
The Sales Machine · 2026-06-10 · 19 min
Key moments - from our scoring
Substance score
30 / 100
Five dimensions, 20 points each
Aaron Ross, author of Predictable Revenue and From Impossible to Inevitable, explains the fundamental shifts making traditional cold outreach obsolete. Response rates are down, churn is accelerating, and sales cycles are lengthening - trends driven by a more chaotic world post-COVID, generational buyer preferences for digital-first engagement, and exponential noise across channels. Rather than copying playbooks from competitors, Ross emphasizes investing in relationships as a hedge against uncertainty. This includes building community through events and mixers, strengthening customer success partnerships to generate referrals, and creating content-based relationships at scale (social media, LinkedIn, thought leadership). He also introduces a framework on income operating systems covering employment, freelancing, and investing, arguing that most people should start with stable employment while building entrepreneurial skills through freelancing before scaling to business ownership. The conversation touches on AI acceleration of tactic commoditization, the importance of personal authenticity versus parroting trends, and practical referral strategies SaaS companies typically neglect.
Multiple structural trends are converging: response rates are down across channels, buyer noise is increasing as technology makes it cheaper to send messages, younger digital-first buyers demand higher justification for meeting time, global chaos makes predictions harder, and the half-life of tactics is shortening because anything that works spreads rapidly and gets commoditized.
Aaron Ross recommends investing in relationships through community building, partner ecosystems, in-person and virtual events, referral systems (especially leveraging customer success teams), content-based relationship building at scale (social media, thought leadership), and personal authenticity rather than copying playbooks.
The challenge Ross identifies is that customer success or account management teams have strong customer relationships but lack motivation to refer (they're not compensated on new business), while sales teams are motivated but lack relationships; bridging this gap requires deliberate processes connecting customer success to prospecting teams to generate referrals.
It covers three ways to make money - employment (pros: stability; cons: risk of job loss), freelancing (pros: flexibility; cons: unpredictable income), and investing/business ownership (pros: scalability; cons: higher risk) - with a recommended pathway: start with stable employment, layer in freelancing to build skills, then gradually transition into investing and business building over 5-10 years.
As AI commoditizes copied tactics faster, differentiators like genuine authenticity, personal hunches, and following your own interests create sustainable value; leaders should question whether they're parroting popular approaches or developing unique, interest-driven positioning that AI can't easily replicate.
Our reviewer’s read on each dimension, with quotes from the episode.
There are a few genuinely interesting observations - particularly about the shrinking half-life of tactics and the structural problem of referrals being orphaned between CS and sales teams - but they are buried under extended personal tangents about fiction writing, Scottish property, board positions, and a generic personal-finance framework that has no relevance to B2B operators.
the half life of techniques and tactics is shortening because if something works just gets spread around faster, which means more people see it, which means it doesn't work as well
how do I work with the customer success team to get customers to refer me to the people I want to talk to? It's kind of like a bit complicated
The episode recycles Aaron Ross's own decade-old specialization thesis from Predictable Revenue, leans on the well-worn 'relationships are the future' argument, and pivots into a generic employment→freelancing→investing wealth-building framework that is entirely off-topic and unoriginal; almost nothing here challenges or reframes conventional thinking.
people, people in, you know, no, shocker. No, it's not the only thing, of course
Taylor Swift obviously is, you know, a master at that
Aaron Ross has genuine practitioner credentials - he built a real outbound system at Salesforce before it was a household name - but in this episode he presents largely as a reflective author-advisor between projects rather than an active operator with fresh at-scale experience; much of the conversation is personal life navigation rather than hard-won operational insight.
I'm figuring out this process to get a point appointments. I don't want to have to wonder how I'm going to make my quota every month
I've got a business in Brazil and I've got a different sales consulting business and kind of a partner runs it all. And I get like a percentage
Concrete data is almost entirely absent - claims about falling response rates, rising churn, and longer sales cycles are stated without a single number, study, or named company beyond Salesforce cited in the host's intro bio; the one figure offered ('30,000 connections on LinkedIn') is personal vanity data, not evidence for a claim.
Response rates are down across whether it's in marketing or whether it's in sales. And churn is up
I have 30,000 connections on LinkedIn
The host contributes almost nothing beyond a bio recitation and a single factual error about publication dates; there are no follow-up questions, no pushback on any claim, and Aaron is essentially left to free-associate for 19 minutes, resulting in long detours into personal memoir and an unrelated personal-finance book pitch.
2019, predictable revenue and then from there from impossible to inevitable. And both of them are copyrighted in 2019.
Gratitude of jumping on the show?
Computed from the transcript - who did the talking, and the words that came up most.
