What CEOs Should Expect From Their Sales Leader: Part 2
The four qualities all great sales leaders share (and how to test for them)
This is part 2 of a series on what CEOs should expect from their sales leader. If you haven’t read part 1, I’d recommend starting there first.
Missing on a senior hire hurts, no matter the position. But there’s one executive hiring mistake that’s uniquely expensive and uniquely painful: getting your head of sales wrong.
The miss rate on sales leaders is surprisingly high. You don’t have to look hard to find stats on how short the average CRO’s tenure is. The reason isn’t hard to figure out: these people get other people to say yes for a living. They’re good at it. The longer you’ve been in the working world, the more likely it is that you’ve run into a sales leader who talks a great game but can’t remotely back it up. The kind who probably sounds great in the interview and then quietly wastes everyone’s time for a year while doing everything but delivering the results they were hired to produce.
In Part I, I laid out the three go-to-market situations I run into most often in my work as a PE operating partner (Figuring It Out, Fixing It Up, and Scaling It Up) and argued that what you need from a sales leader depends on which situation you’re in. Hire for the wrong stage and you’ll pay for it — in time, money, and opportunity cost.
What Part I didn’t cover is the other side of the coin: the traits that matter regardless of which phase you’re in. Every stage has its own demands, but there are four qualities I look for in every sales leader evaluation (new hire or incumbent) that always matter.
The Four Universal Traits of Effective Sales Leaders
Here are the four traits that actually predict whether a sales leader will drive growth in your business. Every strong one I’ve worked with has them. Almost every bad hire was missing a few.
1. They Learn From Customers
In my world of B2B technology, there’s almost always an opportunity to position your product more clearly in the mind of the customer. Most sales organizations never fully nail that opportunity. The ones that do seem to grow faster than everyone else.
If your sales leader isn’t hunting for the most clear and relatable way to talk about what you do (and is instead blasting people with product specs and hoping they just buy the thing) they’re just a brochure with legs. A very expensive brochure with legs.
The best sales leaders are bloodhounds. They’re customer-obsessed. They’re like Tom Cruise in that famous scene from A Few Good Men: They want the truth.
They make it their responsibility to go find out what customers are struggling with, what it’s costing them, what they think is so valuable about their product, and what caused them to finally say yes. Because they know that once they know that, they have what they need to give every future prospect what competitors won’t: Expert perspective on the market, and credible help navigating their options.
That’s what earns trust. And trust is what closes deals.
What separates customer-obsessed sales leader from everyone else isn’t that they listen. It’s that they change things because of what they hear. They rewrite the messaging. They kill the talk track that isn’t landing. They shift who they’re targeting when the evidence points somewhere new. They use what they learn to make intelligent changes to how they and their team do their job.
The quality underneath all of this is curiosity. My best sales leaders are all genuinely, almost restlessly curious about customers. Not because someone told them to be. But because they know that truly understanding their customer gives them everything they need to win.
How to test for this: Ask them to tell you about a time they heard something from a customer that surprised them. Then ask them what they changed because of that surprise. What you’re listening for is the second half of that story. If the surprise didn’t lead to action, you’re talking to someone who listens politely and then keeps doing what they were doing. That’s not who you need.
2. They Have a Nose for Value
Some sales leaders will tell you they need six months of assessment and a full consultant-led diagnostic before they can tell you what needs to happen with your go-to-market strategy. Others stick their nose into what’s going on and know within a week where the biggest challenges or opportunities are (and have probably already started doing something about it).
I want to hire the second person. Don’t you?
I call this having “a nose for value.” It’s an almost involuntary ability to walk into any sales situation and immediately pick up on what matters. These people aren’t processing everything equally. They’re pattern-matching against a deep library of what an effective sales process looks like, what solid deal management feels like, and what the absence of those things looks like in the numbers and in the field.
You can’t fake it. It comes from years of paying close attention to the small things that actually create results — enough pipelines, enough customer calls, and enough sales motions that the patterns become second nature.
What separates this from simple experience are opinions, speed, and specificity. A lot of sales leaders have seen enough to have opinions. The ones with a real nose for value have seen enough that the read is fast, precise, and almost always pointed instinctually at the right thing first.
How to test for this: Send them something real before the interview. A pipeline export. A sample call recording. A look at your recent numbers. Ask what stands out, what they’d want to fix first, and why. The candidates who don’t have a nose for value will try to spin you around with a brainstorm: “here’s everything I noticed.” The ones who have it won’t be afraid to prioritize. They may give you a list, but they’ll also take a stance - on what the biggest challenge, opportunity, or insight is, and what they would do next to address it. That stance and that prioritization (and the instincts behind it) are what you’re looking for.
3. They Build Systems That Outlast Them
Go-to-market strategy can get endlessly complicated. The best sales leaders resist that pull. They know that building a sales team is mostly about teaching people, and that complexity is the enemy of teaching. You can’t hand something to someone else and expect them to use it if you can’t explain it simply.
What I look for here is a bias toward simplicity. Specifically, I’m looking for the ability to throw a lasso around the business and get it under control. To identify two, three, maybe four moments of truth in the sales process and organize everything around those. What they teach. What they coach. What they measure. What they’re listening for when they join a rep on a call or review a recording on their own. The system doesn’t have to be complicated. It just has to be clear enough that other people can carry it out when they’re not in the room. And to believe in it enough to want to.
That’s the real proof of a system. It’s about full transference to the team and commitment from the team. Not that the sales process exists, but that it lives in other people. Pulling that off requires simplicity. You can’t transfer something complicated. You can only transfer something someone else can understand, repeat, and internalize.
