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The Decade-Long Journey to Product-Market Fit: What Clockwise Learned Building Time Management Software

Most founders obsess over speed. Ship fast. Iterate faster. Get to revenue yesterday.

Matt Martin took a different approach. In a recent episode of BUILDERS, the Co-Founder & CEO of Clockwise shared how spending a decade solving calendar productivity taught him that conventional startup velocity wisdom breaks down for certain business models—particularly PLG products dependent on network effects.

The company took three years to launch publicly and four years before monetization. By most standards, that’s an eternity. But Matt argues this extended timeline was precisely what allowed Clockwise to build defensible distribution mechanics in a space littered with failed productivity tools.

The Problem That Refused to Get Better

Matt’s founding insight was deceptively simple: time is the fundamental economic constraint in knowledge work. “The most valuable thing we have on the face of the planet is our time,” he explained. “It is the primary limiter of all of our economic organizations.”

Coming from Salesforce, Matt saw how even well-run companies with talented people hemorrhage productivity. “Despite all those constraints, we spend it so stupidly,” he said. “Anybody who’s been in a large organization knows how infuriating it is to get scheduled on a bunch of meetings that don’t move the ball forward.”

A decade later, the problem hasn’t improved. There was a pandemic-driven spike as remote work forced meeting-heavy collaboration, which partially receded. Google and Microsoft now include focus time concepts in their calendar products—”I will plant a flag for us as being the pioneer in this regard,” Matt noted—but calendars remain fundamentally inefficient.

The Distribution Hypothesis That Required Years to Prove

Most PLG startups validate product-market fit through conversion rates or revenue velocity. Clockwise validated something more fundamental first: whether their viral loops would actually function at scale.

The company tracked 1,400 weekly active users as the threshold to open public beta. “The number isn’t really as important as what it was a proof point of—that we thought the distribution elements actually had legs,” Matt explained.

The specific mechanics they needed to prove: users would penetrate organizations by accessing colleagues’ calendars, recruit additional users through network effects visible on shared calendars, and those recruited users would retain despite product imperfections. “It wasn’t a great experience at that point, but they would survive,” Matt admitted.

This patience was strategic. Opening wider distribution without proof that calendar-based virality functioned would have wasted their one shot at growth. By the time they removed gates, they had complete confidence in what would happen.

The ICP Paralysis Every Technical Founder Recognizes

Even with clear advantages—they were software engineers solving a software engineer problem with obvious ROI—Clockwise still fell into classic founder paralysis.

“I think one of my learnings is there’s a tendency to overthink the problem,” Matt reflected. “We spent a lot of cycles being like should it be software engineering, should it not? Does that pigeonhole us?”

The targeting logic was obvious. Software engineers provided clear ROI translation because “it’s primarily heads down time that produces output.” Unlike salespeople who should be in meetings or support teams managing queues, engineering productivity directly correlates with uninterrupted time blocks.

“The reality is you just got to find your wedge and move and that was the wedge that we understood,” Matt said. His pattern recognition from a decade later: Type-A founders tend to overindex on first-principles analysis when the answer is already evident. Choose where you have authentic problem understanding and clear ROI articulation, then execute.

The Graveyard of Calendar Productivity Companies

After watching competitors rise and fall for a decade, Matt outlined three distinct failure modes with surgical precision.

Wave one focused on calendar UI superiority. The fundamental problem: “You have a space where the dominant platforms are also the dominant clients.” Most end users don’t differentiate between Google Calendar as a database and Google Calendar as UI. Platform owners have insurmountable distribution advantages, and IT buyers ask “why do I need another calendar when I already bought one?” Matt cited Fantastical as great software that “you just can’t build a VC backed business off that.”

Wave two targeted consumers instead of enterprise. The unit economics don’t work. “People are just really shitty at valuing their time and unwilling to spend on it,” Matt said. “Partly because they’ve been trained to do that. They get a calendar on their iPhone for free, they get all sorts of productivity tools for free.”

Wave three is more subtle: failing to balance end user and buyer needs. This bifurcation defines all productivity software—Notion, Figma, Google Docs face identical dynamics. “If you go too much in the direction of just satisfying business needs, it’s really hard to get the distribution and penetration,” Matt explained. “But if you just focus on the end user, you’re stuck in that trap where you’re not solving a business problem.”

The winning approach requires solving an enterprise problem while maintaining end-user love strong enough to drive adoption—threading a needle most companies miss entirely.

Why Microsoft and Google Still Haven’t Competed

Matt spent the first 2-3 years worried about incumbents. The opportunity seemed obvious—surely Microsoft or Google would move aggressively into intelligent time management.

They didn’t. The reason reveals critical dynamics about platform competition.

“Microsoft and Google often won’t move into something until it’s a proven market,” Matt observed. “They’re not going to get out of bed in the morning for something that’s under a $10 billion opportunity and we’re not there yet.”

More fundamentally, platforms operate at entirely different scale with different problems. “The primary barrier that the Outlook Calendar team works on is how to get people to use Outlook Calendar,” Matt said. “That is so foreign to me that I couldn’t conceive of it at the start.”

