Pradeep Thirukumaran
Pickering,ON
Summary
Accomplished IT Project Management leader with 20+ years of experience shaping enterprise PMO structures, guiding complex transformations, and aligning technology portfolios with organizational strategy. Recognized for building resilient governance models that strengthen transparency, accelerate decision-making, and elevate cross-functional delivery.
- Skilled at unifying diverse teams across global regions, balancing strategic vision with operational execution, and translating priorities into measurable outcomes.
- Adept at leading large-scale initiatives spanning M&A integrations, digital modernization, security, and cloud platforms, consistently achieving accelerated timelines and measurable efficiency gains.
- Respected as a collaborative strategist and decisive leader with strong financial acumen, regulatory knowledge, and the ability to cultivate high-performing teams that deliver enterprise value.
Overview
30
30
years of professional experience
Work History
Head of Operations and Project Management
All Seasons Insurance Brokerage Inc.
Toronto, Ontario
07.2024 - Current
- As a member of the executive leadership team, led enterprise-wide programs to drive operational excellence, modernize technology capabilities, and scale delivery across the brokerage.
- Led cross-functional projects to improve operational efficiency, implement new technologies, and drive business growth within the insurance industry
- Managed the implementation of broker management systems (SIG, EPIC) and digital customer-service platforms, increasing adoption and enhancing customer experience
- Streamlined workflows and introduced automation tools to optimize customer service operations and improve team productivity
- Developed and executed strategic plans to improve business performance, align delivery with regulatory requirements, and enhance customer experience
- Collaborated with internal teams, vendors, and insurance carriers to deliver high-impact projects and ensure alignment with business objectives
- Ensured compliance with RIBO and industry regulations through structured risk assessments, process audits, and staff training
- Initiated and led e-commerce enablement initiatives, including development of a self-service portal and integration of digital quoting platforms
- Oversaw the configuration and deployment of Microsoft infrastructure, ensuring timely patching, system security, and regulatory compliance
- Guided teams through organizational changes and technology transformations, achieving high user adoption and minimal business disruption
- Leveraged analytics, dashboards, and scorecards to monitor key business metrics and enable data-driven decision-making and continuous improvement
- Cultivated strong relationships with key stakeholders, including customers, vendors, regulators, and community leaders to promote collaboration and long-term success.
- Led cross-functional teams for the successful completion of major projects, resulting in increased efficiency and client satisfaction.
Professional Services Manager
Talkdesk
01.2023 - 07.2024
- Masterminded and executed PMO and enterprise delivery functions across North America and EMEA, leading 10 Program and Senior Project Managers on SaaS implementation programs generating $2–3M annually.
● Established a global delivery framework and playbook, standardizing governance, reporting, and resource management practices to improve predictability and executive visibility. - Reduced 25% delivery cycle times, increased 90% project success rates, and achieved 100% client satisfaction.
- Defined program scope, milestones, and success criteria in partnership with executive stakeholders in alignment with organizational strategy and client objectives.
- Mitigated risks and resolved delivery challenges through structured evaluation, corrective action planning, and cross-functional collaboration, including with sales and marketing teams, to strengthen client relationships.
- Delivered process improvements that reduced delivery cycle times by 25% and increased project success rates to 90%
- Partnered with executive stakeholders to define program scope, delivery milestones, and success criteria, and maintained 100% customer satisfaction across completed projects
- Collaborated with sales and marketing teams to promote professional services.
- Investigated and evaluated risks and issues to formulate solutions and implement corrective actions.
Program Manager
Talkdesk
01.2022 - 01.2023
- Mentored and led a 20-person delivery team of Program Managers and Project Coordinators, overseeing concurrent strategic projects for 600+ enterprise clients across multiple regions.
- Instituted program management strategies, governance frameworks, and resource optimization practices that cut delivery times by 25% and increased execution predictability.
- Orchestrated end-to-end project delivery, maintaining scope, budget, timeline, and quality compliance while mitigating risks and resolving issues proactively.
- Forged partnerships with Sales and Customer Success to strengthen client engagement, achieving a 98% satisfaction score, and cultivated stakeholder alignment to support organizational objectives.
