Aligning Sales and Marketing with Data, AI, and Automation

Gerhard, Scott, and Dennis discuss aligning sales and marketing through data and AI. Scott emphasizes strategy should be 70-80% of marketing work. One campaign mined buying signals from SugarCRM, sent wine to prospects, and generated $350k pipeline from a $10k spend in two weeks.
Questions this video answers
April 11, 2025.
About 15 books (over ~10 years).
Approximately 70–80% strategy.
Four (working toward five).
About 75% connection rate.
Chapters
I want to make an observation. This is a rare occasion where we have sales and marketing in the same room.
And they're not fighting.
They'Re not living in their silos.
So why don't you. We start with you, Scott. What is a fun fact about you that is not in your LinkedIn profile?
Well, not in my LinkedIn profile, but it's buried in my LinkedIn profile. But outside of work, I love writing, I love history. And so I've published over the last 10 or so years, about 15 books on many aspects of military history. Um, so, yeah, it's a hobby that keeps me, keeps me out of trouble in the evenings. So. So, yeah, that's a. I don't know if it's fun. Fun to some people, boring to others, but yeah, that's, that's a fact for me.
And judging by your accent, you're in the middle of England. Somewhere in Leeds.
Not Leeds, I'm towards the south. But yes, I'm definitely in England. It's. And it's sunny, it's not raining. Makes a change. So we're happy about that.
And you love soccer.
I love. You can call it soccer. Yes. Association football. Absolutely. Right, yes.
So since you wrote 15 books about military history, you obviously, I would assume that, that you a fan of strategy.
I am a fan of strategy, actually. It underpins. Without stretch, you got nothing. Right. So, yes, big, big proponent of strategy. I class myself as a. Over the years, I've become, you know, more of a thinker. You know, I like to think things through slowly. Well, not slowly, but, you know, completely. But yes, strategy. As I say, without strategy, you've got nothing. So it's super important.
So what, what would be your estimate? What percentage of marketing is about strategy and what percentage is about tactics?
Good question. I would say the thing is you can have, you know, you can have the, the, the, the best thought through campaign, you can have the most beautifully written email or the, you know, the most colorful website or the, the most creative kind of trade show booth. If you're, if, if you're unsure of who your target audience is, if you're unsure of what your story is and how relevant you. You are to your target audience thing, it's all wasted. So I would say, you know, it's 70, 80% strategy. You've got to know, you got to know who you are as an organization. You got to know what your story is, you've got to be comfortable telling your story and you got to, you got to understand.
Who is your story relevant for. Okay. And you know, that's the strategic piece you got to get right. You got to get all that right, and then everything will. It becomes much easier to get the right tactics in place, and you become. It's much easier to become relevant. You know, relevance, relevancy is the key to marketing success. And, you know, it's what differentiates a spam email to. To an email that people action and click through and engage with. Right. Is whether you are resonating and being relevant to the recipient. So strategy is how you become relevant.
Awesome. Dennis, fun fact about you.
I guess I'm an avid juggler.
Takes my mind off a lot of things sometimes.
How many. How many balls can you keep in the air?
I can keep four in the air. Five. Yeah. Five seems to be something that my brain can't process yet, but I continue to. To try. I find it's almost a good meditative routine to kind of calm your brain out because you can't really think or do much else while you got four balls in the air. And juggling a sales team is. Is much like keeping four balls in the air often. So, you know, it gives you a moment to clear your head either before a presentation like this or post one to kind of get your heart rate down and get a singular thought in your head for a bit.
It improves your ability to focus, definitely, that.
I taught myself how to juggle at like two in the morning on a beach in Nice with those little flat rocks where it just sat there and kept going, kept going, kept going. We're waiting for a hostel to let us in the following morning. And that's where it took off from some 30 years ago.
And you started with three around the clock or crosswise?
Three around the clock. And then, you know, everything else comes in line.
That's awesome.
So I think the most interesting thing about that for me is that it always looks like, difficult if you've never done it before, but it's really just a learned event. So, you know, it's a. It's. If you spend time doing it, you can learn. Anybody can.
