Jasdip Dhindsa

Enterprise Transformation Executive | Scaling AI-native product organizations | Chief Information Officer (CIO) | Business Executive | Strategy & Innovation Enthusiast | TD Bank | Gore Mutual

Canada

About

Highly accomplished result-driven senior technology and business executive with more than 20 years of progressive experience in digital transformation, strategic planning, successful agile delivery of large scale programs and cutting edge innovative solutions by leveraging matrixed teams, to address business opportunity. Recognized for being visionary and creative with a positive attitude and commitment to delivering legendary experiences. Collaborative communicator who excels at fostering strong business relationships and creating alignment of corporate strategies. Dynamic team builder with an outstanding expertise in building and leading high performing teams with constant focus on coaching and developing leaders. Performance driven problem solver who has been consistently recognized for outstanding ability to deliver critical technology solution on time and on budget

Experience

  • Executive Advisor - Financial Services Technology at Independent
    Jan 2026 - Present · 6 mos

    Strategic technology advisor to banks, insurers, and wealth management firms across Canada and the United States. Specializing in: • Generative AI strategy, deployment, and governance in regulated environments • Cloud-native modernization on Microsoft Azure and AWS — legacy decommissioning, microservices architecture, data platform re-platforming • Intelligent automation and agentic AI for back-office and client experience • Cybersecurity and zero-trust architecture under OSFI / OCC oversight • Engineering organization design, agile transformation, and global delivery • Emerging technology evaluation — Blockchain / DLT, smart contracts, AI/ML productivity tooling Open to fractional CTO / CTIO engagements and selectively evaluating senior executive opportunities aligned with scale and transformation mandate.

  • Senior Vice President - Canada Business Technology & Global Corporate Technology at Canada Life
    Mar 2024 - Nov 2025 · 1 yr 9 mos

  • Head (Business) of TD Wealth - Direct Investing (Trading & Long Term Investing) at TD
    Dec 2021 - Apr 2024 · 2 yrs 5 mos

  • EVP - Chief Information Officer at Gore Mutual Insurance
    Mar 2020 - Dec 2021 · 1 yr 10 mos

    Enabling Gore Mutual to become an Industry Leader in Digital Insurance Transformation :- - Winner of “The 2021 Global Insurance Innovation Award” - Gore Mutual Insurance Company Becomes 1st Canadian Insurer Using Guidewire Cloud to Deploy the Full InsuranceSuite (Policy, Billing, Claims) and advanced Data Warehouse delivering real-time analytics. - Successfully launched the Digital National Call Centre (on Cloud), powered by Amazon Connect.

  • TD (16 yrs 1 mo)
    • Vice President (North America) - Digital Banking & Branch Banking Technology
      Aug 2019 - Feb 2020 · 7 mos

      Accountable for $450 Million portfolio - strategy, application technology, delivery and innovation of TD Bank’s North American “Online Banking”, “Branch Banking” and “Open Banking” for all Lines of Business - Personal Banking, Business Banking, Credit Cards, TD Wealth, TD Insurance, Public Sites, Enterprise Content Management and Branch Systems (Sales & Servicing).

    • Associate Vice President - Wealth Management Technology & Public Cloud (Devops Automation)
      Sep 2017 - Aug 2019 · 2 yrs

      Elevated TD Direct Investing to #1 RANKING (2019) amongst ALL Online Brokerages in Canada - awarded by “The Globe and Mail”. Pioneered the design and implementation of transformational Public Cloud (Azure) Solutions for multiple applications within TD Bank - IaaS, PaaS and Containers (Kubernetes).

    • Associate Vice President - TD Insurance, Digital Sales Platforms & Enterprise Content Management
      Feb 2004 - Sep 2017 · 13 yrs 8 mos