About Jackie Barbieri

Jackie is the founder and CEO of Whitespace. She began her career supporting the counter-IED mission during the surge in Iraq, working as a red-team analyst. She was a threat emulator who studied the tactics, ideology, and bomb-making techniques of adversary networks, often in Arabic on the dark web, then fused that with classified collection. That experience, and witnessing what timely intelligence does for operators downrange, became the through-line of everything she’s built since.

Jackie returned to grad school to study what changed after 9/11, and got pulled into an R&D community around Activity-Based Intelligence (ABI) — a methodology that made trained analysts roughly 300x more effective. Notably, Jackie has a liberal arts background, not an engineering one. And, fun fact: she founded Whitespace in 2014 when her first child was six months old (there’s something about young parents as founders…)

About Whitespace

Founded in 2014 and headquartered in Alexandria, VA, Whitespace builds sensemaking AI for defense and intelligence. The company bootstrapped for roughly a decade, funding technology development through consulting revenue, before raising a small seed round in 2025 (~$3.2M per public reporting) backed by family offices and a few VCs.

Its early IP, Worldline, is a simulation engine that creates a digital twin of a city-sized population observed by a synthetic sensor architecture, to generate realistic, multi-sensor training data. That capability won Whitespace its first prime contract with the National Geospatial-Intelligence Agency (NGA) in 2017 to build the ABI curriculum for the entire intelligence community, which the company then instructed for nearly eight years.

The flagship product today is Iris: an agentic AI “analyst” that lets operators self-serve pattern-of-life intelligence in natural language. Under the hood, Iris is built on ABI tradecraft translated into a toolkit of deterministic algorithms, wrapped in an agentic system carrying the persona and judgment of experienced analysts. Iris can run standalone, alongside human SMEs, or headless via API — and is designed for a future where her biggest user group may be other agents and autonomous platforms, not people.

Notably, by the time the company raised venture capital, it had flipped from ~80% services / 20% product to ~80% product / 20% services, 4X’d ARR, doubled revenue, and roughly doubled headcount.

Key Takeaways

1. Whether it’s services or product revenue, proximity is the most important early return. Whitespace’s consulting work kept Jackie embedded with the exact analysts and operators who would later define the product, and bought time to figure out the right way to deliver before committing. Revenue close to the mission is the next best form of R&D funding because it pays you to stay in the room.

2. Sequence hard problems rather than stacking them. Early on, Whitespace needed to navigate two meaningful transitions: services to product, and government-only to dual-use. Each is a company-defining transformation on its own. Founders rarely fail because a transition is impossible. Instead, we see time and time again they fail because they’re running several major transitions all at once and starving all of them from the attention they need.

3. Successful products are often the translation of expertise into software form. Whitespace’s hardest, highest-leverage bet was converting a qualitative analytic methodology into production-grade algorithms. This is where most expertise-driven companies stall, for two structural reasons: data science and engineering are genuinely different disciplines (“works in Python” is not “works at scale”), and the engineer has to deeply understand the analyst’s intent. The companies that bridge that gap (in Jackie’s case, by hiring the rare people who have both areas of expertise), are able to build something competitors can’t easily copy.

4. Discipline is knowing when to stop discovering. Growing in the software market can create a seductive trap: every new use case is a chance to prototype, deliver value, and move on. The risk is that you end up producing a pile of one-offs that never become a repeatable product. Crossing the valley requires deliberately cutting off the discovery process and forcing the work to coalesce, even when the next shiny problem is tempting and the customer paying you isn’t the one with the most interesting problem. In a word, focus is the difference between crossing or dying.

5. Brand is strategy when it tells the truth. Whitespace’s bright, almost psychedelic identity is a deliberate departure from defense tech’s default black-grey-gamer aesthetic. The logic is substantive, not cosmetic: the people who do this work are fiercely optimistic, and breaking the visual pattern creates room to rethink intelligence itself. In a crowded category of near-identical “thing-drops-from-the-sky, coming-soon” launch videos, refusing the template has garnered significant organic attention for Jackie and co. That’s because their brand aesthetic signals a genuinely different way of approaching a known problem.

What Stood Out to Me:

The decade-long bootstrap. We are in an era of fast, rapid raises. Jackie’s path — 11 years, one small seed by choice — is almost unfathomably today.
A non-technical, liberal-arts founder built a hard-tech AI company. And she did it before the ubiquitous LLMs made it such that every one of us is a coder. Jackie is candid about the false starts (an entire AR/MR company she founded alongside Whitespace in 2018 that was too early) and the scars from chasing one-offs.
Young parents = great founders. Something about having a six-month-old requires radical focus. The realization that time, not money, is the truly scarce resource.
The product philosophy is sharp and forward-leaning: Iris is “she,” headless, and built on the bet that the biggest future user of intelligence agents will be other agents.

For more on Whitespace: inthewhitespace.com

Follow Jackie: https://www.linkedin.com/in/jackie-barbieri/

For more Crossing the Valley: valleycrossers.com | youtube.com/@CrossingTheValley

Follow Noah: https://www.linkedin.com/in/noahsheinbaum/

Crossing the Valley

Ep. 86: In the Whitespace