EXCELLENCE AWARDEE: CEO of the year

Amanjot Sidhu

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@diamondinsurancegroup

@transalta

When Amanjot Sidhu co-founded Diamond Insurance Group in 2016 alongside his brother Simar Sidhu and father Mohinderpal Sidhu, few could have anticipated the impact this family-run brokerage would have. Today, as the company’s CEO, Amanjot stands as a testament to how unwavering commitment to integrity, innovation, and client service can drive remarkable success in a competitive industry. From its humble beginnings, Diamond Insurance Group’s expansion to 100 brokers from three represents a success story rooted in family values and genuine care for clients. The Brampton-based brokerage has expanded beyond Ontario to Edmonton, AB, and is positioning itself for national growth with plans for British Columbia, Quebec, and Atlantic Canada. A people-first philosophy Amanjot’s leadership philosophy centres on authentic human connection and ethical business practice. He articulates this philosophy clearly, noting that “our family business includes all of our employees, who are more like friends than colleagues; we know them personally and have formed a strong connection.” This people-first approach has become the foundation of Diamond Insurance Group’s distinctive culture and operational success. Amanjot credits his own meteoric rise to the mentorship of his father, who built his own distinguished career as a broker. This intergenerational knowledge transfer has been instrumental in shaping Diamond Insurance Group’s ethical foundation. Supported by Vice President Raman Grewal and Managing Partner Gurvinder Basi, Amanjot leads a team that embodies shared values and mutual respect. The company’s philosophy is grounded in Punjabi cultural values centred on helping people and putting client needs first through honest, transparent dealings. Client education, service excellence, and comprehensive offerings The company’s achievements have been swift and substantial. Within just one year of launching, the company earned recognition as a Rising Star by Insurance Business Canada, and Simar Sidhu was named one of the Top 50 Brokers in Canada. Most impressively, exceptional performance during 2022 and 2023 earned the brokerage Insurance Business Canada’s prestigious 5-Star Brokerage of 2024 award. Under Amanjot’s direction, the brokerage has established itself as a leading provider of comprehensive services spanning auto, commercial, life, investments, bonds, farm insurance, and coverage for small to medium-sized home-based businesses. This breadth of offerings coupled with its multi-provincial offices positions the company as a true one-stop solution for Canadian clients with complex insurance needs. Critically, the company has distinguished itself through education-focused client engagement. Rather than simply selling policies, Amanjot and his team educate clients on coverage options, empowering them to make informed decisions that protect their assets and livelihoods. Blending tradition with innovation The company has built a reputation for fostering long-term relationships with clients, community, and loyal staff. The stability of Diamond Insurance Group’s original team speaks volumes about Amanjot’s leadership. Several founding brokers – including Asif Alam, Dupinderpal Buttar, Gurkarmsher Dhindsa, and Ravinder Grewal – remain with the company today, providing continuity and deep client relationships. Amanjot stands out for the way he honours long-established practices while pushing his organization toward what the industry will demand next. His focus on building an inclusive, opportunity-rich environment has drawn in emerging professionals who want to contribute, not just observe. By keeping that talent engaged and giving them room to grow, he has helped shape an organization that is agile, ambitious, and ready to advance even as the sector faces real pressure. With over 30 national insurer partnerships, Diamond Insurance Group serves diverse clientele from visitors to Canada to rideshare drivers. Amanjot’s CEO of the Year recognition validates his transformative leadership and the values-driven vision that continues to shape Canadian insurance for the better.

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Diamond Insurance Group

@blackfishfinance

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