John's Recent LinkedIn Posts

Reflection, warning and slight humble brag. I've been cleaning out my folders and hard drives to get ready to make the switch from ChatGPT to Claude CoWork and am coming across a few gems of info that are bringing me down memory lane. One was a Master spreadsheet I used to track EVERY SINGLE opportunity and conversion rate for every stage of every deal at my first startup selling IT services to the SMB market in Boston. It starts in 2004 and goes through our acquisition by Staples. If you want to see how OCD I was about tracking back then feel free to check out out here: https://bit.ly/4bFeZZZ The other item I came across was this image I put together of all the clients I've trained over the years. It's a great reminder of what I'm calling the "Golden Age of Sales" (in SaaS between 2010-2022) in my Keynotes when money was free and there was a grow-at-all-cost mentality. I'm not sure how good we all were back then or if we were all just riding the wave but sometimes I sit back and sip my Dunks coffee remembering the good ol days and how relatively easy things were. It's a whole different ball game with what's going on these days. The entire SaaS industry is in serious trouble and so are the reps who grew up in it. I did a Keynote at Pavilion's conference a few months back called "Anything But Predictable" where I talked about how I think the Predictable Revenue model (segmentation of roles) ruined Sales in my opinion. I'm a huge fan of the 'Science' of Sales but we waaaay over scienced it and took the Art out completely. We need to get back to this and fast because AI is better at the science than we ever will be. We need to get back to being true problem solvers and giving a sh-t about the client instead of treating them like another dial we have to make, sequence we have to send, MEDDIC form we need to fill out etc. I've sold through a lot of transitions, this one is by far the biggest shift from a sales perspective and I'm genuinely concerned for the profession of Sales and the professionals in Sales. If you don't think we're in trouble I encourage you to go into your favorite AI platform and pretend like you're a potential customer for your services and ask it a few questions. When you realize that in a 5 minute conversation with any AI tool you'll get more value that you would out of a a 22 year old SDR who's going to give you a generic pitch and then ask a bunch of BANT questions to then schedule a call a week later with an AE who's going to ask you the same questions and then give a canned demo and then wait another week for an SE to ask the same questions and hopefully give you some insights you realize there is no comparison between the two experiences. That's why I'm not worries about all these AI tools that are automating Sales. I'm worried about when the customer wakes up and realizes they don't need us. We all need to level up and level up fast. Who's coming with me?

I’m excited to share that I’m partnering with Apollo. If you’ve followed me for a while, you know I don’t sit still. Sales is evolving fast. AI is evolving faster. And I make it a priority to constantly test new platforms, workflows, and tools so I can see what actually works in the field. I don’t partner with companies because they’re popular. I partner with companies when I see real impact on execution. Here’s why Apollo earned that spot: • It connects data, sequencing, dialing, and enrichment in one workflow • It reduces tool sprawl and simplifies the prospecting stack • It drives daily activity instead of adding complexity • It’s powerful enough for growth teams and practical enough for early-stage orgs • Reps actually use it That last one matters most. The best tech in the world fails if adoption fails. What also stood out to me is how Apollo is approaching AI. They’re not slapping AI onto random features and calling it innovation. They’re integrating it across the workflow. From their AI Assistant to the new connector with Claude announced yesterday, the focus is clear. AI is being built into the execution layer. Not to replace reps. To accelerate them. That’s the difference. Technology should reinforce fundamentals like clear ICP, strong messaging. and consistent activity. AI should make you more effective at those things. Not distract you from them. When humans stay in control and AI becomes the accelerator, that’s where real leverage happens. I’ll be using Apollo in my own prospecting and sharing what I learn along the way. If you’re evaluating your stack and want something that simplifies the execution layer while building AI in the right way, it’s worth a look. If you sign up for a paid plan with this link you'll get 2500 bonus credits: https://lnkd.in/eEHtj8Cw What's the biggest bottleneck you have in your outbound process?