Coming from Salesforce where everyone lives in their calendar created a distorted view. The mass market reality: most people don’t consistently record time in calendars—a completely different problem than optimizing efficiency for knowledge workers who already live in their calendars.

This creates a longer runway than founders expect when building in “obvious” spaces adjacent to massive platforms. If you’re solving for sophisticated users while platforms optimize for basic adoption, you’re not competing in the same market.

The Trust Signal Hidden in Monetization Timing

When Clockwise introduced paywalls after four years, Matt expected stakeholder anger and account churn.

The opposite happened.

“Users felt more confident that we weren’t just stealing their data,” Matt explained. “We had a lot of objection, people thought we were just going to steal their data and sell it.” The formal business model resolved the “what’s the catch?” skepticism plaguing free enterprise tools.

Enterprise buyers welcomed formal security agreements and real contracts. “The stakeholders and buyers were happy to have a real security and enterprise agreement,” Matt noted.

The timing calculation: monetize late enough that product value is unquestionable and viral loops are proven, but recognize that a transparent business model resolves trust issues rather than creating them. Matt wishes they’d done it earlier.

Paywall Placement as the Highest-Leverage PLG Optimization

Beyond the decision to monetize, paywall placement became Clockwise’s most critical optimization lever.

“That paywall becomes a really delicate balance of getting people in and hooked and habit formation early enough such that they’re not going to churn when you ask them for money, but not so late that you never get the opportunity to ask or push them,” Matt explained.

Clockwise has iterated multiple times on this single variable because it directly governs PLG economics. The strategic framing: “In the PLG world, largely what you’re doing is you’re trying to create a big pond of users to fish out of.” Sales does inbound conversion into existing user base rather than pure outbound.

The paywall determines pond depth versus conversion rate—get it wrong and you either have no users to convert or users who never convert. Getting it right requires multiple iterations informed by cohort retention data.

The Stubborn Economics of Organic Growth

After extensive experimentation across LinkedIn campaigns, influencer co-marketing, referral programs, and various channels, Matt’s conclusion is stark: organic distribution and personal referrals still dominate despite everything they’ve tried.

“I would pay much more to have somebody refer and talk to us with five friends than for some influencer on Instagram to say that Clockwise is the next best thing,” he said. “We just see that organic growth and personal referral to be the most prominent thing that gets us more business.”

His candid assessment on marketing: “Our bread and butter is still that organic distribution.”

The strategic implication: when one channel produces disproportionate results, enable and accelerate those mechanics rather than forcing paid acquisition parity. Clockwise now focuses on referral programs and improving product-led distribution instead of fighting uphill battles making other channels work at scale.

This isn’t the inspiring marketing playbook most founders want. There’s no growth hack. No channel that suddenly unlocked scale. Just persistent reality that requires accepting and optimizing around.

The Transition from Pure PLG to Blended Motion

As Clockwise matured, their GTM evolved beyond pure product-led growth. “The initial motion was exclusively PLG,” Matt explained. “We worked a lot off of the early adopter crowd and a lot off of that initial evangelism from engineers to bring it into an organization.”

But inbound enterprise deals changed the equation. “As we gained maturity, we started to get more inbound. And in a lot of ways the inbound deals are much better for us because we can actually implement holistically and educate people on how to use the product instead of pocketing up in these little bubbles.”

Matt cited Instacart as an example: “One of the founders saw us, saw the meeting problem they had internally and wanted to deploy a pilot. The pilot went really well and so we’re deployed quite widely there.”

The company now layers sales involvement and customer success onto the PLG foundation. “It’s not just pure PLG or self serve, but there’s actually sales involvement and a CS team that helps enable that account.”

The broader pattern: PLG works well for productivity products with broad applicability and high evangelism from initial markets. But expanding beyond early adopters to traditional roles may require blended motions rather than exclusive PLG.

Building Toward AI-Powered Personalization

Matt’s vision for the next decade centers on embracing individual complexity that deterministic systems couldn’t handle.

“Every individual has their own unique set of preferences, their specific way of doing things that are in their head,” he explained. “In a deterministic system where you have to hard code every lane of that, it’s just too complex. You’ve got to reduce the complexity to get it done.”

AI changes the equation fundamentally. Matt envisions Clockwise becoming “even more background than we are today, where there’s even less UI around Clockwise” as it evolves into an agent acting on users’ behalf.

The technical architecture he describes: “We know how to operate calendars, we know how to operate the complexity of time. We know how to interoperate with other LLMs and assistants that are using. And so whether you’re talking to Clockwise directly through text message or Slack or some other venue, or you’re talking through ChatGPT, we can help you manage your schedule very nimbly.”

For a founder who spent a decade on what seemed like an obvious problem, Matt’s patience offers a counternarrative to conventional startup wisdom. Some distribution mechanics require years to prove. Some markets need time to develop. And sometimes the standard advice about velocity is exactly wrong for the business you’re building.