use it all the time. But I don't think I don't think some of this stuff is going to change or is really meaningfully going to go away.

So what does the future hold for go-to-market, for outbound, specifically for top of funnel? What's the future hold? Let's talk next six months. What are you seeing? Because you work with so many companies who are really top-of-funnel focused right now. And I would argue everyone's top-of-funnel focused right now. It's the number one problem we hear.

Yeah, I mean, I think that in a word, it's specialization. Like, we're seeing people really specializing in these different channels and the best way to do it. It's like we're not just making phone calls anymore. We've got multiple layers of validation, and we're finding we're calling people with a high propensity to respond. And then for those, we use a power dialer. And then for these other lists, we're using a parallel dialer. To me, in every single area, you're going to get more and more specialization in order to get that delta, to get that return.

So I think most of the market is behind. I think that the next, I think for people that are behind, I think they've got catching up to do. You know, if they're still like, "What's Clay?" they've got some catching up to do. And then I think for the people that are ahead, I think the next six months are going to be less interesting than the last six months because they're ahead, they're getting bigger and bigger clients. And I'm seeing companies with 1,500 employees and stuff like that are now saying, "All right, you know, let's set up a smart lead."

Um, the next like six months of meetings are going to be like with this CRM administrator being like, "Okay, so it's really important for our data hygiene that we have the territory mapped, you know?" And whereas they're used to just gripping and ripping—"Hey, I got a list, boom, we're sending, replies are coming into Slack, let me know if you have any questions"—now it's going to be like, "Whoa, whoa, whoa, whoa, whoa. We need this, this, this, this done. These are our requirements, sir." So I think it's like a good thing. It means it's more money. It's working with bigger companies that have bigger problems. But so to me, that's like a tale of two levels of adoption. The winners, growing up—um, you know, are like having to, like, not grow up. That's like condescending, but having to like slow down. I should say.

I'm condescending all the time apparently.

So you're good. Don't worry about it. Winners having to slow down basically. And then for the laggards, just definitely needing to catch up and just kind of get up to speed. Because I think, yeah, I mean, stuff's just going to stop working. It's going to be like pushing a rope. And so, you know, you can solve that a lot of ways. You don't need to use our product. You don't need to use, you know, work with Revenue Reimagine, whatever. There's a million ways to do it, but it's not going to work. Some of these things just are going to completely stop working at some point. That's what I think.

Yeah, it's an interesting time, man. It's an interesting time. Um, thank you for sharing. Thank you for your knowledge. I love what y'all are doing. I've seen the product be used. We're using it at some clients. I'm excited to see what the future holds for you.

Let's, before we depart, as we wrap up, let's jump into some rapid fire here. Um, when you look at the go-to-market gap—stabilization, foundation, repeatability, scalability—what in your mind is the number one thing you need to move from stabilization to foundation?

Um, well, I have—I'm going to faint a little ignorance here. Help me understand this model a little better.

Yeah, just differently, what needs to be fixed? So when we come into companies, a lot of times they don't know what's working and what's not, and we have to come in and stabilize it, right? Any company needs to be stabilized before you start rebuilding that foundation. What is the number one thing that you think needs to be fixed before you could rebuild?

I think people are focusing on the wrong metrics. I think like for most organizations that are before they're ready to lay the new foundation, they're still talking about like open rates and stuff like that. And so it's like, listen, the dashboard—if you're on that previous model, the dashboard you're looking at, we're probably going to delete like at least half of it basically. And the numbers that you're used to looking at, like we're going to have to stop looking at those. I think that's like the first step.

Not alignment on that, then probably not going to get anywhere. Love it, 100%. So one of the things that we're looking at a lot is how often you should revisit those go-to-market foundations—ICP, buying persona, value propositions. How often do you think you should be revisiting those or pressure testing them at least to make sure you're in the right realm?

Yeah, I mean, if you look at like Octave by Zack Vividor, it's a really interesting software company. We know Zack well. I spoke with him for an hour yesterday.

Okay, there you go. There you go. Hopefully you were nice to him. He's a nice guy.

He's always Zack's great. We're a partner.

Okay, there you go. Adam's just condescending to everybody.

Everyone named Dan. So this was not coordinated at all, but that's great to hear. So I think if you talk to like a Zack, you'd say yeah, continuously we need feedback loops on this and we need to be looking at it and looking at changes in the market. I think if you're not doing that, defining a cadence that's sustainable for your organization—whether that's monthly or quarterly or something like that—but it's definitely not a set-it-and-forget-it kind of thing.

That's not it. Okay, cool. I think quarterly is probably the right place for most people right now. But that's a lot. I mean, that's a huge change versus a deck that marketing gave sales three years ago.

A year ago.

Two years ago.

Three. I'm working with a client now where the deck is six and a half years old. True story.

Harris, early bird or night owl?

Both, unfortunately. We have young kids.

First app you check when you wake up in the morning?

Slack.

Adam too. Interesting. No, my first app is Aura.

Favorite guilty pleasure snack?

We talked about Brian Johnson. He's got this cocoa powder. I have that in the afternoons. It's like a little hot chocolate kind of thing with a Blueprint cocoa powder.

Cool. Last one: dream vacation destination?

Right now, the one that we're talking about a lot is New Zealand. I've been doing Lord of the Rings—I've been telling Lord of the Rings to our four-year-old, and she's like obsessed with it. It's our fifth time through the whole series, and so we talk about Ring story all the time. She asks me questions about Gandalf and stuff. So that's our dream. And I've wanted to go to New Zealand for a long time, so I'm going to say that one.

Cool. Definitely on my list as well. I've heard that's a very bumpy flight, but that's a whole separate conversation.

Over the ocean.

Yeah, big water.

Yeah, big water. Listen, any flight these days that lands successfully is a good day. I say that getting on an airplane first thing tomorrow morning.

Harris, thank you for joining us, man. Everyone, go check out Outbound Sync. Find Harris on LinkedIn. And thanks for joining the show.

Thank you, guys. I really appreciate what you're doing. This is great.

Thanks.