It's actually a weird story. I was at Charter Communications, Spectrum, running their contact center operations. We were consolidating from 360 call centers down to 12, and I took three vendors to RFP: Verint, Witness, and Nice. I ended up choosing Witness, not because they had the best technology, but because I trusted the sales rep the most to help me get the ROI I needed. Then I realized Witness didn't have the best practices I needed to make it work, so I walked in and told them they needed to hire me to run a consulting division. I named off three things I knew how to do and they said, "You know what that means?" I said yes, because I had to build it myself. That's how I got into software. 💡 She chose the vendor she trusted most, not the best technology. That's a masterclass in relationship-based selling.

Every company says they're so different from their competitors, but they're all trying to solve the same problem. C-level will tell you they want to improve customer experience. But when you peek behind the curtain, what they really want is to reduce the cost of doing business without hurting the customer experience. That's a hard balance. Technology helps you find that balance, but you have to get underneath the stated goal to understand what's actually driving it. Right now I'm working with a large MSP on a two-year sales cycle. It's multimillion dollars. The key is having the right C-level involvement so you can withstand that long of a cycle. 💡 C-level says "improve customer experience." They mean "cut costs without breaking anything." Your job is to bridge that gap.

The devil is in the detail. When a company says they want to implement AI, I always ask, "What do you mean by that?" And every single time, they don't really know. AI means something completely different to everyone you talk to. I've been fighting against stereotyping what AI is for years. The only way through it is to slow the conversation down and get specific about the outcome they need, not the technology they think they want. Once you understand the outcome, you can figure out whether AI is even the right tool, and if so, which version of it. 💡 "What do you mean by AI?" is one of the most powerful qualifying questions in SaaS sales right now.

The buying group. Before, you might have one buyer and a few influencers. Now the buying group is enormous. So many people have to be involved in the purchase decision, which on one hand is good, you're building consensus across the organization, but it makes the sales cycle significantly longer. That's the biggest difference between selling 15 or 20 years ago versus today. And the objections? Same as they've always been. No budget. We've been doing it this way forever and it's working. Why invest? The words might be slightly different, but the resistance hasn't changed. 💡 Bigger buying groups mean longer cycles. Map every stakeholder early, don't let your champion play telephone with your value prop.

I love this story. I was working on a large multimillion-dollar deal in Sao Paulo, Brazil. I flew from St. Louis through Dallas, an extra hour, just to get upgraded to first class so I could sleep on an 11-hour flight and walk straight into meetings. When I arrived, my point of contact told me the full C-suite wouldn't be in the room. I said, "That's okay, I'm going to jump back on a flight and head home, and we can reschedule." I walked out. That was the scariest thing I've ever done. It was a fortune to get there, and a massive deal on the line. But I had made one ask at the start of the whole process: when I do my final presentation, I need the entire C-level in the room. Thirty minutes later, they came back and said they'd make it happen. Everyone showed up. And it ended up being the largest deal Verint ever closed. 💡 Willing to walk away = instant credibility. If you can't get the right people in the room, your message will get diluted every time it gets passed along.

I can run a list and have a full prospecting list ready to work faster than most SDR teams can get organized. I have my own CRM with all the modules, my own sales AI platform, Sales Navigator, and my own methodology for sourcing names and contact info. Yaktrak doesn't have any of those tools, I built all of that on my CXpert side. And because I've been in the industry so long, a lot of it comes down to relationships that are already built. I also have a rule: if a meeting is 30 minutes and someone is more than 10% late, I drop. Your time has to mean something or nobody else will treat it like it does. 💡 Protect your calendar like your pipeline depends on it, because it does.

Shadow someone. Find a patient leader in a consulting or sales leadership role and ask to shadow them. Not just sit in on calls, actually watch what a full day looks like. The fun, the challenges, the obstacles, the different personalities. You'll know very quickly if it's for you. I've had people shadow me and I taught at the university level, so explaining the "why" behind what I do comes naturally. But the key is finding someone who will actually take the time to explain their thinking, not just let you watch. That real-world exposure is worth more than any course or certification. 💡 Shadowing a great consultant compresses years of learning into weeks. Find a patient teacher and ask.