Hedberg started his insurance career on the brokerage side in 2003 at Hays Companies in the Midwest. He handled management liability lines in addition to professional and privacy (cyber) insurance covers, representing his clients to the marketplace and placing coverage. In 2013, he moved to New York and joined the underwriting side at Hiscox, a global specialty insurance company based in London. He currently manages a large book of new and renewal technology professional and privacy liability insurance for the Northeast region of Hiscox.