For about 10 years I was on the buying side of this. I started as a software engineer, then architect, then VP of Engineering. Last year my inbox took maybe ~80-100 cold emails a week (if I only count the Inbox) and the phone called a few times a day, with a sales rep on another end trying to convince me I need their observability solution.
I was annoyed by it at first, but then something switched and I decided to start playing along. I must admit, it took me embarrassingly long to understand, that on another side of the phone is another person, and this person makes tens of calls, and it would might make his hard day emotionally easier if I engage in a friendly conversation.
On the other hand, nothing gimmicky ever got a rely out of me. A “quick question” as a subject line in 2025? Seriously? What did get a reply, was recognizing the problem that I would struggle at that moment, and honestly, sometimes just three plain lines with no personalization at all, because at least it wasn't pretending.
The ones who got somewhere with me did things that appear simple, but now I know, difficult to execute. They would be friendly, calm and they would ask the right question and them stop talking, and let me describe the problem in my own words, engage in pleasant conversation. This conversation would build trust and allow me, as a buyer, to see that this “just another sales rep”, although not an engineer, clearly understands the domain. As I would explaining my situation out loud they would help me understand the gaps in it. By that time this call would have provided me with some value already!
Recently switched to running my own startup (B2B SaaS), and while I was busy building the product I first thought of finding someone to do the outreach for me. Everyone I talked to, including people with real B2B outreach experience, got enthusiastic about the same thing: all these new tools, volume, automation, AI. My gut reaction was that they wanted to AI the hell out of my prospects and spam them with generative nonsense, full of “— “ and "no pitch, genuinely interested". And what bothered me, was that you might be able to automate the opening (although it is very hard already), but the part that actually worked on me was empathy and attention. I don't know how you automate trust, and I'm not sure you're supposed to.
At this point I'm a founder with ~2-3 appointments scheduled a month, not a rep with a number to hit. I understand that if you're doing 400 touches a week you can't do what I'm describing.
So, for people who've been doing this longer than 3 months: does the listening part survive quota?
Or is the real skill knowing which small number of accounts get the human treatment and which get the sequence?