1969-1981; Early career with H&R Block

Hewitt began his career in 1969, leaving the University of Buffalo early to become a tax preparer with H&R Block.^[1] Hewitt quickly moved through the ranks of the organization, becoming an assistance district manager for Western New York and then a district manager for the areas of Elmira, Corning, and Ithaca.^[1]

By 1980 He was the youngest regional director at H&R Block running over 250 offices.^[2]

Hewitt perceived a need for technological innovation within the tax industry and he left H&R Block in order to pursue that opportunity. Working alongside his father, he pioneered the development of decision-tree tax-preparation software. However, H&R Block uninterested in the software, leading Hewitt to found a tax-preparation service that would exploit the efficiency of electronic tax preparation.^[2]

1982-1997; Jackson Hewitt

In August 1982 in Hampton Roads, Virginia after Hewitt and other investors acquired the six offices of a local tax-preparation company, Mel Jackson Tax Service and launched the "Hewtax" interview program, the first of its kind in the industry, that had been developed with his father. In 1988, the company changed its name to Jackson Hewitt. By 1986, the IRS began testing an electronic filing process, allowing taxpayers to directly file their taxes, bypassing mailing of returns entirely, benefitting Jackson Hewitt and other providers of electronically produced tax forms. Also in 1986, Jackson Hewitt began offering franchises in the United States.

According to Inc. Magazine, By 1992 Jackson Hewitt had attained a second place ranking within its industry and was one of the fastest growing private companies in the United States. The company became public in 1994. When it was sold for $483 million in 1997, it was operating 1,345 offices.

1997-2017; Liberty Tax Service

John Hewitt had left Jackson Hewitt at the time of its acquisition, and was contractually barred from competing with the company until 2000 within most areas of the United States. In order to avoid infringing on the terms of his non-compete contract, Hewitt initially focused the company's operations in Canada, purchasing a Canadian tax company on September 1, 1997.^[3]

As of 2024 Liberty Tax operated 2,500+ offices in North America. Liberty Tax Service is best known for the costumed "wavers" dressed as the Statue of Liberty used in front of the offices across the country.^[3] During John's tenure at Liberty Tax Service, he wrote and published a book titled iCompete: How My Extraordinary Strategy for Winning Can Be Yours (copyright 2016).

New York-based law firm of Skadden Arps Slate Meagher & Flom found Hewitt had romantic relationships with at least 10 female employees that created a hostile work environment at the company, according to the complaint. Hewitt caused Liberty officials to favor his romantic partners, according to the suit. In one case, he granted a girlfriend the right to buy a tax-prep franchise without a down payment. When she later decided to cash out of the business, he commanded executives to pay her seven times the franchise’s value plus $220,000 in cash and stock, according to the suit. Hewitt was forced out as the CEO at Liberty Tax Service ^[4]

2018-Present; Loyalty Brands

John Hewitt founded Loyalty Brands in 2018. Loyalty Brands is an umbrella franchise company that manages twelve brands. The synergy between the brands allows franchisees to create a portfolio of several businesses that complement each other as a way to diversify and grow their entities. Currently, Loyalty Brands manages several operational and sales aspects for the brands, four wholly owned by Loyalty Brands, including ATAX Tax Service, Ledgers Accounting, Little Medical School, Zoomin Groomin Mobile Pet Spa and Loyalty Business Brokers.