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Fashionpreneur with Rent the Runway’s Jenn Hyman: How and When To Ask for a Raise

Jenn Hyman is the CEO and co-founder of Rent the Runway. Before that she went to Harvard Business School (and Harvard for undergrad too, NBD). She’s w
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Jenn Hyman is the CEO and co-founder of Rent the Runway. Before that she went to Harvard Business School (and Harvard for undergrad too, NBD). She’s writing a column for us that we’re calling Fashionpreneur. In it she’ll dole out advice and lessons learned on everything from raising funds, branding yourself, sales and generally managing a business. She’s also taking your questions.

If you were salivating earlier this week like me over the gorgeous gowns at the Met Ball, you’re likely in my fashion-dazed NY state of mind—if I only looked like Gisele for one day——how will I ever be able to afford to look like that? Naturally, my answer to the latter question is a clear and resounding three words: Rent the Runway. Whether or not you accept my plea to indulge in renting the runway for your next special occasion, please, at the very least, take my advice on this—don’t be impulsive and ask for a raise today no matter how high your fashion lust may be.

Asking for a raise is tough and timing is essential. Throughout the U.S., women do not ask for raises as frequently as men (we should!) and are often satisfied with too little. And, as you move down the corporate ladder, to where positions are the most vulnerable, raises are almost never discussed because who is going to risk angering their boss in this economy?

As a frequent recipient of raise requests, I’ve gathered a few tips that will hopefully increase your chutzpah. Don’t ask for a raise until you’ve been at a company for at least one year. The most classic business mistake is—you start a new job, you’re a rock star, and then you approach your boss after a few months and ask for a raise because obviously due to the stellar quality of your work, you’re being underpaid. Right? WRONG! Implicit in your accepting a job is the acknowledgement that you are going to do A+ work. Great work is the quid pro quo to keeping your job and it is the reason why you were hired. And, by the way, when you signed that offer letter you accepted a specific salary. If you were unhappy with it then, you should have negotiated or not accepted the job in the first place. Raises are rewarded for consistent performance over time.

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But, if you have been at the company for a year, ask away and don’t be shy. It is not always possible to give raises but your boss should always be honest with you about how the company is faring, how you are performing and when he/she will be able to meet your financial demands. Raises are not only rewarded for output but often for how much you are contributing to the culture of your company--Paul English, the co-founder of has a philosophy that there are two types of people in the workplace: people that add positive energy to their environment and others that detract from it. Be an energy creator. Plan a team event for your company. Lead by example. Take on work that you are passionate about simply because you care. Inspire others around you even if they don’t report to you. I guarantee that this will get you a much higher raise than if you just did an A+ on your own. The people who make Rent the Runway a wonderful place to be every single day are the most important building blocks of our organization.

Ask for feedback throughout the year. All too often, employees wait until their annual reviews to suss out how they are performing and how big their raise will be. It’s to your advantage to have these feedback conversations often and consistently throughout the year so you can fix things that are off kilter, be coached, and situate yourself to be more handsomely rewarded later. By the time your annual review rolls around, you should have discussed your accomplishments so much with your boss that nothing is a surprise. Your review should be a recitation of facts you already know.

Finally, asking for a raise is one of those conversations that is unanimously agreed upon as being both an essential yet sometimes awkward and terrifying one. Take it from me (I’ve had my experience asking for money as an entrepreneur!)--it’s like getting a shot at the doctor’s office. The anticipation is always worse than the actual pinch and it’s over before you know it.