AI-driven email outreach is more than just automation—it’s a game-changer for sales and marketing teams. But how do you deploy AI agents effectively while maintaining compliance, preserving inbox health, and ensuring human alignment?
As any good steward of data, we want to ensure that we’re not putting ourselves in a position where we’re gonna get blacklisted or we’re going to run into challenges of not being able to send emails. And the reason why we do that is is we wanna ensure that the health of that box, that sort of inbox and the integrity is held so we can start to email at larger volume. This is Revenue Makers, the podcast by Sixense investigating successful revenue strategies that pushed companies ahead. Saima, it’s time for another AI episode. Are you excited? Another AI episode. I’ll tell you what. I am excited because this is AI for reals. This is not with a z. For reals with a z. This is for reals because this isn’t any old AI. This is number one is Chris Dutton, who we love and we get to work with every day. But number two, this is the nuts and bolts of starting and scaling an AI program, email agents. And by the way, this sort of master class is coming from somebody who started scaling with AI agents three years ago. So he’s been there back in the day before AI was cool. Yeah. And he has not only been doing it for three years, he’s talking about lessons learned. He is talking about how to crawl, walk, run. So it’s really, really tactical considerations and then a little bit of like, hey. You gotta just do it. Absolutely. So this is Chris Dutton, VP of marketing ops at Six Sends. We work with them every day. Great guy to work with, incredibly talented, and we’re just it’s really a case study in how success has been using AI agents, and Chris brings in a huge wealth of knowledge, background, tips, stuff to get started with. I’m gonna shut up now, and let’s do it. Let’s do it. Chris Sutton. Oh, boy. What does the number twenty five mean to you? Twenty five, that’s gonna be my new goal this year for AI email source pipeline. Alright. Good. That was not what I was gonna say, but my number I was probably kicked off my own show if I said anything. Well, Chris, we wanted to talk about all thing you know, we do so many episodes. And let’s say something a decent amount AI and kind of, like, all these pie in the sky concepts and things that are out there. But, like, we work together every day and huge part here running the MOB’s organization along with, the Mangen, and you kinda eat, sleep, breathe, drink AI email right now via email agents. So this made perfect sense to talk to you and have you on the show. Yeah. I absolutely do. I love it. You know, when Saima asked the question about what does twenty five mean to you, immediately what came to mind was, well, oh, we’re gonna go generate twenty five percent of source pipeline this year. Right? We’re gonna beat last year’s goal of twenty percent. Which is crazy to say. But I guess the first question off the bat and again, we’ve asked many people what an AI email agent, what an email agent is, what AI is. Like, in your mind and we obviously have a specific product that six sense offers. But what is an AI email agent, and what does it do? Yeah. To me, an email AI agent is an agent that allows you to scale your business. Right? It allows you to do things that you may not have been able to do with your current capacity in house. And not only just do, but do well. Right? Have it be complementary to, like, what your team is doing and not act as an independent, you know, channel to go generate meetings. It really should be complementary of of your team and your team’s efforts. That’s that’s really what it means to me, and that is across inbound, outbound, and, you know, other demand gen activations. So if we think about how you started on this path, and you are our VP of marketing operations at six cents, that by definition means you are skeptical. You are, rightly so, you are, skeptical. You are careful. You have compliance and things to, you know, to keep front and center. So when three and a half years ago, you were given this tool and, you know, you were told Dutton, go. How did you even start, and and what sort of considerations did you have to take? Well, we started small. It took us a little bit to get kind of ramped up. You know, we were pressure testing. And quite honestly, like, we were trying to break the AI agents. Like, we wanted to see, like, what we could do to make it fail. We had a lot of feedback for the product team, when we initially started using it. A lot of that has been brought into our agents today. You know, it’s gotten a lot better over the years. But, yeah, I mean, everything that we were doing, you know, we were going into it knowing that we’re assuming some level of risk, and some of that was just the unknown. Right? Like, how are our prospects gonna react? How are we going to do this in a way that does not sort of rub people the wrong way internally and have people think we’re trying to do their jobs or replace them? And then just a new sort of, outbound motion that we hadn’t done before. So, you know, getting that sort of operational foundation in place to make sure we’re GDPR compliant. When people are opting out, we’re making sure, like, those data is carrying back