The failure mode shows up in two places. The first is documentation (or the absence of it). If nothing about how your team should sell ever gets written down, that’s a tell. Writing it down forces you to simplify it. It forces you to take a stance on what actually matters. A sales leader who never documents never has to commit to a standard, which usually means they don’t have one.
The second shows up at the executive level, in the language they use to explain what’s happening in their part of the business in board decks and operational reviews. If the slides look different every quarter (e.g., different or unclear definitions, different metrics or methods of displaying them, or different framing for why the number is what it is) that’s not a reporting problem. That’s a systems problem. It’s evidence of a sales leader who’s thrashing reactively to whatever comes their way instead of building something stable and consistent enough to talk about the same way over time.
How to test it: A question I’ll sometimes use: “Tell me about a process you built at a job you left a while ago that’s still running.” The ones who built something real can tell you exactly what they built, how they adjusted it and made it stick, and why it survived. The ones who skirted building systems by playing the hero will tell you a bunch of basic “isn’t that just doing your job?” day-to-day management stories while avoiding talking about process, documentation, or reinforcement.
4. They Know How to Teach
A sales leader doesn’t have to be the best presenter or the sharpest closer on the team. But they have to be able to make other people better. Those are different skills, and confusing them is one of the most common mistakes I see in sales leadership hiring.
Here’s why teaching matters so much in this role: the basics of a great sales organization (e.g., curiosity-driven discovery, demos that focus on what the customer actually cares about, instincts for finding new opportunities inside existing accounts or finding the angle that drives a deal forward) are never really fully installed. They decay over time. Reps who were doing great discovery six months ago start slipping back into pitch mode. Demos that used to be tight start bloating back up to product tours that bore your prospects. The hunting instinct fades and reps start sitting back and waiting for leads to come to them.
Someone has to care enough to keep reinforcing the same things, over and over, long after it stops feeling interesting. That’s the job. And it takes a special kind of teacher to do it well — someone who understands that getting a team of people to master the ordinary things, and to take pride in mastering them, requires patience, high standards, and a willingness to repeat yourself indefinitely without losing conviction.
The best sales leaders I’ve worked with are all great teachers. They don’t dump feedback on people. They translate hard things into simple, teachable standards that sales reps can use in front of customers. And their standards transfer. You can see it when they’re not in the room. The team is running the same plays, using the same language, and holding themselves to the same bar.
How to test for this: Ask the candidate to tell you about an average rep on their team. Not their best. Not their worst. Someone in the middle. (Ask them for their first name. Not because you’re going to call that person, but because it tells you the story is real.)
Then ask: “If I called that person right now and asked them what you’re an absolute stickler about — something you reinforce over and over and over again with your team — what would they tell me?”
What you’re listening for isn’t the technique itself. Which technique or standard they name is less important than (a) whether they have one and (b) can talk viscerally about the time they’ve spent making sure it sticks. The best answers describe something specific (e.g., a moment in a discovery call, a habit in a demo, a discipline around follow-up) and then share stories about the repetition, reinforcement, and individual conversations they had to have to make sure even the average sales rep on the team could meet their standard.
How To Assess The Sales Leader You’ve Already Got
So now you know what to ask to assess for the qualities that matter no matter which stage your business is in. But what if you’ve already hired your sales leader and you’re trying to honestly assess whether they’re the right person to take you into the next chapter?
In theory this should be easier. You’re not relying on interview questions and rehearsed answers — you’re observing what they actually do every day. But assessing someone already on your team can be harder than evaluating a stranger. You have a relationship. You’ve made a bet on this person. And sales is the one function where the results are always visible and the excuses are always plentiful — some you’ll come up with yourself, some they’ll hand to you.
There’s always a deal that slipped, a macro headwind, a rep who left at the wrong moment. The question isn’t whether those things are real. They usually are. The question is whether you’re letting them explain away something that’s actually a leadership problem.
The most common pattern I see in underperforming sales leaders is a focus on activity instead of results. These people will tell you exactly how busy they are, how hard they’re working, how complicated the deals they’re managing have become. They are, in almost every case, complicators rather than simplifiers. They make the business feel harder to understand over time, not easier. If you find yourself getting less clarity on your sales performance every quarter rather than more — if the definitions keep shifting, if the pipeline math never quite adds up the same way twice — that’s not a reporting problem. That’s a leadership problem.
The earlier warning sign, the one CEOs most often talk themselves out of, is reactivity. These sales leaders are trying like hell to bring deals in. Nobody’s questioning their effort or their intent. But they never add anything to how their team performs. They invest in building systems or teaching their people only when that pressure comes from somewhere else — from you, from the board, from a consultant you brought in. Left to their own devices, they don’t view that as the job. They view their job as bringing in deals. Not building the machine, process, and culture that brings in deals at scale.
That distinction matters enormously. Because a sales leader who’s personally closing deals but not making their team better puts a ceiling on your business. And the longer they’re in the seat, the lower that ceiling gets.
So here’s a simple test. Look at the four traits above and ask yourself:
Are they learning from customers and changing things because of what they hear — or are they relying on the same old pitch and process they brought through the door?
Do they have a nose for value (can they walk into a situation and know within a week where the challenges/opportunities are) or do they need months of runway before they’ll commit to a point of view?
Have they built anything that runs without them — or are they barely keeping things together by playing the hero?
And can average people on their team do an impression of their standards — or is all that knowledge still locked inside the leader’s head?
If the honest answers to those questions are making you uncomfortable, trust that feeling. Sales is too important, and the feedback loops are too slow, to spend another quarter hoping things will turn around on their own.
Have questions you’d like to hear me answer on the Hello Operator podcast? I’d love to hear from you. Shoot me a note at podcast@hellooperator.com, and I’ll answer them on a future episode.