But also it. It shifts the brain from a sequential mode into a mode where you have to be 100% in the moment.
Yep, exactly.
So same question percentage wise, sales. As a sales leader, what percentage is devoted to strategy versus tactics?
I think Mike Tyson said it best that, like, everybody has a strategy till you get punched in the face. You know, from a. You know, being in sales, you're on the front line, and so, you know, you need to work with your marketing team. To get you in the room and help you stay relevant in the market. But you have to be able to be fluid in that room. So you're gonna get hit with curve balls when you walk in and somebody who may not be your evangelist is trying to snip at you for something else. And being able to stay fluid in that moment, but also listen and be of value, I think is the most important part. So from a strategy perspective, you have to be prepared, you have to be willing to execute, but you also have to be able to pivot to an alternative strategy right in the moment of interaction in front of a prospect. So depending on what you're doing, you know, you have to have multiple strategies go in the room, all pointing hopefully to the same outcome. But being able to pivot quickly I think is inherent success to any salesperson.
So would you say if you can juggle curveballs, you got it made?
I'm still working, so it's not that made. But from a, you know, I think it definitely helps to, to relieve the pressure.
Right. So I remember doing a, a panel discussion actually in San Francisco between a. Of sales and the, and the VP of marketing. And this is a very similar situation. And in that case they literally could complete the. Each other's sentences because they were so aligned. And Scott, when it, when it comes to misalignment between sales and marketing.
What is the cause of that and what is the promise with AI? Is there a way out so in the future we not going to talk about this anymore?
Great question. I think.
Misalignment isn't done on purpose. We're not sitting here as a marketing team going, yeah, if we do this, we're going really get on Dennis's nerves by doing this. You know, it is not done on purpose. It is, it's mostly if you, if you analyze a lot of the stuff, it's either miss or poor communication. It's nothing more complicated than that really. You know, it could be clunky handovers, it could be incomplete data or whatever, or slow follow ups because they didn't have the right information or whatever. But you know, it's. Yeah, it's, it's communication that underpins most of it.
And from an AI point of view, I think we're already seeing how AI is kind of slowly moving in, in different tools and in different kind of.
Different kind of versions to, to smooth over some of these friction points. You know, I'll give you an example if I can. So let's say one of Dennis's team comes off A prospect call, really good call. 30 minutes, managed to get loads of insight from the prospect. You know, understanding pain points, understanding strategic direction the company wants to go through, competitive layout, the buying group, the hopes and dreams of the organization comes off that call and that person's got, got a choice, right? You got to spend the next 20, 30 minutes trying to remember all the ins and outs of that conversation and then manually type up into the, into the CRM or whatever system you use or, and this is probably more likely you're bouncing to the next call, you're bouncing to the next meeting. Dennis has probably got you in a QBR or a one to one review or some kind of pipeline review call or something like that, right?
And then.
You'Re doing that kind of data entry at the end of the day with four other calls, summaries you've got to put in. It's not scalable, it's not enjoyable and information is going to fall through the cracks, right? But now, and we're already seeing this, right? AI summaries, you know, auto summer summarizations.
These technologies can automatically input all the different bits and pieces from the call, all the pain points, all the challenge statements, all the hopes and dreams automatically in real time in into the CRM. And it's like that is a, that is a whole weight off of that sales person's shoulders, right? And then from a marketing point of view, we can actually, you know, see the insight, do searches in the system for people that are, you know, having whatever hopes and dreams or whatever pain points and tweak the nurture flows, make sure we've got relevant content and we can do all these kind of campaign changes, changes to the messaging or changes to the content on the fly looking at that real time insight. So we're already seeing it, you know, Gerhard, and it's a, it's really interesting to see how, you know, many tools and many kind of solutions are already integrating this kind of.
This kind of technology into the system. Natively.
Then is, is AI.
Transforming CRM into a, a better data universe that offers more guidance to the salesperson?
