Q&A with Kelly Smith, startup founder and ex-Starbucks VP leading digital transformation at car company Hagerty

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Haggerty’s Chief Digital Officer Kelly Smith. (Photo courtesy of Smith)

Kelly Smith Knows a thing or two about digital transformation.

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Before Phrases fully entered the business world, Smith was at Starbucks, where he helped lead the expansion of its digital and mobile apps, from 2014 to 2017. He then took on a similar role at MGM Resorts, using software and data to improve guest experiences at MGM. Location.

Smith – who founded several Seattle startups earlier in his career – is now chief digital officer and chief information officer hagerty, a classic car insurer who just went public The company is valued at over $3 billion in a SPAC deal.

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“I’m really having fun. The cars make it really fun,” Smith said in a recent interview with GeekWire ,See Her Wicked Porsche Collection,

Established in 1984, Hagerty is known for providing insurance for classic vehicles. this is Ride the growth in the classic car market, In a special way amid the pandemic,

(Haggerty photo)
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But the Traverse City, Mich., company plans to grow into something more — with digital at the core of that vision, and Smith is leading the way.

The longtime tech exec and entrepreneur brings a unique perspective as someone who has lived through hyper growth in both nascent startups and decades-old corporations. He previously founded Seattle startups such as RocketVox (sold to The Platform), ImageKind (sold to CafePress) and Zapd (sold to RealSelf).

We spoke with Smith about his role at the company’s SPAC, what digital transformation means, tech trends, remote work, Seattle, and his memorable moments with Elon Musk during an interview for a role at Tesla. The conversation was edited for brevity and clarity.

GeekWire: Kelly, nice to meet you again. We miss you in Seattle. where are you these days?

Kelly Smith: We are living in Idaho but I am traveling to Traverse City once every three to four weeks. Haggerty’s transition to the remote just got a lot better. We were extremely fortunate as our leadership team was really supportive and enthusiastic about adopting best-of-breed equipment for our employees. We made cutovers for Zoom and Slack before the pandemic. And now I think we’ve proven that remote working is a business advantage for us — so much so that we’ve actually redesigned most of our office space to accommodate the remote work model.

Geekwire: Haggerty gigs should be fun. I guess you love cars more than coffee (Starbucks) and casinos (MGM).

Smith: I’m really enjoying it. The cars make it really fun. These old classic cars, they can be money pits. I’m in the middle of two restorations right now. It doesn’t make any sense. But for those who love these cars, it means nothing. Having people around you who enjoy hobbies and are willing to be somewhat irrational in order to create some joy in life is a blast.

Kelly Smith’s wife and daughter, Dasha and Varvara, with a 1994 Porsche with the M030 option – 1 in 99 in North America.

GeekWire: Talk a little bit about Haggerty and your role there.

Smith: Hagerty is probably the largest and best-known insurer of classic and collectible car brands. But we sell a lot of insurance without even talking about insurance. We are one of the largest holders of classic car valuation data. We are one of the largest salary membership programs for automotive enthusiasts. We are one of the largest producers of automotive enthusiast media. We are developing physical spaces that are a combination of storage and entertainment spaces. We have many popular automotive events. And we’re working on a number of new innovations that fuel the automotive hobby, such as a new way to buy and sell cars. We have a lot of platforms that haven’t launched yet.

GeekWire: How is Haggerty using technology and digital to expand, and what is your role in driving it forward?

Smith: It’s fun to go backwards, to unpack it. I moved from the world of entrepreneurial Seattle to a more traditional corporate role at Starbucks. I was curious and interested in how these traditional companies would move forward in the age of technology and whether I could add value to that scale. Then I came to MGM, where I was chief digital officer and was doing a similar role. And then finally, here for Haggerty.

The “why” for me personally has turned into my own fascination and interest in digital transformation stories, even among traditional non-tech companies. It began to become more apparent how someone like me could add value to this type of environment. It’s incredibly challenging, and it’s really interesting work.

As a key gap between my time in Seattle and the chapter in my life now, I see that the cultural divide is so much more significant that almost everyone, including my former peers, could have imagined, in every little way.

How many times have you heard people in Seattle talk about “IT” or use the acronym? not much. And yet, outside of that reality, that’s the phrase people use to talk about technology at traditional companies.

For the rest of the world coming to the tech space, especially those in and around Seattle and California, they don’t really know the real challenges and issues within traditional companies.

Kelly Smith inside Starbucks’ office in Shanghai in 2015. Smith helped lead the digital efforts for Starbucks China. (Geekwire file photo/Taylor Soper)

And what many people don’t realize is that only 30% of digital transformations are successful. So the “why” to me is very curious. Because if everyone is getting the same newspaper in the morning, if everyone is reading the same internet, why do we have stories like Kmart or Sears or Macy’s or even Blockbusters? Interesting question. If we are all getting the same newsletter, why are only 30% of digital transformation successful?

And so it’s that question and because of the results that I find incredibly interesting on the one hand, and incredibly fulfilling from a professional standpoint because you can drive a really meaningful, full impact.

GeekWire: Talk more about “digital transformation” and how you think of that phrase.

BlacksmithDigital transformation is not a topic of discussion that consulting firms have made to sell more services. It’s a real thing with very real challenges.

To maintain business performance and relevance and cost control, you must have the ability to produce innovative products that meet the needs of customers whose expectations are now increasing. They have Airbnb experience, or Netflix experience, or experience with Amazon. Their expectations are rising and this extends to other areas to the extent that how the customer makes purchase decisions. This will have an impact on your profitability and your customer acquisition.

Now, basically, the issue is that businesses generally don’t know how to go about creating a new kind of innovation culture within their traditional culture. And this is usually because they are not aware of the importance of a framework to do it.

What do we mean by structure? Below Board, Does the Enterprise Have a Declared Digital North Star? Or are they throwing money at different initiatives hoping for something good?

Is there support at the CEO level and below to help drive the culture change so that it sticks to senior management all the way through middle management, so as not to sabotage the effort?

For the past 30 years, a business may have operated in such a way that the VP of Sales pioneered the product roadmap. And now all of a sudden, it’s a completely different conversation where there’s this new discipline called product management that realizes how products are realized and it has a different approach to getting them to market. Product management isn’t even a thing at many companies, including my former employer, MGM.

So it’s about bringing in new kinds of people, teaching new subjects, new perspectives, and rethinking everything you used to consider traditional. It is creating a more collaborative, empowered culture that allows innovation to flourish. difficult to do.

GeekWire: What’s an example of technology you’re helping to implement at Haggerty?

Smith: In our case, many people do business with us – adding a car, removing a car, starting a new policy, canceling a policy – over the phone. That’s why we have hundreds of call center agents. As it stands now, we don’t even have a mobile app where you can get your insurance ID card. So we’re trying to pour concrete to get into a table stake situation and then we’re trying to get to the next level where we’re using innovation to drive business value.

And that clearly means a lot of different things. A lot of this means going backward and modernizing legacy technology that’s keeping the company from delivering on those table stakes.

(Haggerty photo)

We’ve certainly shifted from a feature team where you’re basically producing what comes to order in the back kitchen, to a team where most of the innovation is becoming more cross-functional, and you have the strategy to drive There are more people helping and product offerings.

We are building the system. This includes everything the Airbnbs of the world take for granted. We are building basic systems that may have been considered elsewhere.

The reason most of these digital transformation efforts fail is because there is no blueprint. Without a framework or blueprint, you may not get the results you were hoping for. So now what we are trying to do is create a blueprint where we quantify the results. We are investing in digital transformation for five reasons:

number 1. Drive new…

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