A salesperson is losing a deal right now, and nobody told them why
Somewhere a rep is on a call, a competitor's name lands, and the conversation goes quiet. The buyer has done homework the rep hasn't. Jonah Lopin built a company around that exact silence. Crayon, the Boston software firm he co-founded in 2015 and runs as CEO, tracks what rivals are doing across the open web and feeds it back to the people who need it before the call, not after the post-mortem.
His argument is almost stubbornly simple. Most businesses, he says, lose about a third of their sales deals in head-to-head competition, and three out of four tech buyers think the vendors they're evaluating all look the same. Lopin treats that not as a branding problem but as an information problem, and information problems are the kind software can chew on.
So the pitch became a question he keeps coming back to: “What if competitive intelligence could be programmatic and continuous?” Not a deck someone updates twice a year and forgets. A live signal. The explosion of digital footprints online, he points out, means the raw material is already out there. Crayon's job is to make it useful at the moment a deal hangs in the balance.
Notice the verbs. Timely. Hyper-actionable. Lopin isn't selling a report; he's selling a reflex. The distinction matters to him because he's watched the old way fail. Competitive intelligence has traditionally meant a researcher, a spreadsheet, and a quarterly refresh that's stale before anyone opens it. By the time the insight reaches the rep on the call, the market has moved and the deal is gone.
His fix leans on a structural shift he likes to name out loud: companies now leave digital footprints everywhere, and their front lines have adopted messaging and workflow systems that can carry intelligence to the exact person who needs it. The raw signal and the delivery pipe both already exist. What was missing was a system to connect them, which is the company he decided to build.
That conviction didn't arrive in a vacuum. It came from watching the gap up close for six years, at a company most of Boston was still learning to pronounce.
From physics, to Deloitte, to China, to a billion-dollar IPO
Lopin started in physics at Cornell, then did the responsible thing and went to Deloitte's Strategy & Operations group in Boston. He left to get an MBA at MIT Sloan, where in 2007 he met a classmate named John Osborne. They liked each other. They'd eventually build a company together. It would take almost a decade.
In between, he went off-script. He lived and worked in China, focused on entrepreneurship and non-profits, and built and launched social and mobile apps. He is, by his own account, allergic to bureaucracy and the kind of person who'd rather chase value than climb a ladder. His rule of thumb is plain: “create value for the customer and scale a business model around that value.”
Then came HubSpot. He joined as the sixth employee and ran Customer Success, sitting on the management team from zero revenue all the way through the 2014 IPO and a roughly billion-dollar market cap. Over six years he helped onboard around ten thousand customers, scaling the team from a handful of people to hundreds and the customer base from nothing to thousands.
That's a rare seat. Being employee number six at a company that goes public means you watch the entire arc, the part where nothing works and the part where suddenly everything does. You learn what scales and what quietly breaks at ten times the size. Lopin came out of it with operating instincts most founders have to buy with their own failures first.
The itch he couldn't scratch
And here's the thing that stuck with him. HubSpot was brilliant at helping those ten thousand customers optimize their own internal data. It never helped them understand the market moving around them, the competitors circling, the external signals that decide deals.
That blind spot became the brief for his next act. Companies could see themselves in high resolution and the outside world not at all. Lopin decided the outside world deserved a dashboard too.
When he and Osborne finally started Crayon in 2015, the first swing wasn't competitive intelligence at all. It was prettier than that, and wronger.
It began as a mood board. The data had other plans.
The first idea that clicked was Crayon Inspire, a tool that let marketers collect and browse design inspiration from across the web. Think Pinterest, pointed at brand and marketing teams. It launched in 2015 and it was, by the standards of a young startup, working.
But toward the end of that year the founders noticed something underneath the product. To power the inspiration feed, Crayon was quietly indexing and tracking enormous amounts of what companies published online. That tracking, it turned out, was the valuable thing. The mood board was a delivery mechanism for a far bigger idea.
So they pivoted. Crayon Inspire became Crayon Intel in 2016, a platform that watches the market and competitors in real time and routes the findings to sales, marketing, product, and customer success. The pretty version got out of the way of the useful one.
It's a very Lopin move. He'd already learned, at HubSpot, that the unglamorous data underneath a product is often where the leverage hides. At Crayon he got to build the whole company on that hunch.
Read the market as fluently as you read your own numbers
Strip Crayon down to its premise and you get something close to a worldview. Every company has an internal dashboard. Revenue, pipeline, churn, the metrics they refresh obsessively and argue about in Monday meetings. Almost none of them have the equivalent for the world outside their walls, the competitors repositioning, the pricing changes, the market moves that decide whether this quarter's plan survives contact with reality.
Lopin wants that second dashboard to exist and to be just as continuous as the first. His diagnosis of why deals are lost is unsentimental: three out of four tech buyers think the vendors they're evaluating all look the same. When everything looks identical, differentiation collapses and price wins. Intelligence, delivered at the right moment, is how a seller breaks the tie before the buyer ever notices the choice was close.
Why software, and why now
The reason this is a software problem and not a research problem, in Lopin's telling, is scale and speed. A human analyst can read a competitor's website. A human analyst cannot read every competitor's every public surface, every day, and route the relevant change to the right rep inside the hour. Machines can, and the data exhaust companies now generate online makes the input richer every year.
That number is the part he cares about most. Not whether intelligence gets collected, but whether anyone uses it. A battlecard nobody opens is a slide deck with extra steps. The growth in engagement is his proof that intel, delivered where the work already happens, finally gets read.
Six lines that explain the whole thesis
What if competitive intelligence could be programmatic and continuous?
CI can be timely and hyper-actionable in sales, customer success, marketing and product.
Most businesses lose about a third of their sales deals in head-to-head competition.
The explosion of digital footprints on the web means there's a much better way to compete that's software-driven.
Create value for the customer and scale a business model around that value.
You've found my personal website. Make yourself at home!