‘Our sales team speaks directly to decision makers and implements what they need firsthand’

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By Jennifer Glatt | Mint Pillow

Kyle Manning is the National Director of Business Travel Sales at Staypineapple, where bold design, cheeky charm and über-comfy beds are redefining business travel. With fun, funky properties in cities like Seattle, San Diego and Chicago, Staypineapple ditches the bland for something way more memorable. Manning's goal? To deliver all the perks business travelers need—while making every stay feel less corporate and a whole lot more fun. 

How can indie hotels scale sales while staying authentic?
Independent boutique hotels have a unique opportunity to develop true relationships with their clients and learn what is most important to their travel needs. It’s a one-on-one partnership where we can uncover and learn from each company what matters most to them and to their travelers. Large, big-box hotels are burdened with too many layers of salespeople. A client’s needs get diluted as it’s passed from one salesperson to another to another. It’s like a game of “telephone,” where the first message is always misunderstood by the last person that hears it. With Staypineapple, our sales team speaks directly to decision makers and implements what they need firsthand. There is no opportunity for anything to be lost in translation.

What’s your pitch for landing group bookings that want something different?
We are a breath of fresh air in a sea of monotonous brands. We have the ability to ask a client directly: What’s most important to you? If you had a magic wand, what would this meeting look like? Every group, every client, every guest is so different and unique. The only “secret sauce” is finding out specifically what makes a client happy, then overdelivering and knocking their socks off each and every time.

What sales tactics help boutiques stand out from big chains?
We pride ourselves as being disruptors to the big chains. Traditional big box hotels will always be considered by corporate guests. To be honest, I’m glad that they are—it lets us stand out and it lets us shine. Does a company’s traveler really want to stay at the same old hotel year in and year out? Do they want the exact same hotel in one city as they do in another city? Doesn’t the savvy hotel guest want something new? A unique, breathtaking hotel in the heart of the city, where they can actually enjoy their stay and not just count down the minutes until they check out? The majority of our partners include a diverse set of hotels in their travel portfolio. Keep the big box brands for the conservative travelers, and add our upscale boutique hotels for the well-traveled, discerning, adventurous guest. When was the last time that you called a big chain to ask something about your hotel bill? Could you get through? How many automated messages did you listen to before being told to call someone else? We talk one-on-one with every corporate client, whether it’s the decision maker signing a contract or the new hire who is staying at our hotel for the first time.

What’s your best strategy for turning first-time guests into loyal ones?
Personalization. Gone are the days of a hotel guest being impressed by a reservations system seeing that you like Diet Coke in your room or that you want a room away from the elevator. Guests want and expect to be WOW-ed: 'When you checked in a year ago, you had a Seattle Storm hat on, they’re in town tonight, so we got you tickets and have scheduled an Uber to arrive 30 minutes before the first pitch.' That’s the level of personalization that a guest seeking something different and great. That is what we deliver time and time again at Staypineapple.

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