From Kosovo to Sand Hill Road: A discussion with Skyward CEO Jonathan Evans

This interview is with Jonathan Evans of Skyward which simplifies drone logistics, operations and compliance. Full disclosure: DroneSeed is a customer of Skyward. In February 2017, Skyward was acquired by Verizon.

The Drone Series explores the drone industry via discussions with CEOs of leading companies, giving investors and industry analysts the opportunity to hear directly from emerging technology leaders. The series is lead by CEO Grant Canary of DroneSeed which is a drone company positioning to automate and dominate the forestry services vertical.

GRANT CANARY, CEO DRONESEED: I’m going to tout your resume a little bit here. You started out in the Army flying medical evacuation helicopters in places like Kosovo and flying top brass of the Pentagon around in DC. You’ve also served as a medevac pilot in civilian life, and even spent a few years doing a job in Alaska before founding Skyward about three years ago in Oregon. Let me just ask you: what are your two biggest wins professionally?

JONATHAN EVANS, CEO, SKYWARD: Well. I can probably choose any number of the actual missions that I’ve flown as a military or civilian medevac pilot because I think the things I’m most honored to have been part of in my career are probably some of those missions. Probably a little too melodramatic for the purposes of this interview to actually share any of those as “big wins,” though.

On the business side of things, it’s been a wonderful process and I’ve enjoyed every step of it. One culminating experience was being able to go down to Sand Hill Road to Voyager Capital and give a real pitch in the Valley.

It was four meetings from the first cup of coffee to an audience of all the partners. That led to our first institutional round and backing by the sophisticated investors we now have. It was really amazing to connect Skyward with this kind of network and see the company instantly become more sophisticated. It wasn’t even the first round that was the most difficult; our subsequent trips to Sand Hill were much harder.

GRANT: Other drone entrepreneurs are probably very interested in what the experience is like on Sand Hill. What differed from your expectations?

JONATHAN: Fundamentally, it’s a really challenging thing to do. It’s very, very hard but it’s the kind of hard work that tempers you and makes you stronger. I think that there are plenty of clichés about the expectations and the number of “no’s” you have to hear. To really walk that road is to internalize and learn from negative feedback coming from a large cadre of really intelligent people, rather than just saying defensively to yourself, “they don’t get it.” That feedback is powerful, and it can really strengthen your business. It can also be really, really hard and a little demoralizing- there’s no denying that. I had to learn a deep patience for being told ‘no’ over multiple trips. It’s a marathon not a sprint. Realize that this is a process and that there isn’t some sort of TV moment where you get in front of the right shark tank. It’s never like that. Every single one of the paths that you open is going to be a process. It’s like anything else that I’ve done in my life that has been about adversity, from Army basic training forward. If you sign up for it and you really dive into it, it makes you better.

GRANT: That’s awesome. What is Skyward insanely good at and what do you think tipped your investors over to being like “Yes, let’s do this”?

JONATHAN: We’re insanely good at by far the least interesting, least sexy part of the drone ecosystem, which is operations management and compliance with regulations and insurance policies. Global airspace regulatory systems today provide a set of rules that make the air space accessible to a whole new generation of aviators. We’re giving those new commercial drone operators the set of tools they need to access the infrastructure of the air space. We’re really, really good at providing the foundational pieces of joining that infrastructure. We’re an operations management platform, a system of record integrated with a drone airspace map that lets you manage who’s flying what machines, where and when. It’s not just nifty technology. It’s actually business operations. That’s what we’re insanely good at.

GRANT: What I love about what you guys are doing is that you take the part that’s not fun, and you remove that, and make it easy. It takes some of the drudgery out of commercial applications, too. Let’s shift topic just a little bit, still talking about drones but shifting more to the industry side. How game-changing, or not, is drone technology?

JONATHAN: I like to think about what we call ‘drones’ as an emerging network of aerial robots. Picture the personal computer leading to the revolution of the Internet. The net ultimately arrives to our pockets via smartphones, and reaches a confluence with the original technological revolution of aviation, itself. That’s the aerial robotics network we’re arriving to. You could see it as a ‘flying internet’ that can do two major things; collect ‘bits’ or information, or move ‘atoms’ or things across physical space, in real-time, on demand, and programmatically. Or you could look at it as aviation becoming digital; the technological history that started with the Wright brothers and arrives at us being able to move across the globe in pressurized jets is now becoming digital, programmatic, finer grained, and much more on-demand. So the ‘drones’- the aerial robots- are at a sort of tip of this new more diverse league of aviation. They become real-world apps, if you will, physically manifest: bridge inspections, changing light bulbs on interstates, or maybe shooting tree seeds into the ground with great precision.

GRANT: I like where you’re taking that, so let me push this further: So thinking about how manned, commercial aviation has changed things, connecting continents and their previously-separated residents… How might drones similarly connect people or infrastructure? I think a lot of people don’t quite see the big picture, don’t share our excitement or think ‘drones are a fad’.

JONATHAN: We’re starting to understand what is possible when you optimize the connections that compose our civilization today. We started getting a glimpse of this with Uber and AirBnB. People use Uber now in situations when they would never have used a taxi. The ease of technology created the market. When you reorient the sort of nodes and resources that are important to each other- when you optimize civilization- It’s amazing how much that can unlock. One angle is that Jeff Bezos says 86% of Amazon’s shipments are below five pounds. Drones today can easily move five pounds within a 30-minute radius. The technology exists.

We need to mature the eco-system to that tipping point where users can expect immediate fulfillment of requests from a robotic system that moves physical things programmatically in space. The drone is the perfect conduit- it’s the airborne robot that can move rather ubiquitously in space and carry sensors or payloads anywhere it’s requested.

GRANT: What use applications are you most excited about?

JONATHAN: Aerial people-movers are a no-brainer for me. I’m excited for the Jetsons’ future we’ve all already imagined because I come from a helicopter background. Cross that helicopter I flew for so long with my crude human hands and reflexes, cross it with robotic, automated, programmatic aviation systems and a touch of what Uber’s shown us about truly on-demand systems. Now you can ask, “Bring me an air pod that moves me from A to B frictionlessly… I will happily pay the instant market price for that, Sir!

GRANT: Let me ask you: DroneSeed is a customer of Skyward and super happy with the service. You guys provide software that helps clients with FAA compliance, Section 333’s, and all that, but the regulatory system is constantly evolving around the world, and drone operations are always evolving, right?. What can you tell us about what’s next?

JONATHAN: We’re going to continue to listen to our customers who are flying very real commercial drone operations today… this isn’t a ‘future’ set of problems we’re solving. There’s a very real base of ROI-driven operations taking place out there today that we’re addressing. We’ll continue to refine the tools that they need to do that easier and more robustly. You can look for some excellent new features to the Skyward platform coming very soon in: air space intelligence; flight ops management; better workflows and organizational processes for business ops through the aviation lens. In the next quarter or two, you will also see more integrations with Skyward across many of the platforms emerging to support the commercial drone industry today; from drone ground control station software to the data-processing platforms serving up what’s valuable to the customers that need services from drones. We strongly believe in enabling the ecosystem and see ourselves of providing a scaffold of aviation infrastructure upon which this industry can grow.

Have a question you want to ask, send it to

See other interviews in the series here:
The Democratization of Flight by Drones
Drones and Simplifying the Future

One clap, two clap, three clap, forty?

By clapping more or less, you can signal to us which stories really stand out.