You Can’t Automate Your Way to Real Relationships

Traditional tech sales tactics - mass emails, SDR outreach, automated sequences - no longer work like they used to. Robi Ganguly knows this firsthand from his 11 years building tech companies.

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As General Manager of Alchemer Mobile, Ganguly sees a shift in what drives sales success. While most companies push for automation and scale, he points to an overlooked truth: face-to-face meetings create results that digital outreach cannot match.

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Small, focused gatherings bring customers and prospects together in ways automated systems never will. From city-to-city roadshows to local meetups, these personal touchpoints build real connections. Though these activities don't scale easily, they produce lasting relationships.

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The key lies in changing the conversation. Rather than promoting features or products, Ganguly's team focuses on understanding customer problems first. This approach transforms standard pitches into meaningful discussions about business challenges.

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His core philosophy sounds simple but profound: love your customers. This mindset turns every interaction into an opportunity for deeper connection, leading to organic growth through genuine relationships.

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The episode shows sales professionals a different path forward in 2024. As automation fills inboxes and feeds, the human connection becomes the true differentiator.

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What we sell is a solution to a set of problems. When we show up, can we bring any intelligence? Seems like you might have some challenges in this area based upon what we know. If you converse with us and start to unpack that, then we earn the right to talk to you more broadly. -- Robi Ganguly

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Top 3 Reasons to Listen

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Lower Sales Costs: See how relationship-focused outreach reduces expenses compared to mass email campaigns, leading to better returns on your sales efforts.

Fill Your Sales Calendar: Learn how combining personal touch with social media outreach brings consistent opportunities without burning through lists or cold calls.

Keep Clients Longer: Understand how a connection-based sales approach leads to long-term relationships, repeat business, and word-of-mouth growth.

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More About Today's Guest, Robi Ganguly

Giving every customer a voice

Robi Ganguly has a deep appreciation for relationships, valuing the significance of truly meaningful and deep connections that are fostered over time through mutual investment. Driven by this belief, Ganguly is at the helm of Apptentive, alongside a team of exceptional individuals who share a commitment to cultivating great, long-lasting relationships. At Apptentive, they are dedicated to assisting companies, both large and small, in developing deeper and more meaningful relationships with their customers.

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Key Takeaways

• Email Outreach Has Lost Impact - Mass email campaigns and automation tools have saturated decision-makers inboxes. What worked 5-10 years ago needs replacement with more personal approaches.

• In-Person Meetings Drive Results - Post-pandemic, face-to-face interactions create significant advantages. Small group meetings between customers and prospects generate more impact than digital outreach.

• Focus on Problems Over Products - Sales success comes from understanding specific customer challenges first, not leading with product features or capabilities

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A Transcription of The Talk

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Mark Drager: So, having a tech background and having built up Attentive for 11 years before the entire company blew up. And we don't have to really touch on that. I'm most curious about the strategies that used to work in building up tech companies for customer acquisition, working the leads, closing the leads, avoiding churn—all the stuff that is working for our revenue, what used to work, and what people preach, but no longer works today, and what should we be focusing on in 2024, if we're looking to grow these types of companies.

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Robi Ganguly: So, I think that the things that used to work, people wrote books about, and then worked for the likes of Salesforce and HubSpot with the activities around doing outbound, and having a group of young, hungry early salespeople in their career emailing and getting into people's inboxes, that worked really well for like, a good five to ten years, because we were not seeing as much noise in the inbox. And we were seeing new solutions that really unlocked a tremendous new axis of value, that you could subscribe to it. And then you could scale up with your team. And you didn't have to make a commitment. And you didn't even have to do a lot of work to deploy it across all the desktops in your company. So that worked. And then what happened is, some of the companies that started to use those tools built the tools. So you had all bunch of companies, whether it was marketing automation with a local Marketo, or it was, you know, whatever they want to call it sales, engagement platforms like Gong and Outreach, and SalesLoft, etc. That came in and said, "Hey, we're going to effectively give you spam cannons," you know, what it did is, over the course of like two to three years, basically ruined everybody's email inbox that made decisions.

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Mark Drager: So, again, once again, marketers ruin everything.

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Robi Ganguly: Oh, gosh, yeah. Well, I mean, you find the channel, then you flood the channel, and then you ruin the channel.

