What CEOs Should Expect From Their Sales Leader: Part 1

Hard Work and Earned Secrets

Everyone at our PE fund has their own particular area of expertise.

Mine is growth.

Inside the B2B software companies we invest in, our growth strategies typically focus on creating more at-bats. The hypothetical math works like this. If we can find a way to keep our win-rate, price, and retention steady while increasing the number of opportunities we create each month, in theory, the company grows faster and becomes more valuable.

It sounds so simple when you put it like that. In real life, adding five or ten or twenty points of growth to a business that’s been doing things the same way for years is maddeningly difficult. It’s a discipline that spans strategy, change management, training, coaching, data analysis, and — even more important — listening, patience, empathy, and reinforcement.

I’m doing this work for five portfolio companies right now. Five companies with their own unique problems, personalities, habits, patterns, and sticking points. Five companies where it’s my job to find the #1 problem, build a plan to address it, and keep myself and our team honest about whether we’re making progress or not.

I like my job. But it’s hard.

Even when it’s going well.

And the job gets about ten times harder when we pick the wrong sales leader.

Unfortunately, this is an easy mistake to make. Good sales leaders are hard to find. In a job where you’re rewarded for talking a good game, and in an interview process that’s mostly about talking, it can be very, very difficult to separate the right hire from the charismatic horde of almost-qualified candidates. There are so many of them out there — all just dying to close you and then waste your time for the next few years while they talk about the completely forgivable, out-of-my-control reasons why they keep missing their numbers.

Hiring the wrong sales leader is expensive. Forget the dollars — this kind of mistake can cost you years. Feedback cycles in software sales can be long. Once you give your new sales VP a quarter to get their feet under them, another quarter to make some changes, and one more quarter to see if it works… well, you may have wasted close to twelve months on someone who, if you only knew what to look for and how to test for it, could have been screened out much, much earlier.

I’ve been there. It sucks.

Here’s the good news: We’ve gotten much better at finding strong sales leaders. Through lots of trial, error, and reflection, we’re more consistently picking winners and making the growth part of our value-creation plan — and my life as an operating partner — a little easier.

Before I tell you how we do it, a quick warning to the reader. A lot of people out there (consultants especially) present their hiring and assessment frameworks as if they’re guaranteed to work; as if they’re immutable. Not me. I won’t claim to have cracked this code. Not yet. I still miss. But after interviewing hundreds of VP Sales and CRO candidates over the last decade (and working with a few genuinely great ones), I’ve stumbled on some earned secrets that now guide how we hire and assess for this critical position.

As a result, we miss less often.

And missing less is what it’s all about.

In this series, I’ll hit both sides of the topic: Not only what we look for from a new sales leader, but also how we look for it. I’ll unpack the qualities worth considering as you build your scorecard, and explain why they’re especially crucial for emerging tech businesses still finding their go-to-market legs.

I’ll also share everything I know about what to look for, what to ask about, and what to listen for to assess whether the person you’re interviewing (or the one you already hired) is the one that can help you grow faster — or just another pretender, talking a good game and begging for a chance to waste your time, money, and potential for growth.

Sound useful?

Great. Here’s the answer to the question: “What should I expect from my sales leader?”

“It depends.”

It Depends… On What?

Sorry, but there is no such thing as a universally-great sales leader. There is only the right sales leader for where your business is right now.

Below is the simple framework I use with CEOs to diagnose where they are before we start define who they should look for to lead their sales team. The way I see it, there are three “sales phases” every successful business passes through. What you hire for (or how you evaluate the leader you already have) starts with diagnosing which phase you’re in.

Phase 1: Figuring It Out

This is the phase where you’re just getting things going. Maybe you’re a startup emerging out of product-market fit. The founder/s are still doing most of the selling, but there’s no real system, process, or strategy behind your sales efforts. You’re doing your best to get in front of the people you think might want to buy, talking to them about their problems, showcasing what you’ve built, and testing how serious they are about giving it a shot. But you haven’t yet nailed down what works. Your Ideal Customer Profile, your target market, and the building blocks of your sales pitch — all of it still resides mostly inside of people’s heads.

