Driving Disruption: Alex Alioto Of Whimstay On The Innovative Approaches They Are Taking To Disrupt Their Industries

An Interview With Cynthia Corsetti

Personalized Recommendations Based on User Behavior: Utilizing AI and machine learning, we offer personalized travel recommendations to our growing audience of next-gen travelers. This enhances the user experience and allows us to target emerging trends and meet the unique needs of our savvy and spontaneous travelers.

In an age where industries evolve at lightning speed, there exists a special breed of C-suite executives who are not just navigating the changes but driving them. These are the pioneers who think outside the box, championing novel strategies that shatter the status quo and set new industry standards. Their approach fosters innovation, spurs growth, and leads to disruptive change that redefines their sectors. In this interview series, we are talking to disruptive C-suite executives to share their experiences, insights, and the secrets behind the innovative approaches they are taking to disrupt their industries. As part of this series, we had the pleasure of interviewing Alexander Alioto.

Alexander Alioto is the Founder and Head of Growth and Partnerships at Whimstay. Alexander Alioto attended the University of Michigan College of Literature, Science, and the Arts.

Thank you so much for joining us in this interview series. Before we dive into our discussion about disruption, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?

I studied theatre at the University of Michigan, spent 12 years as a theatre actor in New York, and toured across the country. Though I loved it, I eventually moved back to SF and started anew at Yelp. It turns out that the qualities that made me a good actor, like empathy and listening, translated well into sales and leadership. After learning a ton at Yelp and a stint in consulting for several tech startups, my cofounders approached me with the idea for Whimstay, precisely the challenge my soul yearned for.

What do you think makes your company stand out? Can you share a story?

We provide a service that did not exist in our industry when we started. A way for vacation rental hosts and owners to fill last-minute availability — be it vacant weekdays, nights during slower or “off-peak” seasons, or cancelations — while simultaneously offering discounts to savvy and spontaneous travelers looking to get away on a whim. That’s our value in the market: a true win-win.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

  • Seek to Understand: Everyone is unique and beautiful and perfect in their own way. Find out what drives them. Seek to truly understand who people are and why they are doing what they’re doing, and ask how you can support them in a sincere way that meets them where they’re at. This is a powerful character trait when it comes to building culture.
  • Self-awareness: Know who you are and what makes you tick, actively reflect on how YOU can get better- and be open and honest about it. And then be willing to ask others to help fill in where you aren’t great.
  • Empowering with Trust: There’s a fine line between accountability and micromanaging. That fine line exists within the intention of the manager. This is where seeking to understand becomes valuable. When you lead based on empowering with trust — you are going to build an incredible culture. Work to build a community and strive to ensure that every part of that team is equally important. Allow people to be 100% be themselves and manage to their unique strengths instead of strengths you think they should have.

Leadership often entails making hard choices between two good paths. Can you share a story with us about a hard decision or choice you had to make as a leader? I’m curious to understand how these challenges have shaped your leadership.

Years ago, at a former company, we had come off a string of strong quarters when all of a sudden, for reasons inside the markets, things went south. I had a high-performing rep on my team, and we needed every dollar they brought in. But their attitude left a lot to be desired. Their demeanor was highly ineffectual, and I started to sense it was seeping into the team. So, I had a long talk with the rep, told them where I was and how I felt, and basically let my top performer know they had a month to step it up or they were gone. They soon opted to transition to another team, and immediately the team’s energy shifted, and the numbers soon reflected that. From the team’s perspective, I put them above all else, and they met the challenge. Never underestimate the power of trusting the whole over an individual — probably one of the great lessons I learned in all my time in tech sales.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. Let’s begin with a basic definition so that all of us are on the same page. In the context of a business, what exactly is “Disruption”?

I’d say an innovation that shakes up the status quo. Something that changes how people do things.

How do you perceive the role of ‘disruption’ within your industry, and how have you personally embraced it? Is it a necessity, a strategy, or something else entirely in your view?

Stagnancy of ideas will kill anything, including an industry. It’s why competition is necessary. If there wasn’t disruption in our industry, hosts would be limited in how they can produce revenue, and travelers would be stuck with the same products but at a HIGHER price.

What lessons have you learned from challenging conventional wisdom, and how have those lessons shaped your leadership style?

Conventional wisdom will get you close to nowhere. It’s a middle-of-the-road approach that will produce middle-of-the-road results. My co-founder and I have always emphasized to each other and the team the dire importance of creating a unique path. Go where no person has gone before, and if it doesn’t work, gather the lessons, recalibrate, and then keep going.

Disruptive ideas often meet resistance. Could you describe a time when you faced significant pushback for a disruptive idea? How did you navigate the opposition, and what advice would you give to others in a similar situation?