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Mark Drager: Right, but then if you're fast enough to move on to the next channel, I guess. That was something I found really discouraging. You know, I've been part of a few private masterminds for performance marketers, and direct response people, which is not my background, I come from much more on the corporate side. And I was surprised at how fast they jump on a tactic, work the tactic, bleed it for every single thing they can. And then like nine months later, they're like, "Okay, what's the next thing?" And it just seems completely unsustainable to me to be jumping from tactic to tactic to tactic. And it sounds like what you're describing is slow to have tactics that used to work five or ten years ago or too, in your experience. Are people still talking about this and recommending these types of approaches?

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Robi Ganguly: I think it's ubiquitous. I mean, I sold my company to a company called Alchemy. So, I'm now there. And we use it to do outbound. We use emails to ICPs, we use ZoomInfo to get emails, right, we do that stuff. But it's not the only thing we can do.

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Mark Drager: From your website pop-up, you still do webinars, but you still aren't doing all the content marketing, right?

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Robi Ganguly: Yeah, the content marketing is there. And I will say that it's I was referring to the outbound tactic that was most prevalent and worked really well. I think inbound is always valuable and important, like being educational. Our philosophy from day one at Attentive was to educate people. We don't believe that this is necessarily something that one day, folks will just wake up and will dawn on them that they should listen to their customers and their digital channels. We think we need to educate and talk about why and how. We found that that was successful, and it built trust. And it built long-term relationships that we didn't know about, well, before we had the relationship, right? Like, it was kind of one way in the sense that our future customer was reading a bunch of our stuff, and in some ways, copying what we were telling people to do. And then they came in and would say, "All right, so that worked. Can we talk about other things that might work for us?" That, I think, is always valuable, and I would always promote that. But I think the outbound tactic is much less useful.

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And I think what's really your question is like, what's working in 2024? And what's working beyond that? I think really understanding how in-person is used post-pandemic is a very hard skill worth investing in. So if you can get a small group of your customers and your prospects together in person, it's amazing. It's magical. But I say that like if you can get them together, but in order to do that, what needs to be true? Well, you have to have good relationships with your existing customers. So that means that everything about your sales process leads up to selling the customer and then afterward giving them value. If you're really investing in that correctly, you're realizing that now you are creating a happy customer and a real externship where you can call on them to say, "Hey, come with me to dinner with this other person. You guys both live in Chicago, and we're gonna get together." And this person is thinking about making an investment in us. You're much more persuasive than I am. Let's get together and talk. And if we can do that in a small setting, it's extraordinarily powerful. But it doesn't happen just because you call a customer today. And then you call a prospect tomorrow and say, "Let's get together," it happens because your customers are happy that you know where they live, that you have a trusted relationship where you can ask things like, "Hey, where do you live?" You can say things to them, like, could I have you been on the phone with a customer with a prospect talking about this, all that stuff, you can't hurry up, you have to just build into your process, but then it will work consistently. If on the other side, the relationships you're developing with your prospects are ones that are oriented around, even if you say no, today, I'm going to be around tomorrow, and I bet your problems, you're going to still be here. And that kind of approach allows people to say, "All right, I'm ready. I'm ready to actually spend a little bit more time with you. Yeah, I heard from you, you. You did call me. Email me, you got into my inbox. And then you know what I did, I went to one of your webinars, which was pretty good. So then I subscribed to your newsletter. And I've seen three things in there that I actually forwarded on to other people. And now I'm telling you, people are talking about this problem. And you're saying, well, that's amazing. I'm going to be out there next month, and would you like to have dinner, that's what it takes." So that's one of the things that I think will always work. But guess what, it's a ton of work.

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Mark Drager: This is so interesting. One thing that I've been kind of obsessing with, maybe over the last six to nine months, is the idea of non-scalable tactics. And I've talked a bit about it on the show. But it's amazing to me that there seems to be this school of thought out there, where it's like, if I'm going to create something, I better create something that's infinitely scalable. And if it's not infinitely scalable, replicable, well, then it's not going to work organization-wide, or it's not going to work as we scale, you know, from 15 to 30 million, or it might work today, but it's not going to work forever. And then I would hear these case studies. I was just listening to what you were saying and thinking of all of the opportunities I've had. And some of the most remarkable wins. I've seen others in my network or clients have. And they kind of come back to non-scalable activities, they come back to actually calling people like not cold calling, but like actually calling people up and giving them the time to just chat and talk. I was in Arizona last week. And I knew I was going to be there. So a few weeks earlier, I was thinking Who do I know that was in Arizona, and I lined up just a bunch of meetings. But I lined up a bunch of meetings. And so my I flew into my whole afternoon was following, you know, hanging out in someone's recording studio and going here and going there and was great, it was fun. But because I was talking about being in Arizona, the days leading up to it more people I was speaking to, as happened to be in Phoenix, and I didn't even know that. And they're like, "Oh, you need to come by our factory, and you need to see this. Like, next time next time I'm there, I will stop by." But in the back of my mind, I'm going is this a good use of time? It's great. It's networking, it's getting your name out there, it's doing all those things. And I'm the founder and the entrepreneur, I have to imagine if you're a mid-level, you know, rep or if you have a sales team, or if you're a manager, I don't know how comfortable people are just saying, like, just go out there and spend time with people and you know, here's an expense account, and get in front of people and have fun and go do all the soft things. Right, that we know works. But it requires quite a bit of trust.