Yes. I mean, I think it's probably a sales answer and yes, that it certainly is helping. I think, you know, I've been in industry for close to 25 years now, which gets harder and harder to say, right? And there's been a couple of, you know, this is the next thing and this is the next thing and this is what's going to make sales easier. And at the end of the day, people buy from people. It's a people business. And so AI requires data to be effective. And so in order for it to do anything, somebody somewhere has to do something. And so whether that's email communication, chat communication, verbal communication, the art of sales people to people is still true, Right? But the ability to streamline the tools that we use to assist the person, I think is really where AI comes into play. And again, in the light of examples, is primary form of communication is still very email centric. And you're sending emails back and forth throughout the day, maybe through multiple devices at odd times. Being able to get that data back into CRM as a system of record was always the salesperson's responsibility. And the last thing salespeople want to be is a data entry clerk. And so when you look at CRM over its legacy, it's really been a system of record where the rep is typing in information so that the rest of the organization knows what they're doing day to day. It's of no value to the rep to tell everybody what they're doing. It's value to everybody else. And I think what AI is starting to help do, or certainly is doing is being a value to the rep where they no longer have to be that data entry clerk. The action of just working day to day, updating the CRM tool with that information through integration, but then processing it so that I don't have to as a manager read through the last 15 emails that have communication to get the tenor of what's going on within the account. AI summary can show me sentiment analysis, it can show me what contacts are perhaps involved in a particular sales cycle that maybe aren't met yet. Contacts inside of the CRM. And that really helps close the gap between us and marketing and support and everybody else. Because in legacy, the CRM tool only had the information in it that the rep put in it. And now using AI summaries and things like that, we can get a collective idea of what the prospect or customer looks like just by communication. So just the art of doing business is removing another use case that the rep normally would have to sit there and type in and tell everybody what they're doing.
So what you're saying is you're transforming with AI, that system of records, into a tool that helps break salespeople, break.
Records, that's bringing value to the seller. And I think at the end of the day, nobody gets into sales for fun. And I want to know things like I need my CRM to tell me things I don't know, not what I do know. And me typing what I do know into CRM is for everybody else's edification. But it telling me, hey, you not connected to the CEO or this person's on an email chain that you didn't realize you should probably include them in the sales cycle. Or they mentioned this pain point that you haven't glossed over yet or interacted with. Those are things that help coach the rep to the next best step. And I think at the end of the day, that's all any seller really wants, is a tool in their bag that helps them know what they don't know, not tell everybody what they do know.
And I think there's another phenomenon. When you have that AI data in salesforce.com, then marketing can use the data to create better marketing campaigns based on actual.
Customer stories.
Yeah, I would prefer it being Sugar CRM, but we could, you could mention Salesforce as well. But yes, for. Absolutely. From a, from, you know, the collection of data so that we can use it to target campaigns. And so that marketing not only hears the voice of the seller in a room, but they hear the voice of the prospect. And I think tuning our campaigns to what the prospects are saying and how they're reacting to what we're presenting to them and helps us refine how we're going to market and strategy and what works on a whiteboard often doesn't work when it hits the street. So being able to take the reality of what's being heard to product pitches, to slide decks, to examples, to materials, to conversations that are taking place in booths and elevators on airplanes and getting all that information back to marketing so that they can restructure how they go to market. It's invaluable.
So Scott, can you give us a practical example on how you extract that information from sugarcm and then build a better marketing strategy?
Well, since then said, you know, it's about getting those.
Buying signals and finding that insight and then producing the relevant programs. So, you know, a program that we've done previously, actually it was before Christmas, just, I'll give you a very, you know, kind of creative example that we did. We took a lot of the buying signals that we found within Sugar CRM. We can search for different terms, different kind of bits and pieces. So before Christmas, we found about 200.
Prospects that are on the cusp of.
