Ep 359 - Lester Cruz - The Hustle Behind Singlife Philippines

EPISODE INTRODUCTION

In this episode of Hustleshare, we chat with Lester Cruz, CEO of Singlife Philippines, to talk about the journey that took him from his early sales grind and 15 years at Citi to pioneering digital banking at CIMB and Uno before leading one of the country’s most innovative digital insurers. Lester gets real about the rejections that built his grit, the leadership lessons he learned climbing the corporate ladder, and why he chose to take on the massive challenge of closing the Philippines’ insurance gap. He also shares how he’s redefining the insurance experience for Filipinos, and what running, resilience, and family have taught him about leadership and balance.

Episode Timeline: 

[00:02:12] – Lester’s Hustle: Leading Singlife Philippines in digital insurance
[00:03:27] – Early Influences: Lessons from an architect father and banker mother
[00:07:00] – First Sales Grind: Cold calls, rejection, and building thick skin
[00:11:39] – Coping with Rejection: Faith, competitiveness, and staying motivated
[00:15:25] – Foundational Years at Citi: Digital banking and leadership growth
[00:21:30] – Soft Skills Matter: Building relationships beyond technical skills
[00:27:10] – Evolving as a Leader: Managing competition and leading with empathy
[00:34:38] – Jumping Ship: Moving from Citi to CIMB and embracing startups
[00:38:34] – The Bigger Problem: Tackling financial literacy and access gaps
[00:43:39] – Taking the Leap into UNO Digital Banking from CIMB
[00:47:47] – Why Singlife: Taking on the Philippines’ insurance crisis
[00:58:09] – Redefining Insurance: Selling experience, not policies
[01:06:45] – Life as a CEO: Responsibilities, trade-offs, and sleepless nights
[01:14:19] – Building the Justice League: Forming a sharp, values-driven team
[01:24:22] – Sports and Leadership: How athletics shaped resilience and focus

QUOTES
“Life in sales is an emotional roller coaster. Sometimes you're doing all out, everything that you can do, nothing is happening. Sometimes you're just sitting and things are just happening. You cannot predict what's going to happen for the day, but you just have to remain consistent in everything that you do.”– Lester Cruz

CONNECT WITH LESTER:
LinkedIn: https://www.linkedin.com/in/lester-cruz-0243ab122 
Website: https://singlife.com.ph

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Diamond Supporters: Sarisuki, PayMongo, SeekCap, Shoppable Business, Qapita, GoTyme Bank, Sprout Solutions, UNO Digital Bank