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Robi Ganguly: Absolutely. Well, I think there are a couple of things that you said in there that are important details. So one is like the mindset of, "Is this worth the time," right? And recognizing that everybody's doing that calculus, everybody's asking themselves that question. And in my experience, that means most people give themselves a reason to say no. So what you can infer from just that, thinking about that thought process and how people approach it, is it's possibly an opportunity to differentiate yourself. It's probably an opportunity, at least to demonstrate more effort and more work ethic around something, perhaps more care. And then what we can say situationally is post-pandemic, it's clearly differentiating to spend time with people in person. So like, now we're talking about something and it's a clear advantage that I think maps to general trends societally and behaviors from other humans that you're competing with as a salesperson. And so you can differentiate if you think about it.

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And then there's the second thing you talked about, well, you know, what's the capacity? I haven't started my company to do this. So are they gonna fund me to go travel and do this thing? And the answer is, well, it doesn't actually matter. Because if they're not, you can still go to your local area to meetups and find yourself in places in person to make connections. And then you can find yourself digitally in places to make connections. You don't have to travel to meet people in person; your scope of meeting people in person might be smaller, but it's still a skill set and a differentiation you create. What does that mean? Well, if you're investing in that locally, the one time you do travel, you're more likely to be successful in those moments, too. So I think about it as like, how are you going to create some competitive advantage for yourself as a human? There are clear opportunities to being good at being in person and making it a priority that I wouldn't say are going to actually accrue more benefits over time because of what's happening societally.

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Mark Drager: I really appreciate this conversation. The second thing that you mentioned earlier on, which I loved, was the idea of working clients into your messages, especially if you've established tight relationships. Certainly, testimonials case studies, and all of those pre-produced things can help. In September, I was at a private event. One of my friends has launched an AI-driven—well, I guess he's become a friend, I didn't know him when he launched it—but he's launched an AI-driven newsletter, a daily newsletter that uses machine learning to learn the habits based on opens and based on eye tracking, and click-throughs. It pulls, you set all the parameters, kind of parameters, kind of like when you go to Apple Music. And you say these are the genres I like. And like Pandora, it will select what it thinks you should listen to. And so this is a daily AI newsletter, that you set up all your audiences and all your thing, all your preferences, and it goes out and it selects what it thinks your audience might be interested in—all third-party content. And then you select what you want. And then over time, based on click-through rate and other things, it will learn what your audience wants and will tailor the information for your audience—all AI-driven. And this is brand new; he's I think two or three years into the development side. And they have, you know, they've done all their legal stuff before they went to market, but they're about a year into startup. And so he's going to a lot of events. He's talking about this product and service at this event, and he's on a panel. An agency is on a panel and the end client. So it's the tech provider, the agency using it, and the end client. My friend Joe didn't say a single thing for a 30-minute panel did not say a single thing. He sat there the whole time while they talked about his product. And the agency talked about how great it wasn't all the technical stuff. The end client talked about how amazing it was from an ROI point of view, and how they were able to move like open rate from 2% to like 78% on average, and like just these bananas things. And then finally, the host goes, "I'm so sorry, Joe, like we haven't even had a chance to throw it over to you like what do you think?" And he's like, "I'm good. Like, I don't need to get in the way of this love fest. Like, I can just go ahead and put it out there." And it was striking to me. I was like, ah, how do we replicate that in our sales processes where everyone else does the talking for you and you just sit there and go? That's what we do. It was amazing.

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Robi Ganguly: I love that. I mean, it's so repeatable. If you have people who are using your product,

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Mark Drager: If you drive results, yeah, it's repeat, right?

