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Added 1 day ago
H
IT Project Manager
HrBrain
Featured · Posted directly by employer
Waterloo, ON
- $70 CAD / hour
- Contract
Support the end-to-end technology delivery of the MPW Replatform project, translating project priorities into executable plans, milestones, dependencies, and measurable outcomes.
Added 7 mins ago
NC
Program Manager
Native Counselling Services of Alberta
AB · Edmonton, AB
- $70,000 to $80,000 CAD / year
- Full-time
Good working knowledge of computers and information technology.
Added 7 mins ago
Manager, Clinical Practice
Bayshore
Thunder Bay, ON
Bayshore Home Care Solutions is seeking a Nurse to join our amazing team in the role of Manager, Clinical Practice (MCP). MCPs are accountable to implement effective management practices to…
Added 7 mins ago
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Transmission Key Accounts Manager
ATCO
Edmonton, AB
- Full-time
As a Transmission Key Accounts Manager, you will serve as the primary point of contact for ATCO Gas and Pipelines' largest transmission customers. Working closely with customers and…
Added 21 mins ago
FC
Program Lead, Enterprise CRM (Higher Education)
Fanshawe College
London, ON
- Full-time
The Program Lead, Enterprise CRM acts as a strategic liaison between Information Technology and key stakeholders across recruitment, admissions, enrolment services, student services,…
Added 21 mins ago
CC
Retail Shift Leader
Canna Cabana
Ancaster, ON
- $20.4 to $21.6 CAD / hour
- Part-time
Oversee the responsibilities of the Store Manager in the absence of SM or ASM
Added 21 mins ago
Sr. Technical Program Manager
PlayStation Global
Waterloo, ON
…proud legacy of innovation and excellence. SIE is a dynamic technology company, delivering cutting-edge hardware and network services to more than 100 million people and an entertainment…
Added 36 mins ago
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Administrative Assistant (6:30am-3pm)
Veolia | North America
AB · Edmonton, AB
- Full-time
Veolia's Water Technology Business brings together a dedicated team of experienced professionals committed to tackling the world’s most complex challenges related to water scarcity,…
Added 36 mins ago
CF
Technical Product Manager
Centre for Effective Practice
Toronto, ON
- Full-time
CEP is seeking an experienced Technical Product Manager to provide technical leadership across its digital health initiatives. Working at the intersection of evidence-informed care,…
Added 36 mins ago
R&
Senior Delivery Manager
Robots & Pencils
Canada
- Full-time
As a Senior Delivery Manager, you are the senior delivery authority on a cross-functional engagement: owning execution from kickoff through release, leading distributed onshore-and-offshore…
Added 36 mins ago
V|
Administrative Assistant (6:30am-3pm)
Veolia | Water Tech
AB · Edmonton, AB
- Full-time
Veolia's Water Technology Business brings together a dedicated team of experienced professionals committed to tackling the world’s most complex challenges related to water scarcity,…
Added 36 mins ago
GE
Project Manager AI
Global ERP Solutions
Toronto, ON
- Full-time
We are seeking a results-driven and highly organized AI Project Manager to lead the planning, coordination, and successful delivery of AI-powered projects and solutions.
Added 36 mins ago
VB
Specialist, Data Developer (Microsoft)
Vale Base Metals
Toronto, ON
- Full-time
We are currently seeking a Specialist, Data Developer (Microsoft) to join our Data Platforms & Foundation team within Information Technology (IT), based in Toronto, ON.
Added 36 mins ago
CA
Senior Income Tax Analyst
Co-operators Assurance et services financiers
Burlington, ON
- Full-time
…Senior Income Tax Analyst, you will be responsible for the delivery of income tax compliance services to various insurance and holding companies within Co-operators. You will complete…
Added 36 mins ago
MN
Electrical Project Manager
Modern Niagara Building Services
Vaughan, ON
- $100,000 to $120,000 CAD / year
- Full-time
The Electrical Project Manager leads electrical construction projects from planning and procurement through installation, commissioning, and closeout. Based in our Vaughan office, this role…
Added 36 mins ago
ES
Associate Development Manager
EA SPORTS
Vancouver, BC
- Full-time
The EA SPORTS™ Technical Team is seeking an Associate Development Manager (ADM) to manage and coordinate a variety of technical disciplines while supporting cloud infrastructure and live…
Added 37 mins ago
M
Manager, Change Enablement
Manulife
Toronto, ON
- Full-time
…developing comprehensive Change Enablement strategies. The Manager will work closely with delivery teams to ensure effective execution and requires strong leadership skills, including high…
Added 52 mins ago
IF
Manager, Service Delivery – Western Region
Intact FC
Calgary, AB
- Full-time
As Manager, Service Delivery – Western Region, you will play a pivotal role in shaping the future of regional workplace technology services. You will lead a talented multidisciplinary team…
Added 1 hour ago
D
Manager, Secure Digital Builders, Cyber
Deloitte
Moncton, NB
- Full-time
As a Manager, you will lead engagements that address new technology trends and the business challenges our clients face. You set direction, own delivery and grow the team. You drive…
Added 1 hour ago
D
Manager, Secure Digital Builders, Cyber
Deloitte
Halifax, NS
- Full-time
As a Manager, you will lead engagements that address new technology trends and the business challenges our clients face. You set direction, own delivery and grow the team. You drive…
Added 1 hour ago
D
Manager, Secure Digital Builders, Cyber
Deloitte
Fredericton, NB
- Full-time
As a Manager, you will lead engagements that address new technology trends and the business challenges our clients face. You set direction, own delivery and grow the team. You drive…
Added 1 hour ago
D
Manager, Secure Digital Builders, Cyber
Deloitte
Saint John, NB
- Full-time
As a Manager, you will lead engagements that address new technology trends and the business challenges our clients face. You set direction, own delivery and grow the team. You drive…
Added 1 hour ago
D
Manager, Secure Digital Builders, Cyber
Deloitte
Victoria, BC
- Full-time
As a Manager, you will lead engagements that address new technology trends and the business challenges our clients face. You set direction, own delivery and grow the team. You drive…
Added 1 hour ago
D
Manager, Secure Digital Builders, Cyber
Deloitte
Burlington, ON
- Full-time
As a Manager, you will lead engagements that address new technology trends and the business challenges our clients face. You set direction, own delivery and grow the team. You drive…
Added 1 hour ago
D
Manager, Secure Digital Builders, Cyber
Deloitte
Kitchener, ON
- Full-time
As a Manager, you will lead engagements that address new technology trends and the business challenges our clients face. You set direction, own delivery and grow the team. You drive…
Added 1 hour ago
D
Manager, Secure Digital Builders, Cyber
Deloitte
Ottawa, ON
- Full-time
As a Manager, you will lead engagements that address new technology trends and the business challenges our clients face. You set direction, own delivery and grow the team. You drive…

