James Ayoub

Four months into his commercial real estate career, James Ayoub faced an unexpected test.

A pivotal member of his First National financing team in Montreal exited the company, leaving Ayoub alone with an overwhelming number of files to manage. To make matters worse, the COVID-19 pandemic struck a month later.

“It was a true sink-or-swim situation,” said a colleague who nominated him for a Connect 2024 Next Gen Award. “Undeterred, James embraced the challenge with a can-do attitude, putting in 12-to-14-plus hour days and preventing the team from collapsing.”

During that year, he singlehandedly underwrote approximately 70 transactions totalling about $350 million. His responsibilities included liaising with both internal and external parties, successfully leading deals to funding.

“James’ ability to handle immense pressure while still relatively new to the role was not only impressive, but also a testament to his evolving personality and skills,” said his award nominator. “He transitioned from a new team member to a star performer, demonstrating resilience and adaptability.”

While he was adapting at work, Ayoub grappled with a significant personal challenge: The death of his uncle, whom he regarded as a second father, due to a difficult battle with cancer.

“Rather than allowing negativity to affect his work and relationships, James stepped up as a leader within his family,” said his award nominator. “He provided unwavering support to his aunt, cousins, parents and siblings, turning adversity into an opportunity to strengthen family bonds and spread love and hope.”

Ayoub started with First National in October 2019 immediately after graduating from Concordia University with a Bachelor of Commerce degree. His strong work ethic, quick learning abilities and determination enabled him to become a significant contributor to one of First National’s fastest-growing real estate financing origination teams.

He was promoted to senior analyst in June 2022 and became an associate director in January 2024. During his career, he has underwritten about 300 deals with a combined value of $3.5 billion. This year alone, he has underwritten about $1.3 billion worth of transactions.

His portfolio includes a diverse range of deals, such as large term loans, purchaser transactions, construction financing, bridge deals, and conventional term financings. Some notable highlights include a $243-million construction take-out mortgage for a newly built multi-residential complex in Ontario. (A take-out mortgage is a long-term mortgage that replaces a short-term construction loan or other temporary financing.) Additionally, he underwrote a $92-million loan to finance the acquisition of an existing multi-residential property located in Gatineau, Que.

Ayoub’s expertise also extends to larger construction financing deals. For instance, he played a key role in a $62-million construction financing deal for a multi-residential property in Mirabel, Que.

“Another standout achievement was orchestrating the complex acquisition of a portfolio comprising of approximately 2,300 units across 10 clusters of properties,” said his Next Gen Award nominator.

The purchase price was $300 million, making the transaction the second-largest multi-residential deal in Quebec’s history at the time.

Ayoub’s ability to navigate intricate analyses and tight timelines was crucial, resulting in a successful short-term bridge deal followed by a CMHC take-out mortgage, according to the award nominator.

“James’ remarkable journey exemplifies both professional excellence and personal compassion,” said the nominator.