22. Dan McCoy ~ DLM Advisors
Episode Notes
Key moments from this episode
Dan McCoy joins Tailwind for a practical conversation about AI, business development, and the return to more human prospecting: where AI helps salespeople prepare and organize, why AI-generated email and LinkedIn outreach is easier to ignore, how neutralizers and warm introductions improve opportunity quality, why network-building and consistent market presence matter, and how human review, intent, and relationship-building keep AI from flattening the sales message.
Takeaways
- AI works best as an assistant for preparation, organization, and drafting, not as a substitute for human review.
- Generic AI-written email and LinkedIn outreach has made buyers faster at spotting and ignoring automated messages.
- Warm introductions and neutralizers can create fewer touches but much higher-quality opportunities than broad sequences.
- Network-building requires deliberate activity such as meetups, speaking, newsletters, LinkedIn presence, and reciprocal introductions.
- Human intent, proofreading, and relationship-building keep sales messages from sounding automated or misaligned with the buyer.
Key Moments
- 1:34
AI as a sales assistant
Dan frames AI as useful for preparation, organization, coaching, and meeting readiness before turning to the risks it creates in prospecting.
- 3:04
Why AI has oversaturated outreach
The conversation explains how AI-generated LinkedIn and email messages have made prospects quicker to ignore generic outreach.
- 7:46
Grassroots prospecting and neutralizers
Dan describes using neutralizers to create introductions rather than relying on direct cold messages into crowded channels.
- 10:16
Fewer touches, stronger hit rates
Dan compares lower outreach volume with much stronger opportunity quality when sellers put more study into the right introduction path.
- 12:12
Building and working a network
The episode moves into practical ways sellers can grow a network through events, speaking, newsletters, LinkedIn activity, and useful tools.
- 15:11
Keeping a human in the loop
Dan and Austin discuss where AI can assist writing while humans still need to preserve intent, nuance, values, and relationship context.
Transcript
0:03 We have another episode of Tailwind.
0:06 Today we're joined by Dan McCoy. Dan, tell us a little bit more about yourself.
0:10 Great. Yeah, Austin, thank you for having me. So, uh, Dan McCoy, I am the,
0:15 uh, owner of D element. I currently, uh, support uh, from a fractional perspective our Clarota team where I am their acting chief revenue officer.
0:27 excited to be there along with a few other clients where I do some elements of work for uh however I spend a lot of
0:34 my time with the CLOA team uh uh acting on behalf of their investors and their team as the chief revenue officer.
0:43 Uh I've I would say I've spent most of my career in big tech. So I uh uh spent a quite a long time at the time was
0:51 called Pioneer Standard which ultimately got bought by Arrow. Uh and then also at Oracle moved to VMware and decided I
0:58 wanted to right around just right around just before COVID hit I wanted to get into the small business market. So, I
1:05 started to go to companies where I found uh the opportunity to go from a series A to series B or help a company get from
1:12 15 to $30 million or to do those types of elements where I learned a great deal of uh about what it takes to move the
1:20 needle in a small company uh but then also uh help me start my own firm. Very cool.
1:26 So, yeah, that's me. Yeah. So from a from a big tech background, you obviously have been around technology, you've seen the trends and how they play
1:34 out. You how are you seeing this AI trend play at the moment and around business development?
1:40 Uh so you know I think there's it's such a broad conversation. You know I just was at Snowflake Summit uh a week ago.