to our CRM reporting. Right? Because, you know, let’s be honest. Like, when we’re running these, you know, Saima, questions I get from you is how much pipeline are we generating? What are we seeing from Compaq? Is it twenty five percent yet? Yeah. Exactly. She’s never happy. More and more. I’m sorry. I need more. But, no, it’s just, you know, putting that reporting structure in place. You know? And, again, all of these things we hadn’t done before. So, yeah, we’re assuming risk and, you know, we’re we were absolutely taking the crawl, walk, run approach, when we were rolling out these agents, you know, three and a half years ago. So what was the first use case? Again, thinking back to minimizing risk and starting small, what was the initial use case, and then how did you build confidence? Yeah. So the actual first use case, the oldest ongoing campaign we have running is and was built back in April of two thousand twenty two, and that is my very own, peer to peer outreach from my very own c dot n AI assistant. So this was the first campaign that we launched going out to fellow demand gen and ops leaders into our ICP accounts that were top of funnel, looking to engaging conversation, asking open end questions, building trust, creating value. Very first campaign that we’ve launched, still going, strong today. We talk about measurement. Right? So short of, obviously, we’re trying to generate pipeline. When you’re thinking about email that’s or agents that are doing work that are qualifying, like, this is a whole new set of metrics. Right? So what where is the focus on or what are the focus of the key numbers? Because again, like, open rates are so, like, you know, ten years ago and really not even effective anymore. Right? Click through and all. Like, what are the key metrics that are helping you and the team? One, it’s like before pipeline, but certainly those are things have to happen before pipeline. But it really measure the health and the efficacy of of some of these programs that the agents are running. Yeah. That’s a good question. So there’s a few things that we’re looking at. Conversion is number one. That is sort of like the Nirvana. Like, what percentage of these conversations are we able to convert into a qualified meeting? Right? We wanna know what that is. The other ones that we’re looking at might be a little bit more nontraditional, but I actually think they’re more impactful. One is unsubscribe rate. And the reason why we look at that is is we want to know if our message is impacting and resonating with our audience. Because a clear indication or a good indication of that is if it’s not, they’re likely going to unsubscribe, and we’re not gonna have that opportunity to be able to reach out to them again. So unsubscribe is one that we look at. And then lastly, bounce rate. This goes back to, you know, not just your email strategy, but more along the lines of also your contact data hygiene strategy. As you’re building out your database, as you’re building out your marketable contacts, making sure you have buying committee represented, You also wanna make sure that you are keeping a clean database and keeping that bounce rate low. So those are the three data points that we tend to focus on. Now that’s not to say we don’t look at opens and clicks. They just don’t carry as much, weight as they used to. And more often than not, they’re just like a boom stat or a vanity metric. So sort of like conversations well, conversion or conversations is the new black Yeah. In terms of just really, like, what are you because it’s it’s much more outcomes based too, right, if you’re measuring that than, like, openings and click rates. Like, that’s great. You know, thirty eight percent of your email rate was open. That’s a huge number. But versus, like, we send these emails out. We got thirty eight responses that turned into a conversation of which turned into a meeting. I mean, again, it just sort of tells a much better story of what you’re actually trying to accomplish as opposed to just, like, I guess, you see the gambit metrics really. Right? Yeah. No. Ab absolutely. And and I’ll kinda double click on that as well as I think it’s also setting expectations ahead of time on what the outcomes of that particular campaign or goals are going to be. We talk a lot about this with our customers. Right? You’ve got your conversion based campaigns, and you’ve got your progression based campaigns. Right? Which campaigns are going to essentially drive pipeline and revenue? Those are your conversions, so more bottom of the funnel types of plays versus your top of funnel plays, which are your progression plays. We wanna look at advancing accounts through the buying stages within six cents. Right? So being very clear on what the goals are and what the expectations are also very important as well as you’re thinking about not just your AI, you know, email agent campaigns, but just, you know, campaigns in general. And given those different types of campaigns, Dutton, what are your if you had to pick three of your favorite sort of agent led campaigns Yeah. What would you say? Oh, that’s a it’s a no brainer. So the first one would be our inbound agent. This is, I think, a play in a campaign that every organization that has an inbound channel should be leveraging. It