It wasn’t the first time he’d felt this way — Isaac knew firsthand that entrepreneurs face challenges of all shapes and sizes. At Adtuitive, his first startup, the time he spent on hiring, payroll, and compliance kept him from focusing on what mattered most.
Workplaces were evolving. The needs of entrepreneurs, growing businesses, and employees had become more complicated, but the infrastructure to support them hadn’t kept up. The internet had made many things easier, but even people running internet businesses were still hunching over fax machines to hire and pay their team, not to mention struggling to understand complex payroll tax and compliance requirements.
Even people running internet businesses were still hunching over fax machines to hire and pay their team.
After Etsy acquired Adtuitive in 2009, Isaac led Etsy’s HR and payments group, where he worked extensively with sellers, remote and distributed teams, and freelance and part-time employees. Again, he saw the constant administrative and compliance burden stifling people's full potential — there had to be a better way.
So, in 2012, Isaac left Etsy to build one.