1:48 Uh CLOT we are a true blue snowflake partner. So we, you know, we dedicated all of our energy and efforts to the successful consumption of Snowflake
1:56 products, but you know, you you couldn't walk by a single booth without seeing something that was AI generated or it is definitely obviously what consumes
2:05 everyone right now and it's the fastest way to get to market and you know even clar themselves we are a company that was born in the AI era so we move at a
2:15 much faster pace. Now from a sales perspective I think it's good and I think that it's the one area where I would challenge people in technology
2:23 where it's potentially hurt the size of business development. I think from a overall sales perspective,
2:31 uh, if you're talking to any salesperson and in in the anywhere really, I wouldn't say just the United States, but anywhere that isn't using AI as an
2:39 assistant to help them be better prepared for meetings, to help them be better organized, ask solid questions for managers to make sure that they're
2:47 improving on one-on- ones. I mean the the ability to assist and guide uh is so powerful from just a basic AI
2:55 perspective and that's before you even get into all the agentic elements that help make a company run. Uh however from a business development perspective it's
3:04 definitely oversaturated the market. You know I would say uh there isn't a person myself including formerly I was uh chief
3:12 revenue officer for a consumer data company where uh I outsourced our business development. They pretended to be me uh on LinkedIn and that's how we
3:22 went about getting a lot of our warm pro our cold prospecting done. You know what's starting to happen is everyone
3:28 knows that if you get a message from someone on LinkedIn uh and the moment they go back to one or two subtle
3:38 elements of your background you know that it's AI generated so you tend to ignore it right um email campaigns just simply
3:45 don't work anymore because ignore email now that if we don't recognize a person or it goes directly
3:52 into spam. So, you know, those elements are tougher to come by. And of course, prospecting over the phone has gotten incredibly difficult because if you
4:00 don't recognize a number, who answers it, right? Um, you know, I always say that one of the most powerful tools personally ever had to be video
4:08 voicemail. Being able to read or quickly read a transcript of who's calling me so I can ignore it or I can, you know, not, you know, not bother. I I can make sure
4:16 that I keep that 30 minutes of my time in my schedule together. So you know I would say that you know I believe AI has definitely
4:25 uh right now impacted that front end that business development effort uh far greater uh or far negative
4:34 it it's making everyone change the way that they think about how they go about finding new customers.
4:40 Yeah. So what are some of the things where you know you kind of pointed out uh certain things that kind of like diluted. What are certain traps that
4:48 would you would say like, "Hey, watch out for these approaches to using AI in your business development?" Like what are like the basics? You kind of already
4:55 hit them, but I'm just curious like a fun if I'm thinking about it from my own perspective, what should I avoid doing with it?
5:02 Well, I think that the the this is the hard part, right? Because you're asking it to write a lot of your notes for you, right? And you know the the one thing
5:11 that that you know I always talk to anyone that I've ever managed in my entire career is inflection. There's no
5:18 inflection in email, right? So the reality of it is is whoever is reading your email is inflecting based on how
5:25 they would read it. So uh I think all of us that get 200, 300, 500 emails a day quickly can
5:34 disseminate what's been written by a human being and what hasn't.
5:38 Yeah. So, uh, you know, I I wish I I could say, "Well, there's a silver bullet." But I mean, there's certainly easy things and honestly, I don't know
5:45 how to avoid it because you're having an AI engine mass write your your tools, your your programs for you. It's selecting it's pre-selecting certain
5:54 elements from my career. It's saying, "Hey, we have in common. Let's get connected." Um, and you know, I it's
6:01 very difficult for me to pinpoint one of those elements other than the fact that once you read 20 of them, you can quickly identify with them and know. Uh
6:09 and I I think the bigger problem with all of this is um you know uh it's the kind of one bad apple
6:16 theory of you know so now that everyone realizes that let's just say 15% and
6:23 that's probably really low of introductory emails uh or notes are AIdriven well you know as a business
6:32 leader you just ignore them all right so you know I think that that that's in my opinion That's the big challenge and
6:39 I you know that's where you have to get back to you know what seems to be working for us really well is we've gone back to more of a grassroots effort.
6:47 Yeah. Yeah. I I mean I think you know it's tricky because like you could have the human written element in there but
6:55 if everything is so diluted it just crows out and makes it so noisy. And because everything moves so fast now
7:02 it's it's happening ultimately like incredibly fast. And I've noticed the same thing. I used to think it was really cool like at the very very
7:10 beginning when people started being like this is a way to like optimize and personalize emails really fast but then like it just like after you got past the
7:17 party trick it kind of felt like one of those things where it's like you reaching out to say you want to start a you know a relationship with me but you're not actually putting any
7:26 effort into it. You have a bot that you're trying to trick me into thinking I I care about you and it's like that I feel like that kind of once where the luster wore off. I was like, "Oh, okay.
7:36 Wait, there's something on the other end." Um, so what? So, you're saying you're having success with Grassroots.
7:42 Yeah. Do you mind expanding a little bit on that? What exactly that is?
