From the safety of scale to the vulnerability of the unknown

In a world where technology careers often prioritise stability over speed, Jon Lombardo’s decision to leave LinkedIn after a decade might seem, at first glance, like a risky departure from the norm. But what followed was a deliberate move, rooted in evidence, timing, and a sharp sense of when to act. It’s a moment of leadership many organisations would do well to study.

Lombardo co-founded Evidenza to address a problem marketing leaders know all too well: traditional market research is slow, costly, and outpaced by the demands of modern business. During his time at LinkedIn, he saw firsthand how often big decisions were made with outdated insights and limited data. The gap was clear and so was the opportunity to close it.

Now leading an AI-native market research company, Lombardo joined the Pivot Points podcast to unpack what leaders can learn when they choose to back their judgment, embrace uncertainty, and build something better.

The business case for betting on yourself

For ten years, Lombardo operated at the heart of LinkedIn’s brand strategy function, helping some of the world’s largest B2B organizations adapt to a digital-first economy. But ambition, he explains, eventually outgrew opportunity.

“I wasn’t getting promoted. My career was tapped out,” he told host Dave Allen. “You can either stay and stew, or bet on yourself.”

It is a line delivered without sentiment, but with clarity. The type of clarity that defines a pivotal decision: whether to settle for incremental change or to manufacture a more radical kind.

Lombardo chose the latter. And the moment he stepped off LinkedIn’s ship, which he describes as “a huge ship where you didn't feel the highs and lows of the sea”, he stepped into the fray of startup life, “a dinghy where you feel everything.”

Rewriting the scaling playbook

Evidenza was not built with venture capital or a ready-made team. Instead, Lombardo and his co-founders did something far more unusual: they launched with paying clients already in place.

“We had five or seven clients ready to work with us from day one,” he recalls. “Because we hadn’t sold to them—we had advised them—they trusted us.”

This was not a pitch deck dream; it was a revenue-first reality. The firm grew quickly, now serving over 100 clients, without ever raising a dollar. AI became the accelerator—not just of product development, but of company structure. One engineer replaced ten. Feedback cycles compressed from months to minutes.

The result? A lean, profitable business operating at a velocity many larger firms envy.

Leadership without insulation

But the transition from corporate operator to entrepreneur came with its share of discomforts. Chief among them: resourcing under pressure.

“You’re constantly asking, are we hiring too fast? Too slow? You never feel fully in control,” Lombardo admits.

In such conditions, the conventional tools of leadership—long-range planning, process design, managerial hierarchy—begin to erode. In their place, a new set of instincts emerges: judgment, speed, and the humility to course-correct in real time.

Where legacy organizations rely on precedent, Lombardo’s model is based on possibility. As he puts it, “You can’t lie to yourself in a startup. You see the world clearly or you don’t survive.”

What CEOs can learn from uncertainty

For CEOs steering their organizations through inflection points—be it digital transformation, organizational reinvention, or market realignment—Lombardo’s experience offers several lessons.

First, that paradigm shifts are not to be feared but followed. “China, social networks, B2B marketing, AI—each shift created a new opportunity,” he says. The leaders who spot them early often shape the market, not just follow it.

Second, that relationships compound faster than tactics. Evidenza’s earliest revenue wasn’t driven by scale but earned through years of trust.

And third, that AI is not a replacement for leadership but a test of it. The tools may be faster, but the fundamentals remain: insight, decisiveness, and the courage to act before certainty arrives.

“When the world moved from radio to TV, people just read off paper. Then they discovered what the medium could really do. The same is true of AI.”

The case for betting on yourself

In the end, Lombardo’s story is not about disruption for its own sake. It’s about knowing when the environment around you no longer matches your ambitions and having the conviction to build a new one.

“If you want things to be done differently or better,” he says, “you have to go do them yourself.”

That belief now powers Evidenza. It is also the hallmark of every leader who has stepped forward at a pivotal moment and left the safe harbor behind.