Director of Project Management – Enterprise Delivery for Insurance & Pension Leaders

Vitech Systems Group; Toronto; Remote; CAD 120,000 - 160,000; Full time

Job summary

A leading software solutions provider in Canada is seeking a Director of Project Management to lead multi-million-dollar implementations for top-tier clients in the pensions and insurance sectors. The successful candidate will manage complex programs, ensuring operational excellence while influencing senior stakeholders. This role calls for extensive experience in project management and a proven track record in financial oversight. Join us in driving innovation and delivering impactful solutions.

Benefits

Competitive compensation

Comprehensive benefits

Qualifications

• 12+ years of program or project management experience in consulting, software, or pensions.
• Track record of managing enterprise-scale, multi-million-dollar implementations.
• Experience dealing with high-visibility clients in pensions, retirement, or insurance.

Responsibilities

• Lead large, complex, multi-million-dollar software implementations for top-tier clients.
• Own project P&L including costs, budgets, and invoicing.
• Drive operational discipline through structured status reporting and risk management.

Skills

Program or project management

Enterprise-scale implementation

P&L management

Agile methodology

Leadership

Job description

Overview

Director of Project Management – Enterprise Delivery for Insurance & Pension Leaders

Department: Solutions Consulting

Employment Type: Full Time

Location: Canada

Reporting To: Tom Duffy

At Vitech, we believe in the power of technology to simplify complex business processes. Our mission is to bring better software solutions to market, addressing the intricacies of the insurance and retirement industries. We combine deep domain expertise with the latest technological advancements to deliver innovative, user-centric solutions that future-proof and empower our clients to thrive in an ever-changing landscape. With over 1,600 talented professionals on our team, our innovative solutions are recognized by industry leaders like Gartner, Celent, Aite-Novarica, and ISG.

We offer a competitive compensation package along with comprehensive benefits that support your health, well-being, and financial security.

Role: Director of Project Management

Location: Remote Canada

Director of Project Management – Enterprise Delivery for Insurance & Pension Leaders

Lead High-Impact, Multi-Million-Dollar Programs for Market-Leading Clients

Vitech has been named the highest-designated Leader in Group Life Policy Administration Systems for 2025 by Everest Group and was recently featured in Grit Daily for rapid growth built on collaboration, innovation, and integrity.

At Vitech, we don’t just deliver software — we partner with industry leaders who shape markets and influence millions of lives. Our clients are among the largest and most visible organizations in pensions, retirement, and insurance. To meet their expectations, we are seeking a Director of Project Management in Canada — a leader with the presence to influence client executives, the rigor to own P&L, and the passion to deliver multi-million-dollar, highly complex transformation programs.

What you will do

• Lead the delivery of large, complex, multi-million-dollar software implementations for top-tier clients in pensions, retirement, and insurance
• Serve as the executive-facing leader for client programs, shaping strategy, influencing decisions, and constructively challenging when needed to protect delivery outcomes
• Own project P&L, including costs, budgets, earned/non-earned revenue, WIP models, invoicing, and financial reporting
• Partner across Product, Engineering, Cloud Ops, Security, Finance, and Legal to align execution with client and business priorities
• Mentor Deputy Project Managers and provide oversight to solution, technical, and QA leads
• Drive operational discipline: structured status reporting, RCA for issues, risk management, mitigation strategies, and change management
• Lead steering committees and client leadership meetings with clarity and confidence, preparing executive-level materials that inform decision-making
• Champion continuous improvement by embedding efficiency, accountability, and balanced scorecard tracking into delivery
• Identify new revenue opportunities within client accounts, partnering with Sales and Customer Success on proposals, SOWs, and amendments
• Represent Vitech with credibility, consulting rigor, and passion for delivery in every client interaction

What We’re Looking For

• 12+ years of experience in program or project management with a track record of leading enterprise-scale, multi-million-dollar implementations in consulting, software, or pensions/retirement
• Experience managing high-visibility clients in pensions, retirement, or insurance
• Proven success owning and managing P&L, budgets, forecasts, invoicing, and client financial models
• Executive presence and storytelling skills — able to shape opinions, manage escalations, and influence senior stakeholders
• Expertise in complex delivery environments, including Agile, large-scale system implementations, and multi-year programs
• Strong leadership background with a history of mentoring project managers and cross-functional leads
• Ability to manage multiple projects and workstreams while maintaining financial and operational discipline

Bonus Points

• Experience with Canadian pensions, retirement systems, or benefits technology
• Prior consulting experience with Big 4 or large enterprise system integrators

Why Join Us

At Vitech, we believe that diversity fuels innovation, and we’re committed to creating an inclusive workplace where everyone can thrive. We’re an Equal Opportunity Employer and welcome all qualified applicants regardless of race, color, national origin, religion, gender, gender identity, sexual orientation, age, disability, or veteran status.