7:46 Yeah. So, you know, first of all, shout out to uh my my friend Helman at Clos Loop, uh, the training company who does
7:53 a really really great job around explaining how prospecting has changed, right? uh where you know precoid it took
8:02 you nine cold touches to get in front of a human being. You know today it's north of 20. So when you're writing sequences
8:10 you have to write them at such a rapid pace to make sure that you get to the point where someone says okay fine I'll meet with you after you've kind of bludgeon them to death.
8:19 Uh which also is a very poor way to start a relationship. uh you know one of the things that um uh my friends at you
8:29 know one of the things that we do at CLRO is we use a program called neutralizers so uh CLRO is I mentioned
8:36 it a little bit it's a system integrator that is heavily based and founded on Indian principles of you give first
8:43 before you receive right so uh we have strict we have strict guidance to uh
8:50 however your targets are uh you're not to reach out to them uh personally or you're not to reach out to them
8:57 individually. You're to find someone that's a neutralizer that can make that introduction for you.
9:03 Yeah. Because what happens is, you know, there's a thousand partners and they today for uh in in the Snowflake
9:11 ecosystem and if I'm just another partner that sends a a LinkedIn request and tells them that I've got the secret formula to tripling their consumption, I
9:20 know that I'm wasting their time, right? you know, how however if I have a target that uh I can I can put into my
9:28 uh uh into my into my goal sheet and I can identify two or three people that I know of them and I can make that call and make a request for an introduction.
9:37 You're much more likely to make that introduction and then give a value proposition that or a pitch that's going to help them. Yeah.
9:44 Right. Um so I I really think that this getting back to uh grassroots
9:52 build a network, work your network, and also to help others that are coming to see you. Make sure that you're doing the same thing. You're fully reciprocating
10:01 when those opportunities present themselves. Uh creates a a far better avenue. Now, you know what's interesting
10:07 about this is our our outreach numbers, you know, I would say compared to when when I was doing this prior, my outreach
10:16 is 95% less. Okay.
10:21 But my hit rates my hit rates are in the thousand percentile.
10:25 So, you know, you're getting meaningful you're getting meaningful opportunities.
10:30 You just have to put a little bit more work and a little bit more, you know, study in prior to getting those.
10:35 Yeah. Yeah. Warm referrals, those are you can't beat that with outreach.
10:39 There's just no comparison. So when somebody's going to build that network, you know, how would you recommend that they start the process of starting to,
10:47 you know, garner the relationships and be able to do that for them?
10:51 Right. The one thing that I would say uh about that too that I want to be cautious of, you're right. There's nothing like a warm there's nothing
10:58 lead, right? But the reality of it is is what we're creating is we're creating an element where we're saying we're generating the warm lead. So, it's not
11:07 just, oh, you know what? Someone, oh, someone knows Austin and he's a great guy. You know, I'm going to make sure I introduce you to him. No, we're actually going out to those folks
11:16 and saying, we believe we have something that can help someone in your network that uh we would like to get to know.
11:21 Would you be open to it? So, you have to create that warm lead. Um, which is a little bit different of a play than just your standard warm lead. Uh, but it is a
11:31 it is an important differentiator. And Austin, I'm sorry, I forgot your Oh, I forgot your question. Could could you I really like that distinction because
11:39 you're right. This is a proactive thing that you're doing. It's not a I'm just going to sit here and aggressively wait for people to give me like you know the referrals or to you know connect them to
11:48 the network. You have to go out and do it. And I think that's really a good point that you're driving home there.
11:53 Yeah. Um, so if I'm an individual that let's say, you know, maybe I'm newer into my career or I'm breaking into like
12:00 a different industry or for whatever reason I don't necessarily have a strong network and do we have any recommendations on how to start building
12:07 that out so then you can actually start proactively working that network.
12:12 Right. So I think there's a couple things. So first and foremost is uh grow your network. Like if if you're a
12:20 salesperson that's regional or if you're a salesperson based off of that has shares a vertical, you need to start getting into meetups. You need to start
12:28 speaking. You need to start building out, you know, elements that's going to help you grow your network so you can be treated like someone who's going to help
12:35 people. I think that is that is obviously the most important thing. And uh at times, and this is me kind of
12:43 showing my age a little bit, I think that's a a bit of a forgotten uh um a forgotten skill. And it's really
12:50 starting to make a turn back to that because uh we've oversaturated the market with technology to help do that job. That's the first thing. The second
12:59 thing is I you have to find the right tools. Tools are incredibly important, right? So you have things like LinkedIn navigate like Zoom info with you have
13:08 elements that have you know tools that can help you with a lot of different elements. Me personally I'm a big fan of a tool called knowledgeet
13:15 that takes your personal database takes your LinkedIn database and then shows you the multiple connections that might be connected to the person you want to
13:22 get to. So now you have access to all of those folks and you could quickly identify, oh, you know what, potentially
13:29 I I I have a potential opportunity to meet someone through a a a a neutralizing conversation.
