Last September, ZenPayroll’s employees streamed into their San Francisco office at 6 a.m. And then, regardless of their role, hopped on the phone with customers to explain what had just happened: They were now Gusto employees. The company had rebranded, and the change extended much further than the name and logo — they would now be going after the competitive health benefits market in addition to outfitting businesses with payroll software. This could have been frantic and stressful. But their voices lighting up the phones were bright and celebratory instead.
The switch happened fast, smoothly, and got a plum round of press coverage. But it was far from the overnight effort it appeared to be. In fact, CEO Josh Reeves and his co-founders had been plotting the pivot since the company’s incipient days at Y Combinator. They knew their aspirations transcended payroll and that years down the line they’d need to overhaul what they had already meticulously built — a daunting prospect. [Read More]