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Industry Icons Penny Wing and Elaine Macy Disrupt the Sales Status Quo with Reiimagine

Just because something’s always been done one way, does it mean it can’t be done another way? Not according to Penny Wing and Elaine Macy, two industry icons who knew each other for years before deciding to join forces and challenge the commission-based sales representation model by developing Reiimagine, their bold new fixed-fee model that has literally become an extension of the in-house sales team for luxury independent hotels around the world. Although they conceptualized and launched Reiimagine two months prior to the start of the pandemic––not ideal timing––the company has thrived nonetheless. In just over two years, they have grown Reiimagine into an expanding collection of over 60 global properties. Penny and Elaine consider themselves “disruptors” and see no limit to the possibilities for Reiimagine, we chat with them to get the scoop on this game-changing concept.

Penny Wing and Elaine Macy reiimagine

Penny, a look at your LinkedIn reveals a chess enthusiast and a master’s degree in math, what drew you to hospitality? My father was a career Army officer and by the age of 21 I had moved 36 times–all around–from Europe, Asia, and back to the US. I had wanted to be an art major in college but my father refused to pay for art school, so I completed my degrees in business and math. I learned chess by playing with my father’s officers on base. I remember one of them coming to the house and my father woke me up to play one game. I beat him. I was 14 years old. He was a chess master.

I started my career working for engineering companies, then I ended up marrying the president of the company. In those days, husbands and wives couldn’t work together so this prompted a career change. I fell into travel after meeting someone on a flight that owned a large travel agency. It was a natural fit for me. I’ve been in travel ever since! I learned the business and started my first company in 1988. Since then I have started and sold three companies. Now I have a software company called Brojure and Reiimagine with Elaine.

And Elaine, you started as a flight attendant and then worked your way up in group sales? What got you started in travel and what have you loved most about being in the industry?

I took my first flight to another country as a World Airways flight attendant. I went to Tokyo followed by Amsterdam, and this began my love affair with the sights, culture, food, and fun that goes with international travel experiences. I was smitten.

Now, together, you have created Reiimagine. What brought you together and how did you come up with the idea?

Penny: Elaine and I ended up partners when I sold my third company to Peter Ueberroth, who owns Preferred Hotels & Resorts, where she was working in sales. I always wanted to work with Elaine, there was a great deal of mutual respect between us over our careers. When she said she was leaving Preferred to retire…I said, not yet! We need to create a new company and what would you like to do? She told me about her dream of a different kind of hotel sales offering––with a fixed monthly fee––and that was the start of Reiimagine. Elaine and I are similar in our work ethic. She is an amazing connector, creative, and extremely high energy. I am a good business person, tech-driven, and imaginative. It is a partnership made in heaven. We balance out each other very well.

Elaine: I have known Penny for years as we both ran incentive travel businesses earlier in our careers. When I announced my plan to leave Preferred Hotels in 2019, Penny called me immediately. I felt there was an underserved niche with high-end, luxury hotels that wanted broad brand awareness and international reach but couldn't afford what was in the marketplace for sales representation. We decided to call the company Reiimagine because we were creating a new way to sell, Penny made the two “i”s for innovative ideas.

Fox Harb'r Manor Living Room in Nova Scotia
Living Room at Fox Harb'r Manor in Nova Scotia, part of the Reiimagine portfolio

Wow, a flat fee structure when usually hotel sales representation is commission-based. How does it work in practice? Can you still track each booking?

Elaine: We do know the status of each booking but it is not necessary to track as it doesn't matter where the leads come from, the hotel owns the booking once we connect them. We assist them in closing if requested. We truly work as a seamless extension of the hotel sales team.

Are the leads primarily for group business or do you connect properties with individual bookings as well?

Elaine: We cover corporate groups but 65% of our current business is luxury leisure and concierge services as well as high-end luxury weddings.

Where does the travel agent commission fit into this picture?

Elaine: The hotel pays commission as usual to the travel advisor as we are just a member of the sales team and not a third party.

Each of the salespeople on the Reiimagine team is an equity partner? That also seems like a disruptive concept. How does it work?

