Jonathan Sides's guest appearances

Jonathan Sides

CFO THOUGHT LEADER

OwlTail

Among the many SaaS CFOs with whom we have spoken, few have listed their finance leader priorities for us as simply and concisely as did Jonathan Sides, CFO of Fleetio, a Birmingham, Alabama, software company that helps companies to track and manage their fleet operations. “My personal defect is always wanting to take on more—without realizing that I should actually be giving away my LEGOs and finding people who can do things better and faster than I can,” explains Sides, who labels his first CFO priority as “Always be hiring.” According to Sides, between 60% and 80% of Fleetio’s workforce lived in the Birmingham area prior to the pandemic—but now the percentage of local employees has dropped to less than 50% as the company has actively recruited more remote workers. Next, he advises CFOs to work closely with the company’s investors to help them to understand the challenges that a company may be facing.   “The only way that they can help you is if they have the unvarnished truth,” comments Sides, who notes that investors will typically have three responses: “They’ll say, ‘Don’t worry, this is normal’ or ‘Don’t worry, we know how to fix this’ or ‘Good luck, we know that you know how to fix this.’”      The third and last priority that Sides lists is “Achieving work/life balance”—an area, Fleetio’s CFO tells us, with which he has long struggled and that in the past has led him to take some inspired action.   Back in 2014, prior to joining Fleetio and having just completed a 14-year tour of duty as CFO of another Birmingham SaaS firm, Sides scheduled a “gap year” for which he and his wife bought “one-way air tickets” to kick off 12 months of travel during which they lived in 12 different countries. Still, all roads eventually led back to Birmingham and, of course, the SaaS model. –Jack Sweeney

Among the many SaaS CFOs with whom we have spoken, few have listed their finance leader priorities for us as simply and concisely as did Jonathan Sides, CFO of Fleetio, a Birmingham, Alabama, software company that helps companies to track and manage their fleet operations. “My personal defect is always wanting to take on more—without realizing that I should actually be giving away my LEGOs and finding people who can do things better and faster than I can,” explains Sides, who labels his first CFO priority as “Always be hiring.” According to Sides, between 60% and 80% of Fleetio’s workforce lived in the Birmingham area prior to the pandemic—but now the percentage of local employees has dropped to less than 50% as the company has actively recruited more remote workers. Next, he advises CFOs to work closely with the company’s investors to help them to understand the challenges that a company may be facing.   “The only way that they can help you is if they have the unvarnished truth,” comments Sides, who notes that investors will typically have three responses: “They’ll say, ‘Don’t worry, this is normal’ or ‘Don’t worry, we know how to fix this’ or ‘Good luck, we know that you know how to fix this.’”      The third and last priority that Sides lists is “Achieving work/life balance”—an area, Fleetio’s CFO tells us, with which he has long struggled and that in the past has led him to take some inspired action.   Back in 2014, prior to joining Fleetio and having just completed a 14-year tour of duty as CFO of another Birmingham SaaS firm, Sides scheduled a “gap year” for which he and his wife bought “one-way air tickets” to kick off 12 months of travel during which they lived in 12 different countries. Still, all roads eventually led back to Birmingham and, of course, the SaaS model. –Jack Sweeney