Inside Outreach: the hard-charging cloud startup thriving in Salesforce's shadow
for $6.5 billion, suggesting it could move on Outreach or a rival if the time were right. “It’s clear that Salesforce isn't afraid to make big, bold, expensive moves,” says Forrester analyst Mary Shea.But Outreach’s success has had its human costs. Eight former employees who worked at the company between 2017 and 2019 describe a hyper-competitive workplace that led to constant turnover, cutthroat by even software startup standards.
In Outreach's cash-strapped early days, Medina landed in the hospital with a tooth infection; he had quit paying insurance premiums to save costs. A former Microsoft exec, it was hard adjusting to startup life and"barely making things meet."He graduated from the Stevens Institute of Technology in New Jersey in 1997, then received a Master’s in computer science at the University of Pennsylvania and an MBA from Harvard.
In February 2014, Medina had his breakthrough. He was in downtown San Francisco, preparing to head to the Crunchies, the tech industry’s annual award show. The GroupTalent tool, which scraped public Internet profiles to help craft personalized pitch emails, was generating high open rates. But his small sales team couldn’t close enough deals to keep going.
As the funding and product took off, the atmosphere inside the Seattle headquarters and remote offices grew intense. Staff swelled into the hundreds, and turnover accelerated. People were complaining about the culture. Working through weekends and vacation was an unspoken rule, four former employees say. It was common to receive messages from managers past 10 p.m.
“This is not a checkbox for me,” he says. “This is the life I want to live. I want to be surrounded by people who want to feel included, who are doing their best work with peers that they love and respect.” edina estimates Outreach has tapped less than 1% of potential customers. His current clients are the ones that try new tech early.
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