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Robi Ganguly: It's so repeatable. And that's like such a market tell. I mean, it really does matter. The other thing I think is hilarious about it is that you're talking about the tactics that worked but maybe aren't working as much. So everybody copied the SDR system from Salesforce that was written about and would remind me of the book, right? It's like a famous outbound book. So everybody remembers that part. But then behind the cloud, Benioff's book, they all almost always forget that Benioff was super proud of going and having these meetups city to city to city to city to city and the magic of pulling that together. And that means that part's not dying. It's just harder to pull off.

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Mark Drager: That is, that's interesting. The person who I heard the whole idea of non-scalable activities from is someone who's built a massive membership group, I think 17,000 people are a part of it. And they, in terms of paying customers, I mean, and they built it up almost exclusively from doing road shows, and going community to community community paying out of pocket building up this massive following being there. But then now when they go and do podcasts, they do a local meetup. So let's say they're going to be in, I don't know, Vegas for a podcast recording, they will do a local meetup that afternoon, and everyone in their community will kind of come and hang out. They will explain I'm here for this podcast. They will take pictures with fans or community members, then they will do the recording and talk about the fact that they had just done this meetup. Then they will take a photo with the host of the podcast, and then they will share that with everyone locally because they know that they were in town just for that which boosts the listenership of the episode that they're on, which gives them even more love. And that's not even touching, like, the actual revenue side of things. This led to a television show, this led to a bunch of other things. And I was, again thinking like, "Damn, it seems like if you go all in on something, no matter what you pick, you go all in on it, it's gonna work, right?" Like because if it doesn't, you switch to the next thing you go all in on. But this idea of this year, not focusing so much on automation, perhaps maybe the back end, of course, the support, but your main activities not being so focused on automation, not being so focused on digital, and focusing more on people relationships and authenticity. I believe that has to be the thing that combats AI, in the masses of just shit that's being put out by most people.

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Robi Ganguly: I think that's very true, it's always going to be true because real relationships are. They're like litmus tests, you know if your customer is willing to, like, call you up, or text you, if your customer is willing to go to bat and talk for you, that's a real relationship, that's a place where you've got some depth to it. And the tools that we have, you know, as advanced as they might be, are tools to create a relationship. They're not the creators of the relationship in the first place, right? Like, it's a tool to help me do that. And if you kind of forget that it is, I just sort of laugh at the people who, I understand why, but the people who read blog posts, and they point at them, they're like, "Yeah, but over here, this guy said, You didn't have to do anything. And all these people will give you money." And then somebody else is like, "Yeah, this woman over here, she said, I didn't have to do anything, I just use these tools, and I get money." And they're like, the reason that they say those things is so that you will pay them money to get their course or use their tool or whatever they're hawking in order to do that. That's why they're out there telling the story. And if you can look behind the curtain a little bit and understand their motivation, they're just selling you more effectively than you're selling other people. That's what's happening.

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Mark Drager: So as we look forward to the rest of the year, because we still have, you know, three quarters left in this year in front of us, what are you and your team most focused on when it comes to revenue growth or sales?

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Robi Ganguly: I think we are really focused on saying a similar message consistently across the team. As we go up in the market, we have an expanded product portfolio as a result of the acquisition of my company, like there's a much bigger opportunity for us to attack. And if we all show up, similarly saying the same thing in the market, and our marketing and our outbound and our one-on-one conversations, what that does is it supports itself, and people start to understand more of who we are and how we fit in the problems that they have. And I think that alignment, and that like consistent story from an SDR to the customer success manager to the marketing on our site. Really getting that more and more aligned, is clearly going to be powerful for us. Because there's a space in this market that is opening up more and more fully, like our largest two competitors both become private in the last year, it's clear that both of them are cutting staff in a meaningful way and changing the way they serve as customers. So we really have an opportunity to not just be ourselves and strong, we have an opportunity to tell the rest of the market, that we're the ones who are actually investing more in the services we're developing and in the services we're delivering. So I think that's the biggest meta focus. I mean, when we think about tactically because this means...

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Mark Drager: You have nine products in your suite, that I can tell, and maybe you have additional products and services behind the scenes, but you have nine of them. And so is there a concerted effort to suggest to your team, this is the product that's hot right now this is the one in and then cross-sell? Or look at people who happen to have one product and then go and cross-sell and upsell further? Or is it just to have a lot of conversations and whatever our way in is what we'll focus on most?