delivers consistency. The overall experience is far superior because you’re meeting the prospect where they are in their journey. You can likely or most likely reduce your speed to lead time, you know, ultimately providing, like I said, a better overall experience for your for your prospect. The second one is going to be around your six QAs. So as marketers, like, our number one job is to take accounts that are top of funnel and move them to become in market. Right? And that six QA is that outcome of all of those marketing efforts. But the qualified account. A successful qualified account. And QA. Yeah. Yeah. Exactly. And making sure that, you know, you’ve got a mechanism in place that is going to reach out to every single one of those qualified accounts the same way every single time. And then the last one is around engaging your previous lost opportunities from prior quarters. Right? Oftentimes, you know, there are many reasons as to why they didn’t close, some of which we just have no control over. But coming up with a very systematic way to be able to reach out to those and engage the entire buying team, not just the folks that were engaged on those previous opportunities. And I think that was a big moment for us the first time we launched our campaign. We saw personas that were, you know, responding back saying, oh, we didn’t even know we were talking with you all previously. So it was a good way to bring, you know, that team to the table. And it has been one of the our most successful campaigns that we run every quarter. So we got great campaigns. I guess this is a two part question. One, any campaigns that were just I’m gonna say campaigns, more use cases that maybe thought were a great fit and ultimately just kind of fell flat. And then the second opportunities that you saw for them that maybe went a different direction, maybe you went we went into a traditional map campaign or something like that. Like, anything like that that’s been floating around. Yeah. That’s a good question. I always think about where that play should reside and what the best technology we should be using to facilitate that play. This isn’t an this isn’t a scenario where everything we wanna do needs to now go through our email AI agents. Right? We have to look and see what’s the audience size? What are the outcomes? What are the different activations that we wanna be running? So is this a map play? Is this an SCP play? Or are we gonna be leveraging our AI email agents? Right? So I think of, like, intent based nurtures. Like, we had actually talked about leveraging our agents for that, but that just was not a good use case for that particular avenue to go. Right? Map was the better the better avenue for that. The other one that we did, and we’ve done it a couple times, it’s just was a little bit challenging to scale, was, you know, working with reps on and within their particular patch on a set of unique accounts. That worked. But, again, if we wanted to scale that up, that would be a little bit of a challenge because every single one of those scenarios is a little bit unique, and we’d have to essentially go and create, you know, these campaigns and these plays individually. So that one was a little bit of a moment for us as well to say, hey. This worked, but it could we truly scale this, to actually be, you know, impactful for the broader org should we wanna go that route? It it’s an interesting point because maybe when we initially set out creating these email agent campaigns, there was a thought that potentially these could be every seller could have an email AI agent that worked alongside them, and and we quickly kind of moved away from that. How should other ops professionals or teams be thinking about what types of agents to create and Mhmm. How to manage it? Simplicity is your friend. Every agent you add, every workflow you add, every work stream adds an additional layer of complexity, not only from an execution perspective, but also from a reporting and measurement perspective. So those are all things that we’re considering and should be considered when you’re thinking about the approach that you wanna take. Ultimately, where we landed was we wanted to ensure that each segment had a bit of autonomy. So we assigned an AI assistant to each one of the segments. So we didn’t have to necessarily run the same campaign across all three go to market segments. We could use an AI agent for that particular, segment. So it was a good way for us to simplify, have a single work stream be able to report out, but still have a little bit of autonomy within each of those segments. And with AI being a little bit of the wild, wild west, west, right, when you think of all the tools that are out there, how have we, at Sixense in particular, in your in your team, managed the ownership of the agents? Like, it is all centralized within one team really for that purpose. Right? Can you talk a bit about that? Yeah. Yeah. It’s a great question. It has to be owned by your operations team, and that’s really a hard stop. And there’s a lot of reasons for that, but I will highlight a a few kinda captain obvious ones. One is going to be, you know, think about all the other email activations that you have going on. You need to ensure that, you know, from an overlap perspective where you’ve got your