Written By
Rich Miner

Eleven years ago, when I set up GV with three other general partners, we began with the thesis that we'd bet on people as much as companies. Serial entrepreneur Craig Walker was one of the first founders we backed, and we brought him into GV even before he knew exactly what kind of company he would start. Investing in great people is often a better strategy than investing in a great idea.

Craig had already built his reputation in the telephony industry with Grand Central, a pioneering voice-over-IP company that he founded in 2005. I met Craig when Google acquired Grand Central and the platform became the blueprint for Google Voice (now Duo). Craig was already thinking ahead to his next venture. At that point, he thought he might do something with the new level of mobility offered by the iPad, which had just come out. He began experimenting with restaurant ordering systems.

"In 2010, I moved into GV as an EIR," Craig remembered. "We lived in the GV offices and worked with the GV design team. We felt that the restaurant industry posed a huge opportunity to be modernized; fast forward to what Toast has done. But we quickly realized we didn't have any unfair competitive advantages in hospitality."

Some of GV's strongest exits have been pivots (Slack, for example, started out as a videogame company), and we believe that experimentation and reinvention are essential parts of the entrepreneurial process. After Craig's look into the hospitality business, he doubled down on the space he knew best, and decided to build a new type of tool for business communication.

"The world was already transitioning to doing IP voice at scale, and it was all consumer-focused at that point," he said. "I realized that enterprises had moved everything to the cloud — but there was still this one closet you opened up, and there was a PCX." The setup was even more complicated for large organizations, where the PCX system was too big to fit in a closet; it needed its own room. "There are thousands of blue wires. Every time somebody moved desks, you had to hire someone to move the wire."

Craig's first move was to introduce a better conference call product that employees could adopt and manage themselves, without having to go through their company's IT manager. In 2012, he and his team launched their new product, Uberconference, at TechCrunch Disrupt NY and won the event's startup competition.

Employees loved the early Uberconference product because it gave them a degree of freedom, in many ways presupposing today's shift toward remote work. "Our pitch from day one was that work isn't a place you go; it's a thing you do. You do it from anywhere, you do it all the time. Location doesn't matter."

"It's funny when you look back. It all looks high and to the right, but if you zoom in, there are a million gyrations of ups and downs along the way."

With Uberconference gaining traction, the next challenge was turning the solution into something well suited for the enterprise. Craig's engineering team had run Google Voice and understood how to build for scale. They added reporting and analytics and made deployment really simple. Their first enterprise sale, to Motorola, came relatively easily.

After that, things got harder. "We tried to build out a big sales force and aim them at traditional buyers, like an insurance company in Baton Rouge." They were met with skepticism outside of Silicon Valley, and larger companies seemed reluctant to make the switch away from legacy systems. "If I had to do it over again, I would have focused on the mid-market more and longer. Enterprise sales forces are expensive, and the process is slow and long. You hire your enterprise sales team, and you won't know for a year if it's going to work."

For any young company tackling a massive market, I encourage founders to focus on controlled growth — resist the temptation to go after anything that's more than twice the size of your biggest deal. After struggling with long sales cycles for very large enterprise customers, Craig recalibrated with a focus on the mid-market. And things started to click.

Sales really took off for Dialpad after COVID-19 forced most of the world to close offices, transforming how people think about the workplace. "All of a sudden, every one of those legacy CIOs had to support people working from home," said Craig, who estimates that 90% of the enterprise market has had to migrate away from legacy systems. "COVID-19 accelerated that trajectory by eight years."

Dialpad reached unicorn status this year, and in the past 12 months, has exceeded $100M in committed ARR, with cloud contact center business growing fast. Craig said he thinks of the company's journey as a story of incremental growth. "It's funny when you look back. It all looks high and to the right, but if you zoom in, there are a million gyrations of ups and downs along the way. All these things are almost like life and death decisions, and somehow you pick the right door, and the adventure gets to continue."

In short, as Craig put it: "Things generally work out as long as you keep working."