When the shelter-in-place order in California went into effect in March due to the covid-19 pandemic, Chase Roberts found himself working remotely for the second time in his career. The first time came in the middle of last decade, after Roberts joined online sharing and content management company Box.
Roberts, who earned dual degrees in finance and entrepreneurship and venture management from the University of Oklahoma, joined in sales as a remote employee from Dallas. He spent 18 months during his five-year tenure at Box before relocating to the San Francisco Bay Area.
Now a principal with Vertex Ventures, which recently closed on $150 million for its second fund, he tells Venture Capital Journal that while working from home, some of the feelings he regularly felt during his stint in Dallas have resurfaced. Particularly, he misses the serendipitous collisions, or the water cooler talk, that happens when co-workers share an office. Those don’t happen with the structure and scheduled teleconferencing calls.
And although Slack may feel like random chats, Roberts points out that conversations there don’t happen by accident but rather because one person initiated the discussion. “Current tools create a lot of noise and tend to make us feel like responses are imperative at the earliest opportunity,” he says. “Office chats are lost among remote teams, which has been one of the dominant reasons many companies resist going remote.”
Roberts is developing a thesis that a platform should exist to help remote workers decipher what needs to be addressed later and what needs to be addressed right away. He hopes that will bring back the casual office chats that lead to serendipitous moments of collaboration.
“I met a founder [prior to the coronavirus] whose entire team is remote, spread across four continents,” Robert says. “That’s more often the case these days with start-ups. And now in semi-quarantined life, everyone is paying attention to how to do it.”
For Roberts, it’s nothing new for him to develop a thesis and then scour the tech community in search of a start-up.
He did that right away when joining Vertex Ventures last fall. Harkening back to his days in sales at Box, he began rethinking document file management and how files and content are shared online.
His efforts led him to Evisort, a San Mateo, California-based start-up that uses AI to help companies mine legal documents, such as sales contracts and vendor paperwork.
In December, Vertex Ventures and M12 Ventures, the VC arm of Microsoft, co-led the company’s $15 million Series A round, which included Amity Ventures and Serra Ventures.
Vertex Ventures general partner In Sik Rhee describes Roberts as a “star in the making” whose sales background makes him able to carry a conversation with anyone, from investors to entrepreneurs.
“He asks questions and is a quick learner to investing and other areas,” says Rhee, who launched the fund in 2015 with Jonathan Heiliger. “Chase has helped increase our dealflow and raised our awareness as a firm.”
Leaning on salesmanship
Roberts says his secret weapon when it comes to deal sourcing is his sales background. He likes to send emails to entrepreneurs, often guessing the email name based on the company URL.
“The key to a good cold email is to dive right into the conversation,” he says. “I like to share interest and show excitement. And l keep the intro to three sentences.”
Roberts then gives some background on the firm, and adds that he doesn’t try to specify the nature of a meeting in the initial email. “I leave the preference to them,” he says.
But he looks to set up a meeting, ideally via a videoconferencing call.
“I try not to do a phone call,” he says. “I want to look them in the eye. I do better that way.”