12 Qs with Justin Levine, Co-Founder & CEO at Shepherd

5 min read
September 09, 2021

12 Questions with Justin Levine

Welcome to 12 Questions, a Q&A series where we pose the same set of 12 questions to intriguing folks at the intersection of insurance, risk management, commercial real estate, and digital innovation. 

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This week, we chat with Justin Levine, Co-founder and CEO at Shepherd.

1. What is the most interesting idea you’ve encountered in your world lately?

I’m personally most excited by the next wave of innovation for financial services that’s about to really start impacting construction. In particular, I’m impressed by the product and team at Siteline – who are tackling the subcontractor payments space with a really elegant new product. Payments are business critical for every contractor in commercial construction, and today’s processes are highly inefficient. The reality is billing and payments in construction haven't really improved since Textura came on the scene 20 years ago. The time is now. Gloria Lin is a fantastic leader and I’m excited to watch them grow.

2. Where do you think no one is looking right now?

I don’t think construction tech (i.e. SaaS) companies are as focused on loss outcomes as they can or should be. For years, the number one value prop for selling construction SaaS has been efficiency: creating time savings by digitizing existing workflows. PlanGrid, BuildingConnected, and Procore nailed this. But there’s only so much margin you can unlock for contractors if focused solely on efficiency, and we’re starting to hit the ceiling of point-solution saturation in construction. I believe tech companies need to shift their focus to improve the function of risk management – less injuries, mistakes/defects, and higher predictability during the course of construction.

3. If you had a magic wand, what would you change about your industry?

The availability of clean, usable loss data. One of the issues that makes innovation difficult in the insurance space, regardless of vertical, is that it’s difficult to access information about historical losses in order to study them, learn from their patterns, and apply them to new technology.

4. What’s the most rewarding part of what you do?

The best thing we’re building at Shepherd is the people, our team, as cliche as that sounds. Our mission is simple – make construction safe and more financially sustainable for the long term. As we get started, we’re attracting a unique blend of talent – the best engineers in Silicon Valley (former Google, Airbnb, Fanatics) alongside underwriters who have built their careers in the construction industry, but know that technology in underwriting is the future. Seeing this team coming together is the more rewarding part of what I do.

5. What do you envision the next 12 months will bring?

Almost everyone we talk to within the construction industry has been more busy than ever this summer. More jobs have come back online post-COVID shutdowns, and given the progress of the recent infrastructure bill in Congress, I envision the next 12 months will be quite hectic for construction as a whole. For us as a business, we plan on coming to market with our first insurance products within the next 12 months – and I think some of the things we’re doing are going to turn heads and get a lot of folks excited.

6. What’s your favorite building?

The first wrap-up (CCIP) insurance deal I ever worked on at Hunter Roberts was the VIA 57 West project on the upper west side of Manhattan. I was just learning the ropes of risk management (my background is Civil Engineering), so there is a nostalgia and degree of self-actualization anytime I see this building in real life. The structure itself is an amazing architectural feat, the exterior is high complex, and the interior even contains its own green space/park.

7. Please dispel a myth or misconception about your work.

That the construction industry doesn’t use technology or is always highly resistant to adopting new tools. People confuse the challenge of building technology for construction (yes, it’s hard) with the misconception that it’s the industry itself that is the problem. I think most contractors are open to new solutions if you can showcase value clearly and immediately. It’s important to understand the audience you’re selling into as a tech company – contractors are buyers who operate on razor thin margins to begin with, so if your new tool doesn’t provide clear, unique, value (increased revenue or decreased expenses) it’s likely going to be a hard sell.

8. What are the tools, apps, or gadgets that you just can’t live without?

For work – we are heavy users of Slack for all internal communication. I almost never send an internal email to anyone on my team. For fun – I wear the WHOOP strap/band for fitness and sleep tracking. They have an incredible mobile app, and I rely on it daily!

9. What’s your biggest pleasant surprise related to remote work?

I’ve done remote work for several years, but always with the option to come into an office. After a year of COVID, I actually was craving more in-person connection more than anything. I prefer a balance of office and home, rather than all-in on one or the other. That said, I do love that remote work has normalized across all industries and demographics – I’ve done video calls with people in the last year that I would have never expected. It’s fun to see people’s faces, read their reactions/body language, and share a deeper connection than just a phone call.

10. What’s your favorite productivity tip for staying motivated and getting work done?

“Lo-Fi Beats” playlist on Spotify is my perfect work music and is consistently on in the background of our office. In addition, I try to do at least one “no-meeting day” per week. I’m not always successful, but I've found it helpful to get longer stretches of heads-down focus work done.

11. What or who do you read/watch to keep informed?

12. Please nominate folks who should answer this next.

  • Andrew Wynn – Co-founder and Co-CEO at Ascend (premium financing startup)
    Andrew is a serial entrepreneur who sold his last startup to Hippo. He is a founder that knows the problem space he’s tackling intimately and is building an incredibly talented team.
  • Chad Nitschke – Interim President at Vouch Specialty (business insurance for startups)
    Chad was the former founder and CEO of Bunker and is now in an interim leadership role with Vouch. Chad is one of the most knowledgeable people in insurtech, serving as an advisor to several startups (including ours!).

Thank you to Gary Kaplan, President of Construction at AXA XL, for nominating Justin for 12 Questions.

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