Director, Digital DTC Product Management, Prospr

Director, Digital DTC Product Management, Prospr 2 days ago Be among the first 25 applicants You are as unique as your background, experience and point of view. Here, you’ll be encouraged, empowered and challenged to be your best self. You'll work with dynamic colleagues - experts in their fields - who are eager to share their knowledge with you. Your leaders will inspire and help you reach your potential and soar to new heights. Every day, you'll have new and exciting opportunities to make life brighter for our Clients - who are at the heart of everything we do. Discover how you can make a difference in the lives of individuals, families and communities around the world. Job Description Role Overview We are seeking an exceptional and forward‑thinking Director of Digital DTC Product Management to spearhead our product strategy and roadmap for our hybrid advice platform (spanning insurance and wealth). This pivotal role will be instrumental in driving innovation, enhancing customer experience, and achieving ambitious business objectives through our digital offerings. As the Director, you will lead the charge in developing and implementing cutting‑edge technological solutions that position our company at the forefront of the DTC insurance and wealth industry. Your responsibilities will include orchestrating a comprehensive product strategy that seamlessly integrates advanced technology with superior customer experiences, while managing and optimizing the end‑to‑end digital experience. Candidates will have: Extensive experience in both 0‑1 (ideation to launch) and 1‑n (scaling and optimization) product development phases, with a preference to those with digital start‑up environments. You should be adept at taking products from conception to market success, as well as scaling and optimizing products and teams for growth. Demonstrated experience doing so in a DTC (Direct to Consumer) market business model. In this role, you will leverage your start‑up mindset and enterprise‑level experience to foster innovation, drive rapid product development, and ensure the successful scaling of our digital offerings. Your ability to work at both strategic and granular levels, from detailed requirements writing through to high‑level strategy formulation, will be essential in leading our product teams and delivering exceptional value to our customers. Key Responsibilities Product Strategy and Vision: Develop and communicate a compelling product vision aligned with organizational goals and market trends Create and oversee strategic roadmaps for the journey/platform, balancing client needs, business objectives, and technical feasibility Collaborate with senior leadership to ensure product strategy supports overall business direction End-to-End Experience Management: Oversee the entire digital product lifecycle, from conception to post‑launch optimization Continuously analyse and improve end‑to‑end customer journey (including optimization of conversion rates) ensuring profitability and growth of the DTC platform Detailed Product Development: Lead the product development process from granular requirements writing through to high‑level strategy formulation Ensure meticulous attention to detail in all aspects of product development, from user stories to technical specifications Implement and oversee quality assurance processes to maintain product excellence Marketing Optimization and Cost Efficiency: Work closely with marketing teams to optimise customer acquisition strategies Focus on improving key metrics such as Cost Per Lead (CPL) and Customer Acquisition Cost (CAC) Implement data‑driven strategies to enhance marketing ROI and reduce acquisition costs Technology and Data Leadership: Maintain deep understanding of existing and emerging technologies relevant to the insurance industry Ensure consideration of all technical layers in product planning and execution Lead efforts in data stewardship, identifying and addressing data gaps across the product portfolio Agile and Delivery Excellence: Remove systemic impediments to accelerate product delivery Establish risk management frameworks and coach teams on balancing risk with desired outcomes Foster a culture of experimentation and hypothesis‑driven approach in product development Performance and Financial Management: Set and track measurable outcomes aligned with organisational objectives Champion data‑driven decision making in product choices and prioritisation Develop multi‑year financial models to guide investment decisions and communicate ROI to senior leadership Cross‑Functional Collaboration: Work closely with business strategy, marketing and operations teams to ensure alignment of product strategy with broader business goals Foster inclusive leadership by integrating diverse perspectives in product development Required Competencies Product Development Expertise: Proven ability to work at a highly detailed level, from requirements writing to strategy development Experience in both 0‑1 (ideation to launch) and 1‑n (scaling and optimisation) product development phases Strong technical acumen with knowledge of cloud platforms, AI/ML, and event‑driven architectures Client Obsessed: Expertise in embedding client needs into product roadmaps Strong product evangelism skills with the ability to inspire engagement across teams Proficiency in orchestrating complex product launches Tech Fluency: Ability to understand end‑to‑end product architecture and supporting technologies Expertise in data stewardship and identifying data dependencies Accelerated Delivery: Proven track record as an Agile champion Experience in product risk mitigation and management Strong advocate for experimentation and hypothesis‑driven approach Measurable Impact: Ability to set and track outcome‑based metrics Expertise in data‑driven prioritisation and decision making Proficiency in financial modelling and communicating ROI Future Vision: Capability to create and advocate for a cohesive product vision Experience in developing strategic roadmaps aligned with market trends and business goals Commitment to inclusive leadership and fostering cross‑functional collaboration Qualifications Bachelor’s degree in Computer Science, Business, or related field; MBA preferred 10+ years of experience in product management, with at least 5 years in a leadership role Proven track record in digital product development, preferably in the insurance or fintech industry Deep understanding of the DTC market and digital P&L management Experience working in start‑up environments preferred, taking products from conception to market success Strong understanding of agile methodologies and digital product development lifecycle Excellent communication, presentation, and stakeholder management skills Demonstrated ability to lead and mentor high‑performing teams If you are passionate about driving digital innovation in the insurance industry, have a proven track record of delivering impactful DTC products, and excel at optimising the full acquisition funnel, we encourage you to apply for this exciting opportunity to shape the future of our digital advice platform. What’s in it for you? Great Place to Work® Certified for Most Trusted Executive Team in Canada – 2025, 2024 and 2023 Great Place to Work® Certified for Best Workplaces in Canada – 2025 Canada Order of Excellence for Mental Health at Work® certification from Excellence Canada. Sun Life is one of only four companies in Canada to ever receive this certification – 2024 Top Work Places® for Remote Work – Monster Canada – 2024 Great Place to Work® Certified for Best Workplaces in Canada – 2024 and 2022 Great Place to Work® Certified for Best Workplaces for Women in Canada – 2024 Flexible hybrid work model. Pension, stock and savings programmes to help build and enhance your future financial security Work and professional development that is united by our Purpose: to help Clients and Employees achieve lifetime financial security and live healthier lives A friendly, collaborative and inclusive culture Be part of our continuous improvement journey in developing the next greatest digital enterprise experience. Competitive salary and bonus structure influenced by market range data The opportunity to move along a variety of career paths with amazing networking potential Salary Range 125,000 – 195,000 Job Category Product Owner Posting End Date 04/01/2026 Seniority level Not Applicable Employment type Full‑time Job function Product Management and Marketing Financial Services and Insurance Referrals increase your chances of interviewing at Sun Life by 2x Get notified about new Director of Product Management jobs in Waterloo, Ontario, Canada . We’re unlocking community knowledge in a new way. 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