At LendingClub, I ran 4 business units handling 1.4M customer interactions a month. By everyone else's standards I was doing great. I was spiritually dead inside. Before that, I'd built LendingClub's sales team from 5 sellers to 150 sellers. I did it twice, in two different geographies, two different labor pools. When COVID hit, the company went into downsizing and panic, and shut down the entire Sales team. I agreed to become Director for all of Customer Success instead. The job was huge. But it took me away from my first love: the combination of coaching + sales. That's where the dead-inside feeling came from. It also taught me the lesson I still carry: Leaders still need to pour their all into their team members, to mentor and coach them to brilliance. AI can't and won't replace that. So I went out on my own. Now I help small and medium businesses grow and scale their own sales teams, with a coaching, customer-service-centric approach. That company is Cadence. We've built an always-on sales coach that guides salespeople in the moment, when a deal can still be won, rather than after the fact. That typically means a 50-100% increase in conversion rate, on the same ad spend. It's enabled by AI, but it's not a cookie cutter AI solution. We actually listen to the calls ourselves. The mission is the one that started my career: Coaching salespeople to success, with tireless focus on what they actually need in order to learn, and thrive. So much more to come...

Experienced salespeople are the RISKIEST hires you can make. My top 5 hires ever had never held a sales job. (This includes the woman who closed $380k in a single day and the guy who closed over 80% for 14 months straight) Most owners hiring closers want the opposite. They think: "Get someone with 10 years in the game, and they'll hit the ground running." That's actually backwards. If I look at the top 5 salespeople I've ever hired, 3 of them came from about as far outside sales as you can get. One was headhunted out of customer service. Another did multimedia and owned 500 pairs of sneakers. The third had only played semi-pro sports before coming to me. None of the 5 had held a sales job before, and none of them even WANTED one. Selling was never their goal (the customer service hire went on to work undercover as a vice cop after her time in sales). Now flip that around and look at my top 10 WORST salespeople of the last 12 years... every one of them had been in the game for 10, 20, even 30 years. Some had sat in the same role for a full decade. They couldn't: 1. take feedback 2. keep their emotions under control 3. learn to change or grow from their peers who were “less experienced” than them Consequently their results and earnings were wildly inconsistent. That's what a long enough career in sales will do to a lot of people. They get jaded, and the mind locks into place like cement. If they had even a little success, they're convinced they can sell every product under the sun. So when you hire one, you essentially inherit a cup that's already full. Nothing new goes in, plus the bad habits they built over decades, spill over to the rest of your team. And you pay extra for an inflated sense of self-worth, with salary requirements that ballooned to match. TL;DR: The best salespeople are not salespeople. If you’re hiring reps: > I advise you look in the most unlikely places for talent instead. > Hire people with NO sales background > Screen them for EXCELLENT communication skills, and are fun to talk to > Train them to sell exactly the way you want them to sell. It's easier and it's cheaper and you will make loads of money this way.

After reviewing 15,000+ sales calls, this is the cheat sheet I'd hand any founder or closer to read EVERY prospect in the first 5 minutes and know exactly what to say to close them:

Most sales trainers still teach rapport like it's the 1950s. 4 myths that have your closers losing deals: 1. Rapport = the prospect likes you. Real rapport is trust. The prospect trusts your demonstrated expertise and believes you're smart and capable enough to get them results. People buy from people they RESPECT. 2. You build it with small talk. Your rep can talk football teams, hometowns, kids, or weather with anyone. None of it proves you can fix the problem they booked the call about. So it earns you zero trust. Even worse, it labels you as a “Mad Men” or “Wolf of Wall St” salesperson. 3. You have to warm them up before you talk business. There's ZERO need to "build rapport" at the start of a sales call. In 2026, trust gets built by getting to work on their business problems quickly and efficiently. That's where your expertise shows. 4. The more rapport, the better. Chasing rapport is an addiction, and it costs you money. Get as buddy-buddy as you like about brisket recipes and your Shenzhen vacation — AFTER they’ve paid you. Bookmark this.

I've audited 15,000+ sales calls in 12 years. Most objections are caused in the first 5 minutes of the call. On the losing calls I review, the trouble starts in 4 places 🧵

Telling a new closer to "sell like the founder" only works if the founder built a process they can follow. The idea behind it is right. But MOST founders are terrible at building a sales process. So the new closer gets told to “model the founder” and gets nothing that shows how the founder actually closed. The founder thinks if they hire 1 A-player closer and hand them the same leads, they'll close them at the same clip. It almost never plays out like that. A process means a closer knows which questions to ask and in what order. Without one, they're essentially “guessing” on every call. So your whole sales process is the one closer you just hired. And when one A-player IS your whole sales team, here is what will happen: They'll perform well at first. You'll have your best month ever, and they'll make good money. Next month, if there's any wobble in your lead flow or lead quality, they start having doubts. With no process to go back to, all they have is instinct. And unless they've taken over 1,000 sales calls, those instincts are likely pushing them in exactly the wrong direction. Then, they start trying different things. “Switching it up.” Trying that one thing that worked, one time, at another company, in a different industry. And results tank quickly. If you don't add another A-player soon after, nobody shares the load with them. So they start looking around at other offers. By month 4-6, if they haven't left yet, they're already halfway out the door. And you’re left saying “There are no good closers to hire anywhere” ...but it was your fault, not theirs.