Robots & Pencils

Senior Delivery Manager

Canada

The salary range for this role is $ 170.000 CAD - $220.000 CAD. · Full-time

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Job details

Pay: The salary range for this role is $ 170.000 CAD - $220.000 CAD.
Job type: Full-time
Experience: 5+ years of experience in software delivery, technical project management, or engineering leadership
Posting language: English
Posted: Nov 9, 2026

Original job description

Robots & Pencils is an applied AI engineering firm building the next frontier of business architecture. We design and ship AI co-workers that integrate into enterprise operations and deliver measurable results for our clients. We're all in on AWS, combining deep UX capability with senior engineering talent to get AI into production fast and keep it there.

We’ve earned the trust of leaders across Consumer Products and Retail, Education, Energy, Financial Services, Healthcare, and Manufacturing and more, and earned a reputation as the nimble alternative to traditional global systems integrators. Founded in 2009, with delivery centers in Canada, the United States, Eastern Europe, and Latin America, we are smaller, faster, and more senior by design. Our teams average 15+ years of experience. We move fast, sweat the details, and build things that actually ship.

Position Overview

As a Senior Delivery Manager, you are the senior delivery authority on a cross-functional engagement: owning execution from kickoff through release, leading distributed onshore-and-offshore teams, and serving as the primary delivery partner to the client. You bring the judgment to navigate ambiguity, the discipline to keep complex programs on track, and the instinct to make every engagement a foundation for the next one.

Why This Role Matters

Senior Delivery Managers are where Robots and Pencils’ promise of “production-ready AI in 30 to 45 days” actually has to hold. On the engagements you run, you set the pace of delivery, the discipline behind it, and the trust that decides whether the client comes back for more. The work moves only as fast as someone is willing to own the plan, surface trade-offs early, and keep distributed teams pulling in the same direction.

