The Startup Hiring Mistake That Looks Like a Win

In July, WHOOP employed Dirk-Jan van Hameren, Nike’s former chief advertising officer, to run advertising for the wearable-tech firm. On paper, it seemed like a typical senior advertising rent. In apply, van Hameren walked into an organization that had simply closed a $575 million funding spherical at a $10.1 billion valuation, crossed 3 million members and was already cash-flow constructive.

He didn’t construct a advertising perform. He inherited one: a 65-person crew already in place, reporting on to him from day one. 

That’s the half founders miss after they take a look at a rent like this and suppose, “We’re prepared for that, too.” I’ve spent years putting advertising expertise inside growth-stage firms, and the error I see most frequently is making a senior rent earlier than the infrastructure exists to assist it. 

Right here’s methods to inform whether or not your organization is really prepared to rent a advertising VP or CMO, and what to do if it isn’t but: 

1. Learn the indicators earlier than you rent 

These indicators normally imply the infrastructure isn’t there but for a VP or CMO, even when the ambition is: There’s no repeatable method leads or prospects are available but, the advertising funds will depend on whoever’s most cost-effective that quarter fairly than what’s working, and nobody on the crew might inform you which channel really drives income. 

I labored with one founder who received excited a few robust résumé, made the rent after which puzzled, six months in, why nothing had modified. The brand new chief was spending most of their time on hands-on execution as an alternative of constructing a crew or a method, whereas the remainder of the management crew stored anticipating instant development outcomes. That expectation was the actual downside.  

A senior advertising chief‘s first few months ought to go towards diagnosing what’s really working, not producing outcomes off a method that doesn’t exist but. Skip that step, and any development you do see gained’t maintain. Most often like these, the corporate would have been higher served by a powerful director-level advertising chief first, then an govt as soon as the complexity and scale really justified the title. 

A director-level rent prices much less, comes with decrease expectations hooked up and is usually extra comfy doing the hands-on work the corporate really wants proper now. That’s the rent that matches what the corporate can presently assist — nothing about it’s a step down. 

2. Set them up earlier than day one  

A senior advertising chief wants 4 issues within the first 90 days: clear enterprise objectives, actual decision-making authority, entry to knowledge and alignment with the founder on priorities. In addition they want context, together with what’s been tried earlier than, what’s working now and the place the corporate needs to go. With out it, a brand new rent will spend their first month rediscovering issues the corporate already realized the onerous method, resembling channels that by no means transformed or messaging that fell flat with the gross sales crew. 

Founders fall quick right here consistently, altering priorities each few weeks, withholding actual authority whereas nonetheless anticipating possession or demanding outcomes earlier than the chief has had time to construct a method grounded within the firm’s precise knowledge. A 2025 Gartner survey of CEOs and CFOs discovered solely 34% see eye-to-eye with their CMO on advertising’s position in supporting development, which is precisely the sort of misalignment that turns a powerful rent right into a six-month disappointment. 

3. Shut the hole with out the full-time price ticket 

Fractional management exists to assist shut this hole. It is smart when an organization wants senior-level technique and experience however isn’t prepared for the associated fee, scope or workload of a full-time govt — significantly in periods of development or transition, or when the advertising perform itself nonetheless must be constructed earlier than anybody commits to a everlasting chief.  

Alina Vandenberghe, co-founder and co-CEO of Chili Piper, used this strategy after operating advertising herself for a stretch, hitting her numbers however exhausting the mannequin. Relatively than hiring a full-time CMO immediately, she introduced on a fractional advertising govt to check what expertise and attributes her everlasting rent really wanted. A brief, outlined engagement (three to 6 months, with particular objectives hooked up) offers you an identical readability. 

Actual work will get accomplished, and also you study what the position requires earlier than you decide to a wage and a title. Vandenberghe landed on a full-time VP of selling as soon as that was clear. Van Hameren’s transfer to WHOOP reveals the opposite finish of that very same course of. The crew, the funds and the dimensions had been already there ready for him, which is exactly why a full-time rent made sense. 

Earlier than you rent the VP or the CMO, ask whether or not your organization seems to be something like that. If it doesn’t but, that’s not a purpose to attend indefinitely. It is a purpose to construct the infrastructure first, in order that if you do make the rent, you’re not asking somebody to do a job you had been by no means set as much as give them. 

In July, WHOOP employed Dirk-Jan van Hameren, Nike’s former chief advertising officer, to run advertising for the wearable-tech firm. On paper, it seemed like a typical senior advertising rent. In apply, van Hameren walked into an organization that had simply closed a $575 million funding spherical at a $10.1 billion valuation, crossed 3 million members and was already cash-flow constructive.

He didn’t construct a advertising perform. He inherited one: a 65-person crew already in place, reporting on to him from day one. 

That’s the half founders miss after they take a look at a rent like this and suppose, “We’re prepared for that, too.” I’ve spent years putting advertising expertise inside growth-stage firms, and the error I see most frequently is making a senior rent earlier than the infrastructure exists to assist it.