Jackson began his career at PwC, a Big 4 accounting firm, where he built a strong foundation across both audit and tax. At just 25, he went on to open The Vault in Kalamunda, gaining experience in launching and running a hospitality venue from the ground up. He later joined Crown Perth, where he managed budgeting and forecasting across more than 45 bars and restaurants, further developing his commercial and operational expertise at scale. Jackson then spent five years with Varsity, playing a key role in guiding the business through COVID and its eventual sale, while maintaining the strong company culture the brand was known for.