agents going, you’ve got your map going, maybe you have other email, streams that are running. You wanna ensure that from an outreach perspective, you’re not having multiple emails go to the same individuals. That’s typically not going to land well. And the other thing as well is is typically your ops team are going to be very connected with all of the key stakeholders within the right functions of the business. Right? So they’re gonna have that sort of understanding of, like, what the business wants to do from a go to market perspective, but then also have the technical know how of that sort of technical tactical type of implementations, you know, being able to work cross functionally with any of the operational teams as well. Alright. So I’m I’m sitting out there right now. I’m a listener. I’m like, alright. AI email. This is the thing. I’m gonna jump in. I’m gonna I’m gonna get something going today. Tomorrow, I’m gonna start getting meetings. But it’s probably not that easy. Right? So what are some of the things, and this, I guess, key considerations or things that are gonna happen or that need to happen rather for an organization to get started. I know this is something that we continue to to work on, and it’s an important metric for anybody that’s doing AI based email. I speak with a lot of customers. And one of the most interesting data points that continuously comes up in my conversations is the types of campaigns that want to be run. And more times than not, the types of campaigns are progression paced campaigns or low intent campaigns with expectations of driving pipeline and meetings and revenue. So the first thing you’ve got to do when you start with any program, you know, using AI or anything for that matter is back to what I said earlier, make sure you’re very clear on what the outcomes are and how you’re communicating those back to your team. So, like, the number one rule, like, if, hey, we wanna start going with email, we wanna start leveraging AI agents, what are those conversion based plays that you wanna run so you can generate pipeline and be able to associate that back to those efforts? Time and time again, it’s, we’re doing booth scan follow-up from all of these leads that came to our booth, and we scanned them. And they took our swag, and they moved on. And our BDRs can’t get meetings, but we’re gonna use our agents to go after them. Well, it doesn’t work like that. Right? The agents aren’t gonna go be able to generate pipeline and conversion, you know, if your humans are aren’t able to, you know, essentially get that done as well. So I think it’s just going about it the, you know, the right way and just being fair and honest with, like, what your desired outcomes are based off of the quality of the audience that you’re reaching out to. Totally. And, you know, when you mentioned even our your three favorite, our top three best performing campaigns, guess what? They weren’t low intent, you know, lead or account follow-up. Right? It really was the inbounds, the the high intent outbounds, and the, opportunities that we’d already been in a sales cycle with from a closed loss perspective. What other considerations should, again, folks listening have you can’t just turn an agent on and expect to appoint a list of twenty thousand leads against it. Like, what how again, you talked about the crawl, walk, run, but there’s a technical aspect to the crawl, walk, run as well. Yeah. Absolutely. And, you know, if we go back to the crawl and we think about what is that that sort of technical component that we’ve got to do is as any good steward of data, we want to ensure that we’re not putting ourselves in a position where we’re gonna get blacklisted or we’re going to run into challenges of not being able to send emails. So we’ve gotta go through what what is called, like, this inbox warming period, where we’re only sending a few emails a day, call it twenty emails a day, and slowly starting to ramp that up. And the reason why we do that is is we want to ensure that the health of that box, that sort of inbox and the integrity is held so we can start to email at larger volumes. Not map volumes. We don’t ever wanna be there, but certainly volumes that would allow you to be effective in these type of outreaches. So, yeah, this is one that, you know, there’s no getting around it. It’s an absolute must. And if done, you know, right and following the rules, it’s gonna, you know, set you up for success. So if you don’t do that, if you I mean, I guess this the what happens? Right? Because there’s something simple as just, like, your your emails are going to spam, but I would imagine there’s something far more damaging that can happen as well. Oh my gosh. Yeah. You get restricted. Your inbox becomes restricted. Right? And you’re not able to send any emails. And you have to go get it unrestricted and go through another warming. But every time that gets restricted, it impacts the integrity of that inbox. So it’s really important to not become restricted. And, a, that’s done by making sure you’re you’re warming it and you’re sticking to, you know, best practices around daily SEN, limits. Yeah. So it is critical to do it, and there are absolutely, you know, negative impacts if you don’t. Yeah. So follow the rules, follow the process, and and scale