Can we at least agree to stop using AI comments on posts that are more personal than tactical? Yesterday I did a post about how I was feeling uncomfortable right now pretending like everything was normal when its obviously not. It wasn't meant to be a political statement, just about something I was struggling with, specifically related to the content I was sharing on Linkedin. I got a good amount of genuine comments from people I know sharing their feelings and perspective on the matter but then I got a bunch of obviously AI written comments. They were super supportive and eloquently written but instead of feeling supported, I felt frustrated and annoyed. I still don't really understand the value of using AI to auto comment on people posts but I guess I am fine with it when it comes to sales tactics, tips, strategies, etc. BUT, when there's a post that is more personal in nature, using AI to comment makes it feel cheap and diminishes the authenticity of it as a whole in my opinion. Please stop. Stay human. #MakeitHappen

Most companies are still measuring the wrong thing. I had Mark Roberge back on the podcast again to talk about his new book "The Science of Scaling" and he dropped a line seems obvious but is almost always overlooked: “Most people define the end of the funnel as a signed contract… it should be value realization.” Let that sink in. We’ve been trained to chase revenue, new logos and pipeline. But in today’s world, especially with AI, anyone can sell a vision. The real question is: Did the customer actually get value? That’s why the metric that matters most right now isn’t ARR, it's NRR (Net Revenue Retention). Because NRR tells the truth: • Are customers staying? • Are they expanding? • Are you actually delivering on what you sold? If they are, you have product-market fit. If they aren’t, you don’t. Period. Mark said it best: Product-market fit isn’t a revenue number. It’s retention and expansion. And here’s the uncomfortable reality… If you’re working at a company that: • Overpromises and underdelivers • Struggles with retention • Can’t point to strong NRR …it’s not a sales problem. It’s a value problem. And those companies won’t last. The winners moving forward are the ones that under promise, over deliver, reduce risk and consistently create value AFTER the deal is signed. That’s where the funnel actually ends. Watch this clip below and listen to the full episode wherever you get your podcasts. This is one every founder, CRO, and sales leader needs to hear and they should all get a copy of Mark's book too!

I’ve been pretty quiet on Linkedin lately. and it's not because I was busy, even though that's what I was telling myself. Two years ago I posted on LinkedIn asking people how they were really doing after a conversation I had with a colleague who was going through some tough times. When I told him I was struggling he was relieved because he felt like he was the only one based on what he was seeing on Linkedin. That conversation led to the post that then lead to more DMs than comments from people thanking me for giving them a voice and helping them realize they weren't alone. Lately, I’ve felt something similar. Scrolling LinkedIn, everything looks normal. Wins. Frameworks. Growth hacks, etc. Meanwhile, the real world feels anything but normal. And I’ve been really struggling with what to say. My friend Devin Reed had apparently been struggling with similar feelings but had the courage to say something. He talked about feeling like he was lying to himself. Posting about marketing ROI while internally feeling disconnected. That's exactly how I feel/felt when trying to come up with something to post on Linkedin about sales tips, tactics or strategies - hollow. So I asked him to come on the podcast and talk about it out loud. We didn’t solve the world’s problems but we did talk a lot about values, about not sitting silently on the sidelines and about aligning your money, your work, and your voice with what you actually believe. That conversation pushed me to release this weekend’s newsletter and podcast (on youtube) a little earlier than usual. Today is the actual release of the podcast and I encourage anyone who is feeling a bit disconnected to listen to the entire episode. If you’ve felt disconnected, or that everything online feels “fine” when you know it's not, or if you're just unsure or what do to or say right now then watch this clip, listen to the whole episode and hopefully it will help you find your voice. Let me know if you've been struggling with this too. The more we talk about it out loud the more we can make a difference. #MakeItHappen

