His first ever job was working as a delivery boy for Four Square.
The 60-year-old had been thinking about retiring for some time. He said he gave notice of his resignation early to allow enough time to find a replacement.
"The past 20 years has been a fantastic ride, some of the changes in the business and consumer world have been pretty radical," Anderson told the Herald.
"It's never been boring, things have been changing significantly. Twenty years ago it was all about the mass, and you'd talk to the masses through TV advertising, through big IT systems, and now it is all about the individual; data, talking to individual customers and having customers talk to you through social media. There's been huge changes, but great to work through."
Anderson and his team have tripled the size of the South Island business through market-share growth, and expanded outside of grocery with the creation of the Henry's brand.
He has also been contributing to and giving information to the Commerce Commission as part of the Government's inquiry into supermarket food prices.
He couldn't comment on whether the market study was justified, but said Foodstuffs had been working with the commission proactively, "contributing positively towards it".
"I can't comment on whether it is a good idea or not, it is time-consuming and has taken a lot of time and effort, but so far it is progressing well from our perspective and hopefully the Commerce Commission is happy with our response."
Over the past few years he has been focused on digitalisation of the business and using data to source customer insights. In the last year, he has been charged with dealing disruption from the Covid pandemic, and in the supermarket operator's case, extraordinary demand.
"They have been good challenges to have - I'd far rather be running a business that has all of a sudden had a whole lot more unexpected turnover rather than the opposite," said Anderson.
He has had a fair bit of experience with crisis management in his time as CEO, particularly in Canterbury, managing disruption following the 2010 Christchurch earthquakes and the Mosque shooting in 2019, that killed one employee and injured another two in the attack.
A geologist by training, having studied a Bachelor of Science majoring in Geology with Honours, Anderson said the only time he used that training was to brief staff about seismology following the Christchurch and Kaikoura earthquakes.
Anderson always had the goal to become CEO of a company, and during his interview for the role he shared just that: "I was interviewed by the board and one of the questions was 'Did you have any big goals in life when you finished university?' and I said 'Yeah, I wanted to be CEO of a company by the time I'm 40, and by the way I'm 39 years old and 11 months', and they gave me the job."
Russell McKenzie, chairman of Foodstuffs South Island, said Anderson had driven growth and development across all aspects of the business in his tenure.
"Market share has significantly increased with the cooperative delivering consistent growth over the years and a number of critical projects have contributed to this success including the roll out of SAP 11 years ago and the launch of New World's Clubcard in 2014," McKenzie said.
He said Anderson had also been integral in the establishment of the Food for Thought Trust, a Foodstuffs initiative in conjunction with the Heart Foundation, which sees nutritionists go into schools and educate year 5 and 6 students on how to make healthier food choices. The programme has educated over 180,000 students in 2100 schools since inception in 2007.