They haven't converted just yet. They've had conversations, but not quite converted into pipeline, into opportunity and maybe gone a bit cold for, for whatever reason. But we sent, we got, we, we managed to do some data mining within Sugar CRM using kind of buying signals, intense signals that we're searching for within the system, and sent them a bottle of wine with a lockable top. And I'm just looking around my desk to see if I've got the lock. But it had, it was a bottle of wine. Yes. Here we go. I'll show you this.
And it had a lock on top. And the message was, you know, with Sugar serum, you could unlock your potential. Right. So these are organizations where we've got access or we know that the sales leader, the VP of sales, or the sales director. And we're trying to say, you know, with us you can unlock your sales essential. These are customers that have, you know, interacted with us and shown some kind of buying signal in the past, but hadn't quite converted. And you know, from, you know, everyone on the call will know that, you know, when you're cold calling somebody from a, from a BDR or an SDR point of view, your connection rates are pretty small. But we had a 75 connection rate with this because we sent a letter saying, here's a bottle of wine that you can't access. I've got the code. I will call you with the code in a couple of days. So we got through to almost everybody that we sent it to. And you know, that.
That little campaign that costs probably, you know, 10, $10,000 to send out generated about $350,000 of pipeline within two weeks. So, you know, and that was from the insight and the buying signals that we found directly from mining Sugar Serum. So there's a, a small creative example.
Brilliant idea. I love that. It's a great example. I was wondering about how has AI changed the definition of a qualified lead between sales and marketing?
Do you want me to take that one first?
Yeah, go ahead.
Yeah, yeah. Okay. So how has AI changed the definition of a lead? Well, the definition of a lead, I think is one of those eternal kind of questions you ask 700 people. You'll get 700 different answers. Right? But.
For us, how we're seeing AI helping us with this particular kind of conundrum. Well, you know, six months, a year ago, somebody would come onto our website, download an analyst report, flower form. It will come to us. We would throw it over defense to the BDRs. The BDRs will call, try and qualify. Once they've got it qualified, they would then throw over the fence to sales for them to, to do their thing and run off with it. Now, you know, AI is giving us the ability to look beyond the single lead, I. E. That person has downloaded the report and go deeper into, you know, the buying groups. We all know that these days when you're trying to sell anything, really the buying groups that are getting bigger and bigger. Right. It's almost purchased by committee in a lot of organizations, right. So AI is giving us this ability to look and see deeper into that organization and see, oh, the IT guy of the same company went on that webinar last week. Oh, and the head of sales asked for a pricing run through two days ago. So, you know, it's quicker and much easier to be able and automatically build that whole picture of, of the buying group, of the whole view of that organization, you know, and so we now have a lot more context around the account as a whole rather than that just, just that one, that one person that, you know, downloaded that lead. It just gives us that extra depth of vision.
Dennis, what's your take on the same question?
Yeah, I think, you know, the face time that we're getting with prospects is shorter and shorter and shorter. And so, you know, it used to be that somebody would be of interest, you'd go in, you do a demo, you do a needs discovery, try to find the pain, try to build a solution to solve for their individual, individual pains like anything else. Now people are doing 80% of their research before they reach out to a vendor. So how do we maximize screen time, FaceTime, the in person or the phone time that we have? They expect that you've done your homework. You know, they, they, they want a buying experience similar to what they have with Amazon or Apple or whatever it is. So for us, you know, when we show up, we have to make sure we have not only a complete picture of the profile of the company, but perhaps in industry. What are they going through? What pain points are they seeing? Is there a particular tariff situation or something that's going on that's affecting their ability to be a manufacturer in a certain region? So that when you show up, you're showing up as a place of value and not just another software vendor that's pitching individual product skills that they might have. And I think one of the key features inside of our CRM offering is the ability to use predict, which is our AI modeling in our lead sector to say of the leads that have come in here are the ones that are most likely to convert based on the profile of the customer and similar customers that we have in stack and in traditional sales offering. Any sales person or BDR is going to go, here's the largest opportunity, I'm going to chase them in sales value order, right? I'm going to go to the biggest possible one in where the reality is that, you know, 10 tens is better than 150. So if these are customers, but we already have a story, case study, reference vertical solutions that we can show up and be a value from the minute we engage, that's really where we should garner our attention to. So don't get the cat with the laser idea of chasing the largest opportunity that came in. Chances are there's 10 other vendors in there fighting for that business. Concentrate on the ones where we have the best story to tell from day one first and then work down the list. And AI is greatly helping us build that predict score so that we can concentrate on what leads we can convert and make sure that we're prepared and have, you know, value from the moment that we connect. I think the time of having two or three calls before you're able to show a demo are probably pretty much over.
