July 2017
Vol 5 | Issue 130

Q&A with Greg Apple

Chief Marketing Officer at HelloGbye

Principle Series:

Family Office Insights sits down with Greg Apple, Chief Marketing Officer at HelloGbye, to discuss the revolutionary A.I digital assistant that plans, books, and changes travel itineraries with the efficiency and accuracy only achieved by its proprietary algorithm.


Family Office Insights is a voluntary, “opt-in” collaborative peer-to-peer community of single family offices, qualified investors and institutional investors. Join the community here www.familyofficeinsights.com


Tell us about your background and your company, HelloGbye.

In high school, I started my own computer company, similar to Nerds on Site, where we went into university campuses to help students configure their computers and setup their internet. I sold the company when I was 23, and recognized then that I had the entrepreneurial spirit in me. Upon graduating from Huron University College, I was recruited as Account Executive of Salesforce.com, where I quickly became the #1 sales executive in North America. I then was recruited to work at SAS as an Enterprise Account Executive where I sold predictive analytics and data mining technologies to large enterprise accounts for 4 years and again was very successful in my role. With my sales track record and expertise, Google recruited me as Senior Sales Consultant of Digital Advertising in Canada to help the technology sector innovate and shift media dollars from traditional offline advertising to digital advertising. While playing squash with one of the founders of HelloGbye, he approached me about joining his company, but I was content at Google and not interested in leaving such a renowned company. Eventually, they convinced me to take a look under the hood, and after seeing the HelloGbye prototype I was so impressed that I accepted the position as Head of Marketing in November of 2014. Although the travel space is new to me, technology is not, so this has made my job as the Chief Evangelist very interesting, as I am responsible for building out the customer experience and the ‘look and feel’ of the HelloGbye platform and evangelizing our brand.

What makes HelloGbye different is our efficiency to get seemingly tedious and complex tasks done in seconds, hence the name, ‘Hello Goodbye.’ We shortened the ‘Goodbye’ to ‘Gbye’ to exude quickness and brevity to incredibly positive feedback – our name certainly does a lot for us. Founded in 2012 by Jonathan Miller, HelloGbye is an end-to-end digital travel platform designed for frequent travelers, business travelers, luxury travelers, and groups. The HelloGbye experience eliminates the need for restrictive search forms and drop-down menus that characterize the legacy systems. For businesses and groups, you are able to plan and book multi-person, multi-destination itineraries all with unique travel preferences in just seconds, in your own words. HelloGbye also simplifies post-booking changes, allowing users to change booked flights and hotels in real-time without spending hours on the phone with an agent. With the growing number of on-demand features and integrated voice control apps, we aim to be your very own handheld 24/7 digital assistant for travel and beyond.

Who is your target audience?

We have pivoted since we launched back in April. We initially started in the B2C market, because we knew that if we could get the user experience to be seamless and the interface eye-catchingly beautiful, all with an increasing number of users, it would validate our solutions for the big issues in this space. Our strategy is that if we could get the business traveler to fall in love with HelloGbye, then they would naturally convert into personal travel users as well. As a B2C business, we focused on any North American customer who wanted to book an itinerary, but in the saturated market of online giants like Priceline, we shifted our energy and focus on becoming a B2B service catering to the hybrid business travelers, which consist of managed and unmanaged travelers who travel at a minimum of 6-12 times a year. The managed business traveler works with a travel management company through their systems and processes that negotiate rates and packages on their behalf. The unmanaged business traveler typically books through individual channels for each aspect of the itinerary like hotels and airlines by him or herself, through an agent, or executive

assistant. This target market faces arduous and timely issues that HelloGbye alleviates within seconds. And so beyond establishing market fit in the B2C space, our goal to focus heavily in becoming a travel platform for small and large businesses as well as travel management companies and travel agencies.

What are some of the challenges you face in this market?

On the consumer side, the cost of acquisition is very high. We realized very quickly that in order to make a big splash you need a lot of marketing money. Expedia and Priceline (Hotels.Com, Booking.Com, Trivago.Com) spend 47% of topline revenue on advertising, and when in a heavily competitive consumer channel like online travel, you need millions of marketing dollars to compete. We are nowhere near that capacity to fight against them, so we shifted to B2B where our cost of acquisition is much lower, and where strategically we are at a great influx point. These B2B clients will – and have – transitioned into becoming consumer clients as well, and that is how we’ll eventually transition into the B2C marketplace. This also allows us to learn from the market and the customers using our App. To date, we have 5,000 registered users and 15,000 unregistered users who anonymously browse our offerings. We find that this is a great place to learn and see what works and what doesn’t to make the product better and better.

Who are your key competitors and how are you different?

