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 second 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 19, 2025
Daisy Chung believes in sales. Her first tech job was as a sales development representative at an HR management-system company. Even after she rose the ranks to sales development manager, Daisy’s instinct was to keep her hands dirty. In a move that some might mistake for choosing to go backward, Daisy became an account executive. “I decided that I couldn’t be the best manager if I wasn’t selling, which is what all SDRs that I was managing wanted to do. So, I went on to become an AE from there…”
Daisy repeated this type of move during her tenure at Orum. She started at the company in 2020 as an enterprise account executive and worked in this capacity for two years. At the same time, she sensed that something was missing: “I felt like I was more so making money than learning and growing.” She saw herself back to the sales and the management portions of the company, leading the mid-market and enterprise-AE team as a sales director. “I realized that revenue is a team sport. It’s not just sales. Sales influences customer success; customer success influences sales. It’s kind of a whole tandem for a company to grow revenue, and so [I] decided to kind of take a leap to try out this new role where I’m working with both the sales team and the CS team and coming out with our strategy to elevate our revenue.” This feels more aligned with Daisy’s approach to making an impact at her firm. And it must have been a good move since she is now head of revenue strategy at the live-conversation platform.
Cold calling is still very much a part of her everyday job, which, at Orum, is not unique. “Oh, at Orum, everyone cold calls. So, our SDRs for sure, our AEs, our CSMs, myself, our CEO—everyone’s cold calling. I mean, to varying degrees, and SDRs will cold call more than me, but I’m still cold calling to this day.”
To be clear, Daisy sees this as a plus. “This is why I love Orum. That’s why, for a salesperson, it’s really fun, because when you sell to sales, they kind of know what you’re saying and doing. And we do live cold calls at Orum, so they see us. They get really excited. We get really excited. So literally, sometimes when we’re selling Orum, we’re building pipelines for me to sell Orum. I’m showing you how Orum could book meetings, and I’m booking meetings as I’m selling you. So it’s a win-win for me. I get a free meeting, and I’m doing my demo here.”
We asked Daisy to talk a little about different eras of cold calling since 2015. Daisy focused on the following periods: 2015–2020, 2020–2022, and 2022 onward.
She sees the first period as a time of “old-school cold calling.” What this means: “You pick up the phone, dial. Most sales orgs are expecting a hundred dials a day… It was all about dials, dials, dials. And then over time, towards the tailwind of that [they] started being focused more on connects. I’ve been in and have led an SDR team. I’ve worked with a lot of clients [who have] SDR teams. Metrics always change, and focuses always change year after year, just like quotas and comp changes in sales.”
In addition to all of its other colossal impacts, the pandemic changed cold calling. “Everyone was in a frazzle,” said Daisy. “They were like, people aren’t in person anymore, and you have to rely on the phone. Everyone’s at home.” This ushered in the premium status of mobile numbers. “You’re not going to catch anyone on the office line. You’re not going to catch anyone with the dial sheet because everyone’s at home. And candidly, there was a period [at] Orum [when] we were like, ‘Oh gosh, no one’s buying. The economy’s down.’” That reality, however, went both ways at Orum. A market in the eye of a mobile-outreach storm produced a whole lot of potential customers for the AI dialing platform.
The end of the 2020–2022 period saw a major change that both came out of and impacted dialing tools such as Orum. “Since that time, the conversation has shifted. It’s no longer about dials, especially when there are tools like Orum out there. It was about connects and quality conversation because, end of the day, dialers like Orum can get you a lot of calls really quickly, drop all your voicemail, but how many conversations are you really having?”
What took its place was revenue. “Unfortunately, the cold-calling team’s the first to go during a down recession unless you can tie it back to revenue. And a CRO does not care that you’ve booked 20 meetings if those meetings don’t actually land revenue.”
When Daisy looks ahead, she sees a new question driving the cold-calling conversation: “Most companies aren’t there yet, but the narrative is: would you rather have a hundred calls, ten connects, five meetings, four of them with managers, one of them with a gatekeeper? Or would you rather have a hundred or fifty dials, that same time conversation, two meetings, and they’re both with CFOs that can get the job done?”
Not according to Daisy Chung. The major differentiator? Empathy. “It’s human relationships, it’s trust, and that’s what AI can’t build. People buy from who they trust. People buy when they feel like you’re empathetic to what they’re looking for, that you care about their problems. You’re not just shoving a product. And that’s where AI can never win, at least in today’s world.” In other words, Daisy isn’t predicting a complete AI takeover that obviates the need for human communication and effort in sales any time soon.
Some of AI’s capabilities, and an over-reliance on it in personalized outreach, can really backfire. “There’s so much technology that gives you intent data, that gives you research, and there’s everyone customizing: ‘Hey Alicia, I noticed you went here for college. Go mascot!’” That kind of content is probably pretty repelling to most people.
Daisy has an alternative that’s more authentic but doesn’t exponentially increase research time. “You have to go two, three layers deeper in customization…” Here’s her method. “I look at the start date of someone at that company and tie it back to how excited they are for what they’re doing. So, if someone’s been there for a while, my first thing is, ‘Hey, thanks for picking up. So excited to chat. Oh, wow. I noticed you’ve been there for ten years. That means I’m sure you’ve seen all the changes. Have you heard of Orum before?’ If I notice you just started. ‘Hey, congrats on your new role. It’s awesome. I’m sure you have a bunch of priorities and your calendar’s probably full as you’re onboarding. Just curious…’ So you can tell it’s very simple, but at the same time, you’re speaking to the empathy.”
And it really is a better alternative. “You can do that for anything, but it’s layers deeper than ‘Go mascot!’…”
Since number of outgoing calls is no longer the shiniest metric, Daisy recommends that salespeople ensure they are proving their work’s financial value. It’s important to demonstrate “what kind of impact you’re making so that you’re not the first people or technology to churn during a down recession.”
She’d love for salespeople to try and use cold calling as a confidence builder. When “you build that confidence, and you accept the rejection that comes from all that stuff, you can laugh about it.”
She also hopes that people can come to approach cold calling in a way that unburdens them of some of the anxiety it stirs up. “Honestly, cold calling is just that first call. After that, it’s warm calling. Whether they hang up on me or not. That’s where I think it’s so beautiful because you’ve opened the door to send them an email, you’ve opened the door to call them again, you’ve opened the door for more human interaction.”
This is something that Daisy tries to remember at work. She kind of loves cold calling now. And she sees it as a method that’s built from a rich toolbox and skill set—and remains incredibly relevant. After all, she says, “I think billion-dollar deals are made from cold calls…”
Do you need some help at the top of the funnel? Reach out at mastery@maestrogroup.co.
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