What happens when the system you built breaks? Aaron Ross, author of Predictable Revenue, the book that shaped how Silicon Valley sells, is back with a harder truth: outbound is unreliable, buyers are disengaging, and the tactics that worked two years ago have a shrinking shelf life. In this episode, Aaron and John unpack why response rates are falling, what the next growth lever actually is, and how smart sales leaders are doubling down on relationships and referrals to win in a world reshaped by AI and constant disruption.
Transcribed and scored by The B2B Podcast Index.
Speaker A: Most of the people I don't know, they know me, they know me as an author. Relationships could be a lot of SaaS companies are investing in community, in partner ecosystems, events where they're getting people together, often in person, sometimes it's virtual, but they're getting people. Not necessarily even a webinar present. It's often could be a mixer where they have prospects and customers talking or just customers talking with each other. So uh, there's lots of ways you can strengthen relationships and stand out as a brand or as an individual. What doesn't happen lots of companies is.
Speaker B: Ladies and gentlemen, today's guest, Aaron Ross is a globally recognized sales advisor and author of uh, Predictable Revenue and From Impossible to Inevitable, the sales bible of Silicon Valley. His methodologies have powered growth at Salesforce to over a hundred million dollars just in the beginning, before it was a billion dollar company. He's worked with Twilio many, many, many others, generating billions of dollars in revenue. He's on a new journey now. He's a board member for several startups. Aaron helps sales leaders adapt to AI disruptions now and changing buying behavior, offering fresh strategies to thrive in a rapidly shifting market. Welcome to the show Aaron Ross.
Speaker A: There you go. Thank you.
Speaker B: 2019, predictable revenue and then from there from impossible to inevitable. And both of them are copyrighted in 2019.
Speaker A: Yeah, the original predictable revenue was like 2010, 2011 and original impossible was at 2016.
Speaker B: You took your previous experience and failures and you turn them into winners and then win winning systems.
Speaker A: Hopefully we all do. Think about any sports team. Do uh, you know any sports teams that don't put people in specific positions so they can do that one thing really well. There might be someone, I don't know any. You got attackers and whatever the different version, you usually have people who attack people who defend a lot different sports. But in sales the tradition was and there's reasons but you know, everyone kind of like does their own prospecting, does their own selling, maybe even manages their own accounts and doing many things. If you have say 10 salespeople once in a while you can get a unicorn, a salesperson who can do all that really well somehow. But you can't build a team of people like that or it's really hard. You, uh, know, I guess in financial services they, that's kind of their whole model. So to me it's like, well, if you create this system, rather than trying to hire and manage a team of rock stars, what if you make the system the rockstar where you could have a good system and then you could hire good people who don't have to be the best. They could be good. And then everything works well. So that included specializing. You've got prospectors who prospect and you know, maybe inbound lead qualifiers who give marketing leads and closers who sell new customers and then people who manage everything after that. And if you do that and you have to do that, then everything else gets easier. You know, that was not a new idea, but a new saying like you have to do this in this way to make it work. Because like you said, having your highest cost people do low value prospecting doesn't make any sense. Not to say that. I mean there is a blog post or some article which is, you know, salespeople shouldn't prospect. Okay, it's being bit dramatic. So salespeople should prospect a little bit, you know, to a small number of key accounts. And again, there's gonna be jobs where salespeople should prospect if you're, you know, a salesperson in a territory going door to door. And there's always ways. But you're just trying to say in this case last to tie this up is it's not that you should do these jobs the way I lay them out. It's the principle is focus. I wrote about this in the impossible book was you may not the way Your business works B2C B2B to ABC may not need these jobs. You know, prospecting inbound, closing post sales. So it's like what are your jobs to be done and how can you divide and conquer with your team so that people are doing fewer things better not spreading themselves too thin. And if you do that as a uh, as the, as the guiding principle, then everything else will be easier. In certain industries where people are very focused on just money and it's easy to attract a lot of people who have, don't have scruples. Even though there's always tons of people who have values around. Like you said, like service helping people meaning and you know, money is helping kind of power that. But that's where people to realize, you know, money is like. Money is. Can be a great thing used for helpful things or not. You can do sales, you can do marketing. Anything you do with that intention of what you want to get out of it. Sales isn't manipulative. It can be. Sales can be helpful. Marketing can be manipulative or helpful. Let's say we have a business and there's a product and we, we want to put in a go to market motion. We want to like sell and Market it. And there's a lot of playbooks or, or processes or techniques that you could just kind of copy and paste. Although of course you always have to iterate it. But you say, look, some company did it this way, you know, they, and we're just going to basically copy what they did and it would probably work. And that's changing for a variety of reasons. Uh, fundamentally there's. If we go back to a lot of. Even this last year, I talked to a lot of sales