Taking ControlUp from Practitioner Favorite to Enterprise Leader

ControlUp grew to $20 million in ARR on Product-Led Growth: IT practitioners discovered the product, tried it, and championed it inside their own companies. But enterprise buyers do not discover software through free trials, and enterprise accounts were exactly where the next $55 million had to come from. Three years of coordinated change scaled the business to $75 million in ARR while cutting marketing spend by 20 percent.

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Executive Summary

ControlUp had grown to $20 million in ARR on an engine most companies would envy: Product-Led Growth. IT professionals discovered the product, tried it, loved it, and sold it inside their own companies. Then the engine began to stall. Enterprise buyers did not discover software through free trials, and enterprise accounts were exactly where ControlUp needed to grow. The model that built the company could not carry it where it had to go.

The timing made it dangerous. Digital Employee Experience was emerging as a new category, and a small group of competitors was moving fast to define it. Categories harden quickly: buying criteria get written, analyst shortlists get drawn, and the companies left outside stay outside. ControlUp had strong technology and loyal practitioners, but limited enterprise visibility, few analyst relationships, and a brand that no longer matched its ambition. The window was open, and it was closing.

I joined with deep enterprise experience in desktop and virtual computing from Microsoft. My mandate was to go after growth and the enterprise: protect the digital engine already producing revenue, modernize the brand, build demand in the United States and EMEA, establish ControlUp in DEX, and create a global marketing organization across Israel, EMEA, and the United States. None of it happened in sequence. For three years, everything moved at once.

Protecting the Core While Building the Next Engine

There was urgency from the beginning. The company needed growth, and I needed points on the board while the broader transformation took shape.

The website was the most immediate issue. The PLG strategy remained sound, but the web experience had drifted away from it. Product discovery, trial, and conversion were no longer the site's organizing purpose. So we worked in stages: repair the existing site and keep the engine running, modernize the brand and rebuild the message, then return to the web experience and refit it around the new positioning.

The brand needed the deeper work. It had evolved through years of decisions by founders and functional owners, each sensible on its own, that together had diluted the company's purpose. It no longer met the expectations of the enterprise customers we were now targeting.

Meanwhile, much of the digital budget was underperforming. I reallocated investment toward programs that served several objectives at once: stronger enterprise engagement, category visibility, and closer alignment with Sales. The strategy was never to stop the engine and rebuild it. It was to protect what worked while creating room for the next growth model to take hold.

Our VMware Strategy

The foundation was commercial. VMware placed the ControlUp offering on its price list, a validation point that told enterprise customers, analysts, and partners that ControlUp belonged in the largest environments. We used it throughout the company's market story.

We built on that foundation with presence. VMware Explore, the industry's flagship event, gave ControlUp its biggest stage. More than 50 VMware User Group meetings a year across the United States and EMEA kept us in front of practitioners, cost-effectively and in their own communities. Any one of these would have been a good tactic. Together they made a strategy, one that made ControlUp relevant and credible to every enterprise customer, no matter what infrastructure they were running.

The alignment between Sales and Marketing was where the combination really paid off. We did not sponsor events and hope the right people appeared. Marketing and Sales planned together, scheduled customer and prospect meetings directly on the show floor, and staffed the booth as a working environment where everyone played a part: sellers, technical experts, and executives advancing real deals. You could feel the energy and excitement.

It was a wall of sound with Sales and Marketing working in harmony, and every enterprise customer could hear it. We leaned in, and revenue followed.

Explore showed what this strategy looked like over time. It was a three-year investment, not a tradeshow appearance, and each year we made it work harder: bringing the modernized brand to life, sharpening our enterprise positioning, and growing from Gold sponsorship to Platinum. By 2023, ControlUp had a 20-by-20 booth staffed by sales engineers and company leadership, a full calendar of customer meetings, and two TechTarget awards: a category win and Best of Show. Our customer party drew more than 500 people and became one of the most talked-about events. The market saw the company the way we did. It worked.