"How do I get my team to work as hard as I do?" I've gotten this question from founders and leaders multiple times in my career. First, let's be clear - you can't. If you're the founder, you cannot expect ANYONE to work as hard as you UNLESS you're going to give them an equal share/ownership of the company. A more reasonable question is - how to get people to do more than what's in their basic job description? My question back to founders and leader when they ask that is - when was the last time you shared your vision of where the company is going and how they fit into that picture? If someone doesn't know how or where they fit into the bigger picture and what impact their role has in achieving success then they're mostly going to just do their job. If there's alignment between the goals and priorities of the company, leadership, front line managers and the rep and they are communicated effectively then people tend to feel part of something bigger than themselves and typically act that way. Obviously compensation has a role to play too but I find that 'purpose' and alignment matters more in the long run. I dove into this topic and much more around leadership and delegation with Stefan Feuerstein, author of ABC DELEGATION, on this week's episode of the Make it Happen Monday podcast. Check out the clip below and the full episode wherever you listen to your podcasts. What are some ways you've seen leaders inspire others to do more that what their job description says? (besides update their job description) #MakeitHappenMonday

AI isn’t replacing sales reps. It’s exposing bad fundamentals faster. What I liked about the Apollo AI Assistant isn’t the “AI” part. It’s how quickly it forces clarity. During setup, it coached me to: - Be specific about who I’m targeting - Stop guessing on intent - Align accounts, personas, and outreach from the start This is where most teams screw up. They rush to sequences before they’ve earned the right to send one. They automate chaos and then blame the market. I haven’t launched campaigns yet, but the setup alone cleaned up thinking that usually takes teams weeks which is a huge win already. Apollo’s AI Assistant is worth paying attention to if you care about execution, not shortcuts. If you sign up for a paid plan with this link you'll get 2500 bonus credits: https://lnkd.in/eEHtj8Cw #ApolloAIAssistant #ApolloPartner

Most people are using AI wrong. Not because the tools aren’t good. Because the context sucks. Right now, here’s what I see most reps and leaders doing: they take a call, export the transcript, copy it into ChatGPT, ask for a summary or follow-up. That’s not a system. That’s a workaround. And it creates two big problems: 1) You lose context across conversations and 2) You now have sensitive data floating around in random places I saw a demo recently from Otter.ai about their new integration tools that made me rethink this. Instead of copy-pasting transcripts into AI tools, they built a way to connect your meeting data directly into tools like ChatGPT and Claude. So instead of saying: “Here’s one call, summarize it” You can ask: • What have all my clients said about pricing this quarter? • Where are my deals getting stuck based on recent calls? • What did this client care about across every conversation we’ve had? Now AI isn’t guessing. It’s working off your actual business and isn't missing details that most people do. Otter stays the source of truth so you're not moving data around and you're searching securely which is a big shift. AI doesn’t get better because the model improves. It gets better when the context improves. That’s where this is all going. Less prompting. More connected systems. Better inputs. I'm curious how many of you are connecting the dots with AI tools today. Are you still copy-pasting… or starting to connect your systems? Check out Otter today: https://bit.ly/4sZi9Pz #sponsor #makeithappen

If something is optional in sales, it usually doesn’t get done. Updating the CRM. Writing detailed call notes. Sending a clean recap. Reps mean well. But friction kills consistency. The same thing happens with recording calls. If it depends on a bot joining the meeting… If someone has to remember to hit record… If IT blocks it… It won’t happen every time. And if you don’t consistently capture conversations, all this talk about “conversation intelligence” is meaningless. That’s why I like the Otter.ai Desktop App. It runs directly from your desktop. No bot jumping into your meetings. No weird delays. No extra steps. You just record the call, whether it’s Zoom, Teams, Google Meet, or something else. For me and Meghan, that matters. We collaborate on every deal. Sometimes she’s on the call. Sometimes I am. Sometimes both of us. We can’t rely on memory or scattered notes. With the desktop app, every conversation gets captured. Then it syncs into Salesforce. Then we organize it by client in Otter so everything is searchable. So when we’re prepping for a follow-up, we’re not guessing. We’re pulling exact language. We’re checking what objections came up. We’re confirming what next steps were promised. No one’s in the dark. The tech isn’t the point. The consistency is. If you’re serious about scaling insight across your team, you have to reduce friction at the capture level. Otherwise you’re building strategy on partial data. That’s why the desktop app matters. It makes recording automatic instead of optional. And in sales, automatic beats optional every time. Check out Otter today! #sponsor #makeithappen

Join me tomorrow for some free training along with free access to the new JB Sales Bot with all my content included.