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Five Burning Questions: Matt Caulfield, Founder & CEO at Boston-Startup, Oort

Matt Caulfield is the founder and CEO of Oort, an early-stage identity security startup. Prior to founding Oort, Matt was at Cisco for a decade where he led the Boston Innovation Team, working with some of the organization's largest clients on innovation projects across cloud networking and security technologies.

Matt considers himself to be an engineer turned entrepreneur. His educational background included studying Distributed Systems and Networking at Cornell.

I read that you run a ‘sanity check’ on Oort’s vision and culture. Can you share what the vision is and whether that’s changed from 12 months ago?

I usually run a sanity check every Sunday where I sit down and ask myself “are we on the right track both in terms of vision, culture and strategy.” It’s a really important part of my week.

This helps me to form my week ahead and prioritize meetings depending on what needs addressing first.

As for the vision, the long-term vision hasn’t changed – I left Cisco to start Oort and build the Oort Cloud, the idea is to deliver a be-all-end-all cyber security platform. How we get there and the strategy to accomplish that has definitely evolved over the past year.

12 months ago we hired our current CTO, Didi Dotan, whose background is identity, that’s his focus now. We truly believe that the future of security is identity-centric and so that has become ingrained into this phase of the company as we march towards that longer term vision.

But, of course, the 3 and 5 year vision has evolved to make sure we are sticking to the longer term vision.

If you didn't evolve during times when it was necessary, do you think the company would be as far along as what it is today?

No, I think one of my strengths is being flexible in my thinking and staying true to that long term vision but being flexible and curious and willing to try different paths to get there.

Why has Boston always been such a hotbed, not just for security innovation but for successful tech start-ups in general?

I think Boston's always been a unique ecosystem.

I'm not a Boston native, I grew up in New York and New Jersey. However, I think the size of Boston is just right; it's not too big, not too small, and obviously the academic ecosystem. Higher education definitely contributes to the influx of new ideas and new people all the time to keep it fresh. That's really important when you're trying to build a vibrant tech or start-up innovation engine.

You are forced to go on Shark Tank for an invention that isn’t Oort… what do you pitch?

It’s a funny question. I think, for me, I am always writing a list of ideas. It's really difficult for me to focus on one project for as long as I focused on Oort because I'm always coming up with something new. Fortunately, Oort has been so exciting that it's held my attention for the number of years I've been working on it.

A pain point that I'm trying to solve lately is how we amplify our social media presence.

So you put out a post and either through automation or just through messaging, everybody in the company can pile on to that post and amplify it. That's something that we do over slack today but you can imagine automating something like that. And for a big company like Cisco you could enlist the entire 60 – 70 thousand person workforce to help you amplify your message on social media in a way that's automated, that would be pretty powerful.

Pick a funding source to marry forever - which one? Bootstrapping, crowdsourcing, kickstarting, go-fund-me, friends, family, VCs, Angels…

That's a hard one but if I could pick with no constraints it would be bootstrapping, but in order for that to be real you need significant personal means and it depends on the business and network.

When I started Oort I didn't have either of those things and so bootstrapping wasn't really an option. I needed to go work with VC's and it's been beneficial, it's helped me to expand my network. They've been partners in building the company so I'm happy.

It’s going to depend if you need to go really big, really fast. If you do, then taking VC money makes a lot of sense. If that’s not the case, I think bootstrapping is definitely beneficial.

I think the difference is really how fast do you want to grow? Bootstrapping has some limitations around the speed with which you ramp and so there's certain businesses that lend themselves really well to that. And there are some that are more primed for the VC model.

How did COVID challenge you as a Founder, and what has it taught you to prepare for going forward?

What this did was solidify our ability to be a remote-first company from the start without having the pain of being in an office and then having to become remote once we’d built an office culture. We were remote from the beginning and I think that was a huge advantage as we were able to build the team based on that environment.

On the flip side, it meant going into Boston a few days a week and having coffee and lunch with prospective employees, customers and investors was kind of impossible for a long time. It’s only now that we're finally getting close to any sort of level of normal face-to-face interactions.

I'm lucky that I had some time before COVID started to bootstrap my network a bit, otherwise that would have been pretty disastrous. Trying to leave and do all my networking virtually in the middle of COVID.

Now where we are today, I think it's going to result in a much healthier attitude towards remote work, which is good.

I've noticed in terms of investors; you’ll go and have initial meetings remotely to get to know each other and then maybe for a second or third meeting you can meet up in person. So, it's a lot more efficient. Same thing goes with customers.

We don't have salespeople flying all over the country to meet with customers in person, and eventually that might return because there's a competitive advantage to it but at least for now we can run entire engagements purely over video tools like Zoom, and that’s definitely a plus in terms of efficiency although it does take some things away.

Last week I was at the RSA Conference in San Francisco and it was just very different being back together in person and beneficial in a lot of ways. But in other ways still wildly inefficient compared to scheduling your day back-to-back with Zoom meetings and meeting with people efficiently and virtually. So I'm happy with where we are now, I think we've got the right mix of virtual and in-person and I think we're going to come out the other side of this whole thing in a better place than we went into it.

Have you still got employees in the business that you've yet to meet?

In person, yes. We're kind of funny as an 18-person company as we have people across three continents, so we have a team of engineers in Israel, a team of engineers in South America, mostly in Uruguay. And then we have a few more engineers here in the US as well as our go to market functions like marketing and sales in the US. I've never met anybody in person from our South America team or from our Israel team, but we're hoping to change that once we close our Series A and can get the whole team together, at least for a few days.

We’re thinking we’ll get everybody together for a few days and work side by side for a little bit and just have a chance to build more of those relationships in person because that will pay dividends down the road when people need to interact remotely.

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