Indirect competitors for all travel management companies and agents are Expedia and Priceline, the gorillas of the online travel space. Our direct competitors are Lola.Com and Mezi.Com, both personal travel concierge services based on messaging platforms that connect users to travel agents. With HelloGbye, users talk to our AI, not an agent. Against Mezi in a head-to head test, it took the travel agent through Mezi 2 hours to put together a moderately complex itinerary, while it took HelloGbye, 14 seconds. Our patented technology houses so much data and access that we have far better efficiency and accuracy than a person can provide. When we launched, we were about 60% accurate in matching locations, destinations, and rates, but in just a few months, we’ve become 77% accurate. As we continue to grow and improve at this rapid pace, we plan to be more than 90% accurate in another few months, which is incredible for anything regarding Artificial Intelligence and natural language. We are also the first to automate and patent post-booking, change management, which allows a traveler to change or cancel existing flights, hotels, and reservations without speaking with the front desk. There is no middleware third wave company like HelloGbye, and we have the patents to prove it – and add value to the company.

How are you changing the landscape of your industry?

HelloGbye is changing the landscape in two ways. From the consumer perspective, we are making it far easier to plan moderately complex to very complex itineraries that include multi-stops and multi-trips. When it comes to business travel, it’s a multi-step process to book and organize everyone’s arrival and departure times. Most executives default to lengthy chain e-mails with their assistants and co-workers, which is as an extra step in their busy days. We change the industry by making it more convenient with the best prices and options. For both travel management companies and individuals, we are a Third Wave company that takes everyday tasks and rethinks how to make them more accessible, efficient, and enjoyable.

On the travel management side, our goal is to change the cost structures of major organizations like American Express that house thousands of agents to plan and book their client travel itineraries. HelloGbye is designed to understand the context and complexity of an itinerary. Using our platform, businesses like American Express, for example, can cut operational costs significantly by reducing 15,000 employees to 5,000 making themselves far more efficient and profitable. Our vision in several markets is to be invisible to the user in the sense that we also act as the middleware making travel planning smoother for travel management companies and agents alike. Middleware is when software acts as a bridge providing services to an operating system or app. Although our platform is designed with A.I., we also believe in having people on-call to satisfy the customer who feels more comfortable talking with a person, but from what we’ve gathered, most people rather not talk to people if they don’t have to. That’s where the ease and flexibility of HelloGbye comes in.

The global travel industry is a $1.7T business, the largest in the world, yet 65% of travel booking is still done through agents. It’s staggering that in this day in age of people watching TV on Netflix and engaging in mobile banking that travel is slow to catch up. We touch every aspect of the travel planning and booking experience with all the players already in our landscape and the customers as well. We hope to be embedded in every piece of the travel industry, every step of the way.

Who is your ideal investor? How much capital are you looking to raise?

Since I joined HelloGbye in 2014, we’ve raised $20M USD in funding from high net worth individuals and Family Offices. We would like to work with individuals that we could cultivate long-term relationships with rather than a one-time investor. As we grow, the profile of the ideal investor changes. Currently, we have been on the market for 3 months, so the ideal investor would be a Family Office or angel investor, whereas in 6-9 months, our ideal investor would be a larger entity like a VC or a private equity company. At our stage of the business, high net worth angel investors and Family Offices who are interested in investing early-stage in Artificial Intelligence companies, would be ideal. We’ve spent the past 4 years developing technology so we work best with investors who are willing to take risks on investing in an early stage company and see the potential for a 10x to 100x exit.

We are seeking to raise $10M USD with a pre-money valuation of $40M USD to further operationalize the business and expand our product offering. We are looking for minimum investments of $250K USD per investor and would love to have 5 investors come in at $2M USD each, each taking 5% equity.

What’s your mission?

To be recognized as the leading global travel company that makes planning and managing travel convenient, fast, easy to do anytime, anywhere, and for everyone. The vision is to be fully integrated into the supply chain of the travel industry to make it more convenient and easy to use.

What’s next for you?

In 2018, we will be adding travel management features like expense reporting and policy management to make it easier for companies with multiple employees to track their expenses, manage their travel, and seek reimbursements for their trips. We are preparing to launch on Android at the end of the summer, as well as speaking to key players like Amazon and Apple about integrating HelloGbye as skills into their voice assistants, lending to enhance their voice control capability. Within the coming year, we will be supporting over 25 languages and adding automatic notifications regarding flight changes and alternative options for the next flight or hotel accommodations right to your phone. In 2019, we will be doing destination content management, expanding on flight & hotel bookings to include tours, experiences, as well as on-demand stores. The HelloGbye on-demand store will allow you to order room service, book safari tickets, and buy sunscreen with the command of your voice, from the comfort of your app. The future value that we bring will never be further away than the palm of your hand.


Greg Apple

Greg Apple spearheads the launch strategy and customer experience for HelloGbye – an app that helps users book and plan travel itineraries in seconds. HelloGbye’s app recently launched on the AppStore and is now available for download. Greg’s keen understanding of management, negotiation, and marketing comes from several years of sales and marketing experience. Over his 17 year career, Apple has been a successful sales executive at some of the largest tech companies in the world, including Salesforce, SAS, and Google. His career has been focused on helping companies grow their business, solve problems through technology, and generate effective marketing campaigns. Greg lives in Toronto, is married and a father of 2 boys. In his personal time he enjoys snowboarding, playing guitar and racing on the track.

For more information, please reach out to Greg at greg@hellogbye.com.