The cold-calling landscape has changed dramatically in the last few years, due to a number of factors, including (writes in broken record) AI. Jokes aside, though, we felt we needed to address the current state of cold calling, what’s different about it, what’s not, and, most importantly, what advice we can pass along to you. This blog is the first in a series in which we consult cold-calling experts. They come from different places, share views on some aspects of cold calling and differ on others. What they have in common is a razor-sharp understanding of the ways in which cold calling has changed and how vital it remains to sales. They generously shared advice, experiences, and keen assessments of cold calling today, yesterday, and tomorrow.
February 12, 2025
Maestro was first introduced to Ryan Reisert when we used one of his products, Phone Ready Leads (now Titan X), which provides sales intelligence and data scoring. Ryan has authored or co-authored four books. He’s founded or co-founded four companies and acted as the head of sales for another four. He’s also staunchly transparent. Sometimes he’ll broadcast himself doing live cold calls on social media. He has a pretty unique take on the introduction—and the pervasiveness—of technological cold-calling tools.
Ryan believes that our preoccupation with technology is actually distorting our perception of market number: “The biggest problem that we see with cold calling right now is that people believe that no one’s answering the phone, and people believe that it’s not effective because they’re seeing a low connect rate and a low conversion rate. But if you take it back to the simple principles, it’s because they’re not actually targeting the right people with the right contact information…”
More on that later, though. First, let’s back up a bit…
Ryan’s induction to cold calling came in the form of telemarketing for political and consumer surveys in high school. He did so in a cubicle farm with a headset. “You’re at a computer, and the computer literally just drives everything for you,” says Ryan. “You logged into the system, you clicked a button, and they had, back then, some crazy dialers, and a screen would pop up. You’d have someone at home on the phone and you would follow the script to a T.”
He excelled at it. And he liked it. “I moved from working at Burger King in high school to this job, and it was air-conditioned, not in front of a fryer, et cetera.”
In 2008, Ryan graduated from college and went to work in tech sales. “I would show up, I would make calls, and I knew what to say. I was successful. That company was actually backed by AIG.” It was, unfortunately, a home-finance product—not what you wanted to be selling in 2008. Ryan got laid off. Basically, everyone in America got laid off.
His next move was into early-stage startups. What was different about this was that no real infrastructure existed. “I was assigned to cold calling for three different senior AEs, and all of them had a different way of getting me a list.”
According to Ryan, the problem of our own technology getting in our way as it pertains to cold-calling is not new. Here’s how he broke it down for me.
2008–2015: Old-school cold calling
When Ryan began cold calling, the directions were relatively simple. He refers to it as “the math of sales.” 100 dials equaled about 10 conversations equaled one meeting.
Circa 2015: The rise of data
In 2015–2016, data began to proliferate—”the rise of the ZoomInfos of the world. Back then, there were some other tools that you could use. LinkedIn was getting more popular, so [it was] easier to target but didn’t necessarily have the contact information. But you could purchase lists with data now and not have to procure this data yourself.”
Circa 2015–2021: More data
During this time period, the amount of available information went up. So did the number of phone numbers per person. “So, you’re having to make four dials per contact just to try to get a specific conversation. We see that average dial-to-connect rate drop from ten percent to something like three to five percent…”
This created an impression of dwindling pickups. Along with “this rise of more automation [people were] saying, ‘Oh, nobody’s picking up the phone.’ That’s what they said. But the reality was you had to dial through more data to get to that same targeted conversation.”
Then came the deluge of technology dialing, including auto-dialers, parallel dialers, and AI dialers. These, of course, were “aimed at trying to help sellers get more conversations. But the reality was it was actually only making the problem worse.” These tools helped people make more calls in less time, but the actual underlying problem of poor data wasn’t being solved.
Circa 2021: Now
At this point, we were well into the pandemic, and work-from-home seemed like it was here to stay for many. “Everyone’s working from home now, so we have to have more mobile data. Mobile, mobile, mobile…what that did was add yet another element that makes calling difficult, because there’s this problem that is called ‘right name, wrong person.’ So these contact databases have, myself included…phone numbers attached to the records that I’ve never owned.”
The result? “‘I’m not interested. Don’t ever call me again.’ Click. So, the perceived feedback is, well, cold calling doesn’t work. People don’t like it. They’re annoyed. Well, yeah, of course…you’re pitching a service to an individual that isn’t even the right individual.”
