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All HAIL: The Power of Improved Payment Systems with Dan Anderson

Driven by a love of great food and a background in computer engineering, Dan Anderson founded HAIL in 2014, a company that focused on the payment component of dining out. Dan made the move from Southern California to New York City in early 2015, when HAIL was acquired by Reserve. And while the extremes of New York weather — bitterly cold winters and swelteringly hot summers — are enough to daunt any new transplant, Dan couldn’t be happier to be living and working in The Big Apple.

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Dan Anderson, HAIL Founder & Reserve’s Director of Payment Systems

When he’s not checking goals off his 30 Before 30 list of challenges, he’s dealing with complex problems as Reserve’s Director of Payment Systems. Dan sat down with us recently to talk about how social media helped him land a job at Reserve, the future of tech and restaurants, and why dining at momofuku ko was an experience he’ll never forget.

What problem did you identify that you were trying to solve with HAIL?

When you’re out to lunch or dinner you want to be able to get up and walk out without having to wait for the check. Often, when you need the server the most they are nowhere to be found. It’s difficult and cumbersome to split the check, and we wanted to help people seamlessly and automatically. The way we go about paying right now is very antiquated — back and forth between you and the server in a day and age where everyone has a mobile device. It’s easier to get a boarding pass for an airplane than it is to pay for a restaurant check.

How did you decide that joining Reserve was the right move?

It started on Twitter. I saw a tweet about Reserve and tweeted back about wishing that you could split the check. I reached out to [Reserve co-founder] Joe Marchese on LinkedIn because I saw he was in LA. We literally met the next day in West Hollywood. We chatted and realized we had a lot of similar thoughts around the payment component of Reserve and HAIL, specifically check splitting. We saw eye to eye on a lot of technical things and shared the same views on the future of where  the industry would go in terms of payment. I went to NYC a few weeks later in January and met with Greg [Hong, Reserve’s CEO and other co-founder]. I saw the caliber of the executive team after meeting with them and knew that this was the future of dining. Reserve is also not just focused on the payment component but on improving the entire experience from end to end. So HAIL was a natural fit.

How would you compare your experience in the corporate world to the startup world?

Prior to starting HAIL, I had previously worked in consulting, as well as worked my way up the corporate ladder. I had seen quite a bit in the corporate world: the sea of cubicles, people going through the motions and the seemingly endless red tape. While this approach is okay for some, I knew there was a better way.

For example, the majority of time spent to get a project completed in a large corporation often times isn’t allocated to getting the actual solution working but spent working through the red tape and “getting everyone aligned.” When a company has more people saying why something won’t work than people putting forward solutions, it’s in a tough spot. This negative culture can persist for years because the company is profitable, but slowly this behavior will eat away at the bottom line as the company’s competitors are able to better serve their customers with superior and more efficient solutions.

I love the startup world. It’s one thing to say you’re results driven, it’s another to be results driven.  At Reserve specifically, we have a vision, and we’re executing on it. Everyone is firing on all cylinders, and it is amazing to be a part of. 

In your time at Reserve, why have you focused getting more data-driven insights?

I started out as Director of Payment Systems, but I saw an opportunity to expand our business intel and analytics so we can make data driven decisions in everything we do — from the operations and marketing campaigns all the way to strategic product decisions. For example, on the consumer side, we can predict for certain restaurants the minimal advance notice you need to give them to increase your chances of getting in based on previous acceptance rates. While my background is computer engineering, Business Intel/Analytics is the perfect fit for me because it’s an intersection of business and technology which is aligned with my areas of interest as well as my professional experience.

Given that so many mobile apps are emerging in the hospitality space, how do you see the future of tech and restaurants?

These are the top 5 things that I think diners will consider weird in 5 years:

  • Reaching for your credit card at the end of a meal

  • Calling to make a reservation

  • Searching through endless online reviews to try and find a place you might like

  • Check-splitting drama

  • Waiting around for the check

 
Tech can help all of the above problems. It’s inevitable that tech and restaurants will continue to merge. Restaurants are in the hospitality industry, and they want to provide the best experience possible. Consumers want to receive the best experience possible. Any solution which can benefit both parties in the experience, without cutting into a restaurant’s already low margins, will be best positioned to lead this space.

You recently moved from Southern California to New York. How are you finding the city?

It never made sense to me that I could live in a nice big apartment a block from the beach in Santa Monica with near perfect weather for less than what it costs to have a one bedroom apartment in the City.  Then I actually moved here, and I still didn’t “get it” while I was walking to work in terrible weather. Now, I finally get it: the culture. The restaurants, the entertainment, the people — I understand why people become so enamored with NYC. It has been an amazing experience so far, and I look forward to continuing my journey here.

What’s the best dining experience you’ve had lately?

It was momofuku ko, hands down. It’s expensive, but it’s one of those things you need to try at least once in your life. It’s a 17-course tasting menu with the option of drink pairings. Every step of the experience is so well thought out.

The Reserve Editorial Team

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