Project Manager

Shift Technology • Toronto, ON

55d • Hybrid

About The Position

Shift is the leading AI platform for insurance. Shift combines generative, agentic, and predictive AI to transform underwriting, claims, and fraud and risk - driving operational efficiency, exceptional customer experiences and measurable business impact. Trusted by the world's leading insurers, Shift delivers AI when and where it matters most, at scale and with proven results.
Our culture is built on innovation, trust, and a drive to transform the insurance industry through our SaaS platform. We come from more than 50 different countries and cultures and together we are creating the future of insurance.
As a Project Manager, you will join our Delivery team in Canada to spearhead the deployment of Shift’s AI solutions for global insurance clients. You will act as the cornerstone between our technical teams and client stakeholders, ensuring projects move from initial scoping to scalable, long-term success. Your goal is to anticipate risks and build strong, trust-based relationships that allow our products to deliver measurable value across diverse markets. This hybrid role is essential for driving the collaborative execution that defines how we win together at Shift, and should expect to be in the Toronto office 2 days per week.
What Your Impact Looks Like:
At Shift, we value ownership from day one. In this role, you will:
Jump In & Get Things Done: Take proactive ownership of project milestones and resolve blockers quickly to keep delivery on track. Coordinate with our technical program management team to ensure alignment between product roadmap and project plan as well as the execution of the release process
Simplify the Complex: Translate technical requirements and project plans into clear, accessible language for both internal teams, customers, and C-level stakeholders.
Decide with Data & EQ: Manage complex client relationships by balancing hard project data with emotional intelligence to navigate high-pressure situations.
Test, Learn, Scale: Experiment with new project management methods and share these learnings to help the delivery organization improve speed and quality.
Fix Issues Without Drama: Address delivery challenges directly and objectively, focusing on collaborative solutions rather than placing blame.
Communicate with Impact: Adapt your communication style to align diverse stakeholders, from operational teams to senior management, around shared project goals.
Cross the Finish Line: Ensure projects are delivered fully and meet agreed-upon standards, validating that outcomes truly meet client expectations before closure.

Requirements

• At least 5 years of technical project management experience with a consulting or SaaS company.
• Proven track record of managing complex projects and understand how to turn project milestones into measurable business impact.
• Hold a PM certification (PMP, Prince2, or CAPM) and use a structured approach to build scalable processes and implementation plan, but understand how to apply these frameworks flexibly.
• Fluent English speaker with a professional command of French (written and spoken) to effectively manage our global and local stakeholders and lead complex discussions and technical scoping in both languages.
• Always looking for a better way to do something - you are eager to test, learn, and adapt your project management methods by integrating AI-driven tools into your own workflow, using technology to automate the routine and scale your impact as Shift grows.
• Thrive in cross-functional environments, partnering naturally with Product, Engineering, and GTM teams to deliver unified outcomes.
• Committed to exceptional service but prioritize the project’s long-term success over short-term requests.
• Have the professional courage to stand your ground under pressure and navigate difficult client conversations with data and integrity.

Responsibilities

• Take proactive ownership of project milestones and resolve blockers quickly to keep delivery on track.
• Coordinate with our technical program management team to ensure alignment between product roadmap and project plan as well as the execution of the release process
• Translate technical requirements and project plans into clear, accessible language for both internal teams, customers, and C-level stakeholders.
• Manage complex client relationships by balancing hard project data with emotional intelligence to navigate high-pressure situations.
• Experiment with new project management methods and share these learnings to help the delivery organization improve speed and quality.
• Address delivery challenges directly and objectively, focusing on collaborative solutions rather than placing blame.
• Adapt your communication style to align diverse stakeholders, from operational teams to senior management, around shared project goals.
• Ensure projects are delivered fully and meet agreed-upon standards, validating that outcomes truly meet client expectations before closure.

Benefits

• Flexible remote and hybrid working options
• Competitive Salary and a variable component tied to personal and company performance
• Multiple Learning and Development opportunities, including Focus Fridays, a half-day each month to focus on learning and personal growth
• Generous PTO and paid holidays
• Mental health benefits
• 2 MAD Days per year (Make A Difference Days for paid volunteering)

What This Job Offers

• Job Type: Full-time
• Career Level: Manager
• Education Level: No Education Listed