Automated products seemed great for callers, but they were an increasing nuisance for, well, everyone else. “There’s a mandate that came out called STIR/SHAKEN,” Ryan told me. “So, STIR/SHAKEN is aimed at combating robo-dialing…You’ve started to see on your mobile phone where numbers come up as ‘spam likely,’ ‘scam likely,’ those types of things. So, what does that do? Continues to plummet the dial-to-connect rate. What does that do? Solutions come into the market and say, ‘Hey, no one’s picking up the phone. Let’s do more dials.’ And so, you can see this proliferation occurring where people are not solving the right problem in the right order. So, this change that occurred didn’t just start in ’21, but we started to see it really happen [then] because of that mandate with STIR/SHAKEN and this rise of more data, more automation, which has changed the game for cold calling.”
Ryan has a remedy to offer: go back to the basics. “If you remove all this bloated tech stack and you get scientific with understanding the process behind identifying, ‘Do I have the actual right contact information for somebody?’ … ‘What percentage of that list will actually pick up the phone if I call enough times?’ Then you’re in a position where cold calling becomes very efficient.” And by that, he means very efficient. “Connect rates on a list of people that are actually likely to pick up the phone, the ones that are worth calling, are not three to five percent. They’re more like twenty to thirty percent…When enabled properly, you can effectively book meetings every, let’s say, fifty dials.”
To Ryan, neither automated tools nor number of dials do quite as much as people think they might. Rather, “the list is the strategy. It doesn’t matter how good you are at cold calling. If you’re calling people who are not relevant for your offer, you’re not going to have success.… Process is what’s going to drive results. And what I discovered very quickly is that obviously when you’re cold calling, the number one thing that matters most, it’s not how many dials you do every day, it’s how many targeted completed conversations you have every day. How many people on your list that you’re trying to get on the phone do you actually get on the phone, and they hear your message? That’s the number-one thing that matters. So, I’ve obsessed over that for my entire career.”
According to Ryan, too many people have forgotten this. For him, everything he learned from his first cold-calling job remains important. “If I have sales reps or if I am a sales rep…I want to have a system or a process, just like I did in high school, that gives me the next best person to call with the right message…What’s happening is companies are buying these inflated, bloated tech stacks with all these crazy insight signals and data, and here’s all the information, here’s all the automation, putting it on the rep to go put the list in the process, not enabling them with the message, and just spamming the crap out of their market.”
One of the things Ryan is most famous for is his “buckets” approach. He uses four buckets to describe the successful sales process.
Uncontacted
The first bucket involves collecting targeted data of your buyer persona. In this stage, automated tools are not totally anathema to Ryan: “We can use those tools to get the enrichment, but in order to move from uncontacted to the next bucket, which is working, we should run a validation process. And that validation process allows us to understand which numbers are worth calling and which ones are not worth calling.”
The working bucket
In fact, one of the tools out there—Titan X—is something Ryan fashioned himself. Titan X deploys an algorithm that predicts which prospects are likelier to answer the phone. It’s also something that can be done manually: “We want to try to look at the propensity of someone’s likelihood to pick up the phone… In order to be a validated record, I need to be able to get to a working voicemail, and I want to hear your name in the voicemail.” A personalized message indicates that the owner is likelier to pick up. “It makes sense, right? If I take time to program my voicemail, I probably am more receptive to people calling me. I want you to know this is my number versus if I don’t…”
A generic voicemail, on the other hand, is labeled non-validated. The logic behind this is that, “my valid records are going to have a one-and-a-half to two-times higher connect rate than my non-valids.”
Another method of determining the likelihood of a pickup is whether a call sends you to an IVR (dial tree) as opposed to a live answer. “Companies who staff a human that transfers calls are also two times more likely to pick up the phone than people that use an IVR. Again, makes sense if you think about this. If I’m paying someone at my company to push calls to my employees, I want my employees to be picking up the phone versus if I’ve included an automated dial, like a dial tree, I’m not really prioritizing people calling my company.”
Here’s some of Ryan’s math: human answer + voicemail with name = 4x more probable pickup than IVR + generic voicemail.
Priority
“The next phase is, once someone picks up the phone, that becomes a priority lead…People who pick up tend to pick up again and again and again and again. People who don’t, don’t.”
Priority-lead math: priority leads x multiple calls = probably 80–90% additional pickups.
Meeting Scheduled
Enough said.
In many ways, everything Ryan knows about cold calling, he learned in high school. Maybe not everything. But he does hold many of those longstanding lessons dear. Ryan believes that sales is about trust. That’s something you’ve got to earn. But, according to him, that’s a more achievable outcome than you might think.
Do you need some help at the top of the funnel? Reach out at mastery@maestrogroup.co.
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