Establishing ControlUp in the DEX Market

ControlUp had invested little in relationships with Gartner, Forrester, or the broader analyst ecosystem. As competitors moved to define DEX, the risk was real: ControlUp would stay known as a strong VDI monitoring product while the enterprise category formed without it.

Working with a strong Product Marketing leader who combined field sales engineering experience with deep product knowledge, we rebuilt the ControlUp story around the changing market and the needs of enterprise buyers, then took it to the analysts. Our first efforts were largely ignored. Competitors like Nexthink had invested heavily in shaping the category and its buying criteria.

Our competitors were helping set the rules while ControlUp was still trying to get into the room.

That gradually changed. The enterprise credibility we had built across the VMware ecosystem gave analysts a reason to listen, and ControlUp could explain why its practitioner strength, real-time insight, and technical depth belonged in a broader conversation about employee experience. We were not yet defining the category, but we were at the table, and the company was increasingly seen as a credible DEX player.

Building a Global Team, and Earning a Place on It

The organization was changing as fast as the market strategy. We established strong digital leadership in Israel and built field and partner marketing teams in the United States and EMEA. These were not support hires. They were central to enterprise growth, which depended on regional execution, Sales alignment, and partner influence. As the teams came together, lead performance improved, enterprise engagement deepened, and deal sizes grew.

Building the organization was one challenge. Becoming part of ControlUp's leadership team was another. I was an American executive joining an Israeli team that had largely been together since the company's founding. Israeli companies operate differently: people say what they think, argue directly, and use disagreement to harden the plan. Once a decision is made, everyone commits without looking back. The unvarnished feedback took adjustment, but it was energizing to be part of a team willing to challenge itself so openly.

The Head of Sales was employee number three and functioned in many ways as a founder. He had previously led Marketing and believed deeply in the PLG strategy that had built the company. Convincing him to support new approaches required more than a title or a presentation. My approach was to preserve the most important elements of PLG while creating room to experiment with new ways of driving enterprise growth. Protecting PLG was the right thing to do, and he knew it. That was where we found our agreement.

I also knew those relationships could not be built through video calls. I committed to traveling to Israel every quarter, generally for a week of leadership meetings and working sessions. My first trip took place during COVID, requiring special permission and three days of quarantine alone in a hotel room. It was inconvenient, but the commitment mattered.

I was not asking the Israeli team to adapt to an American executive working from a distance. I was making the effort required to become part of their team.

Over time, working relationships became friendships, and trust made the direct debate more productive. Our willingness to challenge one another and commit fully once decisions were made became one of the reasons the transformation worked.

Business Outcomes

No single initiative produced the results. The work across PLG, brand, analyst relations, events, partnerships, and organization was deeply interconnected, and together it scaled ControlUp from $20 million to $75 million in ARR. High-intent leads increased 62 percent, demos grew 44 percent, and marketing spend declined 20 percent.

Along the way, the company increased deal sizes, established a credible DEX position, developed meaningful analyst relationships, and built a coordinated global marketing organization across Israel, EMEA, and the United States. We did not abandon the model that had built ControlUp. We protected it, improved it, and built the next growth engine around it.

Three Leadership Lessons

The first: transformation does not always begin by replacing what exists. PLG had built a successful company. The right move was to preserve what still worked while creating room to build what the business needed next.

The second: a macro strategy is the product of hundreds of micro decisions. Brand, website, analysts, events, partnerships, hiring, and regional execution all evolved together. The leadership challenge was keeping those decisions aligned while the company continued to operate and grow.

The third: distributed leadership requires personal commitment. Trust does not develop across cultures and time zones through scheduled calls. Traveling to Israel every quarter, learning how the team worked, and joining the debate directly made the difference.

ControlUp challenged me to respect a successful past while helping build a different future. It required urgency, experimentation, and the humility to earn influence inside a team that had already accomplished a great deal. It remains one of the most rewarding transformations of my career.

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