By Robert Sison, Chief Financial Officer, Shift5

From 2017 – 2018, I took a step back from corporate life, tucking away my work-sanctioned laptop and the long deskside hours, and said farewell to teammates who I’d bonded with through the rigor of the startup world. My sabbatical came after more than two decades in finance. I’ve worked with companies at every stage of growth, from public to private; methodically explored every role in the finance team, from M&A to investor relations; and gone deep in multiple industries, from enterprise and semiconductors spaces to AIOperations and video games. This diversity of experience gave me a unique perspective on the role of finance in business successes, and provided a concrete platform for identifying the type of company I’d work for next.

During that year, I took a keen lens to my priorities. I reassessed every variable, especially considering how work fit into the puzzle. I spent time reflecting upon my experience across the corporate world, the best attributes of the companies I worked with, and set specific expectations about the kind of company I would align myself with going forward. It was following this introspection that Shift5 entered the picture, and I began to immediately identify the attributes of a company that I had set out to align myself with.

While there are several reasons I chose to join Shift5, here are the most significant:

The People

Startup life is difficult. All at once, you are developing foundational processes and policies, executing on them in real time, and sharing battle-tested opinions on how to deploy the proper strategy for long-term success. Amid the hard conversations and the late nights, the constant variable is your team. You spend 8+ hours with your teammates daily, relying on their domain expertise, skills, and commitment to navigating the journey together. You’ll be in the foxhole together, and you must have confidence in those in the foxhole with you.

From my earliest conversations with Shift5, it became clear that the people at every level of the business are those who would get their hands dirty and break down walls to move forward. I’ve worked with many of the individuals at Shift5 in different phases of my career, and I’ve seen what happens when they work together. Shift5 is entering the game with a team that’s already built trust, established unique working styles, and can execute. The Shift5 leadership team brings significant experience and knowledge from a number of different fields, and their openness to collaboration is unparalleled. It was an easy decision to jump into the foxhole at Shift5.

The Culture

The problems Shift5 is addressing are extremely complex and difficult. No one person can do it on their own, it requires a team. And one measure of a team is its culture. A company’s culture can never be manufactured; rather, it’s developed organically through personal engagements, commitment to solving a problem together, and through mutual respect.

At Shift5, there are industry experts who have built technology that has changed industries. There are national security veterans who’ve been on the frontlines of combat, and who’ve engaged with the top echelon of national intelligence and defense. And despite the differences in career histories, they all share similar values: operating with integrity; being collaborative; solving hard problems with rapid, quality solutions; and maximizing real world impact. The team that’s steadily grown at Shift5 has reflected this caliber of excellence and embodies the values of the organization. The culture that has developed across the company gives me confidence that – even though Shift5 is tackling such a complex problem in the road ahead – it will fulfill its mission.

Solving a Real Problem

Shift5 protects the assets that defend our country and the planes and trains that the vast majority of people use to travel. The economy relies upon transportation infrastructure to operate as expected, just as the Department of Defense relies upon tanks, aircraft carriers, and jets to operate with resilience. Defending these assets, and enabling their operators to use them as strategically as possible, is a matter of national security. The Shift5 team is laser-focused on making these vehicles and modes of transportation safer for everyone. In this way, Shift5 is focused on maximizing our real-world impact.

And this effort is getting noticed by those in the field who share the same mission. Shift5 has seen significant growth over the last few years –  revenue, customers, opportunities, and headcount. The investment community has taken notice, as evidenced by our Series B round, which attracted Insight Partners, and AEI HorizonX. The market timing, the founding team and senior executives, coupled with investors and adoption across federal spaces, commercial aviation, and rail markets indicates Shift5 is at the right place at the right time, and that we are solving a real problem. Based on the opportunities in front of Shift5, this growth will only continue. 

Being part of a startup is an exciting journey. It’s working together and helping where you can. My main goal at Shift5 is to develop a team, and work with the organization to move the company forward. As Shift5’s first-ever CFO, I’ll take the lead on developing the company’s financial infrastructure, which will allow the brilliant people here to build the product and get it into the market, so we can scale the company efficiently and effectively.