Summary
Overview
Work History
Education
Skills
Servant Leadership Roles
Timeline
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Pradeep Thirukumaran

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 School

Certificate - Sustainable Business Strategy

Harvard Business School
Hardward

Certificate - 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
Pradeep Thirukumaran