You can also find the markers of the figuring-it-out phase within older, more-established companies who have never seriously invested in their go-to-market machine. They might have a couple of sales reps and might even be tracking their results in a CRM, but they’re lacking the sort of clarity and direction they know they need. Clarity about who they should pursue. Clarity about how they’ll make a good first impression. And clarity about how they can get their their sales process to feel more predictable, repeatable, and authentic.

When you’re still in the figure-it-out phase, what you’re really trying to do is what one of my favorite business thinkers, Niko Canner, calls “finishing the work of founding the company.” It’s when you follow the advice of Dolly Parton and “figure out who you are and then do it on purpose.” It’s when you take the reason your business exists and the raw ingredients behind what’s already working and distill it all into something that you can start to do with a little more intentionality. Something that not only brings you more customers, but actually feels like you.

The figure-it-out phase is about filling the obvious gaps. Maybe you aren’t tracking or interrogating your pipeline. Maybe you don’t have one consistent message or pitch deck — or the one you do have needs a serious refresh. Maybe you’ve never started doing outbound, or attempting to upsell/cross-sell your products, or asking your existing customers for referrals. Sure, in the figure-it-out phase, you have some happy customers. What you don’t have yet is a plan or a process that answers the question “How can we go find more?”

What Matters Most In the Figuring-It-Out Phase

In this phase, you need a sales leader who can do multiple jobs and then quickly fire themself from those jobs. In the figure-it-out phase, your sales VP needs to commit to spending ~6 months or more establishing what a single quota-carrying sales rep does to create, work, and close deals. Then they need to teach that standard to the team that they hire. It’s a unique mix of excavation, content creation, experimentation, and lots of time spent listening to both teammates and customers — the two kinds of people who can help them stitch together the real story behind not only how the business works, but also the value that it can deliver.

If you’ve hired a big-company sales leader during the figure-it-out phase, I’m sorry, but you’ve almost certainly made a mistake. You don’t need someone to manage a 50-person team here. That’s hard, but it’s not this. You need someone who can jump in, get messy, create and close pipeline through quick cycles of trial-and-error, and then become an agent in their own rescue — documenting and building the minimum-viable-system that allows them to climb the ladder from doer to manager. These people are hard to find, period. But they’re impossible to find if you’re only looking inside of big technology companies. (More on that in Part II.)

Phase 2: Fixing It Up

This is the phase where your go-to-market machine needs a tune-up. Maybe your growth has stalled out. Maybe you’ve lost ground to competition. Or maybe you’ve pulled up after a few years of work and realized that you’ve picked up some extra baggage along the way. People that aren’t quite the right fit. Processes that have been left to decay. And an accumulation of little inefficiencies that, after a while, start to drag down your results. “This isn’t good enough. We need a reset,” you think. “We need a better way.”

That feeling — whether expressed aloud or nagging at you silently — is the sign that you might be in the fixing-it-up phase.

The difference between figuring-it-out and fixing-it-up is all about the value of a good diagnosis. Even if you nail it, a good diagnosis isn’t that useful in the figuring-it-out phase. You already know that what you’ve got isn’t that great. You’re fully aware of the gaps. You just haven’t gotten around to filling them yet (probably because you’ve done just fine living off early wins, word-of-mouth, and referrals from your happy customers).

In the fixing-it-up phase, you’re further ahead. Here, you’ve spent time and money building out your sales team, and you know that at least some of it is working. But (and here’s the key) you’re not quite sure what’s working, what isn’t, and (most importantly) where the biggest problem is. Before you change things, you need to decide what needs fixing first. A good diagnosis is the unlock a fix-it-up situation demands. As the saying goes, “The man who chases two rabbits catches neither.” The right sales leader at this stage will keep you focused — making a clear declaration that we should chase this rabbit instead of that one. And in doing so, they can transform what seems like a total, overwhelming overhaul into a smaller, more manageable tune-up.

What Matters Most In the Fixing-It-Up Phase

The most important quality of an effective sales leader in the fixing-it-up phase is the thing enables a strong diagnosis. I call this quality your managerial palate. A fix-it-up sales leader needs to have a strong sense of taste — a well-honed view on what good looks like. They need to have high standards and the means to detect where they are and aren’t being met. These are the people that can make quick, almost instinctual judgments about where the waste in your sales system is. They can listen to five calls with your reps and hone in on a short, clear list of improvement opportunities — the controllable, fixable things that, if we change them, will predictably lead to more at-bats, higher win-rates, or (ideally) both. They have the balanced ability to identify problems and communicate how they plan to solve them, all while bringing their peers on the management team along for the ride.

