The Startup Hiring Mistake That Looks Like a Win

The Startup Hiring Mistake That Looks Like a Win
A senior marketing hire can look like proof you’ve made it, when it’s really proof you’ve moved faster than your company can support.
Opinions expressed by Entrepreneur contributors are their own.
Key Takeaways
- Many founders make the mistake of hiring a senior leader before the infrastructure exists to support it. They expect the leader to produce results off of a strategy that doesn’t exist yet.
- Read the signs before you hire: no repeatable way leads or customers come in, the budget depends on whoever’s cheapest rather than what’s working, no one knows which channel actually drives revenue.
- Set them up before day one: They need clear business goals, real decision-making authority, access to data and alignment with the founder on priorities.
- Consider fractional leadership: Real work gets done, and you learn what the role actually requires before you commit to a salary and a title.
In July, WHOOP hired Dirk-Jan van Hameren, Nike’s former chief marketing officer, to run marketing for the wearable-tech company. On paper, it looked like a typical senior marketing hire. In practice, van Hameren walked into a company that had just closed a $575 million funding round at a $10.1 billion valuation, crossed 3 million members and was already cash-flow positive.
He didn’t build a marketing function. He inherited one: a 65-person team already in place, reporting directly to him from day one.
That’s the part founders miss when they look at a hire like this and think, “We’re ready for that, too.” I’ve spent years placing marketing talent inside growth-stage companies, and the mistake I see most often is making a senior hire before the infrastructure exists to support it.
Here’s how to tell whether your company is actually ready to hire a marketing VP or CMO, and what to do if it isn’t yet:
1. Read the signs before you hire
These signs usually mean the infrastructure isn’t there yet for a VP or CMO, even if the ambition is: There’s no repeatable way leads or customers come in yet, the marketing budget depends on whoever’s cheapest that quarter rather than what’s working, and no one on the team could tell you which channel actually drives revenue.
I worked with one founder who got excited about a strong résumé, made the hire and then wondered, six months in, why nothing had changed. The new leader was spending most of their time on hands-on execution instead of building a team or a strategy, while the rest of the leadership team kept expecting immediate growth results. That expectation was the real problem.
A senior marketing leader‘s first few months should go toward diagnosing what’s actually working, not producing results off a strategy that doesn’t exist yet. Skip that step, and any growth you do see won’t hold. In most cases like these, the company would have been better served by a strong director-level marketing leader first, then an executive once the complexity and scale actually justified the title.
A director-level hire costs less, comes with lower expectations attached and is often more comfortable doing the hands-on work the company actually needs right now. That’s the hire that fits what the company can currently support — nothing about it is a step down.
2. Set them up before day one
A senior marketing leader needs four things in the first 90 days: clear business goals, real decision-making authority, access to data and alignment with the founder on priorities. They also need context, including what’s been tried before, what’s working now and where the company wants to go. Without it, a new hire will spend their first month rediscovering things the company already learned the hard way, such as channels that never converted or messaging that fell flat with the sales team.
Founders fall short here constantly, changing priorities every few weeks, withholding real authority while still expecting ownership or demanding results before the leader has had time to build a strategy grounded in the company’s actual data. A 2025 Gartner survey of CEOs and CFOs found only 34% see eye-to-eye with their CMO on marketing’s role in supporting growth, which is exactly the kind of misalignment that turns a strong hire into a six-month disappointment.
3. Close the gap without the full-time price tag
Fractional leadership exists to help close this gap. It makes sense when a company needs senior-level strategy and expertise but isn’t ready for the cost, scope or workload of a full-time executive — particularly during periods of growth or transition, or when the marketing function itself still needs to be built before anyone commits to a permanent leader.
Alina Vandenberghe, co-founder and co-CEO of Chili Piper, used this approach after running marketing herself for a stretch, hitting her numbers but exhausting the model. Rather than hiring a full-time CMO right away, she brought on a fractional marketing executive to test what skills and attributes her permanent hire actually needed. A short, defined engagement (three to six months, with specific goals attached) gives you the same clarity.
Real work gets done, and you learn what the role requires before you commit to a salary and a title. Vandenberghe landed on a full-time VP of marketing once that was clear. Van Hameren’s move to WHOOP shows the other end of that same process. The team, the budget and the scale were already there waiting for him, which is precisely why a full-time hire made sense.
Before you hire the VP or the CMO, ask whether your company looks anything like that. If it doesn’t yet, that’s not a reason to wait indefinitely. It is a reason to build the infrastructure first, so that when you do make the hire, you’re not asking someone to do a job you were never set up to give them.
Key Takeaways
- Many founders make the mistake of hiring a senior leader before the infrastructure exists to support it. They expect the leader to produce results off of a strategy that doesn’t exist yet.
- Read the signs before you hire: no repeatable way leads or customers come in, the budget depends on whoever’s cheapest rather than what’s working, no one knows which channel actually drives revenue.
- Set them up before day one: They need clear business goals, real decision-making authority, access to data and alignment with the founder on priorities.
- Consider fractional leadership: Real work gets done, and you learn what the role actually requires before you commit to a salary and a title.
In July, WHOOP hired Dirk-Jan van Hameren, Nike’s former chief marketing officer, to run marketing for the wearable-tech company. On paper, it looked like a typical senior marketing hire. In practice, van Hameren walked into a company that had just closed a $575 million funding round at a $10.1 billion valuation, crossed 3 million members and was already cash-flow positive.
He didn’t build a marketing function. He inherited one: a 65-person team already in place, reporting directly to him from day one.
That’s the part founders miss when they look at a hire like this and think, “We’re ready for that, too.” I’ve spent years placing marketing talent inside growth-stage companies, and the mistake I see most often is making a senior hire before the infrastructure exists to support it.