A 'warrior's warrior': Why insiders say the first-time CFO running Lyft's $20 billion IPO is the perfect fit

Brian Roberts, who joined Lyft as chief financial officer in 2014, had no experience as a CFO.Instead, the 50-year-old brought a wealth of tech, retail, and financial knowledge acquired at Microsoft, Walmart, and two banks.He's playing a lead role in the company's IPO, helping convince prospective investors understand Lyft's financials and growth potential.Former colleagues describe Roberts as a “warrior's warrior” who can see problems before they arise and making him the perfect person to oversee the company's roughly $20 billion IPO.Lyft had never had a chief financial officer before hiring Brian Roberts from Walmart in 2014.And Roberts, for all his experience in consumer retail and banking, had never been a CFO.But now, with Roberts now in the ride-hailing company's C-suite alongside founders John Zimmer and Logan Green, Lyft is quickly racing toward an IPO.This week, the team, along with bankers, will meet with prospective investors across the US before pricing its roughly $20 billion offering next week.Former colleagues say Roberts, a seasoned veteran of banking, technology, and retail, is the perfect person to oversee the first ride-hailing IPO to hit stock exchanges.Here's how the 50-year-old found himself in the driver's seat of one of the world's hottest companies as it chases a historic first.It all started in the Bay AreaAfter studying economics for an undergraduate degree from UC Berkeley, Roberts headed to Harvard Business School for an MBA. He worked his way up through the ranks at investment bank Lazard to vice president, according to his LinkedIn.It was back on the West Coast, however, where his interests would shift from banking to business development.In 2001 he joined Microsoft. At the time, former colleagues say, the corporate-development office at the software giant included a wide range of bets, including updates to the Office software suite, the X-box video-game console, and online efforts like MSN.“These were very different products, with different go-to-market strategies, and different capital modes,” John Connors, a former Microsoft CFO, said of the company's efforts while Roberts was on the team.“He was also excellent at recruiting talent and working across the company on complex issues that covered product, tax, accounting, and integration.”Back to Wall StreetRoberts was then lured back to financial services when investment bank Evercore poached him in 2006 to help build out the firm's West Coast advisory practice. Over five years at the bank, Roberts worked his way up to senior managing director.“Brian is a warrior's warrior,” former Evercore colleague Michael Price told Business Insider. “He is so concerned about what could go wrong, that he's worried about it before you have even though about it.”From an investor's standpoint, I would sleep very well at night knowing that Brian is watching.“Walmart's e-commerce beginsIn 2011, Roberts joined Walmart to oversee merger-and-acquisition strategy for the world's largest retailer. In the span of three years, the chain snapped up more than a dozen high-profile retailers that would set the wheels in motion for Walmart's major push into e-commerce.The groundwork laid by Roberts and his work with Walmart Labs would see the chain snap up big names like Bonobos, ModCloth, Moosejaw, Jet.com and more.Landing at LyftRoberts hit the ground running at Lyft, which was still in its infancy when he arrived in 2014. That same year, Lyft raked in a $2 billion investment from backers including Chinese internet giant Alibaba and activist Carl Icahn.In the time since, Lyft has raised more than $4 billion in venture capital ahead of its IPO in a handful of deals. The company has also acquired Motivate —a bike-share operator with active fleets in New York, Chicago, Boston, San Francisco, and other cities — now branded as Lyft Bikes.”What I love about my job is that it is about so much more than just the numbers,“ he told the Financial Times of his new gig at Lyft in 2016. Though his expertise with the numbers will certainly come in handy as Lyft reinvests the roughly $1.9 billion in proceeds from its IPO back into the business.There will be high pressure too. Take Facebook's David Ebersman, for instance. The social network's CFO oversaw in 2012 what at the time was largest-ever internet IPO — and ended up taking most of the heat when that offering delved into chaos.By the time the dust had settled, more than three months later, shares had fallen more than 50% and the company was facing government probes and dozens of lawsuits. Ebersman was accused of pushing 25% more shares on the market when Facebook went public and allowing the price to set well above the company's initially planned range.Still, Ebersman stuck around at Facebook for two more years, by which time shares had climbed far above their IPO rut.And with an industry as nascent as ride hailing, all eyes are on Lyft to test the waters. Uber, after all, is likely watching with bated breath as it awaits launching its larger IPO this year.A variety of experiences to draw upon can only be a good thing for Roberts at Lyft.As Price, of Evercore, summed it up: ”He's adaptable.“”I crack up when I watch his career,“ Price said. ”He's seen it all.Do you work at Lyft？ Have a news tip？ Get in touch with this reporter at grapier@businessinsider.com. Secure contact methods are available here.