leaders around the world and what a lot of them said, marketing leaders, sales leaders, revenue leaders, and they said is everything is getting harder. Response rates are down across whether it's in marketing or whether it's in sales. And churn is up. So customers are leaving faster. And there was a slowdown recession too. So churn is up. Sales cycles are taking a bit longer. Response rates are on, sales and marketing are down. Salespeople are getting ghosted more often by prospects and customers. All these factors, right? And there's some reasons for that. There's not one reason, but I'd say there's a few major reasons and most of them are not going away. So for example, the world is, is more chaotic, less safe, less predictable. I think Covid really broke that open. The sense of you think you can have some plan. You kind of, you used to feel like I, I used to feel like, okay, I can kind of guess at what the next few years will people that that illusion has been dispelled. So people still feel like that bit of unsafeness in the world, what's next? And that's going to continue because as, uh, the world gets more connected, the chaos factor will increase because one thing in one part of the world will just ripple faster to the other parts. There's a generational change, right? So now you've getting, you're getting younger buyers and well, the buyers and sellers who are of this kind of younger generation growing with being more digital first. And so yeah, they're not going to just take a sales meeting and a buyer based because they need to learn something. Like, well, do I actually need this to learn something? Can you send a video? Can you send a thing? Do I want to look online? So the bar to get a sales meeting is going to go up to justify the time spent. So that's affecting things. There's just noise. So another third trend is just there's always going to be increasing noise in the world, right? There's more channels, more content, more messages, more stuff. Right. That's inevitable from the way Technology works and how the it's easier to make technology cheaper to send messages. And so the clutter in email boxes, messaging boxes, online screens, that's always going to be there. So getting that attention is going to be more competitive. Your main competitor is not actually like a true competitor. It's just, you know, for someone's attention, all that stuff they deal with. So there's uh, all those things are combining and then you have AI on top of it. So to me, if I step back right, I think, huh, there is a parallel between when I started at Salesforce and created predictable revenue and what that was, was I'm figuring out this process to get a point appointments. I don't want to have to wonder how I'm going to make my quota every month. How can I solve this once? So it just keeps working. So now what is the case is, you know, if techniques didn't work, techniques from two months ago may not work today because things are changing or you know, from last year, the, the half life of techniques and tactics is shortening because if something works just gets spread around faster, which means more people see it, which means it doesn't work as well. Outbound, inbound, marketing, ads, whatever. So for me, I'm like, huh, huh. If I was going to solve this once. So we have this unpredictable world. Who knows what's happening with AI and everything else or uh, when the next kind of COVID type thing is. And now like our old home area in Los Angeles just went up in flames basically even yesterday. So to me the thing to invest in like one thing that if you invest in it, there's not just one thing, but one of the, one of the things you can invest in, no matter, and no matter what happens, it will be valuable, it will help you succeed is relationships. So to me, one of the keys of the future and I think where my lens is, people, people in, you know, no, shocker. No, it's not the only thing, of course because you could invest in technology and so on, but with all the change and how you stand out in the future, people in relationships are in the area that will always serve you well, no matter what happens. Because the shortest path between two points isn't. It's just trust, right? So that's why if you have a big audience or if you have. It doesn't even have to be big, a big audience. If you have any audience or if you know people and they trust you. It doesn't if you're doing AI or not, or there's Covid or Not. Or you're going to have more leeway in more opportunities and more advantages. So that might look like there's a lot of ways that can translate to a business. And this is kind of the part where I'm still developing the, uh, playbooks. But what that can look like is how your relationship, relationships with your internal team. If you have a team, because if you're a CEO, the way you treat your team will set the example for how they treat their customers. So that can be then. Or the relationships that you salespeople or people who sell have with the customers. It can look like how, if you say you're a leader again, how you're treating your own people, it could be how you present yourself at scale through marketing. I start content, social media, content, whatever form of content. So you can create relationships at scale. Taylor Swift obviously is, you know, a master at that. So it doesn't have to be, hey, having coffee with somebody. It could be any way that you're forming a bond of trust with someone, whether you know them or not. Like, I have 30,000 connections on LinkedIn. Most of the people I don't know, they know me. Not all. I mean, some, but they know me as an author, I may not know them, and that's okay. So in relationships could be a lot of SaaS. Companies are investing in community, in partner ecosystems, events where they're getting people together, often in person. Sometimes it's virtual, but they're getting people. It's not necessarily even a webinar present. It's often could be a mixer where they have prospects and customers talking or just customers talking with each other. So, uh, there's lots of ways you can strengthen relationships and