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

Pradeep Thirukumaran

Pickering,ON

Summary

Dynamic PMO and Project Management leader with 20+ years of experience across IT infrastructure, SaaS and insurance domains. Proven track record in establishing and scaling PMO functions, leading multi-million-dollar programs, and driving enterprise-wide operational excellence. MBA and PMP certified, with additional credentials from Harvard Business School in sustainable business strategy. Recognized for aligning complex delivery initiatives with executive strategy, implementing effective governance frameworks, and improving execution, visibility and value creation. Adept at leading large cross-functional teams, optimizing resource utilization and delivering high-impact projects on time, under budget, and with measurable results. A collaborative leader who thrives in matrix environments and believes in combining performance with empathy to empower teams and build sustainable success.


Overview

30
30
years of professional experience

Work History

Vice President Operations and Technology

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
  • Led PMO and enterprise delivery functions across North America and EMEA, overseeing a team of 10 Program and Senior Project Managers and driving large-scale implementation programs for enterprise clients.
  • Directed complex SaaS implementation programs generating $2–3M in annual revenue, ensuring alignment with client objectives and organizational strategy
  • Developed and implemented a comprehensive delivery playbook, establishing governance standards and PMO processes across regions
  • Improved project predictability and executive visibility by introducing standardized reporting and resource management practices
  • 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
  • Managed a 20-person delivery team (Program Managers and Project Coordinators) supporting over 600 enterprise clients across multiple regions.
  • Developed and implemented program management strategies and best practices to align delivery operations with organizational objectives
  • Partnered with Sales and Customer Success teams to strengthen client engagement and achieved a 98% customer satisfaction score
  • Oversaw simultaneous delivery of multiple strategic projects, ensuring adherence to timelines, budgets, and quality standards
  • Introduced process improvements and optimized resource allocation, reducing delivery times by 25%
  • Proactively managed risks and maintained strong relationships with internal and external stakeholders to support successful delivery outcomes
  • Managed and supervised administrative and daily program operations, complying with policies and regulations.
  • Established strong relationships with key stakeholders, ensuring support for program initiatives.

Senior Project Manager - Professional Services

Talkdesk
01.2021 - 01.2022
  • Led cross-functional delivery teams through full project lifecycle, including planning, resource allocation, budget forecasting, and execution
  • Ensured timely and on-scope delivery of complex projects by coordinating closely with internal teams and external stakeholders
  • Gathered requirements and defined project objectives in collaboration with key stakeholders to ensure alignment and satisfaction with deliverables
  • Implemented and enforced project quality standards and best practices, conducting regular project reviews and driving continuous improvement
  • Maintained clear communication throughout execution phases to support stakeholder engagement and successful project outcomes
  • Maintained schedules to meet key milestones at every project phase.
  • Directed changes to project scope and cost and implemented appropriate change management processes to keep project on track.

Senior Director Information Technology

Chemtrade Logistics
01.2006 - 01.2021
  • Led a multinational IT organization of 45 team members (including 20 direct reports) and drove enterprise-wide technology strategy and PMO delivery across 72 locations in North America and Brazil.
  • Spearheaded large-scale transformation initiatives—including M&A integrations, cloud modernization, cybersecurity frameworks, and IoT automation—delivering programs 30% faster and under budget
  • Established enterprise governance and delivery standards across infrastructure, security, ERP, CRM, business intelligence, and cloud services (AWS/Azure)
  • Negotiated multimillion-dollar service contracts and optimized operating costs across network and cloud environments
  • Increased productivity by 65% through digitalization of IT service delivery and improved threat detection efficiency by 75% with new security frameworks
  • Implemented IoT-enabled process automation that increased operational efficiency by 90% and enhanced real-time monitoring capabilities
  • Deployed disaster recovery protocols for mission-critical systems and guided enterprise architecture design to support long-term organizational growth
  • Optimized project timelines by effectively delegating tasks and prioritizing workload among team members.
  • Cultivated a culture of innovation by promoting creative thinking and encouraging employees to take calculated risks in pursuit of solutions.

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

Vice President Operations and Technology

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 Director 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