Amazing. So I would.
Guess that when I look at the evolution, and I've known sugarcm since its inception, that you have transitioned gradually.
From that system of record CIM solution to creating a predictive tool that allows you to.
Get consistent success and have more accurate sales forecasts.
I think from our side, we'd like to say, like, we want our customers to interact with the platform. We don't want users, right? We want them to log in, be told something that they should do based on the data that's being fed to it, whether that be from outside systems, ERP systems, you should go speak to these customers for these reasons and, you know, then the user wants to log in because they're interacting. If you think of CRM much the way that people configure their social profiles, whether that's Instagram or Facebook or YouTube, they've told that algorithm what they're interested in. And when they log in, they're presented with similar things and maybe some outside things that are close to what they're interested in so they stay engaged with the platform. CRM really needs to go in that direction. You know, the idea of static dashboards and static layouts is over. You want users to log in and interact with the data and be coached on who they should direct their attention to based on buying behaviors through their ERP system based on product selections. They're buying, you know, bananas, but they're not buying grapes. You should go try and sell these people grapes. Those type of things again, help sellers direct their attention to where they should be doing things instead of guessing. And AI has a huge influence on that impact.
I wonder, Scott, how often do you get a chance to sit in a sales meeting?
Oh, I sit in dozens of them. I sit in regional forecast calls, global forecast calls, weekly meetings, QBRs. I present, I make sure that we present or my team presents at the every QBR and weekly. So you know, the EMEA team have a weekly call, the APAC team have a weekly course and the, so does the US teams and either myself or, you know, the regional marketing director is there, engaging, presenting. As I say, it comes back to the communication thing that we talked about right at the top of the show. Right? So you've got to, from a marketing point of view, you've got to be able to. I want to know that the sales team know what our plans are, what tactics we're doing, why we're doing the, the, the programs and the tactics that we've chosen. It all add us up to the higher strategy of who the ICP is, who our target market is, the core, the core geographies, the message that we've got, the story we're telling. And so they can see that it's not just random acts of marketing. This is a, you know, this is a joined up plan. But more than that, you know, the, the sales leaders and almost every account manager is actively encouraged to get involved in building the plan. We want, we want them to feel it's, they've got a bit of ownership in this plan. It's not just marketing telling you this is what we're doing. We're marketing. We know marketing best. Leave us alone to do our, it's, it's a joint thing, right? So yeah, the short answer is loads.
Scott. What, what is a tool that you can't live without?
Well, from a personal point of view, I would be lost without my Kindle, but that is probably not what you or the audience want to hear. Okay, but from a, from, from an AI point of view.
I'm, there's two tools, right? I'm going to, I'm going to cheat and say two tools. Okay, so, but the first one's got a caveat. So Perplexity is an AI model. It's, it's a Chat GPT kind of.
Similar kind of system. But what I found is it, it has a much more reliable and predictable deep search capability. Chat GPT can get a lot of things wrong, especially when you want to go deep and you're trying to do a lot of kind of like industry analysis or you know, address market analysis and you want to really try and figure out what's going on in, in a certain topic. Chat GPT can make stuff up, get things wrong. However, the caveat is they've just launched their pro version of Chat GPT which is a significant level, a step change, right. But previous to that, Perplexity is much more reliable. And so I recommend it everybody for that deep kind of, if you want, if you need to, you know, prove references and you know, just, you know, really have.
Strong, solid research. And then.