Senior Project Manager - Professional Services
Talkdesk
01.2021 - 01.2022
- Supervised cross-functional teams through full project lifecycles, including planning, requirements gathering, resource allocation, budget forecasting, execution, and change management.
- Coordinated with stakeholders to define objectives, align deliverables, and maintain engagement, ensuring projects met scope, schedule, and quality commitments.
- Instituted project management standards and reviews to enforce quality, drive continuous improvement, and mitigate risks through structured change control.
Senior Manager Information Technology
Chemtrade Logistics
01.2006 - 01.2021
- Oversaw a 15-member multinational IT organization, including 7 direct reports, shaping enterprise-wide technology strategy and PMO delivery across 72 locations in North America and Brazil.
- Drove large-scale transformation programs, including M&A integrations, cloud modernization, ERP/CRM deployments, cybersecurity, BI platforms, and IoT automation.
- Completed initiatives 30% faster, under budget, and achieved up to 90% efficiency gains.
- Instituted enterprise governance, disaster recovery, and security frameworks that cut operating costs, boosted productivity by 65%, enhanced threat detection by 75%, and enabled sustainable organizational growth.
Information Technology Project Manager
End to End Networks Inc.
01.2005 - 01.2006
- Delivered more than 50 infrastructure projects—including national WAN/LAN deployments—by effectively managing scope, cost, resources and timelines
- Partnered with business stakeholders in retail and manufacturing industries to identify needs and implement technology solutions that improved operational efficiency and reduced costs
- Led one of the largest Citrix thin-client implementations in the retail sector, deploying a Metaframe-based solution across 120 locations nationwide
- Consistently exceeded customer expectations through proactive communication, risk management and high-quality delivery practices
- Interviewed, hired and trained staff, leading performance reviews, and offering constructive feedback.
- Guided implementation of company-wide enterprise security strategy for network and hardware, disaster recovery and endpoint protection.
Information Technology Manager
Polytainers Inc.
01.1996 - 01.2005
- Managed and maintained corporate IT infrastructure across four North American locations, supporting over 400 end-users
- Planned, configured and implemented LAN and WAN solutions—including frame-relay and Cisco-based wide-area networks—to ensure secure and cost-effective operations
- Designed and deployed a corporate VPN infrastructure to enable secure remote access, significantly reducing travel costs and enabling remote work capabilities
- Provided technical leadership and operational support to internal users, ensuring system reliability and optimal performance
- Streamlined helpdesk operations, reducing response times and increasing end-user satisfaction levels.
- Researched and recommended innovative and automated approaches to routine tasks.
Education
MBA - MBA
Aston Business School
Aston Business SchoolCertificate - Sustainable Business Strategy
Harvard Business School
HardwardCertificate - Management Fundamentals
University of Waterloo
Project Management Professional - PMP
Project Management Institute
08.2025
Skills
- Project and PMO Leadership
- Relationship building
- Decision-making
- Critical thinking
- Coaching and mentoring
- Strategic planning
- Operational leadership
Servant Leadership Roles
- Global Ambassador for International Students – Aston University
- Mentorship and Leadership for MSC Students- Aston University
- Global Ambassador – Friends Lanka Child foundation - https://www.flcf.lk/ambassador.php
- Program Director - Leadership for upcoming Leaders- Kenya and East Asia Program
- Volunteer and Helper- Sick Kids Foundation
Timeline
Head of Operations and Project Management
All Seasons Insurance Brokerage Inc.
07.2024 - Current
Professional Services Manager
Talkdesk
01.2023 - 07.2024
Program Manager
Talkdesk
01.2022 - 01.2023
Senior Project Manager - Professional Services
Talkdesk
01.2021 - 01.2022
Senior Manager Information Technology
Chemtrade Logistics
01.2006 - 01.2021
Information Technology Project Manager
End to End Networks Inc.
01.2005 - 01.2006
Information Technology Manager
Polytainers Inc.
01.1996 - 01.2005
Project Management Professional - PMP
Project Management Institute
MBA - MBA
Aston Business School
Certificate - Sustainable Business Strategy
Harvard Business School
Certificate - Management Fundamentals
University of Waterloo