A company hits 60 or 80 employees and the founder realizes they can’t do it all anymore. Revenue is growing, operations are getting complicated, and the leadership team — if you can call it that — is a handful of people who were there early and grew into roles that nobody formally defined. The founder decides it’s time to make a real leadership hire. A VP of Operations. A Head of Sales. A second-in-command who can take half the load.
The job description gets written over a weekend. It’s based on everything that’s currently on fire: the operational problems that keep surfacing, the projects that are stalled, the decisions that are waiting on the founder’s desk. The company posts the role, interviews a handful of people, and hires the candidate who best understands the current problems and seems most capable of solving them.
Six to twelve months later, the hire isn’t working. Not because the person is bad at their job — they’re often excellent. But the job they were hired to do is no longer the job the company needs. The business moved. The role didn’t. And the company just spent a year and somewhere between $150K and $400K learning a lesson that was avoidable from the start.
The Pattern: Hiring for the Company You Are, Not the Company You’re Becoming
I’ve seen this pattern play out at every stage of growth, across every industry. A PE-backed services company that hired a VP of Operations to fix delivery problems — but 12 months later needed someone who could build scalable systems for a company twice the size. A tech startup that hired a Head of Sales who was brilliant at closing deals personally but couldn’t build and manage a sales team. A professional services firm that hired a COO to “run the business” without defining what that meant, and ended up with a very senior person doing project management because nobody scoped the role properly.
The underlying mistake is the same in every case: the role was defined around today’s pain, not tomorrow’s need. The job description was a list of current problems dressed up as a position. And the evaluation criteria during the interview were “does this person understand what we’re going through?” rather than “can this person lead where we’re going?”
This happens because founders and CEOs are, understandably, living in the present. The problems are real. The urgency is real. But the first leadership hire at a growing company isn’t a problem-solving hire. It’s a capacity-building hire. The difference between those two things is the difference between a 12-month solution and a 3-year asset.
Three Ways the Role Definition Goes Wrong
1. The role is a collection of tasks the founder doesn’t want to do anymore. The job description reads like the founder’s to-do list: manage vendor relationships, oversee office operations, handle customer escalations, coordinate hiring, run the weekly team meeting. The problem isn’t that these tasks don’t need to happen. It’s that bundling them into a single role creates a job that no experienced leader wants — and that doesn’t match any real career path. The person you hire for this role will either be overqualified and frustrated (because the role has no strategic substance) or underqualified for the strategic challenges that will emerge in six months (because you hired a task manager, not a leader).
2. The title is aspirational but the scope is tactical. A company posts a “VP of Operations” role, but the actual day-to-day work is project coordination and vendor management. Or they hire a “Chief of Staff” whose real job is scheduling meetings and managing the founder’s inbox. The disconnect between the title and the work creates a credibility problem internally (“why is our VP doing admin work?”) and a retention problem within a year, when the person you hired realizes the strategic scope they were promised doesn’t exist yet.
3. The role is scoped for one person when it needs two. This is the most common version. The company needs both strategic leadership and tactical execution, so they write one job description that requires both. They end up hiring someone who’s strong at one and adequate at the other — and then wondering why half the role isn’t getting done. At many growth-stage companies, the right answer isn’t one senior hire. It’s a senior part-time leader (fractional or advisory) who provides the strategy plus a full-time operations person who handles the execution. That combination usually costs less than a single senior hire and produces better results — because you’re getting the right person for each type of work.
How to Define the Role Before You Write the Job Description
The fix starts before you open a single recruiting channel. You need 90 minutes and a whiteboard — or a conversation with someone who’s seen this decision go right and wrong across dozens of companies.
Start with the 18-month picture. Where is the company going in 18 months? Not aspirationally — concretely. How many employees? What revenue? What geographic footprint? What operational complexity? The role you’re designing needs to be right for the company at that stage, not just at the current one. If you’re at 70 employees and expect to be at 150, you need someone who’s operated at the 150-person scale before, not someone who’s an excellent operator at your current size.
Separate the strategic from the tactical. List every responsibility you’re imagining for this role, then sort them into two columns: decisions that require judgment and experience (strategic), and tasks that require execution and consistency (tactical). If the strategic column is thin, you may not need a senior hire — you need a strong manager or individual contributor plus periodic strategic guidance. If both columns are full, you need two roles, not one underpaid person doing both.
Define success in outcomes, not activities. Instead of “manage the operations team,” write “in 12 months, our delivery quality metrics will have improved by X and our operational costs will be Y.” Instead of “build the sales function,” write “in 18 months, we’ll have a repeatable sales process with three reps consistently hitting quota.” Outcome-based role definitions attract people who think in terms of results. Task-based descriptions attract people who think in terms of activity — and you don’t want to evaluate candidates by how busy they plan to be.
Evaluate for the 18-month role, not just the current fire. Your interview process should assess whether this person can do the job the role will become, not just the job it is today. That means asking about their experience building systems, scaling teams, and navigating the kind of complexity your company is heading toward. A candidate who’s brilliant at solving today’s problem but has never operated at your next stage is a 12-month hire. You want a 3-year hire.
Three Things You Can Do This Week
1. Review any open leadership role descriptions through the 18-month lens. Is the role designed for where the company is going, or for what’s on fire today? If the job description is mostly a list of current pain points, pause and redesign it before you invest in sourcing candidates who’ll solve the wrong problem.
2. Separate the strategic and tactical for your most critical open role. Use the two-column exercise. If one column is dramatically heavier than the other, that’s a signal about what kind of hire you actually need — and it might not be the title you originally had in mind.
3. Ask yourself: am I hiring one role or two? If the honest answer is that you need both strategic leadership and full-time tactical execution, don’t force them into one position. The cost of a mis-scoped senior hire — in salary, in lost time, in the organizational disruption of unwinding it — almost always exceeds the cost of structuring two roles correctly from the start.
Your first leadership hire sets the tone for every hire that follows. Get the role definition right and you build a foundation. Get it wrong and you spend a year cleaning up a mistake that compounds with every month.
We help growing companies build recruiting infrastructure that produces better hires — starting with role definition and working through structured interviews, evaluation frameworks, and quality-of-hire measurement. Whether you’re making your first leadership hire or building the team that will take you to the next stage, the process matters more than the posting.
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