What You’ll Do

Delivery

Lead end-to-end delivery of complex, multi-phase engagements, ensuring alignment across scope, budget, timeline, and quality to meet delivery commitments and achieve successful outcomes
Facilitate sprint planning, backlog refinement, and delivery execution across one or more cross-functional teams
Manage phased releases, production readiness, and transitions into operations and maintenance models
Identify and proactively manage dependencies, risks, scope changes, and escalations before they become blockers
Define, track, and report delivery KPIs, using data to guide decisions, manage delivery health, and inform tradeoffs across scope, timeline, and budget
Support QA and UAT efforts, ensuring quality is validated and outcomes meet agreed acceptance criteria
Bring an AI-forward mindset to your daily work, using tools like Claude to enhance delivery planning, reporting, and stakeholder communications

AI Enablement

Help implement the AI Development Life Cycle (AIDLC) across your engagements, and set the standard other delivery managers follow for standing it up
Use AI yourself day-to-day, and set the standard for how your engagements run an AI-augmented delivery process - modeling and coaching the delivery managers you mentor on how planning, building, and review change when agents are doing part of the work
Know observability for agentic and AI-driven work well enough to partner credibly with an AI product manager and AI engineers across your engagements - judge whether their approach is actually solid, catch risks early, and drive them to resolution - and hold the delivery managers you mentor to the same bar. You’re not the one building the instrumentation, but none of it should be a black box to you.
Define what “success” looks like for an AI-augmented delivery process and set the metrics standard across your engagements - quality, rework, review overhead, and velocity, not just tests passed
Build - or direct the building of - status-visibility tooling for complex AI-driven pipelines, using AI yourself, and expect the delivery managers you mentor to do the same
Understand context management and latency trade-offs deeply enough to make the call on when an agentic approach is the wrong tool for a client’s needs, and defend that call to the client
Set the standard for what infrastructure an agentic delivery pipeline needs - compute, orchestration, logging, guardrails - and know enough to hold engineering accountable for it, even though you’re not the one building it
Own the delivery approach for AI-native and agentic engagements: partner with AI/ML engineering leads on model risk, data readiness, and evaluation strategy, and translate technical uncertainty into a delivery plan and risk register the client can act on
Work with AI product managers and AI engineers to set the standard, across your engagements, for what a “definition of done” looks like for probabilistic or AI-driven features - evaluation thresholds, human-in-the-loop checkpoints, post-launch monitoring - well enough to judge whether it’s actually good, and hold the team to it
Coach delivery managers and delivery coordinators you mentor on the difference between shipping an AI product, using AI to accelerate a traditional delivery, and running an agentic development process to build the work itself - and help them adapt scope, staffing, and risk management accordingly
Serve as a credible voice with clients and internal leadership on what “production-ready AI” actually requires - setting realistic expectations for iteration, evaluation, and drift over time

Collaboration & Communication

Serve as the primary delivery contact for clients, building trusted relationships through transparency, consistency, and clear communication while identifying opportunities to expand value within the engagement
Lead stakeholder working sessions, roadmap alignment discussions, and delivery forums with confidence
Communicate progress, risks, and tradeoffs clearly to executive and non-technical audiences
Partner with Client Partners to spot expansion opportunities inside the engagement (scope, follow-on work, new use cases) and help shape the case for what’s next
Translate delivery progress into business impact for client stakeholders (ROI, milestones, decisions) so executives see ongoing value, not just status

Leadership & Influence

Lead distributed delivery teams across onshore and offshore locations, fostering accountability, collaboration, and delivery excellence
Coach junior delivery managers with concrete feedback and stretch opportunities, contributing to their development plans
Foster a culture of transparency, continuous improvement, and high performance across the engagement
Contribute to improving delivery practices, tools, and frameworks across engagements
Assess team strengths and gaps on your engagements, and partner with Client Partners to flag staffing needs and high-potential talent for the firm
Conduct executive interviews for engineers, designers, and other roles joining your engagements, and serve as an essential voice in go/no-go hiring decisions across the firm

What You’ll Bring

5+ years of experience in software delivery, technical project management, or engineering leadership
Strong understanding of agile delivery practices across complex, multi-team engagements (e.g., Scrum, SAFe, Kanban)
Experience managing distributed teams across onshore and offshore locations
Proven ability to deliver complex, multi-platform digital systems in agile environments
Strong client-facing communication and relationship management skills
Experience with delivery tooling (e.g., Jira, Confluence, GitHub, Azure DevOps, CI/CD pipelines)
Familiarity with cloud-native architectures and AI-enabled platforms
Demonstrable usage of AI tools to enhance delivery planning, reporting, and documentation (e.g., Claude)
Track record leading at least one engagement where AI/ML or agentic capability was core to the solution - including how you managed model risk, evaluation, and client expectations, not just how you used AI tools to work faster
Able to set delivery standards for AI-native work across an engagement or practice - evaluation criteria, human-in-the-loop checkpoints, monitoring - and coach other delivery managers on them
Track record leading a team through an agentic development/delivery process yourself - not just using AI tools personally - including how you approached observability, success metrics, and status visibility for a process that isn’t fully deterministic
Comfortable setting the standard, across engagements, for the infrastructure, context-management, and latency trade-offs an agentic delivery pipeline needs - enough to hold engineering and delivery managers accountable, even though you’re not the one implementing it
PMP, Scrum Master, SAFe, or equivalent certification preferred
Instinct for spotting where an engagement can grow, and the credibility with clients to bring those conversations forward with Client Partners