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Robi Ganguly: I think that's a good way of posing the question. It's, it's closer to the latter, but with this bent, which is we have all these products, but they're not in and of themselves, what we sell. What we sell is a solution to a set of problems. And so what we are doing more aggressively is going to the accounts we're targeting and say hey, what problems do we think they have from the outside looking in? And when do we show up? Can we bring any intelligence? Like we have an understanding of public feedback in some places? Can we bring any intelligence to that first set of conversations that says seems like you might have some challenges in this area and this area based upon what we know? And based on what we think you do and your role? And if you converse with us and you start to unpack that, then we can we earn the right to talk to you a little bit more broadly about the things we can do as we grow over time. And I think a lot of the customers that we show up and come into contact with this year are going to be surprised to find out how many things we can solve for them. But none of them are gonna care how many products we show up with. Like, "Oh, cool, you're offering nine products now, that's great. I totally want to work with you." It's more like, "Oh, you can solve that problem that I have right now. Cool. Wait, you can solve this other problem that my team member's been talking about? That's awesome. That's more of..."

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Mark Drager: Yeah, you ever know, what is, our reticular activator is in our brain, right? You think about buying a Jeep and suddenly you see Jeeps everywhere, you buy a white car and suddenly see white cars everywhere. It's the filter in our brain that the bodyguard is trying to keep all the crap that we don't need away. Literally, just on Friday, I'm listening to a lecture and the person just goes, "Guys, come on, it's not about the work. It's about the problems. It's not about the work. It's about the problems. Nobody cares about the work, just what are the problems you're solving." And so perhaps it's just my RAs, which is like kicked in by the fact that you are going to spend the next months and years and hopefully forever, I suppose, focused on having conversations around problem-solving, as opposed to solutions, products, tech, feature benefits, you know, we've helped XYZ with is like all of that stuff is just the credibility or you know, the rationale that one might need to be able to help move forward on solving the core business challenges that people have.

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Robi Ganguly: Yep, absolutely. Absolutely. And I think it's really one of the things that is super unfortunate about the flooding of the email channel is how many people show up in my inbox with awful, awful emails, because what they're trying to do is tell me about their product, right? They're trying to tell me like, "Here, I've done all this work. Like, this is my 17th email to you. I'm like, I don't care about your 17 emails. And this is what this product does. And like, I also don't care about that. But if you showed up one day, and you're like, 'I know exactly how your business works. And I'm going to solve this specific problem for you. And it only will take five minutes for us to talk about it. I work with somebody just like you.' I'm much more likely to like, 'Okay, cool. Yeah, that is a problem I have. Let's give five minutes.'"

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Mark Drager: There we go. There we go. I do have one final question for you. I do appreciate your time so much. What would be your number one, pick it out of the air, pick it out of experience, anything you want? What's your number one tip or strategy to sell more?

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Robi Ganguly: Love your customers. If you really love the problems you're solving and the customers you're solving them for, and you keep showing up to sell to other people, it's going to shine through. They will care about you. You will care about them, and it will build on itself, and you'll be a happier person.

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Resources & Go Deeper

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A Guide to Customer Acquisition in 2024 [Strategies, Tools and More]

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This article provides a comprehensive overview of customer acquisition strategies, emphasizing the importance of understanding the target audience, choosing the right channels, and creating engaging content. It highlights the necessity of sustained business growth through new customer acquisition, market expansion, and building brand awareness. The article suggests that customer feedback and data analytics are essential for refining strategies and improving conversion rates.

A Guide to Customer Acquisition in 2024 [Strategies, Tools and More] (hiverhq.com)

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Customer Acquisition in 2024

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A Glimpse into the Future from Buyapowa emphasizes the shift towards deeper human connections, the significance of being human in the age of AI, and the evolving concept of value beyond just money. It discusses the importance of managing uncertainty, operational agility in eCommerce, and the integration of machine learning and AI to offer personalized shopping experiences. This aligns with the discussion on building genuine relationships and leveraging technology to enhance but not replace human interactions​.

Customer Acquisition in 2024: A Glimpse into the Future - Buyapowa

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Best B2B Customer Acquisition Strategies in 2024

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The Full Guide from Scaleo Blog focuses on B2B customer acquisition strategies, highlighting SEO marketing, customer feedback, and lead generation and scoring as effective methods. It underlines the importance of not overlooking long-term marketing methods and tailoring surveys to include all types of users. The article also points out the challenges B2B companies face in customer acquisition and suggests genuine and honest connection-building as crucial​

Best B2B Customer Acquisition Strategies In 2024 - The Full Guide - Scaleo Blog

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