Scaling Toggl from $10M to $20M ARR

Toggl was loved by solopreneurs and SMBs, and that love was the problem's disguise. To keep growing, the product needed to move upmarket without losing the ease-of-use DNA that made it successful.

Underneath, the product organization wasn't built for that journey. Teams were structured around features and projects, not outcomes. Discovery was inconsistent, analytics were siloed, and the roadmap was effectively an engineer-driven backlog with dates attached. PLG itself was showing cracks: acquisition through word of mouth was strong, but fewer than 20% of users kept tracking time regularly after the first month, free-to-paid conversion sat around 0.5%, and monetization — from public web through trial to upsell — was treated as an afterthought.

I joined as a product manager and grew into the CPO role over five years, so the transformation wasn't imposed top-down, it was rather built gradually, and every system I later rolled out across the department was one I had first proven as an individual contributor.

As Head of Product, I defined a dual upmarket / PLG strategy with the CEO and Board, then rebuilt the organization to deliver it: six outcome-driven squads, each owning a measurable goal; dual-track agile with a continuous customer feedback loop; product analytics as default infrastructure rather than a luxury; and business casing for critical milestones so alignment held at every level of the company. Over the years I hired and levelled up an A-class product and design team, screening thousands of applicants.

Betting on the hard thing. As an IC, I noticed Premium customers churning after four weeks, while those who stayed became some of our most durable MRR. Discovery traced it to a missing capability so technically complex the team had deprioritized it for years in favor of quicker wins. I built the business case that avoiding it wouldn't make the churn go away, won stakeholder buy-in, and led a delivery that took nearly two quarters. The result: 25% higher four-week retention in the cohort using the feature and a top closed-won reason for sales, because most competitors had been avoiding the same problem for the same reasons we used to give ourselves.

Building the upmarket wedge. All I had at the start of the New Analytics project was a vague, recurring complaint: "we need better reports." Through user interviews and data digging, I turned it into a full strategy for the data visualization domain: problem statements, roadmap, success metrics, and built a new product capability later used by 98% of Toggl's enterprise clients.

Fixing retention by not fixing retention. Preparing the first annual strategy as Head of product, I dedicated a task force to the post-week-4 retention drop. The data showed the real problem was upstream: users weren't reaching their habit moment, and what they achieved in the first minutes and hours determined everything after. We redesigned onboarding around early activation and doubled early activation rates within a couple of months.

Learning that friction can be a feature. One of our products struggled across the board: new MRR, engagement, retention. We removed an "extra" explainer step during signup, and conversion skyrocketed... followed a week later by a major drop in activation and retention. The screen we deleted had been filtering for intent. We restored meaningful friction and learned to design the journey to be opinionated, not just short.

Monetization as a system. Pricing hadn't been touched in years. The team I have gathered to work on it built a business case showing that lifting free-to-paid conversion from 0.5% to just 1% would hit the annual revenue target with no other efforts. Within three months of the team becoming fully functional, conversion had grown to 0.7%, navigating the realities of pricing work: limited A/B testing, delayed impact, and the stakeholder patience that only trust can buy.

• Revenue: ARR doubled from $10M to $20M over my five years, PM to CPO.
• Enterprise adoption: New Analytics used by 98% of enterprise clients — the upmarket proof point.
• Retention: +25% four-week retention for the Premium cohort on the strategic feature.
• Activation: Early activation rates doubled within months of the onboarding redesign.
• Monetization: Free-to-paid conversion up 40% (0.5% → 0.7%) within the new team's first quarter.
• Organization: Six outcome-driven squads with owned metrics, dual-track discovery, and business casing as standard practice.