13:37 Yeah. And then so, you know, you work on that getting out there, going to the meetings, going to different events, making sure that you're getting to know
13:44 people, then you start analyzing it. Um, you know, is it as simple as just making a phone call? Do you just try to stay in touch once a quarter with everybody? How
13:52 are you doing like your practical application on a on a regular basis?
13:57 Right. Right. Right. Great great question. I think there's two elements to that, right? So, one is uh part of the fun of doing things this way is you
14:04 get to connect with people you might not have connected with for for a while. You know, I've gotten to talk to some old friends of mine that you know that have
14:12 I haven't gotten to see and to catch up and and that part is great. I think the second piece of this is you have to have effective marketing too. You have to have a good newsletter. Mhm.
14:21 You know, a good newsletter will help you immensely to help you get to those different types of people and to continue your reach out and just great
14:28 friendly reminders. Um, you know, I think that I know I believe I know that that is a huge element to to success.
14:36 Uh, I also would say uh activity on LinkedIn that's positive is really good.
14:42 Uh, also company and corporate activity on LinkedIn I think is also a huge help.
14:48 Yeah. Now would you say that the you know we've talked about the the personal aspect of it you know do you think that those newsletters and that LinkedIn
14:55 activity needs to be like human and like written by a human maybe assisted by AI or is that one of those situations where
15:03 that's fine because it's more of summarizing information getting it out. Um well that's that's a great question.
15:11 I I just I I fundamentally believe that uh yes, you you should use AI to assist you in just about anything you can to make your life more efficient, right?
15:21 And that's where I was talking about at the beginning of, you know, uh there's no better executive assistant for any
15:28 individual contributor than AI. And frankly, if you're a really good one, you have a lot of heavy activity, if you're the type of salesperson that
15:36 every sales manager loves, you need that kind of help. And I always say, man, I wish I had it when I was, you know,
15:42 carrying a bag. Uh, however, you also have to be smart enough to know that someone can say, Dan McCoy didn't write
15:50 that, or your marketing team didn't write that. Yeah.
15:53 So, you know, there it's it's it's all nuance. I there's no there's no better answer to that. Uh, of course, you want
16:01 someone to help and guide you write something. And whether it's AI and technology or whether it's another person, of course, you want it, but just don't forget to do the hard work of
16:10 proofreading and making sure that you know it it does things like matches your corporate values, that it it hand it
16:18 your mission statement, and that it's targeting what you want to target. Too often do we just rely on a tool like that and just hit send and um that's
16:26 when you know you're in trouble. I mean, is it almost fair just to say like have it run and do as much as you want it to do, but you have to be that
16:35 intermediary. You can never not have the the human in the loop making sure that when the humans interacting, the AI isn't just not getting the uh the
16:43 intercept at some point, right? I I mean, I'm I think that there's there's just elements of creativity that
16:51 Yeah. you know each person or each company owns and you you have to abide by those
16:59 principles and you know you can train AI as much as you want there's always going to be elements that might not make sense
17:08 at least right now may maybe three years maybe six months from now that might be different but for today especially in
17:14 the in terms of business development uh I I'm starting to see more and more getting back to basics grass fruits of, you know, effective networking.
