Leonardo da Vinci
Ross Sylvester, Co-Founder & CEO, Adrata | Feb 2026 | ~5 min read
In 1482, a thirty-year-old artist from Florence sat down and wrote what might be history's first sales pitch. Leonardo da Vinci needed a job, and the Duke of Milan, Ludovico Sforza, was hiring. Leonardo composed a letter listing ten capabilities he could offer the Duke.
Nine of the ten paragraphs described military engineering. Portable bridges that could pursue or retreat from enemies. Siege techniques for draining moats. Designs for bombardment machines, armored wagons, cannons, and catapults. Tunnel-digging methods. Hydraulic systems.
Only in the final paragraph did Leonardo mention that he could also paint and sculpt.
This was not modesty. This was positioning. Milan was at war. Ludovico needed someone who could help him defend his duchy, not someone who could paint a nice portrait. Leonardo was an artist to his core -- painting was his life's work and his deepest passion. But he understood that the buyer's problem was not his problem. So he led with nine paragraphs of military engineering and buried art in the postscript.
He got the job. He spent seventeen years in Milan. The Duke eventually commissioned The Last Supper.
Walter Isaacson, in his 2017 biography Leonardo da Vinci, builds the case that Leonardo's genius was not innate supernatural talent but a method -- "based on skills we can improve in ourselves, such as passionate curiosity, careful observation, and an imagination so playful that it flirted with fantasy." That method, examined carefully, contains at least four lessons that translate directly to how revenue leaders should think about their work.
Sell to the Buyer's Problem, Not Your Passion
The Sforza letter is worth studying not because it is old, but because the instinct it overcame is so persistent. Most sellers lead with what they are proudest of. Leonardo was proudest of his art. He led with bridges and cannons.
The structure of that letter -- nine paragraphs of the buyer's priority, one paragraph of the seller's identity -- is a ratio most pitch decks invert. CROs should ask their teams a simple question: in our last ten presentations, what percentage of slides addressed the customer's stated problem versus our product's capabilities? If the answer is not overwhelmingly weighted toward the customer, you are writing a letter about painting to a duke who needs fortifications.
Observation Before Action
Between 1494 and 1498, Leonardo painted The Last Supper on the wall of the Santa Maria delle Grazie convent in Milan. The novelist Matteo Bandello, a contemporary who watched Leonardo work, recorded his method: some days Leonardo painted without interruption from sunrise to sunset. Other days he stood before the wall for an hour or two, studying it, and never touched a brush. He would go two, three, four days without applying paint, yet spend every day in the room -- contemplating, considering, examining.
The Prior of the convent complained to the Duke that Leonardo was wasting time. Leonardo's response, recorded by Vasari: "Men of lofty genius sometimes accomplish the most when they work least, for their minds are occupied with their ideas and the perfection of their conceptions, to which they afterwards give form."
This was not procrastination. Leonardo was solving the composition mentally before committing pigment to plaster. He walked the streets of Milan studying faces, mapping how emotion shows in the muscles around the mouth and eyes, working out how light would fall across thirteen figures seated at a table. The brushstrokes were execution. The observation was the work.
The parallel for revenue leaders is direct. The CRO who spends a week studying pipeline data, listening to call recordings, reviewing win-loss analyses, and mapping competitive positioning before committing to a new sales strategy is not stalling. They are doing the highest-leverage activity available. The danger is the opposite instinct -- the leader who walks in on Monday and starts reorganizing territories before understanding what is actually happening in the pipeline. Action without observation is paint without composition.
Cross-Domain Pattern Recognition
Leonardo was, as Isaacson documents, a "pioneer in disciplines including fluid dynamics, optics, cartography, engineering, aviation, and anatomy." But his distinguishing capability was not depth in any single domain. It was the ability to see patterns across domains. He noticed that the spiral flow of water eddies resembled the curls of human hair, which resembled the vortices created by bird wings. These were not metaphors to him. They were the same underlying phenomenon expressed in different materials.
He wrote in his notebooks: "First I shall do some experiments before I proceed farther, because my intention is to cite experience first and then with reasoning show why such experience is bound to operate in such a way." He signed a document calling himself "Leonardo da Vinci, disscepolo della sperientia" -- disciple of experience. His method was empirical and cross-disciplinary a full century before Galileo and Bacon formalized the scientific method.
The revenue application: the best CROs are pattern matchers who work across functional boundaries. They notice that the churn signal in customer success looks like the onboarding friction signal in implementation, which looks like the competitive displacement signal in new logo deals. Siloed leaders see separate departments with separate problems. Cross-domain leaders see a system, and they intervene at the root cause rather than treating symptoms in each department independently. Leonardo's spiral showed up in water, hair, and wind. Your pipeline problems show up in sales cycles, win rates, and expansion revenue. They are often the same problem wearing different clothes.
Build Expert Networks
One of the most revealing documents in Leonardo's notebooks is a to-do list from the early 1490s in Milan. It is not a list of tasks to complete. It is a list of things to learn, and nearly every item involves seeking out a domain expert. He assigned himself to study proportion with a professor of medicine. To learn medieval mechanics from a Benedictine friar. To find a hydraulics master who could teach him canal and lock repair. To get optical mathematics from a library in Pavia. To examine a crossbow with a military engineer named Mastro Giannetto.
Leonardo did not try to be the smartest person in every domain. He tried to find the smartest person in each domain and learn from them. As Isaacson observes, he was "open to others and often gave himself over to experts" for education.
CROs who build expert networks -- genuine relationships with specialists in product, engineering, finance, customer success, and adjacent industries -- make better decisions than those who rely on their own experience and whatever their direct reports choose to escalate. The to-learn list is a better operating model than the to-do list.
Vision Without Shipping Is a Clay Horse
The cautionary tale. In 1482, the same year Leonardo arrived in Milan, he was commissioned to create the largest equestrian statue in the world -- an eight-meter bronze horse for the Sforza family. He spent eleven years on the design. Seventy tons of bronze were collected for the casting. In November 1493, he unveiled a full-size clay model at a Sforza wedding. It was magnificent. It made him famous.
Then the French threatened to invade. The Duke gave the bronze to his father-in-law to forge cannons. In 1499, French soldiers entered Milan and used the clay model for archery practice. The statue was never completed in Leonardo's lifetime. A modern recreation was finally unveiled in 1999 -- five hundred years later.
Leonardo completed fewer than twenty paintings in a forty-seven-year career. Some scholars count as few as fifteen. He abandoned the Adoration of the Magi when a better opportunity appeared. He experimented with an unproven fresco technique on the Battle of Anghiari and watched it fail. He was still refining the Mona Lisa when his right hand was paralyzed in 1517, fourteen years after he started it.
The lesson is not that thinking is bad. The Last Supper proves that deep observation produces the greatest work. The lesson is that observation must eventually yield to commitment. The Sforza Horse is what happens when you perfect the prototype while the market window closes. The bronze goes to cannons. The budget gets redirected. The competitor ships.
The Takeaway
Leonardo wrote in his notebooks: "He who loves practice without theory is like the sailor who boards ship without a rudder and compass and never knows where he may cast." The inverse is equally true -- theory without practice is a ship that never leaves port.
The CRO's job is to hold both. Sell to the buyer's problem, not your own. Observe before you act, but act before conditions change. See patterns across domains. Build networks of people who know more than you do. And when the clay model is ready, cast it in bronze before someone turns your bronze into cannons.
Leonardo was the greatest mind of his millennium. He still finished fewer than twenty paintings. Genius is not the bottleneck. Shipping is.