slowly. What has surprised you in a good way, though? Right? We’ve talked about compliance. We’ve talked about oversight and ownership, but I know you are a, I’m just gonna say it, you’re a nerd when it comes to this sort of stuff. You’re in the platform. You’re reading the emails. You’re looking you’re looking to see I I include myself in that. It’s it’s coming from a place of love. You’re in there, and you’re looking to see what the AI agent is sending and also how it’s replying. What surprised you the most? Yeah. So I’ve got a couple things that I’ll hit on here that has surprised me the most. One, when we talk about just the the quality of the interactions that we’re seeing the AI have, It has absolutely blown me away. We’ve seen our AIs reply with empathy. We’ve seen our AIs reply with just acknowledging the questions that are being asked to the point where we had to go back and look at the thread to determine whether or not our AI had lost its mind talking about Christmas lights. But the reality was is Christmas lights were mentioned in that email correspondence. So just even seeing things like that tells me just how smart and how impactful that AI can be and just how relatable it can also be as well. And I think that’s also important to remember as well as AI has the ability to still feel and act like a human. And when I see empathy and when I see those types of things, like, those are the types of things to me that that really kinda stick out to me as just, you know, like I said, if done well, if done right, it can be really impactful and provide such a positive experience. The other thing as well I would kind of hit on is I absolutely, like, live for art of the possible. When someone tells me, like, something can’t be done, I’m just like, no. Hell no. Like, we’re gonna go do it. We’re gonna crush it. Break it. We’re gonna try. We’re gonna break it, and we’re gonna prove people wrong. And I think we had a lot of reservations around some of the plays that we wanted to run. Look. I mean, Adam, you’re on right now. We told you we were gonna set up our eight our inbound in agent. I think you went, like, all white. Like, you just no. Well, yeah. I mean, I had you know, we have an inbound goal that, you know, it’s it’s on my head, and they take my head if I don’t meet it. So it was like We do take his head. I mean, Simon does she, like, laughs maniacally, and there’s blood splatter. But sorry. That was violent. And so, yeah, I was I was like, oh, really? And what wound up happening was remarkable because, again, like, there’s a was a segment of this of our business that was, you know, high volume, and we gave it off to the AI. There’s certainly human intervention coming in on the other end. And, like, we saw conversion rates just, like, go up and go up significantly. I think it’s your point earlier about speed to lead. Like, speed to lead is that’s never a metric that goes out of style. And the results were to the point where I was like, alright. Why don’t we just doing it all and letting the you know, letting every single inbound at least start with an AI touch. So, yeah, I was definitely yeah. I know. It’s coming. Yeah. Hesitancy is definitely something, but I think people start to see results and they forget very quickly. Yeah. Yeah. I mean, we are a Slack culture. Right? We live and operate by and through Slack. How amazing was it to see our BDRs shouting out our email agents when they were booking their meetings. Like, I never in a million years expected that. Like, there was massive reservations from that team on launching that qualified account outreach to work in parallel with our BDRs working those accounts, and now they’re shouting them out on Slack. That to me was just like, alright. We’ve arrived. We’re here. Like, our agents are certainly going to have an impact, continue to have an impact. And one of the things I didn’t touch on, and I actually just had to confirm this number before before us chatting was we have reduced and and mind you, this was actually not a stat we were measuring. We wanted to generate twenty percent. Right? That was our North Star. That’s where we were laser focused. But when we look at last year, we reduced BDR activities by fifty nine percent from a qualified account to a scheduled meeting. And why that’s so important is because we’ve allowed our BDRs more time to be effective in those things that they’re really freaking good at, which is getting on the phone, hyper personalized emails, using all of that intent data, all of those signals, all of those information within sixth sense, and then also reaching out on LinkedIn. And I don’t think we talk about that enough, but that to me is one of the things that has been really cool to see from our our teams. I feel like we should end on this high note because, yes, the email agents have helped us break company records for pipeline. Right? Two out of the last four months were best ever pipeline months at the company. And so there’s a lot to be said about just how AI can support that. But we promoted more BDRs than ever to AE roles. And and so fewer touches, meaning fewer repetitive touches from BDRs, but more selling. Quality. Yep. And I think the the thing right at the opening when we were saying ask you the question, like, what’s your what do you think an agent