17:26 Yeah, definitely. I I'm not going to claim to be like a mass a master at message writing or like any anything like that. Um, but I almost feel like
17:35 there's almost like the uh imperfection of the human element and it just being like, you know, maybe a misspelled word here. I mean, not do it don't do it on
17:44 purpose, but like, you know, like just adding the human element of just being like, hey, this is my best attempt at writing it the way I write it. and
17:51 that's kind of who I am. And it allows them to kind of see you and maybe they don't want to work with a person like you, which is not an insult. It's just kind of, you know, they're not a match
18:00 on how you behave. But then you got a person over here who's more receptive to your guys's strategy or how your company operates and they want to talk to the
18:08 person that's there, not the thing that's always nailing its punctuation and doing grammar right all the time. I don't know. I I think Yeah, I've seen
18:16 the smirk. I'm so curious what your thoughts are. I mean, I I certainly want someone that has a can grasp the English language to write their emails for
18:23 themselves, but uh uh you know, it is funny what you say phrasing. You know, I I have my I have my AI engine on all the
18:32 time when I'm writing emails and I always get you know, I would say every every there you you can't write an email without a suggestion. It's almost impossible these days, right?
18:41 But do you take them all?
18:42 No. because there are time because I'm like this doesn't sound like me or I don't want to shorten this this sentence or you know there there are elements
18:50 that yeah that you're right that I kind of make that uh that that human
18:56 connection that in in my opinion they definitely matter people can tell people can read that well let me say I know I
19:04 can if I'm taking something something that's serious yeah I think I think there's a lot of I don't know if AI literacy is the right way to
19:12 put it, but a lot of people are getting really good at being able to pick that out. And then like even with like the videos as we're getting exposed to more and more of
19:20 those videos which are just mind-blowing, right? to see the AI creative videos that are just complete pull out of thin air and then like you see the first couple you're like this is
19:28 so realistic but then eventually like that it seeps in whatever is there you start noticing the tiny little nuances or like things are just barely off and
19:36 an inhuman way off and it becomes like you know where I think it's just become more and more where it's going to be more difficult to hide that the AI is
19:45 being used but I mean at the same time you know you you made me think of just you made me think of just a couple of
19:52 things that I I say are always important in sales and probably the biggest one is intent. Yeah.
19:59 If you know if your buyer feels that you actually truly want to help them and you're not doing this for a commission check, uh you have a much higher probability of being successful, right?
20:10 And you know, can AI pick up your intent with your customer?
20:16 And if it hasn't Yeah. And if it hasn't, maybe maybe that's a a great thing to evaluate.
20:25 I think the the emotional aspect of the conversation that you're having, like AI is mimicking emotions, but AI doesn't have emotions. And so, yeah, there's
20:34 that when it tries to be empathetic or be like, "Hey, I understand what's happening here." Like, it doesn't. It's, you know, a really advanced clustering of text with I know more math than that.
20:44 But it's it's really powerful tool, but it's not actually having empathy for your situation or not truly looking out for your best interest. It's just
20:52 processing a calculation on what the next best guess is of what that conversation should go to. And I think that, you know,
21:00 that's Yeah, I I think this gets back to, you know, I would challenge anyone on my team to use AI every single day.
21:08 Like it's going to make you more efficient. Uh, is it the has it harmed business development by saturation? I'm
21:17 gonna say yes, it has just because I'm a person who gets called on every single day I get prospected to multiple times.
21:26 And I could open up my email right now and I could assure you that the top five of them were not written by a human.
21:31 Yeah. Yeah. Well, and you know, not to play devil's advocate, but maybe there's something nice about the shift that it's
21:38 forcing us into with like, all right, you no longer can just sit here and write an email and get a response. You need to actually go out and there start
21:46 building networks and building stronger human relationships.
21:49 Um, which makes it maybe a little bit more difficult, but could have profound impacts down the road. And I got to imagine that, you know, if you met somebody, shook their hand, and they
21:58 became a pro or a customer later on, they're probably going to be harder to churn than if you sent them an email and saw them over Zoom once. Um, I don't
22:06 have any data to back that up, but I would I would be willing to bet that would be what would happen. Sales is hard. It is.
22:15 I mean, it is. So, yeah, you gota you gota you got to do some of that heavy lifting.
22:21 Yeah. All right, Dan, we're up on our time. I want to make sure I'm respectful of it. Any final parting thoughts or anything you want to summarize before we sign off here?
22:30 No, this was great. I really enjoyed it.
22:32 I I appreciate the time. I'm glad you reached out and uh I'm I'm always curious to hear if there's other people that kind of see things the same way I
22:41 do or they think I'm crazy or may I'm sure there's a a combination of both of them out there. So, yeah, I'm super
22:48 interested to see uh what the feedback is. Yeah, me as well. All right, Dan. Appreciate you.