stand out as a, as a brand or as an individual by building your relationships. So there's one last area that I think the most practical area that will be the most kind of playbookable is referrals. Because even in these books, right, I wrote like, you know, word of mouth is the hardest thing to grow. It's the best. It's hard. But now that outbound, inbound is often a lot less reliable. Sometimes it works, but, you know, there's always this like, huh, uh, is it going to work next month? I believe referrals are going to be as, or more important than ever. Well, and what doesn't happen in lots of companies is often because there is specialization of salespeople and I helped create that. Of course, you have the people with really strong customer relationships, let's call them the customer success team. It could be or let's just use that label. Or because it could be account management, they have these relationships that the people motivated who need business are the salespeople or prospecting team. And so it's a lot of steps and people don't do this, which is how do I work with the customer success team to get customers to refer me to the people I want to talk to? It's kind of like a bit complicated. It doesn't have to be. So that's an area I'm looking to kind of come up with a better solution at least for SaaS companies in the next maybe even few months. I'm not really sure. But relationships to me are one of the areas where at least I'm interested in doubling down on. And that also if you, if we can, if we kept going, which I'm going to inform again, how well do you know yourself? You know, what are you actually interested in? How do you kind of, uh, connect with people or not? Are you just kind of parroting all the same stuff out there, like kind of copying what's popular? Or are you really kind of following your, your own interests, your own hunches, your own path to kind of say something or be something that unique and interesting and different and everything else that is getting copied faster than ever by AI, uh, you know, salesperson, sales leader or a CEO who's selling any C level or executive or founder who needs to kind of a bigger picture. Uh, like, what does it take to grow a company? So in China they had a great the. They renamed it from 1 to n. Peter Thiel wrote a book from 0 to 1. So how do you go from nothing to like something? So this was the book which is you something. How do you get, you know, grow a lot of okay, well what do I do next to make money? And so naturally advising companies and looking at boards or something I was interested in doing, I thought, okay, I could do that, that type of work. Feels the time easier to do closer to what I'm known for, versus I'm just going to use things like writing novels. You know, I think joining board sounds, you know, growing up it's like, sounds prestigious and you can make, you know, uh, you can make a lot of money at it. And for some I did some not. Some boards were really interesting because I was learning and they're smaller and some were just boring af and it's like, oh, you know, I really don't like this. They're saying, you know, I've joined a couple because I like them and it's like, okay, keep my hand in. I'm kind of learning as good people, but I don't want to do a bunch of boards. Okay, so I'm still on this journey, like, what do I actually want to do that I'd like to do for the whether if I wasn't paid, but I still do this. That actually still feels really interesting. Although I quite haven't figured out how to do that in a way that fits how I want to do it. And I'll give you one example I think this will hope helpful is, um. I think, let me tell the backstory was we wanted to buy this other property out west in Scotland. Didn't have the money through doing this. I talked to some people who were like, oh, yeah, we want your help in like writing a book. I was like, oh, okay, that resonates with the market. That feels good to me. I've been interested in that for a long time. But timing wasn't right. Messaging with people on LinkedIn and they'd send, you know, hey, I have this book idea. And I'd look at the idea like, oh, wow, yeah, that's not. It's too general. Can remember this little feeling of, oh, I liked doing that. And that little subtle feeling was really important. Those little clues that turns out it's really not the right time to do that. Do much of it. I still think I will do more of that. I just can't say when yet. But this last three years is kind of looking for those little clues and to kind of continue to build more clarity on, like, what do I want to do? What area do I want to work in? How do I want to work in there? You know, how am I in. A third area is like, how am I going to make money at it? And I'm still evolving that. And so boards are a small part of that industry sometimes. So partnering is a big thing for me. I like working with people. And by partnering it means, for example, I've got a business in Brazil and I've got a different sales consulting business and kind of a partner runs it all. And I get like a percentage. So I help with, like, ideas, content and advice and some introductions and things, but they kind of run it. Um, endgame is to make more money doing this things I really like to do than I did doing sales consulting, which I was great at. But I didn't have that same. I didn't feed my soul. I worked with some good people, you know, reasons these in a lifetime. And I want to write fiction that's more for fun. Could I make money at some point? Yeah, but that's more of a, a creative exercise that would be completely different than writing non uh fiction books. So I'm kind of drawn to these different areas and it's again there hasn't been like one lightning bolt. There's been lots of little clues, some bigger than others to kind of evolve this. And I still got to make money. I still got, I got rent to pay, I got this, that, uh, the other. So it's not like I made so much money that I don't have to worry about that. So I'm still there and what I'm doing is. And trusting it's all going to work out. After so many years of this, it's like