AI Engagement Manager

Greenlight helps organizations solve complex business challenges through intelligent automation, agentic AI, and custom technology solutions. Our teams work directly with clients to understand their operations, identify opportunities, and rapidly build solutions that create measurable business value. We combine deep consulting expertise with hands-on engineering to bridge the gap between strategy and execution.

We’re building a future where consultants and engineers work alongside AI to deliver faster outcomes, stronger businesses, and transformative customer experiences. We run AI-assisted delivery as standard — from discovery through documentation to quality assurance — and this role operates in an environment where Anthropic's Claude is embedded in how we work, not treated as a future state.

• Commercially sharp and client-obsessed — you measure success by what the client achieved, not what was delivered
• Calm in complexity — you manage multiple engagements, competing priorities, and difficult conversations without losing composure or thread
• Fluent across the room — as credible with an executive sponsor as you are with a developer debugging an agent workflow
• AI-forward — you understand enough about how intelligent automation works to lead it, defend it, and sell its value without needing a translator
• Ownership mindset — the engagement is yours; you don’t wait for problems to surface, you find them first

This is the accountability seat on every Greenlight engagement. The AI Engagement Manager owns the client relationship, the commercial track, and the delivery cadence - across AI and automation projects running on tight, high-output cycles.

Engagements operate with an AI Automation Business Consultant who owns process discovery, AI logic design, and technical specification, alongside an Automation Engineer who owns the build. This role sits above both, as the commercial and relational anchor keeping the engagement on track, the client confident, and the value visible.

This means the role requires AI and automation fluency to have credible conversations about what is being built, how long it should take, and what the business outcome looks like - without needing the consultant or engineer to translate. You do not build the solution. But you need to understand it well enough to own it in the room.

Director Project Delivery & Strategy

Automation Business Consultant, Automation Engineers, Client Stakeholders, Vendor Partners

Executive sponsors, business leads, project steering, vendor partners

3–4 concurrent engagements (3–6 month delivery cycles)

UiPath, Microsoft Power Platform, Anthropic Claude / AI Agents

Mid-to-Senior (5–8 years relevant experience)

Onshore Canada - GTA preferred

Hybrid Office - client-facing with occasional travel

• Serve as the primary client contact from kickoff through post-delivery review — the face of the engagement at every stage
• Build trusted relationships with executive sponsors, business leads, and key stakeholders — read the room, sense shifts in confidence, and act before they become delivery risks
• Own scope management and change control — identify creep early, facilitate commercial conversations around change with clarity, and protect margin without damaging the relationship
• Lead difficult conversations: expectation resets, delay communications, scope disputes — directly, calmly, and without escalating to leadership by default
• Maintain commercial awareness across your portfolio; flag risks to margin, timeline, or client satisfaction before they surface in a steering call

• Understand what is being built on every engagement — the automation logic, the AI agent behaviour, the integration points — well enough to represent it accurately to a client executive
• Track delivery against the Week 0-to-go-live cadence: readiness confirmed before kickoff, discovery completed in Week 1, SDD validated before build, test cases parallel with Sprint 1
• Identify when the delivery thread is at risk — slow discovery, SDD delays, build blockers, UAT gaps — and drive resolution before it affects the timeline
• Maintain the RAID log, delivery schedule, and status reporting to client stakeholders — governance that is current, honest, and actionable, not performative
• Manage competing priorities across 3–4 concurrent engagements without losing thread or dropping client confidence

• Create the conditions for the Automation Business Consultant and Engineer(s) to do their best work: resolved blockers, aligned stakeholders, clear scope, no unnecessary noise
• Review Consultant deliverables — PDDs, agent specs, SDD sign-offs — for quality and alignment with client expectations before they go to the client
• Coach the consultant through complex stakeholder sessions and difficult discovery conversations — your experience in the room is a resource, not a rank
• Manage resource capacity and flag resourcing risks early — don’t let a build slow down because of a preventable resource constraint

• Proactively track whether clients are realizing expected automation and AI value — report against agreed KPIs and business outcomes, not just delivery milestones
• Lead go-live communications, confidence management, and post-delivery debriefs — close every engagement with the client seeing what was delivered and what it was worth
• Identify expansion opportunities within active accounts — process gaps, adjacent automation candidates, AI use cases the client hasn’t named yet — and surface them to the account team

• 5–8 years in a delivery, project management, or client-facing consulting role within technology — automation, AI, and RPA, development projects strongly preferred
• Proven track record managing short-cycle software delivery projects (3–6 months) end-to-end across a portfolio of concurrent engagements
• Direct exposure to AI or automation project delivery — you understand what an LLM-based agent or RPA build involves, the risks that are specific to these projects, and how to talk about them with a client
• Experience managing executive and senior stakeholder relationships, including difficult commercial conversations and expectation management
• Background in a consulting, managed services with experience delivering AI or agentic automation projects
• Track record of managing scope, change orders, and commercial conversations in a professional services or managed services environment
• Agile delivery — sprint planning, backlog prioritisation, retrospectives; comfortable running a cadence without a dedicated Scrum Master

• Commercial acumen — you understand project economics, margin, scope risk, and value-based delivery; you protect both the client relationship and Greenlight’s position
• AI and automation fluency — not an engineer, but not a stranger to the technology; you can discuss agent logic, LLM outputs, and automation architecture with enough credibility to hold a client room
• Political intelligence — you read room dynamics, sense wavering confidence, and act before issues escalate
• Clear, confident communicator — you simplify complex technical and commercial topics without losing accuracy for either audience
• Calm under pressure — you de-escalate, not amplify; clients feel steadier after talking to you, not more anxious
• Organised across complexity — managing 3–4 concurrent projects with different clients, consultants, and build stages without losing thread

They know the delivery status before the status call and the client's mood before the client says anything. They understand what the consultant is building well enough to defend the timeline and scope in the same breath. When something goes sideways, they're already in motion — not writing an update, not waiting for the team to surface it. They run a portfolio of concurrent engagements with the same composure they bring to one. And they leave every client at go-live feeling like they got more than they paid for.

We use AI tools to support parts of our recruitment — things like organizing applications and flagging relevant experience. These tools inform our process, they don't drive it. Every hiring decision is made by our team, full stop.

Compensation
The expected salary range for this role is $110,000 – $130,000 CAD Currency annually, based on experience and qualifications. We're happy to discuss further in conversation.

Equal Opportunity
Greenlight is an equal opportunity employer. We believe in fair consideration for all candidates regardless of ethnicity, culture, sexual orientation, religion, age, gender, or disability status.

Great Place to Work™
Greenlight is a certified Great Place to Work™ — 98% score. We're proud of that and we work every day to keep earning it.