Zach Rego is the Chief Revenue Officer at Triple Whale, the AI operating system for commerce used by more than 60,000 brands, where he leads sales, partnerships and marketing. He joined four and a half years ago as the company's first head of sales, starting from an Airtable of 2,000 waitlist names, and has built the revenue org from two sellers to roughly 40 reps across SMB, mid-market, enterprise and international markets. Before Triple Whale he spent seven years at WordStream, rising from individual rep to general manager of the global agency business, and then led sales and marketing at Unstack, later acquired by Elastic Path. He started his career in IT consulting services, selling to Fortune 500 CIOs.
“I think in-person has become so mission critical and personalization is going to need to go to like the craziest degree to work.”
“It was a very scrappy, "How do we collect as many dollars as we can?" We'll figure out the rest later motion.”
“I always had the vision of, what does 12 months from now look like when I hire people? What data do we need to collect today so that one day I can route SMB leads to our SMB rep or mid-market to our mid-market team, et cetera.”
“If you're making that decision, you need to go and try to sell it because the feedback loop is going to be so much faster for you to iterate and you'll know where the friction points are.”
“If I had just looped in an AE, that deal closes because they'll handle the follow-up.”
“I'll let the expansion sales rep do the discovery. I might add a couple things in there, but I want to do the presentation and the pricing because I feel like that's where we're going to hit the most friction and need to uncover the value for the prospect.”
“It worked okay, but it actually inhibited usage. People were fearful of hitting the limits.”
“There's a benefit and a downside to that, in that customers are blowing themselves up when they're like, Opus 5.5 max, and then ask a question, like, "How many sales did I have today?"”