Quiller

In 2011-2012, Dylan, a designer and developer running a micro agency in Sydney, was drowning in proposal work. He'd spend hours juggling Excel for pricing, Word for copy, and Adobe InDesign for layout. Each client revision meant ripping apart the entire design and starting over. One day, frustrated beyond belief, Dylan did what any developer would do: he built a website instead. The magic happened when he sent this web-based proposal to a major prospect at Saatchi & Saatchi New Zealand. The MD called him within hours asking, "Is this a product? How can we use this?" Dylan won the job and the contract was surprisingly large—he hadn't even expected to win it. The seed was planted.

Dylan was initially hesitant about another product business (he'd tried once before with mixed results), but the more he thought about the potential, the more excited he became. When Mark returned to Sydney from New York—leaving Google to move back for his now-wife and rejoin the startup ecosystem—the timing was perfect. Dylan had already built a second prototype (scrapping the first WordPress-based version because it wasn't beautiful enough). Mark immediately saw the potential from a sales perspective; he'd experienced the pain of clunky document tools at Google.

Lucky breaks accelerated development. Dan, a lead engineer from Google Wave's text editor project, was so impressed by Dylan's prototype that he joined the team early on. He'd even written custom libraries to solve dependency injection problems in Angular, the beta framework they were using. The technical bar for a beautiful web-based editor was extremely high in 2014, and having Dan meant they could actually clear it.

Mark and Dylan committed to a two-month experiment: work for free and see if they could find their first 10 customers. Mark's entire job was validation—getting the product in front of as many people as possible, collecting feedback, and talking to potential customers. They heard plenty of nos. Mark once drove 45 minutes for a half-hour coffee to demo the product, then drove 45 minutes back. That person eventually became a customer.

They released a free version and cold-called relentlessly. One breakthrough came from a video producer who realized that embedding video in a web page was vastly superior to static PDFs or PowerPoints. That became their first niche. They discovered something else: Quiller had light virality. Every proposal sent out included a little URL badge leading back to them. After about two months, they had unaffiliated paying customers (at $20/month each), and suddenly it felt real and possible.

Freemium was seductive. The viral loop seemed perfect—why not make it free and amplify that effect? So they tried it, and virality did spike. But everything else tanked. Their sales cycle, which had been 14.5 days with a trial, blew out to 60 days. Worse, activation rates dropped significantly. With a 14-day trial, users spent 50% more time in the app trying to activate (creating and sending their first proposal). Without time pressure, they'd sign up for free and never come back. Conversion plummeted from roughly 3x year-over-year growth to 70-80%, which felt catastrophic.

They also discovered that free users tend to refer other free users (who are cheap), while paid users refer other paid users at higher tiers. The entire unit economics of freemium inverted against them. After experimenting with different approaches—working with growth teams from TypeForm and Intercom, testing 14-day vs. 30-day trials—they eventually shut down freemium and their cheapest plan. They doubled their top-tier pricing as a forcing function.

The bigger realization was their "original sin": focusing on the SMB/prosumer market for too long when they should have been targeting sales and marketing teams at mid-market companies all along. Hundreds of product decisions had been optimized for freelancers and small businesses. Their SEO strategy targeted small businesses. Their pricing and features reflected that. By the time they started closing actual sales teams, the product had to be retrofitted with collaborative editing, team permissions, folders—all the things enterprise teams needed.

When they finally committed to moving upmarket—killing freemium, killing the cheap plan, raising prices, investing in direct sales, and eternally communicating the shift internally—growth accelerated again. Sales teams expanded from 10 seats to 30. They didn't churn. They were 10-15x more valuable than SMB customers over lifetime. Mark realized you can't just announce a direction change; you have to structurally force it through pricing, product, go-to-market, and relentless internal messaging.

Quiller now has 3,000 customers, 45 employees, and has raised $7.5 million. They're focused on helping enterprise and mid-market sales and marketing teams create web-based proposals that integrate with Salesforce, HubSpot, Xero, and Slack. The product has evolved into a truly collaborative tool with powerful integrations and analytics. Mark and Dylan learned that product-market fit isn't a destination—it's clicking through gears. You find first gear (SMB), then have to figure out how to shift into second or third (upmarket, new channels, expansion motions). The journey from two months of free work to 45 people and $7.5M raised taught them that focus is everything, and that the market you start in may not be the market you own in five years.