About Ben
Ben Cipperley spent 26 years in the Navy. The first 18 he served as an Explosive Ordnance Disposal office, with three tours across the Indo-Pacific, three years between Iraq and Afghanistan, and command in Guam. Which is to say, he has more experience than most.
What makes his background unusual isn’t the operational experience; plenty of veterans make the transition. It’s the Pentagon chapter that came after. A fellowship at the Stimson Center led to a resource sponsor role writing the Navy’s budget, which led to being pulled onto the team drafting the 2022 National Defense Strategy (mid-process, while Russian forces were marshaling in Belarus). Which led to working under the CNO on what became the Navy’s first force design document in 50 years. It’s a classified vision for the fleet in 2045 that, he notes, had quite a few robots in it.
He put an “Open to Work” banner on LinkedIn when he retired. The CEO of Havoc called him 20 minutes later.
About HavocAI
HavocAI is a collaborative autonomy software company. The pitch is deceptively simple: one operator, thousands of autonomous systems. The technology is the connective tissue, the software layer that lets a surface drone, an aerial drone, and a ground vehicle share a common operational picture and respond to commands from a single interface, rather than requiring separate operators, separate control systems, and separate data pipes for each platform.
The company was born from a conference convened by then-Undersecretary of Defense Heidi Shyu around the concept of “Hellscape,” IndoPaCom’s deterrence concept for a Taiwan scenario involving massive swarms of autonomous systems. The question in the room wasn’t whether the platforms existed. It was: how do you make thousands of them work together when a human brain can only track so many things at once? Founders Paul Lwin and Joe Turner quit their jobs the next day and started building the answer.
Early validation came through Silent Swarm, an exercise run by Naval Surface Warfare Center Crane. Havoc showed up with 12 prototypes of their Rampage platform. Representatives from NIWC Atlantic watched, then bought the prototypes on the spot. Those units shipped to Portugal to support Task Force 66. That’s the loop Havoc is now trying to close, and why they recently acquired Mavrik (air) and Teleo (ground) to make good on the multi-domain part of the pitch.
The business model is worth understanding clearly. The government is bad at buying software. It tends to need software wrapped in a hardware container before it can conceptually acquire it. Havoc has internalized this and partnered with eight different maritime platform builders, plus air and ground hardware partners, so that their autonomy stack arrives pre-integrated with best-of-breed hardware. They’re not trying to be the OS layer that makes everyone else’s platforms work together. But they’ll sell you the hardware too, because that’s how you get the check.
The Lessons
1. The problem the government actually has isn’t the problem it says it has.
Ben draws a sharp distinction between what defense procurement documents say and what operators actually need. There are no formal capability development documents specifying what a medium unmanned surface vessel needs to do. The requirements that exist are top-level (e.g., speed, payload, endurance) without a mission profile to lay them against. This creates a strange situation: companies are trying to satisfy requirements that aren’t fully written yet, for operators who know what they want but can’t always articulate it in the language acquisition needs.
Havoc’s origin story reflects a clearer version of this: the problem wasn’t the robot. It was the software to make robots work together. Nobody had written that as a requirement. A senior leader named it in a room, two founders heard it, and they went and built it.
2. “Works” is the word doing a lot of heavy lifting.
I am always curious about what people mean when they say “the product works.” I pushed Ben on this at length. His response was that “works” doesn’t mean end-to-end, zero failures. It means you’ve demonstrated a high enough Technology Readiness Level that the government believes you’ve solved a piece of their problem and are worth investing in further.
But there’s a harder version of this. Noah describes watching companies show up to exercises, fail three times, succeed on the fourth attempt, and walk away saying “see, it works” — while the warfighter in the room is mentally writing them off. Ben’s answer: if it doesn’t work, it goes in a Conex box and you never see it again. The military’s decision calculus is binary in a way that startups often underestimate. One bad demo doesn’t just cost you that contract. It costs you credibility with that community for years.
His rule of thumb for whether to attend a government test event: if you can’t define what your success state looks like before you arrive, don’t go. If the government hasn’t clearly outlined the operational problem, and you can’t articulate how your technology solves at least part of it, you need more turns before you’re ready to demonstrate.
3. Scale is the argument, not capability.
The case for autonomy isn’t that autonomous systems are better than destroyers at every task. It’s that you can lose 10% of a drone fleet in a day and replenish it in weeks. You can deploy hundreds of systems fast, replace them fast, and iterate on payloads fast. The learning cycle compresses from years to days. Against an adversary who has spent 30 years developing anti-access/area-denial weapons specifically designed to threaten large surface combatants, the risk calculus of putting a $2.3 billion target in a contested strait is, as Ben puts it, off the charts.
The argument is economic and strategic. And it’s an argument defense tech founders often undersell, because they’re focused on what their product can do rather than what the alternative costs.
4. The insider path is real, but it’s not a shortcut.
Ben’s transition looks clean from the outside: senior Pentagon official with deep relationships joins autonomy company, brings credibility and access. The reality is more complicated. He spent years building understanding at every level of the system, from budget to requirements, acquisition, strategy, and operations.
When he was in the CNOs office, he saw Havoc at an investor conference, brought it back as a recommendation, and helped the CNO’s office start paying attention to what defense tech startups were actually building.
That kind of insider value takes decades to build. Which means the shortcut version (e.g., hiring a recently retired flag officer to open doors) usually doesn’t work the way founders hope. The doors might open, but what matters is what you do once you’re inside.
5. The multi-domain bet is a systems integration bet, not a platform bet.
Havoc’s goal isn’t to own the best aerial drone or the best ground vehicle, but to be the software layer that makes a surface drone, an aerial drone, and a ground vehicle operate as a single coherent system under unified command.
Ben described a hypothetical operational scenario: a maritime ISR platform sees a fast-moving target but can’t track it over the horizon. If it can launch an aerial drone and pass targeting data between them through a common autonomy stack, you’ve created networked warfare from a single operator interface. The value derives from the connections between platforms, and in making those connections simple enough that the person running the operation doesn’t need three separate control consoles and three separate teams.
For more about HavocAI: https://havocai.com/
Follow Ben: https://www.linkedin.com/in/bencipperley/
For more Crossing the Valley: valleycrossers.com
Follow Noah: https://www.linkedin.com/in/noahsheinbaum/
Crossing the Valley explores the journey from proof of concept to production in defense technology. New episodes weekly.
