Judges said Challies' attention to detail and strong leadership skills had contributed to his win.
These skills had been evident since he was appointed chief executive in 2006, but particularly in the last year, with Ryman's expansion into Australia, they said.
The company has recorded 12 years of double-digit profit growth, something the judges attributed to Challies' leadership.
"It is no mean feat and Simon has to be given full credit for Ryman's success," the judges said.
In the company of the year category, the judges said Air New Zealand "seriously punches above its weight in the international aviation arena".
The company reported its highest net profit in a decade after a strong year, and chairman Tony Carter said the company was expecting another positive year in 2015.
Spark boss Simon Moutter (left) and Air New Zealand chief executive Christopher Luxon at the Vector Arena awards function. Photo / Dean Purcell
"With new aircraft offering better operating economics, an optimised network with the right alliance partners, disciplined cost management and a daily focus on improving the customer experience, we are very well positioned to continue growing," Carter said.
The company celebrated a second win later in the evening with Mr Carter named the chairperson of the year.
The judges said his leadership and direction for the company, alongside that of chief executive Christopher Luxon, had resulted in an extremely successful period for the company.
"Tony Carter as chairperson and chief executive Christopher Luxon have transitioned well leading to 2014 as a standout year with the successful execution of the Government's share sale, new strategic alliances and a massive investment in new planes," the judges said.
More than 1000 people attended the event at the Vector Arena last night.
Neil Paviour-Smith, chief executive of Forsyth Barr and one of this year's judges, said that making it into the finalist list was a huge achievement in itself.
"The awards are a special occasion, I hope that all of the finalists can consider themselves winners because they have been identified out of 200-plus companies," he said.
"To be classified in their category as amongst the top three is pretty impressive."
Fletcher Building won the excellence in governance award and Delegat Group the best growth strategy award. The most improved performance went to Tourism Holdings and the diversity leadership award went to BNZ.
The young executive of the year award went to Michael Lewis, northern operations manager for New Zealand Post.
From left, Sara Ford, NZME. group strategy and operations director Caroline Luey, NZME. group marketing director Liza McNally, NZME. chief executive Jane Hastings and NZME. group digital media director Laura Maxwell-Hansen. Photo / Dean Purcell
The judges said Mr Lewis was "a young leader who seems destined to have a profound impact on the organisations he works for, the people he works with and on New Zealand as whole".
A final award recognising a visionary leader was presented to Bruce Plested, founder and chairman of Mainfreight. Mr Plested started Mainfreight in 1978 with just $7000.
"This year the winner is someone who I think exemplifies a lot of the particular attributes of a visionary leader," Mr Paviour-Smith said.
See video: Deloitte Top 200 executive of the year - Simon Challies
Deloitte chief executive Thomas Pippos said the event was important to celebrate the success of New Zealand companies.
"The high level of excellence demonstrated at these awards should give New Zealand great confidence in our business leaders.
"After 25 years of honouring our business heroes, and despite ongoing global and domestic uncertainties, the vision and ability for our top companies to succeed is stronger than ever," Mr Pippos said.
