Sellers Are Drowning in Technology and Starving for Skill: A Conversation with Chris Orlob

Ask most revenue leaders what has changed in the last twelve months and you'll get the same one-word answer: AI. So when I sat down with Chris Orlob, CEO of Caliber, for the Sales Operator Series, I asked him to look past it. What are the CROs, VPs of sales and enablement leaders he talks to every week feeling pressure to fix?

His answer was a skills crisis. Sales skill levels are lower than they've ever been, and sellers now have more technology than ever but not the skills to use it well in front of a buyer.

Chris is well positioned to say so. He helped Gong grow from $200K to $200M in ARR, and I've always credited him as one of the first people to do truly analytical, actionable content in our industry. Today he runs Caliber, which he describes as a revenue skill development operating system: it measures seller skills, trains people on their specific gaps, gives them practice before they hit live calls, and then measures whether it worked.

Here's a recap of our conversation. You can also watch the full episode below.

Why is there a skills crisis in sales right now?

Chris talks to three to five VPs of sales or CROs every week, plus heads of enablement. AI dominates most of those conversations, and understandably so. But underneath it, he sees something else.

He was careful to say this isn't a knock on the newest generation of sellers. The reasons are structural. We went from a hot economy to a cold one to a confusing one. Buyers are more sophisticated than ever, partly because of AI. The revenue workforce is younger. And earlier generations of sellers learned by working alongside each other and getting good together, which is harder to replicate today.

Chris's line for the result: sellers are "drowning in technology but starving for skill." Eventually a seller still has to get on a call and quantify value and pain, multi-thread without alienating anyone, and reach the economic buyer. Most leaders he talks to have serious gaps in exactly those areas, and it's costing them revenue.

Did Predictable Revenue take the judgment out of selling?

I have a pet thesis here. We took the ideas in Aaron Ross's Predictable Revenue to their end state: prescriptive activity targets and tightly segmented roles, each with a very confined job. Somewhere along the way, I think we took out some of the critical thinking.

Chris agreed. He started his career as an SDR when the model was just taking off, and he says it worked at the time. But he thinks we trained a generation of SDRs to follow a process, and he draws a sharp line between a process and a skill:

• Process is here's what to do.
• Skill is here's what to do, here's why, and here's how.

When you have all three, you can participate in the market with judgment instead of brute-forcing a hundred emails. Chris's read is that emails and calls can still work, but a decade-old playbook of high volume and hyper-specialized roles no longer cuts through. And nobody has landed on what replaces it. We're in an era where the profession doesn't yet know what the next outbound playbook is.

I added my own view: as AI produces more spam, systems for catching it will improve too. That leaves room to break through if you're authentic, and it puts the weight on your perspective and your reason for reaching out.

What does a real point of view look like in sales?

I shared an idea Morgan Ingram floated on an earlier episode: that we may be headed back to 1990s-style selling, with SDRs physically showing up at accounts in ways an AI agent can't.

Chris didn't disagree, but he said something more fundamental has to be true for that, or anything, to work: you need a non-milquetoast point of view. Most so-called points of view aren't one, because a defining feature of a good one is that it's a little polarizing.

Then he asked me a question. Of the discovery calls and demos I've taken from AEs over the last five years, how many had someone say something sharp enough to fundamentally change how I think about the problem they operate in?

I estimated I've taken somewhere between 100 and 150 of these calls. My honest answer was fewer than three.

Chris sees that as the opportunity. It's rare because it's hard, so any seller or sales leader who gets there stands out. His warning is that showing up door to door with the same product pitch just moves an ineffective approach to a new channel, and you become a pest.

The reason most calls fall flat, I think, is that reps have a perspective on their product and not on the market. Chris's answer is that you have to be an expert in your buyer's world. He can do this well with CROs and VPs of sales because he has spent 15 years selling to that exact persona with a problem-first, product-second mindset. When you do that long enough, you see the patterns in how everyone deals with the problem. The trap is being so eager to talk about your product that you bury any point of view that might have shown up.

How do you break a transactional sales mindset?

I pushed on this one. We've trained sellers to treat calls as a way to fill CRM fields: who's the economic buyer, what's the budget, who's the competitor. How do you get out of that?

Chris's answer was that the process can be there, but it shouldn't be the north star of the call. The process serves the seller. The north star is putting the spotlight on the buyer: understand their problem and desired outcomes, and be a problem-solving partner. Yes, you still qualify the economic buyer, because you're a professional. But job number one is solving the problem with them.

He also made a point I keep thinking about: without that mindset, even the right behaviors feel forced, like techniques. With it, many of those behaviors show up on their own. "I'm not a vendor, I'm a partner. I might not be able to help you, but let's find out."

What is synthesis, and why do great sellers do it more?

Chris shared research from the Caliber Index, which benchmarks selling skills anonymously across Caliber's customer base. The study analyzed just under 1,600 sellers and about 300,000 of their calls, looking at skills (not just behaviors) that separate great sellers from everyone else.

One of the first things that surfaced was synthesis: while you're in a discovery conversation, you give the problem back to the buyer sharper and clearer than they articulated it themselves.

On the surface it looks like summarizing. In practice, you're taking the messy inputs of a discovery call and playing them back in a way that creates epiphanies. The buyer trusts you more, sees you as credible, and views the conversation as time well spent. If you get it right, they go on long monologues afterward.

According to Caliber's data, great salespeople scored 69% higher on their proficiency scale for this skill, yet only 17% of sellers do it effectively.

What I love about this is that it's both obvious and almost never trained. Most organizations coach metrics like connect rates. And it's something a team can start on tomorrow. Ask your sellers to listen more actively, bring back trends they've heard, and connect what they heard on earlier calls to the conversation in front of them.

Will a highly skilled sales team become a moat?

To close, I asked Chris what sales leaders will be talking about twelve months from now that isn't on their radar today.

His prediction: a highly capable, highly skilled revenue organization becomes something of a moat. He was careful not to oversell the word, and he framed it over a two-to-three-year horizon. His logic is that with AI, you can match a competitor's product almost overnight, and every company will be "AI-pilled," so AI stops being an advantage and becomes the ticket to play. What separates teams is what can't be switched on overnight: reps who run exceptional discovery, sell to the economic buyer, multi-thread well, and close on time without pressuring the buyer. Some leaders will have had to move people out and bring in people with those capabilities. That takes time, and it can't be mirrored fast.

He also clarified what he doesn't mean. This isn't the old line that people buy from people they like. Picture a buyer choosing between two sellers at similar prices with similar products. One runs through budget, authority, need and timing. The other partners with them, says "your situation reminds me of another client," and challenges their assumptions about the cause of the problem. Chris's point is that acumen, not charisma, wins that deal.

What I'm taking away

The AI conversation isn't going away, and it shouldn't. But my main takeaway from Chris is that efficiency gets everyone to the starting line. The gap that opens after that is skill: knowing the buyer's world, having a real point of view, and keeping the buyer's problem at the center of the call.

For managers, skill also only develops through practice and coaching, which is why we keep saying coaching should be a system and not an event.

To hear the whole conversation, watch the episode on the Sales Operator Series. You can find Caliber's latest research here, and connect with Chris on LinkedIn.

To stay up to date on the latest from the Sales Operator Series, connect with Brian on LinkedIn here.