Overview

As a Senior Delivery Lead - Deploy, you will lead complex, customer-facing enterprise SaaS implementations for top-tier airline customers. You will own delivery outcomes across the full implementation lifecycle, from kickoff through go-live, stabilization, and transition to BAU.

This is a hands-on senior delivery leadership role, not a PMO coordination role. You will be expected to step into ambiguity, establish structure quickly, drive alignment across customer and internal teams, and maintain confidence with senior stakeholders throughout the implementation. You must be able to manage scope, challenge assumptions, hold the line when needed, and protect product integrity while still building strong customer trust.

Success in this role requires maturity, judgment, executive presence, and strong critical-path management in a fast-paced environment.

What You'll Do

• Own end-to-end delivery of complex enterprise software implementations for airline customers
• Lead implementation planning, governance, critical path management, risk management, and delivery execution
• Drive alignment across customer stakeholders, Delivery, Product, Engineering, Support, and other internal teams
• Establish structure, ownership, and momentum in ambiguous or fast-moving situations
• Run steering committees, status reviews, risk discussions, and executive updates with clarity and confidence
• Manage scope, dependencies, tradeoffs, and change control while maintaining customer trust
• Identify technical and delivery risks early and bring the right people together to resolve them quickly
• Create clear implementation plans and keep teams accountable to milestones, decisions, and outcomes
• Balance customer needs with product boundaries, delivery realities, and long-term scalability
• Improve delivery quality and repeatability over time through stronger frameworks, planning discipline, and practical process improvement
• Support successful go-lives, hypercare, and transition into steady-state operations

What Success Looks Like

• You quickly build credibility with customers and internal teams
• You create order in unclear situations and keep teams moving
• You lead large enterprise customers with confidence, calm, and authority
• You manage scope and expectations without drifting into custom-services behavior
• You identify risk early, escalate appropriately, and drive decisions to closure
• You improve both customer outcomes and delivery discipline
• You help raise the overall bar for Delivery

About You

Delivery Leadership

• You have substantial experience leading complex, customer-facing enterprise software implementations
• You are comfortable owning outcomes, not just coordinating tasks
• You know how to establish control quickly in a messy delivery environment
• You are highly proactive, organized, and disciplined in how you drive execution

Customer Leadership & Communication

• You are an excellent written and verbal communicator
• You communicate clearly and directly with customers and internal teams
• You are comfortable presenting risks, decisions, and tradeoffs to senior stakeholders
• You can push back professionally and maintain trust even in difficult situations
• You combine confidence with sound judgment and strong listening skills

Product Mindset

• You understand the difference between implementing a configurable product and running a custom services engagement
• You know how to manage customer expectations without defaulting to yes
• You can protect scope, timeline, and product integrity while still delivering an excellent customer experience

Technical Fluency

• You are technically fluent enough to lead implementations involving APIs, integrations, connectivity and security models, data flows, and platform dependencies
• You can challenge assumptions, identify technical risk, and coordinate effectively with technical leads
• You do not need to be the architect, but you must be able to lead confidently in technically complex situations

Ambiguity & Execution

• • You perform well in high-ambiguity environments
  • You anticipate challenges, create clarity, and move teams forward
  • You are comfortable leading without authority across competing priorities and stakeholders
  • You follow through relentlessly and take full responsibility for delivery outcomes

Skills and Experience

• 10+ years of progressive experience in delivery, implementation, program management, or related leadership roles
• 5+ years of experience leading enterprise SaaS or platform implementations with meaningful systems integration complexity
• Proven track record delivering complex customer-facing implementations on time, within scope, and with strong stakeholder alignment
• Experience managing executive stakeholders, steering committees, and formal delivery governance
• Strong experience with change control, dependency management, and implementation risk management
• Strong working knowledge of software delivery and agile development
• Hands-on familiarity with common delivery tools such as Jira, Excel, PowerPoint, Teams, and project planning tools
• Undergraduate degree in business, information technology, project management, or a related field
• Airline, travel technology, or other operationally sensitive enterprise software experience is an asset, but not required if you can ramp quickly and demonstrate strong delivery leadership in similarly complex environment

This Role is Not

• A junior project management development role
• A PMO reporting or task-coordination role
• A custom consulting role where every customer request becomes committed scope

Why Join Us

• High-ownership role with direct impact on company growth and customer outcomes
• Opportunity to help shape how Delivery scales
• Exposure to complex global airline customers and mission-critical operational environments
• Product-led environment with meaningful cross-functional influence across Delivery, Product, and Engineering
• Strong supportive management team
• Collaborative and ambitious team environment with office hubs in Toronto and Montreal

The salary range for this role is $150,000 to $200,000. In addition to salary, new hires may be eligible to receive stock options. The salary range shared is intended as a guide; the final salary offered may vary based on factors including the experience and skillset of the candidate. Our company is committed to providing a fair, equitable, and competitive salary that reflects the value an individual brings to the organization.

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.