Sharp takes on
sales hiring.
Not a generic recruiting blog. Specific, opinionated writing on what makes sales leadership hiring hard in IT services and consulting — and what to do about it. Written by Monica Sethi.
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Why IT Services Firms Keep Mis-Hiring Sales Leaders
It's not that the candidates are bad. It's that the profile is wrong — and no one takes the time to define what "right" actually means.
We've run hundreds of searches for IT services and consulting firms over the past 14 years. And the single most common pattern we see isn't a bad hire — it's a mis-hire. A talented sales leader, placed in the wrong environment, failing for reasons that were entirely predictable.
The most common version of this story goes like this: a $150M IT services firm hires a VP of Sales from a $2B systems integrator. The candidate has an impressive resume — big logos, big numbers, big team. They come in with confidence and a clear plan. Six months later, they're struggling. Twelve months later, they're gone.
What happened? The candidate was good. The firm was good. The fit was wrong.
At the large firm, the VP had a brand that opened doors, an SDR team that filled the top of the funnel, a marketing engine that generated inbound, and a support infrastructure that handled everything from proposal writing to contract negotiation. At the boutique firm, they had none of that. They were expected to build pipeline from scratch, sell on expertise rather than brand, and navigate complex multi-stakeholder deals with a fraction of the support they were used to.
This is the pattern we call the 'infrastructure dependency' problem. And it's almost never surfaced in a standard interview process, because no one asks the right questions.
"The most expensive hiring mistake isn't hiring a bad salesperson. It's hiring the right salesperson for the wrong environment."
The three questions that predict fit
Before we start any search, we ask three questions that most firms never ask. First: where does this candidate's track record actually come from — their own ability, or the machine behind them? Second: what does their typical deal look like, and does that match what we're asking them to sell? Third: what environment do they thrive in — high-autonomy or high-structure, brand-led or expertise-led, inbound-heavy or outbound-first? The answers to these questions tell us more about fit than a resume ever will.
The comp plan problem
The second most common reason searches fail — and the one clients are most reluctant to hear — is that the comp plan is below market. We see this constantly. A firm has a budget in mind, they build a comp plan around that budget, and then they wonder why the candidates they want keep declining. The answer is almost always that the OTE is 15–25% below what the candidate can earn elsewhere. We tell clients this before we start the search. Sometimes they adjust. Sometimes they don't. The ones who don't usually come back to us six months later.
What to do differently
The fix isn't complicated, but it requires discipline. Before you write a job description, spend an hour answering these questions honestly: What does our go-to-market actually look like? What infrastructure will this person have? What does a typical deal look like — size, cycle, stakeholders? What happened to the last person in this role, and why? The answers will tell you what profile you actually need — which is often very different from the profile you think you need.
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