Stay Flexible and Over-Communicate: Lessons From Building Oscar's Sales Team

Bobby Guelich is no stranger to taking risks. After beginning his career at mega hedge fund Bridgewater Associates, he headed west to attend Stanford University’s prestigious Graduate School of Business. He spent his summer interning at Oscar, when the company was still in its nascent stage and had only a handful of employees. As his internship came to a close, he met with the CEO, who asked him to join the team permanently. After a significant amount of soul-searching, Bobby realized that given the team he’d be working with, and the company’s mission, this was a no-brainer; “I was confident enough in Oscar’s mission, team, and the opportunity to know it was worth it for me to take this risk. Honestly, it didn’t seem like there was any real risk. I knew it would be a great learning experience either way.” During his tenure building and leading the business operations and sales teams at Oscar, the company underwent explosive growth, which showed Bobby the value of flexibility, over-communication, and transparency.

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He likened those early days to jumping into the deep end. For example, as the head of the sales team, one of Bobby’s key responsibilities was forecasting. Forecasting can be pretty straightforward when you have years of data and predictable revenue, however as veterans of early stage startups can attest, it takes many years to reach that level of comfort. Further complicating the forecasting model was Oscar’s unique business cycle. The company holds an open enrollment period from November to January, during which the vast majority of business occurs. The sales team ramps up significantly during that period to handle the increased demand. In Bobby’s first year he scaled his team from six employees to 40 in a matter of months, and during his second year his team grew to 130. With so many moving pieces, building a strong team and a cohesive training program was essential.

Bobby’s first open enrollment period (only the company’s second) came only a year after the launch of healthcare.gov , and its myriad issues. The craziness of that period though made it all the more difficult for him to forecast when he first began leading the Inside Sales team. This meant that there had to be a significant degree of flexibility built into Bobby’s forecasting plan, and the processes he built for his team for the subsequent year. As Bobby stated, “there’s no real science in the early stages, and the data is often incomplete. You just have to know that you have a process in place, and a strong team to execute against the plan. As you get more open enrollment periods under your belt it becomes more about iterating. The level of uncertainty goes down a bit- but it’s always there.” Processes inevitably broke, especially on hectic days during the open enrollment period, in which inbound traffic was multiples higher than on most days. However, Bobby’s team was able to cut through the chaos and uncertainty of those early days and be successful, because he had built such a strong and resilient team.

Missions allow you to find and retain the right people who are motivated for the right reasons. This was huge. In my experience, being an authentically mission driven company allows you to recruit and retain a much higher level of talent than you would otherwise.

For Bobby, a critical component uniting Oscar’s team was the company’s mission-driven environment, because “missions allow you to find and retain the right people who are motivated for the right reasons. This was huge. In my experience, being an authentically mission driven company allows you to recruit and retain a much higher level of talent than you would otherwise.” Having a base of individuals who were on the same page engendered continuity. To continually ensure that everyone was aligned, Bobby and the rest of Oscar’s senior management relied on over-communication. This tactic paid dividends as the company spread its footprint and built a Customer Care Center, comprised of individuals handling every customer issue, in Arizona.

You can’t communicate enough. There’s no such thing as over-communication. Even if you feel like you’re saying the same thing, people are still just picking up on it for the first time, on your tenth time saying it.

As Bobby asserted, “you can’t communicate enough. There’s no such thing as over-communication. Even if you feel like you’re saying the same thing, people are still just picking up on it for the first time, on your tenth time saying it.” This level of communication naturally bred transparency and visibility across the organization, which was yet another piece of the company’s strong foundation. In addition to the firm’s heavy emphasis on regular all-hands meetings, executives would visit the Customer Care Center regularly.  As Bobby declared, “when we built the large contact center we had to do a lot more to make sure that company felt connected and we were disciplined about making sure business leaders from virtually every department visited regularly.”  It may be tempting for companies to neglect satellite offices, but Bobby and the rest of the executive team recognized how invaluable the feedback the Customer Care team was collecting, since they were Oscar’s front lines. In fact, Bobby had someone on his team whose job it was to synthesize feedback from the Customer Care team, and that data and analysis would be shared on screens across the company.

Transparency was a defining theme at Oscar, and that carried over to the company’s interactions with customers. Bobby realized that to build an impactful and effective sales team, he needed to create an educational process that promoted diagnosing the best solution for the customer. Many startup sales teams espouse that same ethos, but few are able to follow through on that impulse. As Bobby asserted, “we wanted to be an education-based sales team, and not a pushy team. We didn’t want to set up a structure that incentivized people to stay on the phone and close.” This approach was embedded in sales training and compensation structures, and reinforced along the way through regular reviews.

Oscar is a truly unique company, in terms of its business model and sales cycle. However, many of the lessons and strategies Bobby learned and employed throughout his time there can be applied more broadly. Flexibility is essential, and the key to effectively scaling is building a strong team, comprised of individuals who are united around a singular mission. Finally, transparency at every level of the company, and in every external interaction is a powerful driver of success.

5 Fast Facts

 First job: "My first job was being a basketball camp counselor."

Most humbling life experience: "When I started at Bridgewater, I took an investment class with all of the new investment hires, that was led by one of the firm’s Chief Investment Officers. It was an intense atmosphere, and you never knew when you were going to get cold-called. I’ll never forget during one of the first classes, I was asked to ‘explain the business cycle.’  I mumbled something and the Chief Investment Officer just tore me apart, in the most unvarnished way. I remember sitting there thinking, the most senior guy at Bridgewater thinks I’m an idiot and I’m never going to survive. Fortunately long term everything worked out - this situation was indicative of the firm’s culture, which definitely motivated me and compelled me to constantly improve."

Random fact:  "I danced on stage with Girl Talk at the Treasure Island Festival - it made me briefly consider being a rockstar!"

Productivity hack: "My simplest and most effective productivity hack is to accomplish the most important task first thing in the morning"

Favorite book: "A Prayer for Owen Meany"


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