Head of O2O Sales and Insurance Advisory

MoneySmart Group is a trusted personal finance platform in Southeast Asia, helping consumers compare and apply for financial products such as loans, insurance, and credit cards. Founded in Singapore in 2009, our mission is to simplify complex financial decisions and empower people to make informed choices with confidence. We are growing and we’re looking for exceptional talent to come onboard to lead our O2O business units in SG & HK as the Head of O2O Sales and Insurance Advisory (SG+HK) Mission MoneySmart's O2O business is at an inflection point. With a clear insurance-first strategy and expanded regional ambitions ahead, this role exists to turn a high-potential advisory channel into a scalable, retention-driven revenue engine across Singapore and Hong Kong. Your mission is to lead and build the systems, team, and culture that makes O2O MoneySmart's most differentiated capability. This is a leadership role and reports into the Chief Business Officer (CBO). Responsibilities • Accountable for SG & HK P&L for O2O - Life Insurance, Car Insurance, and Home Loans, delivering revenue, margin, and retention targets • Drive sales conversion and advisory practices through a high productivity tech enabled specialist team, robust lead and CRM management and best in class sales process and training • Actively champion and drive post purchase engagement, cross sell, loyalty and retention for the O2O business • Own CRM adoption and execution across the full O2O journey — ensuring hygiene, automation, and data-driven sales management • Strengthen and expand partnerships with insurers, banks, and lending institutions • Build, standardize and enforce SOPs, SLAs, Advisory and Sales playbooks/frameworks that enable scalability and effectiveness • Partner with Marketing, Product, and Tech to: • • Improve lead volume, quality and profiling • Strengthen CRM integration with marketing and sales workflows • Deploy automation and AI-driven sales productivity tools • Recruit, lead, mentor, and develop specialists and team leads, instilling ambition, accountability, and alignment with MoneySmart values and O2O strategy Requirements • You've built or rebuilt a high-touch advisory sales operation before — and you're hungry to do it at a higher level, with better data, AI tools, and a platform behind you • Proven learning agility and ability to thrive in ambiguity • Demonstrated success in using AI-driven productivity tools and data-driven sales management • Proven sales track record in direct-to-consumer, advisory, or high-touch telesales environments • Demonstrated success in scaling call centres and specialist advisory teams — including recruitment, training, SOPs, and incentive design • CRM ownership experience — proven ability to enforce CRM discipline across the O2O funnel (lead → contact → conversion → renewal) • Strong commercial acumen with the ability to balance customer-first advisory with revenue and retention outcomes • Ability to be a strong operator as well as a strategic thinker • 5-8 years of people leadership experience MoneySmart Culture Values & Tenets The traits we admire are core intrinsic qualities we look for in someone we want on our team, and we look for people who are Hungry, Humble and Smart. We also expect all our people to uphold the following company values: • Play to win as a team • Solve for the customer • Embrace a personal growth mindset • Step up and own it • Challenge the status quo and deliver outcomes MoneySmart Group is an equal opportunity employer. Please include only relevant details and avoid unnecessary information (e.g., photos, age) in your job application to assist us in ensuring that the interview process is devoid of bias.