Helpful Extras And Unique Skills

Vertical depth in one or more of Consumer Products and Retail, Education, Energy, Financial Services, Healthcare, or Manufacturing
Experience delivering agentic, AI co-worker, or applied-AI initiatives in enterprise
Prior career experience in client-facing roles (engagement management, consulting, account leadership) that informs growth conversations

You’ll Do Well Here if You Are

A doer. You see something broken and fix it. You'd rather move on clarity than wait for certainty.
A fast learner who knows you don't know everything. The AI landscape changes weekly. You're senior enough to know better and curious enough to keep learning anyway.
Direct in a way that makes the work better. You give honest feedback. You'd rather have the hard conversation than blow smoke.
Obsessed with craft. You know genius is in the details. You ship exceptional, not perfect, and you don't put your name on work you wouldn't stand behind.
Built for ownership. You honor commitments, admit mistakes fast, and back your teammates when a decision costs something. No handoffs, no finger-pointing.
All in. You treat clients' businesses like your own. You take the work seriously without taking yourself seriously.
Resourceful when the budget, timeline, or team is tight. Constraints don't slow you down. They sharpen you.
Calm when it gets hot. When scope, timeline, and stakeholders pull in three directions, you slow the room down enough to make the right call. You’d rather raise the hard trade-off in week two than absorb it in week eight.
Glad to be in the room with people who care as much as you do. Our teams average fifteen-plus years of experience. We hire people who push each other to do better work.

The below range reflects the range of possible compensation for this role at the time of this posting. We may ultimately pay more or less than the posted range. This range may be modified in the future. An employee's position within the salary range will be based on several factors including, but not limited to, relevant education, qualifications, certifications, experience, skills, seniority, geographic location, performance, shift, travel requirements, sales or revenue-based metrics, any collective bargaining agreements, and business or organizational needs. The salary range for this role is $ 170.000 CAD - $220.000 CAD.  We offer a comprehensive package of benefits including paid time off, medical/dental/vision insurance and 401(k) to eligible employees.

An offer of employment may be conditional upon successful completion of a background check in accordance with local legislation and our candidate privacy notice. Your current employer will not be contacted without your permission.  We are committed to ensuring equal employment opportunities for all job applicants and employees. Employment decisions are based upon job-related reasons regardless of an applicant's race, color, religion, sex, sexual orientation, gender identity, age, national origin, disability, marital status, genetic information, protected veteran status, or any other status protected by law.

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More about this job

Responsibilities

Own complex, multi-phase engagements from kickoff through release, managing scope, budget, timeline, quality, risks, and production readiness while serving as the primary client delivery partner. Lead distributed teams and establish AI-augmented and agentic delivery standards, including evaluation, observability, success metrics, infrastructure expectations, and coaching for other delivery managers.

Requirements

Requires at least five years of experience in software delivery, technical project management, or engineering leadership, with a record of delivering complex digital systems and leading distributed teams. Candidates should have led AI/ML or agentic engagements, be able to set standards for AI evaluation and delivery processes, communicate effectively with clients, and demonstrate practical use of AI tools; relevant certifications are preferred.

Skills

End-to-End Delivery Management
Agile Delivery
Distributed Team Leadership
Risk and Dependency Management
Budget and Scope Management
Delivery KPI Reporting
AI-Augmented Delivery
Agentic AI Delivery
AI/ML Model Risk and Evaluation
AI Observability
Cloud-Native Architecture
Stakeholder Communication
Quality Assurance and User Acceptance Testing
Coaching and Mentoring
Jira

Benefits

Paid Time Off
Medical Insurance
Dental Insurance
Vision Insurance
401(k)

Visa sponsorship

Not detected in the job text

Keywords

AWS
Claude
Jira
Confluence
GitHub
Azure DevOps
CI/CD
Agile
Scrum
SAFe
Kanban
AI Development Life Cycle
Agentic AI
AI/ML
Cloud-Native Architecture
Model Risk
Data Readiness
Evaluation Strategy
Observability
Context Management
Latency Trade-Offs
Human-in-the-Loop
Production Readiness
Quality Assurance
User Acceptance Testing
Delivery KPIs
Risk Management
Distributed Teams
PMP
Scrum Master Certification

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