When Flexport’s Amy Lance showed up to what she thought was a client onboarding meeting in 2015, she was met with not one but two surprises: Not only had the client not yet signed a deal, but the company hadn’t even seen a demo of Flexport’s supply chain management solution. 

Without hesitation, Lance, then an operations manager, guided the prospect through Flexport’s platform, lending her hand to a deal that the company would later close. In a situation where many might enter a state of panic, Lance said she saw an opportunity.

“I quickly realized that this was a chance for me to fill a role that Flexport needed,” Lance said.

This experience set off Lance’s career pivot to sales, where she now leads as a sales director from Flexport’s LA office.

Like Lance, Taylor Oliver, who began at Flexport as its first sales development rep, shares similar tales of stepping up to support the company’s growth. 

“When I started there were just 10 people in the company,” Oliver said. “The company needed people to step up and fill the gap. We all had to wear different hats, and it was never about titles. It was, ‘How do we solve this problem today?’”

Today, Oliver is the general manager of the company’s Southwest region.

Oliver’s and Lance’s ability to “step up and fill the gap” inspired their paths to leadership and continues to play an important role as the company adapts to changing industry demands. 

“We are used to operating in an evolving chaotic environment,” Oliver said. “This is how we have grown for the last six years, and as a result, we’re very agile.”

How has your career path reflected the “step up and fill the gap” mindset?

Oliver: Flexport has been in a high-growth state for the past six years and every day presented new, complex challenges that someone needed to solve. When I identified these challenges, I always committed myself to diving deep on these problems and solving them in order to provide the most value to the company. Whether that was building out our SDR processes or opening our Chicago office and growing Flexport’s presence in the Midwest, I put the company needs first and ended up having many opportunities to grow as an individual as a result.

Lance: My transition from operations to sales was also an opportunity to fill the gap. And to preface, I had no intention of ever being in sales. I had a vision of what a salesperson was and I did not fit that at all. I’m definitely an introvert.

In operations, I supported our head of sales. As his plate got full, he started involving me in deals further upstream. In these conversations with prospective clients, I quickly realized I loved selling. It was about learning how companies were set up and listening to what issues they dealt with within their supply chain and then identifying ways we could help. Although I did not have formal sales training, coming from operations, I intimately understood our product and how we’d helped similar companies. I was able to draw on that to build trust and design solutions to make an impact in their business.

Who has helped you throughout your career journeys at Flexport?

Lance: I leaned on my team and peer group within Flexport. With so many people coming into the company with no prior freight experience, there is a culture here built on learning that encourages people to ask questions and help one another answer them. There’s also a lot of cross-departmental movement within the company, which helps to build a support network across the many functions.

Oliver: I have also leaned on and learned from my team and peer group, and have sought out opportunities to learn from the industry experts we’ve hired. I used to interview new hires after they started to pick their brains on their areas of expertise and learn everything I could. I was never afraid to ask someone to join me in a client meeting to provide additional support.

What formal initiatives does Flexport offer to support growth?

Oliver: We have an internal team that’s focused on learning and development. Recently, we held multiple webinars to help our team better adapt to remote work. We also host external webinars and have learning courses via online platforms available for individuals or entire teams to take. 

How does Flexport emphasize a culture of promoting from within? 

Oliver: One of our OKRs this year is to fill 50 percent of our above entry-level roles with internal candidates. This encourages promoting from within and internal mobility, which we think accelerates the learning of our team members. I firmly believe that Flexport’s future leaders will be individuals who have worked in different departments and functions who have developed a thorough understanding of how we operate and adapt across the company. 

Lance: It sounds obvious, but I think it is crucial for leaders to deeply understand the business they are leading. Those who have worked successfully “in the trenches” gain this and understand the actual work we’re doing, what our customers truly value and how the two feed off one another so we can continue to build a better company.