Good fix-it-up sales leaders are also strong, uncompromising judges of talent. They evaluate people against their standard and sort the team into three buckets: The ones who “get it” and are worth investing in, the ones who clearly aren’t willing to rise to the new bar that they set, and the group in the middle — the on-the-fence cohort that needs more of their time, attention, and coaching to clarify what it will take to be part of the team in the next phase, and to give them the clarity they need to decide if they’re in or out.

Phase 3: Scaling It Up

Now you’ve got something. You’ve got a team of sales reps and most of them are consistently hitting or exceeding quota. You’ve got a predictable lead machine that serves up hand-raisers every week. You’ve got lots of happy customers that probably would buy more if you just found the right way to ask them. You’ve got a solid foundation that you can build on — a product that works, a market that’s ready, and a growth opportunity that looks like it could be massive. Now you just need to get out there and grab it. But first, you need a bigger, better sales machine and more lines in the water.

These are the signs that you’re ready for the scale-it-up sales leader.

The scaling-it-up phase is all about predictably replicating and multiplying your early successes. It’s about finishing the work of codifying “how you sell” and putting in place the tools to measure where your sales machine needs tuning as it grows. And, maybe most importantly, it’s about adding capacity to that machine — one unit at a time — that predictably returns the investment required. It’s about understanding and standardizing the inputs so that you can predict what outputs they should yield. And then it’s about adjusting and tweaking things when they inevitably go a little off-course. Scaling it up, more than anything, is about the art of placing smart bets. Bets that add growth potential without accumulating waste.

What Matters Most In The Scaling-It-Up Phase

This is the phase when your sales motion seriously evolves — from artisanal, one-at-a-time sales, to industrial sales. Before the scale-it-up phase, you might be OK with a “Super-AE” sales leader”: Someone who made their way into a leadership position still working in the business instead of on the business. People like this run their sales team like an apprenticeship — spending lots of 1:1 time with their sellers, sharing their earned secrets through personal interactions, and helping their team pick up their habits, routines, and best practices without ever writing much down. But in the scale-it-up phase, your span of control grows too large to manage via 1:1 communication. Instead of relying on apprenticeship-style leadership, you need someone who can run your sales team more like an academy — an institution with standardized ways of doing things and regular assessments that evaluate which components and people need additional attention.

This is the stage where you need a systems-thinking executive. They need to be equally comfortable in front of customers, inside of a spreadsheet, and up at a whiteboard. They need to be able to select the sales play that will find you your next wave of customers, design the steps you’ll use to run the play, teach it to their team, and then honestly evaluate their execution. And the cycles with which they do this need to be short — measured in weeks or months, not quarters or years. Clarity and process matter a lot here, but so does speed.

Buyer Beware

An important note: These phases don’t always happen sequentially. Some companies find product-market fit quickly, and then have to jump from figuring-it-out to scaling-it-up. Some companies have spent years ramping up their go-to-market spend, only to see their growth slow or their financial position change, triggering a fix-it-up phase focused on efficiency. As a business grows, the needs of the sales team evolve less linearly than cyclically, making their way through multiple loops of the three situations above.

Why does this matter? Well, the chances of finding a sales leader who can steward your company through multiple cycles are low. And in my opinion, CEOs and founders need to adopt a March-Madness-like mentality of “survive and advance” when they are evaluating or recruiting a sales leader. Diagnosing which situation you’re in is critical for building the right rubric. Hire the “scale it up” sales leader when you’re actually in a “figure it out” phase can be a fatal mistake.

Sure, they’ll sound good — they just won’t know what to do.

In Part II of this series, we’ll explore the universal qualities of great sales leaders. Then we’ll dive into the nuance of how those qualities get put to work during the figure-it-out, fix-it-up, and scale-it-up phases. I’ll also share the interview and assessment techniques you can use to test for what you need — and ensure you’re backing the right person to lead you into your next phase of growth.

If you’d like to read Part II when it comes out, make sure to subscribe over at Hello Operator (I’ll be publishing it first over there as I continue prioritize my writing on Substack).

Thanks for reading.

-Paul