Clary

In 2017, Thomas Konjapu and Ryan, both at Twitter, noticed something interesting: large tech companies invested heavily in building internal tools for employee experience. Thomas was hired specifically to create products for Twitter's employee base, while Ryan had previously worked in HR tech. They realized this pattern was repeated across the industry—companies like Amazon, Google, Microsoft, Uber, and Dropbox all had similar internal tools solving the same core problems around communication, alignment, and culture. This observation sparked the founding idea for Clary: why not build this solution externally for companies before they needed to invest millions building it themselves?

Rather than immediately launching a product, Clary took an unconventional path. The founders leveraged their network to pitch the idea directly to Square, who was experiencing rapid growth and needed to invest in employee experience infrastructure. Square had around 2,000 employees at the time and multiple VPs involved in the decision—already a true enterprise sale. Critically, Clary proposed a unique arrangement: they would act as service providers, essentially a product and engineering consultancy, but would retain all intellectual property. This allowed Square to validate the solution without committing long-term SaaS spend, while Clary learned how to solve the problem at scale.

What was meant to be a three-month engagement evolved into a two-year partnership. The founders focused obsessively on making Square successful, delivering and over-delivering on feature requests, building trust that made the relationship work despite the unusual structure. They were bootstrapped and didn't raise money during this phase, knowing that "customer revenue tells you where things are going."

After two years, the founders realized they had a choice: continue optimizing for Square's custom needs or build a true multi-tenant SaaS product. By late 2018, they began lifting their heads beyond Square. In early 2019, they closed a couple of customers quickly through their referral network and simultaneously raised a small round "of a few million" in funding. This capital enabled them to hire a broader engineering team and shift focus entirely to building a scalable product.

The path from customer one to ten took roughly a year and a half. The pandemic accelerated demand as distributed work became universal, validating their core thesis about the need for a digital hub when physical offices weren't available.

Early channel experiments—Google Ads, LinkedIn Ads, event sponsorships—largely failed. Thomas realized that paid advertising didn't work for a non-transactional product requiring mindset change. "Ad spend needs to be patient capital with a return horizon well into the months," he noted. Event sponsorships also underperformed compared to digital outreach.

What did work was referrals from satisfied customers. Because the product had to be excellent and the value proposition required deep stakeholder buy-in, customer word-of-mouth became the primary growth engine. Cold outbound also proved effective when targeting prospects similar to existing customers, especially after the team refined their messaging and sales process.

Thomas discovered critical sales lessons in enterprise deals: controlling room attendees matters enormously. Walking into a demo with 20 people created friction and delayed time-to-value. The solution was conducting pre-meetings with individual stakeholders first, so when the larger meeting happened, key decision-makers were already sold and could advocate internally.

Positioning evolved significantly. Initially, Clary branded itself as an "external internal tools team," but this only appealed to companies at the exact moment of deciding to build in-house. The market expanded dramatically when they repositioned around the Chief People Officer persona, emphasizing employee retention and engagement in distributed work. They stopped leading with "we replace intranets" (though that remained a secondary pitch) and instead focused on being a platform for modern employee experience—combining directory, onboarding, internal communications, and cultural programs in one digital hub.

Clary has grown to approximately 15-16 people and recently crossed $1M ARR after raising $7.5M in venture funding. Their customer roster includes major names like Square, DoorDash, and Scale. The sales process remains enterprise-focused: discovery calls, custom personalized demos, trial periods, and typical close times of 2-3 months for mid-market (their bread-and-butter segment) and up to three quarters for enterprise (1000+ person companies).

Thomas credits their success to three factors: building a genuinely excellent product that customers want to refer, maintaining focus on their core market rather than chasing every channel, and learning to adapt their positioning and sales approach based on customer feedback and market signals. The journey from a single services engagement to a scaling SaaS product required tremendous patience, but it provided unmatched market validation and customer intimacy.