I also love Notebook LM from Google and there's a number of reasons why I love this platform. You can take all kinds of documents, so and upload it and it will give you a summary, it will take all the information, disseminate it. And so if you've got analyst reports, industry reports, you want to try and understand, you know, a sub segment of manufacturing, for example, where, what the trends are, how is it growing, what are the key challenges, what, what's the kind of industry commentary and you can, you can put all the analyst reports and the trade reports and the kind of trend analysis up into the system and it will give you a beautiful written summary. Not only that, it will also output an audio summary for you in the, in the shape of two avatars having a conversation, almost like a podcast. And it is, if you haven't done it, I recommend just trying it. It is unbelievable how good this thing is already. And so that is. So those are my two kind of obviously Chat GPT, especially with its image.
Creator now, which is a quick audience question. Do you think that Perplexity is better than Gemini when it comes to research?
I'll be honest, I haven't used Gemini. I've, I was shown Perplexity maybe eight, nine months ago. And that's, you know, my tool of choice. So I'll be honest, I don't have knowledge of Gemini.
I'm sorry.
Dennis, what, what's the tool you can't live without?
Well, you know, as a, as an evangelist of CRM and being at Sugar for the last, you know, 15 or so years, I think Sugar, CRM number one, you know, as a sales leader, using that as a platform to help run my entire business and seeing the adoption of AI come through that, not as a technology component, but as a sales tool for the users to interact better with the application as opposed to being users inside of that. My number one feature that, that I love would be our Sales I offering. So what Sales I does is, is connects to ERP and feeds Sugar CRM on next best actions for the sellers to be following up on based on invoice and order line items. So reps really not getting blindsided. They don't need to run reports. Not going through their inbox to look through complex, you know, power BI or tableau reports is simply code straight at the account level to say you should speak to this account for these reasons because it's using the data that's coming out of one of the cleanest data sources that company has, which is their erp. So you know, again, using the modeling to coach a rep inside of the tool that they have to be in anyway day in, day out and not having it be another source of record for them, but something they can interact with to me is invaluable as a seller.
That's awesome. Do you do roleplay simulations.
From inside from a, from a team coaching perspective? Yeah, yeah, absolutely.
What tool do you use from a.
I mean we are generally using our modeling inside of chat GPT to present a buying experience and then seeing what answers it comes back with compared to what we have so that we're updating our documentation and our rebuttal sheets inside of a BDR call all the way from inside of a presentation.
Scott, audience question. What is the note URL, the AI tool that you mentioned?
I will find it for you and if I give it to you, Gerhard, could you disseminate it out to the audience? Absolutely, yeah. So we'll follow up with that.
Absolutely, absolutely.
Yeah.
I have one more audience question. How do you use AI to close a deal? Dennis?
So you know, at the end of the day, people close deals. AI is not there yet. If it does, we're all sellers are in a little bit of trouble. But I think making sure that you have your blind spots covered. And so one of the, you know, Jorge Arroyo, who's one of our senior network engineers here at Sugar, has a great line where the interactions is really the voice of the relationship inside of the sale and the AI modeling is the voice of the business of what you should be doing. Right. So if you look at the interactions, the people to people interactions, little things like a person being cc'd on the email that are not involved in the direct sales channel and having AI point that out, that the person you think is your point of contact just copied somebody into that sales communication chain and you're not speaking to them. So you know, at the end of any sales cycle, junior sellers get blindsided all the time. Heck, it happens to senior sellers all the time. But the more that you could be prepared to understand who the actual buyer is. In a remote environment where we do 95% of our selling through meetings like this, it's very easy for a seller to pretend they are the buyer or the purchaser, even if they tell you. And there are other influences at work that you need to smoke out. So using AI to show you who else is involved in the deal cycle and then being able to leverage your people skills to get to those people inside of the interaction really increases your ability to close the deal.
Well, I think you, Scott and Dennis, you've both demonstrated through your.
Collaborative efforts that we are all a team, and when we work together in sync with the most intelligent tools, we truly can align people, process and technology to create more customers.
That's the idea.
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