Higgins has been fined $270,000 and ordered to pay more than $494,000 in reparations to the whānau of three Bay of Plenty road workers killed on the job.
The company's safety failings were described as a "significant departure from industry standards" by Judge David Cameron this afternoon.
Rotorua men Haki Hiha, David Eparaima and Dudley Soul Raroa were killed on February 26 last year when a truck veered off State Highway 2 at Matatā.
It shunted another truck that rolled into a culvert where the Higgins road workers were working.
The company pleaded guilty to not ensuring the health and safety of their staff and was convicted and sentenced this afternoon.
The public gallery of the Whakatāne District Court was full of bereaved whānau who comforted each other as victim impact statements were read out.
Anna Nepia-Eparaima told Judge Cameron she found out about her partner's death on the 6pm news.
She described herself as "an emotional mess ... without the love of my life" she suffered "immense loss" and "extreme" pain.
Nepia-Eparaima had counselling and had not been able to sleep for more than three hours at a time since.
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She explained her financial difficulties paying mortgages and bills after David's death, and these worsened when was made redundant earlier this year.
Esther Waretini's statement said she and Dudley Soul Raroa had been together for 30 years.
They had six children and 18 mokopuna - the youngest was born the morning Raroa died and he was "so excited".
"But he never had a chance to see and hold her."
Raroa was the "main provider" for his whānau and had no life insurance.
Waretini went straight back to her job in kiwifruit orchards after his tangi, to distract herself.
Her statement described Raroa as a "brother, uncle, workmate and friend" who had been "stolen away from us all".
"He had so much mana and wisdom to give and share."
It also said the safety changes made after the crash should have been in place beforehand, and Raroa's family felt "ripped off" by this.
Judge Cameron said when the culvert excavation started the site traffic management supervisor was not there, there was no management plan, nor was there a safety briefing.
"Under the Higgins standard operating plan, for culvert cleaning, the shoulder of the road or the nearest lane should have been closed. This did not occur."
Cameron said it was "an understatement to say all of them [the three men] are dearly missed by all of their family members".
He discounted the Higgin's fine from a starting point of $600,000 because of the company's guilty plea, remorse, co-operation and measures taken to address its safety failings.
These included the introduction of a temporary traffic management app requiring staff to input information for a safety plan.
Higgins also stopped all work on highways immediately after the crash, to improve safety measures before work resumed.
Cameron said Higgins had no previous convictions for failing to keep workers safe and the company's commitment to stopping a similar crash from happening was "very clear".
He fined Higgins $270,000 and ordered emotional harm payments of $130,000 be paid to each of the three families.
Higgins had already paid $21,578 to the Hiha family and $55,571 to the Eparaima family before today's sentencing but Cameron ordered further payments for consequential losses.
These were $41,701 for the Hiha family, $8490 for the Eparaima family and $54,420 for the Raroa family.
Higgins was also ordered to pay $3000 in court costs to WorkSafe.
Whānau declined to speak to media about the outcome but Higgins issued a statement from general manager Henare Clarke.
"I know that the whānau of our colleagues David, Soul and Haki will live with their grief forever and nothing can change that. We can only hope that today's sentencing has gone a small way towards healing the hurt felt by them and the wider community.
"This tragic event has deeply impacted our whole organisation. Everyone has the right to go home at the end of their work day and we are devastated that three of our people did not last February."
He said the three men were "never far" the thoughts of staff.
"We talk about them often. We talk about the impact this has had on their families. I can only offer them our deepest sympathy to them and a commitment that we will continue to work every day to make sure this never happens again."
Higgins is a subsidiary of Fletcher Construction and chief executive Peter Reidy and head of safety Carla Tonks joined Clarke for the sentencing via audiovisual link, from Auckland.
They had applied for an exemption to leave the Covid-19 lockdown in Auckland to attend the sentencing in person but this was denied.
The man driving the truck that caused the crash last February pleaded guilty last year to three charges of careless driving causing death, laid by police.
Tauranga man David Cox was ordered to pay $21,000 in emotional harm reparations, complete 250 hours' community work and was disqualified from driving for 21 months.