I, I do believe 100% in a higher power. Everything leads to another thing and when you get knocked down it's because you need to learn a lesson to get to the next step. The impossible to inevitable is less. I worked with a publisher. There's some off of that not as much. The predictable revenue book sells more people. People newer say oh I need to build something that does recurring revenue. But you know sometimes to get there you have to start with things that are non recurring and unscalable and very manual to learn enough that you can kind of evolve that. I mean sometimes you can make a jump. But I think people are often so afraid to oh, I don't want to sell my like I don't want to sell my time or I don't want to do this or I don't get a job or like they're so SC of trying these things that might give them really important tools to get to the place they want to get to. So it's just kind of be open to whatever is there you need to do. Like I think one of the lessons I love to share is that when I went from being a CEO of a company which failed but still taking this entry level job, I didn't let ego get in my way. I was like I need to learn this skill. I'm not gonna, it's not gonna pay shit. I need to learn the skill and I'm not gonna. I don't care what people think. I don't care. I need, I need to learn the skill. Even if I got a job. There's pros and cons of uh, I mentioned this income operating system books hopefully come out this year. The essence is talking about the pros and cons of three ways to make money. Employment part time, full time pros and cons of that. Pros and cons of freelancing. People might get excited about consulting and setting your own hours, but you know, unpredictable income. Pros and cons of investing, which includes having your own business. And there's. I made a conscious choice where, you know, if I, I could make, you know, even if I could have gotten a job which not very employable, I could even make a lot like $300,000 a year, you know, see what happens here with projects. And speaking again, that was that path I had to walk, like what felt important. And you know, I've learned a lot through that which again is going back into, you know, this next book on money. One of the key ideas is this again, three ways to make money. Employment, freelancing, investing, businesses. We're going to lump mostly into that investing side. So that's kind of in this bucket. Pros and cons of each, right? Because there's a lot of older people who've been in safe jobs for a long time who feel like jobs are safe. Freelancing and starting your own business. Investing can be risky. However, you know, jobs are risky too because you can get fired or if things change, you get let off and so on. Freelancing, lots of younger people think, oh, jobs are for losers, don't want to sell my time and I'm going to like do the, you know, build my thing and well, good luck because it's hard to build your own freelancing, whether freelancing, consulting, cert, whatever, all that lump of services into something where you can support yourself and, well, a family. And it's unpredictable. So there's pros and cons. Pros you can design, you can design a product in five minutes on a word doc. Cons are you might not have regular income. And pros and cons of investing, which could be, you know, stocks, bonds, businesses and so on. So pros and cons of all these ideas, hey, people can kind of pick the right tool for where they are. And the, the basic recipe, because again, this world is really confusing, is to say start with employment. So get a full or part time job based on what you need. Part time job, sure. Or remote, even full time. And then once you kind of have some stability there and you feel like, okay, I got this, start adding freelancing. Freelancing can mean lots of different things. Could be consulting, gigging, upwork, who knows. And uh, my personal opinion is that freelancing for most people isn't even about making money or lots of money because you, it's hard is to learn entrepreneurial skills because to do that, you have to force yourself to learn, you know, things like sales or marketing or servicing customers and all, you know, and over time, because this is probably over the course of years, not months, you can kind of ease into investing, starting with index funds or the equivalent, because that's kind of like relatively safe and simple. And as you start to build your confidence and income and other things, you can start looking at other steps. Whether you invest more in your turning freelancing into like a business or your investments into, you know, buying or investing in a business, which is another form of investing. And kind of over time, five or 10 years, try to build your, your wealth. It might even be long for some people. The idea is to give people clarity and to do it is in as unbiased a way as possible. Like we're, uh, not trying to sell stuff. It's just trying to help people like you said, to have fewer, better choices, to see where, where are you, what's next and to realize, you know, you see all this million dollars in 30 day stuff online, but come on, like people win the lottery. It's like cinnamon saying, hey, get a gold medal in 30 days. Do some people win gold medals? Yeah, lots of. Actually, lots of people do. Are you going to be a millionaire this year? Are they selling that to sell you something? Yes. Let's just be honest. They're more concerned with them making money than with you actually getting results. And why do they care about you getting results? So they can look good? Do they actually care about you?
Speaker B: Gratitude of jumping on the show?
Speaker A: Sure. The goal is to help a lot of people with it. That's a wrap, folks.
Speaker B: Thanks for joining me today. And if you got value from this episode, do me a favor, like subscribe and refer a friend. And if you want even more value, go to thesalesmachine. Com, click on resources, and there's tons of resources there to increase profits and drive performance in your business. Right on, right on. Come on.
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