Top Group Financial Services Director 2022
A leader is one who knows the way, goes the way, and shows the way.
John C Maxwell


Top Group FSD 2022
MDRT COT Qualifying & Life Member 2023

My Team

Winnie & team

About Winnie

“A leader is one who knows the way, goes the way, and shows the way.” - John C Maxwell

Formerly a banker for five years, Winnie Cheah joined AIA in 1997. In 1998, she won the companywide Top Rookie Award and transitioned into leadership in 2001. Over the past 22 years, Winnie has focused on agency building and spun off 4 districts. She achieved a career milestone by becoming one of the few Master District Directors in 2018, having groomed more than 10 leaders.

Despite overseeing an agency, Winnie has impressively maintained her Million Dollar Round Table (MDRT) qualification. In 2020, amid very challenging times, she achieved her first Top of the Table (TOT) qualification, which she repeated in 2021. In 2022, she achieved her Court of the Table (COT) qualification and won the Top Group Financial Services Director Award.

With a strong belief in the power of discipline, Winnie emphasizes the need for consultants to develop proper habits in their daily work. She integrates supervision, training, activity and reward systems within her organisation. Leading by example, Winnie is a role model to her consultants as she carried on doing her personal sales in order to share knowledge and mentor her team. She continues to invite advisors to attend her sales appointments, enabling them to learn from real-life experiences. Winnie encourages her consultants to be activity-driven, goal focused and have a growth mindset. To effectively manage her district and serve her clients, she delegates most of the administrative tasks to her support staff, allowing her to focus on her primary responsibilities.

A strong advocate of paying it forward, Winnie began her community giving in 2015 by donating bursaries to universities and supporting various charities. She established her own "Win Advisors Scholarship" at NUS Business School, her alma mater. Ultimately, Winnie aspires to leave a lasting impact on the financial services industry by creating sustainable systems for generations of advisors nurtured under her agency, Win Financial Group.

Congratulations to Winnie, for trailblazing a path of success and inspiring countless financial advisors to reach new heights!



  • Top Group Financial Services Director 2022
  • MDRT District 2023
  • Pinnacle Gold District 2023
  • Prestige Club Member 2023
  • Prestige Club High Net Worth District 2023
  • MDRT Court of the Table - Qualifying & Life Member 2023
  • Bachelor of Business Administration (BBA)
  • Diploma in Life Insurance (Dip SCI (LI))
  • Certified Financial Planner (CFP®)
  • Chartered Financial Consultant (ChFC®)

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