• Smarking

High-Tech Products for Non-High Tech Industries


Our Esteemed Panelists


War stories from the hottest Silicon Valley start-ups and how teams of hard working engineers are making it happen.


A panel of world class engineering leaders gathered at Smarking in San Francisco last week, to share best practices about “Building High-Tech Products for Non-High-Tech Industries”, with over 80 software engineers attending the get together. We polished off at least 20 Goat Hill Pizzas, on top of some craft beers, and wine, and surprisingly didn’t make too much of a mess of our offices.


Smarking plans to make this the first in a series of discussions designed to engage, teach and learn about interesting topics in high-tech. So, please stay tuned!

You can watch the full recording here. It’s about 45 minutes long, but well worth listening to — and you can always fast-forward.


Panelists: The following executives led our panel:

Randy Shoup — VP of Engineering at WeWork Randy has been a senior engineering leader at Google, eBay, and Stitch Fix, among others. He is currently VP of Engineering at WeWork.

Ralph Gootee — CTO & Co-founder at PlanGrid Ralph is Co-founder and head of product at PlanGrid. Prior to that, he was a systems SW Engineer at Pixar, and a SW Architect at Sony.

Lee Edwards — Former CTO & VP of Engineering at Teespring Lee Edwards was until recently CTO & VP Engineering at Teespring, after having built software and robots at Pivotal Labs, iRobot, and a small startup he helped start that was acquired by Groupon. He’s now actively investing in startups, with the mission of supporting technical founders.

Chien-Liang Chou — VP of Engineering at Flexport Chien Liang is the VP of Engineering at Flexport. Prior to that. Chien-Liang was VP Technology at Lending Club, Head of Engineering at Stockpile, VP of Engineering at Loyal3, and many others.

Wayne Fenton — Wayne has led engineering teams at big companies, such as Oracle, eBay and Qualcomm, as well as startups, such as Latitude Communications (IPO), iSkoot (acquired), and Icontrol Networks (acquired).



I had the great honor to moderate the panel and hear some incredibly insightful thoughts on building great products, growing valuable companies, and developing software engineering powerhouses. Here’s my recollection of what was discussed. Remember…there was craft beer involved.


The underlying premise is that industries evolve over time and companies come-and-go as disruptions occur. However, some industries are more resistant to change based on factors such as labor intensity, amount of capital required, structure of incumbents, and barriers to entry, just to name a few. As technology changes occur, opportunities to enter legacy markets can open up a disproportionately large market value. So, in last week’s panel discussion, we heard from technology leaders from companies that are attacking laggard markets to learn how they are doing it. What challenges are involved? How they are not only addressing those challenges, but also thriving.


The speakers all had similar founder’s stories with themes of how they were able to penetrate large, historically low-technology, industries. Each of their startups had targeted enormous markets (parking, commercial real estate, construction management, apparel, and global shipping). Most of the speakers found it difficult to break into calcified industries with a large global presence, with most of the legacy providers and their customers not familiar with technology or how to incorporate it in their daily workflow.


As a result, each of our startups was forced to identify structural gaps, supply chain inefficiencies, or excessive fragmentation in these markets in order to transform the way business is done. Further, timing was found to be essential. These companies were able to take advantage of technological shifts or advancements that “opened the door” to entering these markets and providing significant value.



Entering a large, global industry as a startup does not come without many challenges along the way. Like all start-ups, but especially with tech-adverse types of industries, customer satisfaction is essential to solidify a company as a legitimate player in the market.


Ralph had a great story about trying to remotely debug a SW problem on an iPad, with a customer who was out in the woods, and didn’t even know what Google, or the Internet, was. Beyond just customer satisfaction, as a first mover in these markets there is no technological pattern to draw from. In many cases there is no clear roadmap for moving forward in these industries, and as a result the companies must forge their own path.

Chien-Liang had a good story about putting four people on a plane to Hong Kong to figure out how to build an airplane freight management system. Lee also made a great observation about scaling, which is “management debt is at least as big a challenge to growth as technical debt”.



WeWork has a good angle here. Randy described their model as “Space as a service” (I’m sure that will go in the Gartner deck). Just the way Amazon purchases servers and rents them out, WeWork purchases long term leases to spaces, divides them up, and rents them out to people.


We discussed how our companies made money in these markets, and what adjustments we had to make to reflect market dynamics. SaaS is a popular model used to improve scale and keep costs down.



We finished up by discussing open opportunities. Common theme: these companies are rocket ships. If you’re interested in a wild ride, check ’em out!


o Smarking o WeWork o PlanGrid o FlexPort o TeeSpring / Lever / Daisie / Skydio


Finally, I’d like to thank the folks at DevJobs for helping organize/host the event, all the engineers that attended, the esteemed panelists that led our discussion, and finally, my co-workers here at Smarking for helping set up. This was a great discussion, with a lot of insights, and great perspectives. The Q&A was interesting as well, so please watch the video to see a lot more details.


Stay tuned for our next event highlighting more interesting topics and technology leaders.


PS: We have fun here



About Smarking

Smarking is a fast growing tech company that solves the notorious parking problem via a unique angle. By providing the leading business intelligence and yield management enterprise SaaS solution to the parking industry, Smarking is rapidly elevating how parking businesses are operated cross the North America. Here’s a 2min video if you'd like to learn more. In the long term, Smarking aims to empower highly connected, autonomous, and efficient urban mobility with fully digitized parking inventory.

Backed by a group of top tier VC firms/investors including Y Combinator, Khosla Ventures, and Slow Ventures, Smarking is growing furiously.


Smarking is looking for some of the best engineers in the world to solve the last piece of puzzle in the urban mobility landscape, together with a group of MIT data scientists, transportation experts, and seasoned business professionals. Smarking’s growth is stunning, culture is amazing, and benefits are insane. If you know engineers that are open to new opportunities, we have a $10,000 referral reward. Additional details here: https://www.smarking.com/careers




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