is? And you said you went specifically to capacity, but working together and cooperatively. And I think that of all the people on LinkedIn that tell, you know, everyone’s dead, the BDR role is dead, being dead is dead. It’s very much like AI is not coming for the jobs in the sense that AI is coming to make people better. And it’s again, that’s the perfect point. Right? The BDRs can focus on what they’re good at. The AI is doing its thing and they’re working together and now they’re shouting each other out. AI is a career accelerator. It is not a career detractor. It’s not going to prevent you from moving on in your career. It’s gonna help expedite and get you there faster. Love it. Dutton, we have a question that we ask everyone who comes on the show. What is the most ridiculous thing you’ve been asked to do in your career? And, hopefully, I didn’t ask. I was just gonna say it could have been my son. If you would ask me this question, you know, probably right after it happened, I probably wouldn’t have thought it was ridiculous at all. But, you know, because I’m a lot older and wiser, in my years and have had a lot of time to reflect, I would say the craziest thing that I was asked to do was I was a bouncer at one of our corporate parties, and this was eons ago, working the door with a list that was everything was written down on paper, and I had to manage a line of just people that were not all that nice. I can’t even imagine having to do that today or putting anyone in a position to do that that if you’re not a trained professional. There you go. Dutton, if there’s any MOPS professional listening who is looking to dip their toes into email agents, AI for outreach, for working inbounds? Number one, should they? And number two, how should they go about it? Maybe should they reach out to you? Like, what is your advice? Yeah. No. Absolutely. First off, yes. Reach out to me. I am, like I said, very passionate about this, particular topic. Love to have a conversation. But I would also recommend just leaning in. A lot of people have just been talking about AI. I think there’s some some hesitancy perhaps around it. But the reality is is it’s here. It’s here to stay. So we’ve gotta make sure, you know, we’re we’re going about it, a, the right way. But, you know, we’ve gotta we’ve gotta lean in. We’ve gotta understand, you know, what’s out there. What are the potential outcomes? What are the potential impacts? So my recommendation would be lean in, reach out to me if you have any questions. And then lastly, as MOPS professionals, we often struggle sometimes with how can MOPS have an impact on pipeline and revenue. And this is a clear way for marketing operation professionals to have a direct impact on exactly that pipeline and revenue through those efforts that you are ultimately going to be leading. And also to be a truly successful MAS professional, you have to be called by your last name. I think we’ve definitely determined that. It’s it’s a given. That’s how it Thank god that’s my last name. Well, sir, thank you for for hopping on with us. Always a pleasure. Enjoyable. I think great great actionable tips for the folks out there. And we love working with you every day. Likewise. I appreciate the both of you. You’ve been listening to Revenue Makers. Do you have a revenue project you were asked to execute that had wild success? Share your story with us at six cents dot com slash revenue, and we might just ask you to come on the show. And if you don’t wanna miss the next episode, be sure to follow along on your favorite podcast app.
In this episode, Chris Dutton, VP of Marketing Operations at 6sense, breaks down how his team has scaled AI email agents over the past three years, long before AI became mainstream. He shares the key lessons learned, the crawl-walk-run approach to implementation, and how AI enhances rather than replaces BDRs.
Chris unpacks the metrics that matter beyond vanity stats, the campaigns that work (and those that don’t), and the impact of AI on pipeline generation and team efficiency. From reducing BDR workload by 59% to achieving record-breaking pipeline months, this episode is packed with actionable insights on integrating AI into your outbound strategy.
In this episode, you’ll learn:
- How 6sense successfully scaled AI email agents without compromising compliance
- Why AI email agents complement BDR efforts instead of replacing them
- The key metrics that matter when measuring AI-driven outreach
- Best practices for inbox warming, campaign selection, and maintaining email health
Jump into the conversation:
00:00 Introducing Chris Dutton and the AI email revolution
02:16 The importance of AI agents in scaling outreach
04:48 How 6sense started with AI email agents—cautiously
07:24 Key metrics for success beyond open and click rates
10:29 The three most effective AI email agent campaigns
12:48 Common pitfalls and when not to use AI for outreach
15:42 How 6sense centralizes AI ownership and ensures compliance
18:20 The technical crawl-walk-run approach to AI email implementation
22:03 Surprising AI interactions: empathy, engagement, and success stories
The 6sense Team
6sense helps B2B organizations achieve predictable revenue growth by putting the power of AI, big data, and machine learning behind every member of the revenue team.