I tried to bring meditation to my previous work. We’d meet every Friday morning. Mostly we spoke about the power of intention and the importance of being and then we taught a group meditation. If misunderstood this could seem like a pretty radical idea on the sales floor. But it all tied in to how we can work more effectively. It’s very powerful. Eventually, sadly, we were shut down. But years later I’m still in contact with people from that group that say that work changed them. Sometimes being disruptive just seems like the logical next step — and it won’t always work the way you want it to, but don’t let that stop you.

What are your “Five Innovative Approaches We Are Using to Disrupt Our Industry”?

  1. Dynamic Pricing for Last-Minute Bookings: Leveraging advanced algorithms, we dynamically price last-minute vacancies in vacation rentals, ensuring they’re the best available during the last-minute booking window, but also during slower seasons throughout the year. This approach maximizes occupancy and revenue for hosts while offering exclusive deals to travelers.
  2. Seamless Integration with a vast number of property management systems: We’ve worked hard and fast over the past two years to integrate directly with all the major vacation rental software companies — allowing property owners the ability to seamlessly sync their listings with Whimstay and diversify their distribution in an instant. This means that owners can manage their properties across multiple platforms without additional hassle, increasing their potential earnings and market reach while maximizing availability by targeting unique audiences.
  3. Personalized Recommendations Based on User Behavior: Utilizing AI and machine learning, we offer personalized travel recommendations to our growing audience of next-gen travelers. This enhances the user experience and allows us to target emerging trends and meet the unique needs of our savvy and spontaneous travelers.
  4. Advanced Analytics for Property Owners: We provide property owners with advanced analytics and market insights to optimize their listings. This service includes data on peak demand periods, pricing strategies, information about optimal requirements for minimum lengths of stay, and traveler preferences. By empowering owners with this data, they can adjust their offerings to maximize occupancy and revenue. For instance, an owner might find their property particularly popular with families during school holidays and can tailor their marketing and amenities accordingly.
  5. Hyper-Localized Market Expansion: We are focusing on hyper-localized expansion in markets often overlooked by major rental platforms. This involves targeting smaller towns or unique destinations with the potential for growth based on our research and 1st party analytics. By doing this, we’re offering new, undiscovered locales to adventurous travelers and helping local property owners tap into a broader market. For example, a quaint town with unique cultural attractions or natural beauty could become a new favorite for travelers seeking hidden-gem experiences at a great deal. This strategy disrupts the usual focus on major tourist destinations and supports local economies while diversifying our portfolio of properties.

Looking back at your career, in what ways has being disruptive defined or redefined your path? What surprises have you encountered along the way?

What defined my disruption was to always be authentic — to just be me. For a long time, folks told me that wouldn’t work. The biggest surprise I found was that when I started a company with a co-founder who also bucks convention and trusts me implicitly, my department’s identity would be flavored by how I did things. And it worked. I am amazed by what we have built every day. What we have on our hands is serious business doing serious things to help people build their own businesses.

Beyond professional accomplishments, how has embracing disruption affected you on a personal level?

My great takeaway from starting Whimstay is this: allow life to unfold the way it will unfold. That does not mean being passive. It simply means that how you approach the small things is how you must approach everything. If you are at every peak and every valley through the course of a start-up, you will burn yourself out in a year. Hold fast to the knowing that if you have a market fit, and your timing is right, and you have good people — success is inevitable. It might take longer than you prefer, but you’ll eventually get there.

In your role as a C-suite leader, driving innovation and embracing disruption, what thoughts or concerns keep you awake at night? How do these reflections guide your decisions and leadership?

Details keep me up at night. Knowing those details are covered allows for greater execution. So, I tend to over-communicate. Leaving a meeting without pre-assigned next steps is fodder for my nightmares.

If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

The power of being. The inherent knowing that everything is connected. Just knowing it allows for such a deep relaxation into what and who you are. We can stop chasing feeling good and start to embrace the whole panoply as it comes.

How can our readers further follow your work online?

Follow Whimstay on LinkedIn to keep updated on what’s new and what’s next for us and visit www.whimstay.com to see for yourself.

Thank you for the time you spent sharing these fantastic insights. We wish you only continued success in your great work!

About the Interviewer: Cynthia Corsetti is an esteemed executive coach with over two decades in corporate leadership and 11 years in executive coaching. Author of the upcoming book, “Dark Drivers,” she guides high-performing professionals and Fortune 500 firms to recognize and manage underlying influences affecting their leadership. Beyond individual coaching, Cynthia offers a 6-month executive transition program and partners with organizations to nurture the next wave of leadership excellence.