Penny: For the first time in my career, I wanted to create a company with Elaine that allows our loyal team members to participate in the equity of the company. Most people would never get a chance to own shares where they work. We are still building and once we are breaking even, we will formally set up the shares. We want them to be part of the upside, not the struggling start-up. We are turning the corner soon due to the very exciting expansion of our unique collection, even in this pandemic and post-pandemic times, due to the new representation model Reiimagine has established.

You started during the pandemic, how much has the company grown?

Elaine: So far we have a collection of 60+ properties globally in 2.5 years, and we have lots of prospects.

the terrace at The Mandrak, London
the terrace at The Mandrake, London, part of the Reiimagine portfolio

What types of hotels do you think benefit most from Reiimagine’s services?

Elaine: We only work with 5-star independent luxury properties that are under 250 rooms. The hotels need to meet five criteria:

  1. Experiential––they must offer guests interesting and immersive

  2. Unique––luxury doesn't always just mean 5* but they need to offer something different. The Mandrake in London is a great example, the scene at that hotel is so special, with their artist-in-residence program and internal courtyard which belies the hotel's central location.

  3. Wellness component––the hotel must have a spa or wellness offering

  4. Sustainability––this has to be a core focus of the hotel. A good example of this Potato Head in Bali, everything was built locally and sustainably, and they offer regenerative travel experiences.

  5. Design forward––no big box hotels, each property is one-of-a-kind and done with flair.

Lately, we have had several larger hotels requesting our services, so we are considering opening a division for larger properties that have been renovated or reinvented themselves but the largest would be 400 rooms.

What are you doing to drive business?

Elaine: Events! Roadshows! We're planning IMEX and ILTM right now. We are in constant contact with our member hotels, seeing what they need and how we can help them. I am working harder than I have ever in my career and I love it.

Penny: In the past, representation companies seemed to compete with the internal sales teams at the property. Mostly because it was commission based. Reiimagine is literally an extension of their sales team. We all work together as one team for new sales and opportunities for the property. It is an absolute pleasure not to be arguing about who found the lead, who closed the lead, who gets the commission, etc. It’s just one big happy family now. And I love how Elaine is forever checking with the hotels on what they need immediately. We are nimble and can shift direction–does a hotel need more Leisure or do we concentrate on short-term MICE business or Weddings? Our team is extremely talented, creative, experienced, and well connected, along with diversified in many markets.

Penthouse Deck at Chedi Lustica Bay in Montenegro
Penthouse Deck at Chedi Lustica Bay in Montenegro, part of the Reiimagine portfolio

Tell me more about your team?

Elaine: Because of COVID, suddenly several brilliant talents became available and we scooped them up! Our team of sales professionals includes legends in the biz including Dan Beschloss who was with Valerie Wilson Travel for many years and Gary Stram who you know from working at Loews Hotels. We have people in New York, California, Texas, Canada, and London––key markets for luxury agents.

What trends do you see coming in the luxury travel space?


  1. Luxury leisure is more interested in experiences and wellness.

  2. Incentives are looking for more remote and unusual destinations.

  3. High net worth clients are willing to fly private with their friends and families to have an experiential luxury.

  4. Weddings are looking for our beautiful castles and estates.

  5. International travel is booming and Asia is especially coming back


I agree with Elaine and would add other key trends are centered around technology and storytelling. With Brojure, we have a comprehensive software platform in which I invested $5 Million over the past nine years. We want to make it easy for Travel Advisors to find the stories of our properties and share those with their customers. It's not just booking rooms anymore, it’s booking experiences and creating special memories. Our Brojure software is all about visuals, stories, and evoking emotions. That is how people buy travel. Not off an OTA with small photos and prices. Especially in the luxury world.

Here's what is next: by the end of the year, an Advisor will be able to pull a hotel Brojure off the platform into their own account, and customize it with their logo, customer name, contact page, and a personalized Day-by-Day itinerary before sending it to the customer. The presentation will look like a mini Vogue magazine personalized to each customer. It will just take minutes to create, and the impact will be amazing.

Thank you both for your time! Wishing you lots of success with Reiimagine!

Penny Wing and Elaine Macy reiimagine


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