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On first glance, Ra Medical Systems CFO Andrew Jackson\u2019s 20 years as a finance executive in life sciences and technology companies seems have progressed in a traditional, orderly manner. A closer inspection of Jackson\u2019s experience reveals that taking early-career risks can pay off handsomely. Jackson joined the manufacturer of laser-based solutions for the treatment of cardiovascular and dermatological diseases two weeks after the company decided to go public, and he filed the company\u2019s initial S-1 with the SEC four weeks after his start date. One high-stakes career decision involved Jackson taking a title demotion, moving from controller to assistant controller. The move was strategic, though, in that it transported him from a privately held firm to a publicly listed company where he rapidly accumulated the SEC reporting skills he knew he would one day need as the CFO of a public company. It was a \u201ca risky move to take a step down,\u201d Jackson says, \u201cbut it ended up paying off in the long run.\u201d