Delivery Lead - Deploy

About Us Air-tek is a Canadian-based software company with a powerful suite of products that has already achieved significant traction in a large global market. Our customers are global airlines operating in complex, high-stakes environments where delivery quality, product quality, and customer trust matter deeply. We operate in stealth mode during this growth phase. Our team is united by a passion for solving hard problems, building great products, and creating the passenger-centric travel industry. Based in Toronto, our culture is built on trust, collaboration, high standards, and continuous growth.

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.